Author Topic: Wanted references  (Read 7978 times)

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Rhodium

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Wanted references
« on: September 27, 2001, 06:29:00 PM »
Reaction Byproducts of Common Cold Tablet Ingredients Via Hydriodic Acid/Red Phosphorus
Oulton-S-R; Skinner-H-F
Microgram 32(10), 257-285 (1999)

Abstract
In southern California, the current method of choice for the synthesis of illicit methamphetamine is the reduction of ephedrine or pseudoephedrine with hydriodic acid and red phosphorus. However, as a result of restrictions on the availability of both precursors, common cold tablet preparations are increasingly being used as a source of ephedrine and pseudoephedrine. Such tablets also contain other ingredients such as paracetamol, chlorpheniramine, dextromethorphan, diphenhydramine, doxylamine, guaifenesin, and triprolidine. Depending on the isolation method used, these other compounds may be present in the reaction mixtures and subsequently produce other by-products. This paper describes the by-products formed as a result of the reaction between the tablet ingredients and hydriodic acid/red phosphorus. The identification of the by-products found in clandestine methamphetamine laboratories would help to determine the exact cold preparation used as the source of the precursor.
____ ___ __ _

Synthesis of deuterio-l-amphetamine, d1 sulfate
Foreman RL, Siegel FP, Mrtek RG.
J Pharm Sci. 1969 Feb;58(2):189-92.
____ ___ __ _

The Identification of Cathinone in Khat (Catha edulis): A Time Study
Lee MM
J. Forensic. Sci. 40(1), 116-121 (1995)

Abstract
Previous studies on the khat plant (Catha edulis) illustrated the importance of using freshly harvested young shoots and leaves such that cathinone, the principal active component and Schedule I controlled drug contained within the plant, could be suitably isolated and identified. Upon drying and storage of the cut plant material, cathinone readily converts to the reduced product, cathine, which necessitates rapid extraction and chemical analysis for cathinone identification. This study demonstrates that by air drying the young khat shoots at ambient temperature, cathinone may be detected in khat samples that have been harvested for more than 10 days. Refrigeration for two weeks and freezing for one month of the khat samples also yield identifiable levels of cathinone. Cathinone and cathine are both specifically determined and differentiated by vapor phase infrared detection, which is the method of choice in relation to mass spectrometry.
____ ___ __ _

MS data of some metabolites of the amphetamine derivatives MDA MDMA
Verweij AM
Arch Kriminol. 197(1-2), 27-30 (1996) [Article in German]

Abstract
Mass spectrometric data are presented for the detection of metabolites of the amphetamine derivates 3,4-(Methylenedioxy)amphetamine (MDA) und 3,4-(Methylenedioxy)methylamphetamine (MDMA, Ecstasy) as well as some other derivatives.
____ ___ __ _

Intermediates/byproducts in the illegal production of fentanyl, and its p-fluoro- and N-acetyl analogues
Fritschi G, Klein B.
Arch Kriminol. 196(5-6), 149-55 (1995) [Article in German]

Abstract
The aim of the present work was the gaschromatographic and mass spectrometric characterization of intermediates and artifacts in the illegal synthesis of fentanyl and fluorfentanyls. These data provide the means to recognize fentanyls from illicit production.
____ ___ __ _

Fentanyl analogues with a modified propanamido group as potential affinity labels: synthesis and in vivo activity.
Essawi MYH.
Pharmazie 54(4), 307–8 (1999)



LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors
Watts VJ., Lawler CP., Fox DR., Neve KA., Nichols DE., Mailman RB
Psychopharmacology 118(4), 401-9 (1995)
____ ___ __ _

Complex stimulus properties of LSD: a drug discrimination study with ?2-adrenoceptor agonists and antagonists
Marona-Lewicka D., Nichols DE
Psychopharmacology 120(4), 384-91 (1995)



High atomic yield bromine-less benzylic bromination
Mestres, Ramon; Palenzuela, Jesus
Green Chemistry 4(4), 314-316 (2002)
DOI:

10.1039/b203055a



Abstract
A two-phase mixture (sodium bromide, aqueous hydrogen peroxide/carbon tetrachloride or chloroform) under visible light provides a simple and convenient system for benzylic bromination of toluenes. A high atomic yield for bromine atoms is attained. Substitution of the chlorinated solvents by other more environmentally benign organic solvents has been attempted and good results are obtained for methyl pivalate.

Found in

Post 468080

(moo: "Another one", Methods Discourse)




The Synthesis of a New Homologue of Mescaline
Hey, P.
Quarterly Journal of Pharmacy and Pharmacology, Vol. 20, 129-134 (1947)



Could anyone fetch these two revolutionary articles by Channe Gowda, published back-to back in Ind. J. Chem?

Hydrazine/magnesium mediated cost-effective and selective reduction of nitro compounds
Srinivasa GR, Abiraj K, Gowda DC
Ind. J. Chem. Sect. B,  42(11), 2885-2887 (2003)

Abstract
Hydrazine aided catalytic transfer hydrogenation has been employed for the reduction of both aliphatic and aromatic nitro compounds to corresponding amines. The use of low-cost magnesium, as catalyst leads to high yields of amino compounds under ambient conditions of temperature and pressure. Many commonly encountered functional groups like ethene, nitrile, acid, phenol, halogen etc. are compatible with the present system.
____ ___ __ _

Magnesium/ammonium formate promoted rapid, low-cost and selective reduction of nitro compounds
Srinivasa GR, Abiraj K, Gowda DC
Ind. J. Chem. Sect. B,  42(11), 2882-2884 (2003)

Abstract
The reduction of nitro compounds, both aliphatic and aromatic into corresponding amines has been achieved at room temperature in good yields by employing ammonium formate in the presence of low cost magnesium powder. The hydrogenation is fast and selective in the presence of other sensitive functionalities such as halogens, -OH, -OCH3, -CN, -COOR, -COOH etc. It was observed that, this system is equally compatible with existing methods, which employ expensive catalysts like palladium, platinum, ruthenium etc.



Wanted Amphetamine Syntheses:

Preparation of 2-phenylisopropylamine
F.M. Jaeger and J.A. van Dijk
Proc. Acad. Sci. Amsterdam, 44, 26-40 (1941) [CA 37, 6219 (1943)]

Reduction of phenylhydrazone-p-sulfonic acids
R. Fusco and L. Canonica
Chim. Ind. (Milan) 32, 208-210 (1950) [CA 45, 4645a (1951)]



Catalyst selection for the lactonization of 1,4-butanediol
Srinivas B, Subrahmanyam M, Kulkarni SJ, Rao YVS, Rao AVR
Indian Journal Of Chemical Technology 3(4), 237-238 (1996)

Abstract
Chromite catalysts have been studied with and without modifiers for lactonization of 1,4-butanediol. The reaction on majority of the catalyst proceeds giving rise to cyclodehydration product, tetrahydrofuran (THF) mainly rather than cyclodehydrogenation product of gamma-butyrolactone (gamma-BL). The lactonization of 1,4-butanediol increases when the zinc chromite catalyst is modified with Pt metal. Few methods are discussed regarding the preparation and modification of the catalysts and their effects in selectivity from THF to gamma-BL.



Synthetic approaches to cocaine and its analogs    
Simoni, Daniele; Rondanin, Riccardo; Roberti, Marinella   
Targets in Heterocyclic Systems, Vol. 3, pp. 147-183 (1999)

Abstract
A review of the most important synthetic approaches to cocaine and its analogs with 95 refs.  It is presented in the following chapters; (1) Introduction (2) Total synthesis of cocaine via Mannich-type cyclization, nitrone-based approach, and Dieckmann cyclization (3) Synthesis of anhydroecgonine methylester (4) Synthesis of cocaine's analogs (5) Conclusions.  Particular attention has been devoted to the recent synthetic acquisitions esp. regarding the synthesis of two-carbon bridge substituted cocaines as well as to conformationally restricted cocaine derivs.
(Please scan the pages in an OCR-friendly way, as in completely straight and in 200 DPI. Do not compress with jpg/djvu.)



Synthesis, Stability and Analysis of MDA analogs
J Alabama Academy Sci 64, 34-48 (1993)

Methadone NMR Analysis
Sci. Pharm. 68(3), 229-234 (2000)



Reactions of aliphatic epoxy compounds. IV. New route for DL-ephedrine synthesis.
Lunge, Jerzy; Belzecki, Czeslaw
Acta Polon. Pharm. 18,  177-81 (1961)

Ref found in in

Post 290749

(foxy2: "Novel route to Ephedrine and possibly its analogs", Novel Discourse)




Synthesis of benzyl chloride by solid-liquid phase-transfer catalysis method
Bui Thi Van Nga; Chu Pham Ngoc Son
Tap Chi Hoa Hoc 23(4), 6-7 (1985)

Abstract
PhCH2Cl was prepd. by chlorination of PhMe with Ca(OCl)2 using tetrabutylammonium hydrogen sulfate or tetrabutylammonium bromide as phase-transfer catalysts.  With suitable ratio of PhMe-catalyst, the yield was high and the reaction was quite selective.
____ ___ __ _

Chemical Reagents 21(4), 231-232 (1999) Synthesis of 1-(2-bromophenyl)-2-propanol
Chemical Reagents 21(5), 264-265 (1999) Synthesis of 2,5-dimethoxy-4-methylbenzaldehyde
Chemical Reagents 22(6), 356-357 (2000) A new synthetic method for phenylacetone

Title: Hua hsüeh shih chi = Huaxue shiji = Chemical Reagents
ISSN: 02583283
Homepage:

http://huaxsj.periodicals.net.cn/default.html



Libraries in the western hemisphere carrying the journal:

Linda Hall Library

(http://www.lindahall.org) (Kansas City, Missouri, USA)
British Library Science Reference Library (London, England)
Universitaets Bibliothek und TIB (Hanover, Germany)

algebra

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wanted refs.
« Reply #1 on: May 29, 2003, 01:58:00 PM »
This reference which discusses DXM would also be a very useful addition to the Levorphanol synth on Rhodium's by DopaMan,

https://www.thevespiary.org/rhodium/Rhodium/chemistry/levorphanol.html



The synth for this powerful opiate is very straightforward except for the difficulty in obtaining 2-(1,4-Cyclohexadienyl)ethylamine. This compound can be made from PEA (decarboxylate phenylalanine) with a controlled birch reduction of the ring, however the reference given here would seem to procede from cyclohexanone or cyclohexanol which would offer a far simpler route.

Preparation of useful intermediates of dextrorphan
Passarotti, C. M.; Valenti, M.; Grianti, M.
Boll.Chim.Farm. 1993, 132: 11 472-474

Abstract
Dextrorphan is the main metabolite of Dextromethorphan, a drug with high anti-tussive activity.In this preliminary work we report on the synthesis of two essential intermediates for its preparation: 2-(1-cyclohexenyl)ethyl amine and (R;S)-1-(4-methoxy-benzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline.

ChemisTris

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Progress toward the total synthesis of salvinorin
« Reply #2 on: September 14, 2003, 08:34:00 PM »
This is from the 225th ACS National Meeting. I hope that someone can post more about it  :) .
As far as i can tell, it is not yet available through

http://www.cas.org/Support/dds.html



Progress toward the total synthesis of salvinorin A: A potent, non-nitrogenous kappa-opioid receptor selective agonist.
Vangapandu, Suryanarayana; Phillip, Ashok; Stewart, Jeremy D.; Zjawiony, Jordan; Avery, Mitchell A.; McCurdy, Christopher R.  
Department of Medicinal Chemistry,  University of Mississippi,  University,  MS,  USA.
Abstracts of Papers, 225th ACS National Meeting, New Orleans, LA, United States, March 23-27, 2003 ORGN-421.
Publisher: American Chemical Society,  Washington, D. C  CODEN: 69DSA4  Conference; Meeting Abstract  AN 2003:184914

Abstract
Salvinorin A (1), a nonnitrogenous, neoclarodane diterpine, obtained from Salvia divinorum, has been reported to be the most potent naturally occurring hallucinogen, with an ED in humans in the 200- to 1,000- micrograms range when smoked with a typical duration of action being several minutes to an hour.  Salvia divinorum exts. and salvinorin A have become widely used in the U.S. as legal hallucinogens.  The site of pharmacol. activity remained a mystery until the recent report that identified salvinorin A as a potent and selective ligand for the kappa-opioid receptor.  Thus representing a unique structural class of nonnitrogenous opioid ligands.  In order to investigate structure-activity relationships of salvinorin A, analogs must be made.  One approach to analog synthesis is from a total synthesis perspective.  To our knowledge, there are no known syntheses of salvinorin A. Here we report our progress toward the first total synthesis of salvinorin A.


Surya N. Vangapandu

(http://webmail.olemiss.edu/~suryav/)


azole

  • Guest
the only ref. on MMA human use
« Reply #3 on: October 27, 2003, 10:32:00 AM »
de Zorzi, C., Cavalli, A., Zacchia, 10, 3 (1974)

Journal info: Zacchia: archivio di medicina legale, sociale e criminologica
Roma, -, 1921-  *  Non pubbl. dal 1981 al 1982  *  ISSN 0044-1570

The experiments on animals suggest that MMA (3-methoxy-4-methylamphetamine) can be considered as a non-neurotoxic analog of MDMA (

https://www.thevespiary.org/rhodium/Rhodium/pdf/mmai.pdf

). A quote from PiHKAL:

Some years ago a report appeared in the forensic literature of Italy, of the seizure of a small semitransparent capsule containing 141 milligrams of a white powder that was stated to be a new hallucinogenic drug.  This was shown to contain an analogue of DOM, 3-methoxy-4-methylamphetamine, or MMA.  The Italian authorities made no mention of the net weight contained in each dosage unit, but it has been found that the active level of MMA in man is in the area of 40-60 milligrams.  The compound can apparently be quite dysphoric, and long lived.

There are several questions that may be answered in this article:
1) Are there anecdotal reports on the effects of MMA in humans?
2) How was the structure of the seized substance elucidated? Is there any possibility that it could be actually an isomer of MMA, say, 4-MeO-3-Me-A, PMMA, or 4-MeO-3,5-diMe-PEA?
3) What method was applied to synthesize the substance?

Chimimanie

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Wanted Articles
« Reply #4 on: November 16, 2003, 08:41:00 PM »
Methoxyamphetamines and fenfluramine compared to amphetamine for antagonism of electroshock seizures
Davis, W. Marvin; Hatoum, Hind T.; Hatoum, Nabil S.   
Research Communications in Substances of Abuse  (1982),  3(3),  297-305.
____ ___ __ _

Synthesis of Ar-S-R from Ar-Br with Cu2+

New synthetic method for 2,5-dimethoxybenzaldehyde.    
Chen, Zhi-tao; Xiang, Jian-nan; Li, Zhi-liang.   
Chongqing Daxue Xuebao, Ziran Kexueban  (2002),  25(2), 109-111. 
CODEN: CDXZF2  ISSN: 1000-582X.  Journal  written in Chinese.    CAN 138:73048    AN 2002:335010   

Abstract
Reimer-Tiemann reaction and a methoxylation through di-Me sulfate are employed for the prepn. of 2,5-dimethoxybenzaldehyde from p-methoxyphenol in this paper.  Comparing different phase transfer catalysts, it can be demonstrated that the PEG-10000 is the most favorable catalyst used in Reimer-Tiemann reaction.  The yield and quality are improved through the methoxylation of 2-hydroxy-5-methoxy-benzaldehyde in a buffer soln.  The diverse factors influencing the yield are examd.  Some explanations are given from theor. viewpoint.  The proper exptl. conditions are found and the overall yield reached 68%.
____ ___ __ _

Analysis of the essential oil of Zingiber cassumunar Roxb. from Indonesia.    
Taroeno; Brophy, J. J.; Zwaving, J. H.    Fac. Pharm.,  Gadjah Mada Univ.,  Yogyakarta,  Indonesia.   
Flavour and Fragrance Journal  (1991),  6(2),  161-3.

Abstract
The compn. of the Z. cassumunar oil from Indonesia was examd. by gas chromatog. (GC) and GC-mass spectrometry.  A major part of the oil consists of monoterpenes with sabinene and terpinen-4-ol as main constituents.  Sesquiterpenes accounted for a small part of the oil with sesquiphellandrene being the principal constituent.  In addn. to these terpenes the oil contains a no. of phenylbutanoids.  The essential oil obtained by steam contained about 25% of these phenylbutanoids whereas, the oil obtained by extn. with light petroleum had about 46% with trans-1-(3,4-dimethoxyphenyl)but-1-ene, trans-1-(3,4-dimethoxyphenyl)butadiene and trans-4-(3,4-dimethoxyphenyl)but-3-ene-1-yl acetate as the main constituents.

Zamboni

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Dissertationes Pharmaceuticae
« Reply #5 on: February 01, 2004, 04:35:00 PM »
Can anyone get this article?  Volume 1963 was gone at the only library I found in my area that carries it.

Dissertationes Pharmaceuticae 15(4), 419-426 (1963)
Infrared absorption spectra in the 1-14 micron range of apiole, 1,2,3,6-tetramethoxy-4-allylbenzene, myristicin, etc. obtained from various essential oils are recorded and discussed.

This is found in Chemical Abstracts (year = 1964) 4145b (volume 61?)


Some things I found using

http://www.google.com

:

Prace Komisji Nauk Farmaceutycznych Dissertationes Pharmaceuticae

Dissertationes Pharmaceuticae

http://www.if-pan.krakow.pl/pjp/986_1.htm




Polish Journal of Pharmacology and Pharmacy (1973-1992) (ISSN 0301-0244 POL)
Dissertationes Pharmaceuticae et Pharmacologicae (1966-1972) (ISSN 0012-3870 POL)
Dissertationes Pharmaceuticae (1954-1965) (ISSN 0301-1615 POL)
Dissertationes Pharmaceuticae (1949-1952) (ISSN 0477-4795 POL)

http://unionlist.sti.sci.eg/data/00013/00013835.htm


Purepacker

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Traces of metals in Ecstacy tablets
« Reply #6 on: February 27, 2004, 01:03:00 PM »
Could someone retrieve the following article?

Traces of metals in Ecstacy tablets
S. Comment et. al.,
Probl. Forensic Sci., 66, p. 131 (2001)


Nicodem

  • Guest
OK, I know...
« Reply #7 on: March 17, 2004, 11:20:00 AM »
...this time I ask nearly the impossible but anyway:
Nikolova M., Daleva L. Marinova V. Farmazia (Sofia) 19 (1969) 31.
and/or
Vasileva E., Natova L. Compt. Rend. Bulgaria 44 (1991) 37.
The papers are probably in Bulgarian but that is OK


Megatherium

  • Guest
Wiss. Z. Techn.
« Reply #8 on: April 04, 2004, 04:39:00 AM »
Has somebee access to the (german) Wiss. Z. Techn. article about the Mannich reaction on primary amines?

H.G.O. Becker, W. Ecknig, E. Fanghänel, S. Rommel    Wiss. Z. Techn. (1968) vol 11 p 38

josef_k

  • Guest
quaternary N-methyl-4-piperidone methiodide
« Reply #9 on: April 21, 2004, 01:10:00 PM »
Could someone get these articles drone mentioned on the reaction of the quaternary N-methyl-4-piperidone methiodide with amines to get N-substituted 4-piperidones.

Chem. Heterocycl. Compd. 21(12) 1327

Also, in an article I saw they alkylated 4-piperidone pyrrolidine enamine with allylbromide to get 3-allyl-4-piperidone but they didn't give reaction details or references. That kind of reaction would be useful for making 3-methyl piperidones.

Chem. Heterocycl. Compd. 21(12): 1362

Vitus_Verdegast

  • Guest
side-chain modifications of amphetamines
« Reply #10 on: April 27, 2004, 02:52:00 PM »
Here is something interesting in the pursuit of AMT from isatin:
3-Methyleneoxindoles can be selectively reduced at the carbon-carbon double bond using sodium dithionite in aqueous ethanol.
Isatylideneacetones are reduced to the corresponding 3-acetonyloxindoles in 57-92% yield.

Joshi, K.C. et al, Pharmazie (1984) 39, 153



As posted in

Post 475500

(Nicodem: "Modifications on the side chain (again)", Novel Discourse)
:

“The alpha-methyl group of amphetamine itself can be replaced by allyl, ethyl, or ethynyl groups of electron-donating character, without deleterious effects on centrally-mediated actions [1,2], but replacement by electron-withdrawing groups, such as cyano [3] or trifluoromethyl [4], abolishes amphetamine-like properties.”

[1] Burger, Zimmermann, Ariens (1966), J. Med. Chem. , 9, 469. [Retrieved]
[2] Shamano, Hitchens, Goldstein, Beiler (1968), Arch. int. Pharmacodyn. Ther. , 172, 251.
[3] Pinder, Burger, Ariens (1970), Arzeim.-Forsch. , 20, 245. [Retrieved]
[4] Pinder, Burger (1967), J. Pharm. Sci., 56, 970. [Retrieved]

If anybody can find and post them, these are the refs for the phenoxyethylamines:
Julia, M. and de Rosnay; European Journal of Medicinal Chemistry, 4 (1969), 334.
Julia, M. and de Rosnay; European Journal of Medicinal Chemistry, 5 (1970), 337.
(European J. of Med. Chem. stil had the title Chim. Ther. in those times)
Rougeul, A.; Laval. med., 40 (1969), 37.
Rougeul, A. and Verdaux, J.; Rev. Can. Biol., 31 (1972), 49.


7is

  • Guest
GHB vs. GBL
« Reply #11 on: April 29, 2004, 07:13:00 AM »
Improved pharmacological activity via pro-drug modification: comparative pharmacokinetics of sodium gamma-hydroxybutyrate and gamma-butyrolactone
Lettieri J, Fung H-L
Research Communications in Chemical Pathology and Pharmacology 1978, 22(1)107-118

Abstract
Although gamma-butyrolactone (GBL) rapidly converts to gamma-hydroxybutyrate (GHB) in vivo, the lactone gave significantly more prolonged hypnotic effects than GHB when equimolar doses were compared both parenterally and orally in rats. Plasma drug concentrations were higher after GBL administration through both routes, consistent with the observed differences in the pharmacological activity of these two compounds. Oral GBL was absorbed much faster than oral GHB, with the dual effects of decreasing potential first-pass metabolism and elevating plasma drug concentrations to the region where capacity-limited elimination is operative. Parenteral GBL produced a slower initial drug plasma clearance than parenteral GHB. In spite of the rapid metabolism of GBL to GHB, the apparent tissue distribution of these two compounds may be different.

Ganesha

  • Guest
Shulgin
« Reply #12 on: June 04, 2004, 06:55:00 AM »
Medicinal chemistry and structure-activity relationships of hallucinogens.
Nichols, D.E., and Glennon, R.A.
In: Jacobs, B.L., ed. Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. New York: Raven Press, 1984. pp. 95-142.



The replacement of two adjacent methoxy groups with a methylenedioxy ring generally increases potency...
I would be grateful if someone could supply me with this paper covering the details:

C. Naranjo, A. T Shulgin, and T. Sargent, Med. Pharmacol. Exp., 17,359 (1967)

Bibliography data on the latter, found by Major_Armstrong:
Medicina et pharmacologia experimentalis
Basel ; New York : S. Karger, 1965-1967, 6 v. : ill. ; 26 cm, Vol. 12, no. 1-v. 17, no. 6.
See:

http://www.scd.univ-rennes1.fr/sante/perab_m.html




pericles

  • Guest
Shulgin 5-MeO-DIPT article
« Reply #13 on: June 13, 2004, 02:59:00 PM »
Someone must have access to Communications in Psychopharmacology. I'd love to read this.

N,N-Diisopropyltryptamine (DIPT) and 5-Methoxy-N,N-Diisopropyltryptamine (5-MeO-DIPT). Two Orally Active Tryptamine Analogs with CNS Activity.
Shulgin AT, Carter MF.
Communications in Psychopharmacology 1980; 4():363-369

armageddon

  • Guest
wanted
« Reply #14 on: June 16, 2004, 01:25:00 AM »
Hehehe....

"Isolation of Lysergol from Kaladana", C.I. Abou-Chaar and G.A. Digenis, Nature 212, 618 (1966)

BTW, the plant's full latin name is "Calonyction-Ipomoea (Choisy) Hallier f. nova species"....

THX A


GC_MS

  • Guest
TMA
« Reply #15 on: July 07, 2004, 01:58:00 AM »
First human trials with TMA
Peretz, D. I., Smythies, J. R., and Gibson, W. C.
J. Mental Sci., 101, 317 (1955)

Shulgin refers to this article a few time. It describes the first human trials with TMA. You can also read about it in PiHKAL under TMA.


moo

  • Guest
Please
« Reply #16 on: July 07, 2004, 06:17:00 PM »
Raney Ni catalyzed Leuckart reaction

J. Gen. Chem. U.S.S.R. (Engl. translation) 25, 1377-81 (1955)

Abstract in

Post 512060 (missing)

(moo: "Nickel catalyzed Leuckart reaction.", Methods Discourse)



Lego

  • Guest
Wanted
« Reply #17 on: July 12, 2004, 03:22:00 PM »
Zhurnal Organichestroi Khimii, 1965, 1(11), 1973-1976

Hopefully related to butyraldehyde acetals - If it is of interest please translate it....

Thanks!



A novel metal promoter for the Sandmeyer reaction.
Anon. UK. CODEN: RSDSBB  ISSN: 0374-4353. CAN 103:87565 AN 1985:487565      
Research Disclosure  (1985),  252  171.

Abstract
Fe2+ halide or Feo-Fe3+ system as a promoter for the Sandmeyer reaction, wherein Cu+ causes detrimental side effects in the case of Me-substituted or ortho-substituted arenediazonium salts, was discussed.  The oxidn. of pendant Me groups was not evident in the Fe system and the reaction was applicable to a wide variety of functional groups.  The Fe system is less expensive than Cu+ and more friendly environmentally.


Disciple

  • Guest
Phenylpiperazines
« Reply #18 on: July 28, 2004, 06:06:00 PM »
Hi
I've hada bit of a fish aroundlooking for this but haven't found anything yet if someones got access to this thanks.
Physical characterization of the new bis(N-phenylpiperazines).
Journal of Pharmacy (University of Karachi) (1985), 3(2), 89-94.

Stalin

  • Guest
Drugs of Abuse: historical context
« Reply #19 on: August 05, 2004, 01:26:00 AM »
I would be interested in the following two articles, especially because of their historical context:

The Drug Problem in the Military: an American Lawyer's Point of View. Medicine, Science and the Law 9(2) (1969) 122-124
Hallucinogens and Narcotics Alarm Public. Chemical and Engineering News 48(47) (1970) 44-45

Thanks in advance


Kinetic

  • Guest
Retrieved reference
« Reply #20 on: August 05, 2004, 10:47:00 AM »
Here you go psyloxy:

Heterogeneous catalysts in the preparation of 2-aryl-1,3-dinitropropanes from beta-nitrostyrenes or benzaldehydes
Angélica Fierroa, Marcos Caroli Rezendea,* Silvia Sepúlveda-Bozab, Miguel Reyes-Paradab and Bruce K. Casselsc
J. Chem. Research (S)
, 2001, 294–296

Abstract
The use of heterogeneous basic catalysts (KF, NaHCO3) in the preparation of 2-Aryl-1,3-dinitropropanes from beta-nitrostyrenes or benzaldehydes is described, with one example followed kinetically by HPLC analysis of aliquots of the reaction.


psyloxy

  • Guest
wanted
« Reply #21 on: August 06, 2004, 10:11:00 AM »
J.Chem.Res.Synop.; EN; 7; 1996; 334-335

bromination of vanillin with hydrogen peroxide, HBr, sodium tungstate in GAA; 30 min, 45°C, 73%

I know even better yields are reported here at the hive with H2SO4 / NaBr / H2O2 (hest, I think) - but reading this article surely can't hurt.



reaction of P2O5 with various metal salts (research target: POCl3 from P2O5)
H. Kolbe, Ann. d. chem. u. pharm., 103, 240 (1859) EDIT: according to legal this ref is in error, issue/volume and year don't match
--psyloxy--

Lego

  • Guest
Synthesis, 2004, 1947-1950
« Reply #22 on: August 12, 2004, 10:27:00 AM »
Enantioselective Henry Reaction Catalyzed by Salen-Cobalt Complexes
Youichi Kogami, Takahiro Nakajima, Taketo Ikeno, Tohru Yamada
Synthesis, 2004, 1947-1950
DOI:

10.1055/s-2004-829157



Abstract: The enantioselective Henry reaction catalyzed by the optically active salen-cobalt complexes, proceeded to afford ?-hydroxynitroalkanesin good-to-high yields with high enantioselectivity.

Thanks!  8)


java

  • Guest
Enantioselective Henry Reaction ........
« Reply #23 on: August 12, 2004, 01:13:00 PM »
..........for Lego

Enantioselective Henry Reaction Catalyzed by Salen-Cobalt Complexes
Youichi Kogami, Takahiro Nakajima, Taketo Ikeno, Tohru Yamada

Synthesis, 2004, 1947-1950

DOI:10.1055/s-2004-829157



Abstract: The enantioselective Henry reaction catalyzed by the optically active salen-cobalt complexes, proceeded to afford ?-hydroxynitroalkanesin good-to-high yields with high enantioselectivity.


lugh

  • Guest
Four Retrieved Requested Articles
« Reply #24 on: August 13, 2004, 02:25:00 AM »
For Rhodium:

The Identification of Cathinone in Khat (Catha edulis): A Time Study
Lee MM
J. Forensic. Sci. 40(1), 116-121 (1995)




Complex stimulus properties of LSD: a drug discrimination study with ?2-adrenoceptor agonists and antagonists
Marona-Lewicka D., Nichols DE
Psychopharmacology 120(4), 384-91 (1995)




LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors
Watts VJ., Lawler CP., Fox DR., Neve KA., Nichols DE., Mailman RB
Psychopharmacology 118(4), 401-9 (1995)




For GC_MS:
A New Hallucinogen: 3,4,5-Trimethoxyphenyl-?-Aminopropane
(with notes on a stroboscopic phenomenon)

Peretz, D. I., Smythies, J. R., and Gibson, W. C.
J. Mental Sci., 101, 317 (1955)



;)


Rhodium

  • Guest
Selective NR1/2B NMDA Receptor Antagonist
« Reply #25 on: August 13, 2004, 09:16:00 PM »
For Nicodem:

4-Hydroxy-1-[2-(4-hydroxyphenoxy)ethyl]-4-(4-methylbenzyl)piperidine:
A Novel, Potent, and Selective NR1/2B NMDA Receptor Antagonist

Z.-L. Zhou, S.X. Cai, E.R. Whittemore, C.S. Konkoy, S.A. Espitia, M.Tran, D.M. Rock, L.L. Coughenour,
J.E. Hawkinson, P.A. Boxer, C.F. Bigge, L.D. Wise, E. Weber, R.M. Woodward, and J.F.W. Keana

J. Med. Chem. 42, 2993-3000 (1999)



Abstract
A structure-based search and screen of our compound library identified N-(2-phenoxyethyl)-4-benzylpiperidine (8) as a novel N-methyl-D-aspartate (NMDA) receptor antagonist that has high selectivity for the NR1/2B subunit combination (IC50 = 0.63 µM). We report on the optimization of this lead compound in terms of potency, side effect liability, and in vivo activity. Potency was assayed by electrical recordings in Xenopus oocytes expressing cloned rat NMDA receptors. Side effect liability was assessed by measuring affinity for 1-adrenergic receptors and inhibition of neuronal K+ channels. Central bioavailability was gauged indirectly by determining anticonvulsant activity in a mouse maximal electroshock (MES) assay. Making progressive modifications to 8, a hydroxyl substituent on the phenyl ring para to the oxyethyl tether (10a) resulted in a ~25-fold increase in NR1A/2B potency (IC50 = 0.025 µM). p-Methyl substitution on the benzyl ring (10b) produced a ~3-fold increase in MES activity (ED50 = 0.7 mg/kg iv). Introduction of a second hydroxyl group into the C-4 position on the piperidine ring (10e) resulted in a substantial decrease in affinity for 1 receptors and reduction in inhibition of K+ channels with only a modest decrease in NR1A/2B and MES potencies. Among the compounds described, 10e (4-hydroxy-N-[2-(4-hydroxyphenoxy)ethyl]-4-(4-methylbenzyl)piperidine, Co 101244/PD 174494) had the optimum pharmacological profile and was selected for further biological evaluation.


Rhodium

  • Guest
Wanted halogenation
« Reply #26 on: August 14, 2004, 04:10:00 AM »
Monohalogenation (bromination and iodination) of electron rich arenes by tetraalkylammonium halides in presence of conc. H2SO4
Pasha M. A., Myint Y. Y.
Indian J. Chem., 43B, 357–360 (2004)


java

  • Guest
For Lego...Metal promoted Sandmeyer Reaction
« Reply #27 on: August 16, 2004, 05:53:00 PM »
A novel metal promoter for the Sandmeyer reaction.
Anon. UK. CODEN: RSDSBB  ISSN: 0374-4353. CAN 103:87565 AN 1985:487565      
Research Disclosure  (1985),  252  171.

Abstract
Fe2+ halide or Feo-Fe3+ system as a promoter for the Sandmeyer reaction, wherein Cu+ causes detrimental side effects in the case of Me-substituted or ortho-substituted arenediazonium salts, was discussed.  The oxidn. of pendant Me groups was not evident in the Fe system and the reaction was applicable to a wide variety of functional groups.  The Fe system is less expensive than Cu+ and more friendly environmentally.




demorol

  • Guest
(Post deleted by demorol)
« Reply #28 on: August 17, 2004, 06:38:00 PM »
(empty)

fogged

  • Guest
For demorol: The Mechanism of the Sandmeyer...
« Reply #29 on: August 18, 2004, 02:32:00 AM »
For demorol:

The Mechanism of the Sandmeyer and Meerwein Reactions
Jay K. Kochi
J. Am. Chem. Soc. 79, 2942 (1957)



java

  • Guest
(Post deleted by java)
« Reply #30 on: August 19, 2004, 06:57:00 AM »
(empty)


azole

  • Guest
for java
« Reply #31 on: August 19, 2004, 02:28:00 PM »
For java:

Reduction of Fluorenonecarboxylic Acids to Fluorenecarboxylic Acids
D. C. Morrison
J. Org. Chem.
, 23, 1772-1774 (1958).


Reduction of the keto group in fluorenonecarboxylic acids (1-, 2-, 3-, and 4-) with red phosphorus / conc. aq. HI / AcOH (EtCOOH) is described.

longimanus

  • Guest
D. W. Wooley
« Reply #32 on: August 23, 2004, 10:50:00 PM »
Wooley, D. W.
The Biochemical Bases of Psychoses or the Serotonin Hypothesis about Mental Diseases. New York/London: John Wiley and Sons, Inc., (1962).


 Harder to find than I thought. :(

lugh

  • Guest
Exactly What Pages Do You Need?
« Reply #33 on: August 24, 2004, 02:25:00 AM »
   The biochemical bases of psychoses; or, The serotonin hypothesis about mental diseases.
Woolley, Dilworth Wayne,1914-
New York, Wiley 1962
Description    331 p.  illus.  24 cm.
aka The serotonin hypothesis about mental diseases.


Unfortunately it will probably bee impossible for most contributors to this thread to obtain all 331 pages, you need to bee more specific  ;)


longimanus

  • Guest
pages, pages, pages
« Reply #34 on: August 24, 2004, 06:32:00 PM »
Uh, let`s just say that I need the part(s) about medmajine (hope it`s spelled this way) and 2-methyl-3-ethyl-5-nitroindol. Nothing more specific - I`m sorry.

Edit: To make things more clear - this article is ref #5 from

"Ïñèõîòîìèìåòè÷åñêèå âåùåñòâà" (Psychotomimetic Compounds)

(http://chemister.da.ru/Books/Toxbooks/psihotomimetyc.djv)

psyloxy

  • Guest
wanted
« Reply #35 on: August 27, 2004, 03:46:00 AM »
Formic acid methyl ester is chlorinated in the dark w/dibenzoylperoxide yielding methyl chlorocarbonate (reflux over lead oxide to get dimethylcarbonate).

Yura; Kogyo Kagaku Zasshi; 51; 1948; 157
Chem.Abstr.; 1951; 5476


--psyloxy--

lugh

  • Guest
CA Citation in Error
« Reply #36 on: August 28, 2004, 03:31:00 AM »
That CA citation is erroneous, sorry to say  ;)


moo

  • Guest
I hope you didn't compare to the electronic...
« Reply #37 on: August 28, 2004, 05:06:00 AM »
I hope you didn't check from the electronic database... CAN and the pre 1967 CA are two different indexing systems. :o


psyloxy

  • Guest
found
« Reply #38 on: August 28, 2004, 02:33:00 PM »
Good news everyone: my library does carry Kogyo Kagaku Zasshi, though I believed otherwise. It was Java providing me with the English name of the journal that made me find it in the database, the Japanese version is spelled differently in it.

Sorry for the hot air.

--psyloxy--

java

  • Guest
Physical characterisations of the New Bis.....
« Reply #39 on: August 28, 2004, 03:46:00 PM »
For Diciple


Physical characterisations of the New Bis (N-Phenylpiperazines)

A.W.Baloch and M.Iovu

J.Pharm.Univ.Kar.3(2) 89-94, 1985




fallen_Angel

  • Guest
Ohmefentanyl
« Reply #40 on: August 31, 2004, 12:27:00 PM »
Ohmefentanyl and Its Stereoisomers
G. A. Brine, F. L Carroll, T. M. Richardson-Leibert, H. Xu and R. B. Rothman
Chemistry and Pharmacology. Pp. 247-270, Volume 4, Number 4, 1997

Rhodium

  • Guest
Wanted Stuff
« Reply #41 on: September 02, 2004, 09:42:00 AM »
Behavioural Effects of 4-Alkyl-2,5-Dimethoxyamphetamines
RD Morin, JR Smythies, Experientia 31, 93 (1975)
____ ___ __ _

Rapid TLC identification test for khat (Catha edulis)
T. Lehmann , S. Geisshüsler and R. Brenneisen
Forensic Science International 45(1-2), 47-51 (1990)
DOI:

10.1016/0379-0738(90)90220-S

 

Abstract
A rapid and sensitive method for identification of Catha edulis (khat) basing on a simple extraction and TLC separation is described. The test is specific for the main khatamines cathinone and norpseudoephedrine.
____ ___ __ _

Synthesis of deuterium labelled drugs of abuse for use as internal standards in quantification by selected ion monitoring. I.
Methamphetamine: 2,5-dimethoxy-4-methylamphetamine (DOM); phencyclidine (PCP); and metaqualone

Fentiman A.F. Jr.; Foltz R.L., J. Label. Compounds Radiopharm. 12(1), 69-78 (1976)

Abstract
Four deuterium labelled compounds were prepared for use as internal standards in the quantification of methamphetamine, DOM, PCP, and methaqualone at low levels in body fluids by selected ion monitoring. The need for standards containing more than three deuterium atoms per molecule and having high isotopic purity is discussed.
____ ___ __ _

Use of MDA (the Love Drug) and methamphetamine in Toronto by unsuspecting users of Ecstasy (MDMA)
Kalasinsky, KS; Hugel, J; Kish, SJ; J. Forensic Sci., Vol. 49, No. 5, pp. ?? (2004)

Abstract
It has recently been reported that purity of illicit tablets of ecstasy (MDMA) is now high. Our objective was to confirm whether hair of drug users, who request only ecstasy from their supplier, contains MDMA in the absence of other drugs. GC-MS analysis of scalp hair segments disclosed the presence of MDMA in 19 of 21 subjects and amphetamine/methamphetamine in eight subjects. Surprisingly, seven subjects had hair levels of the MDMA metabolite, MDA, equal to or greater than those of MDMA, suggesting use of MDA in addition to that of MDMA. These amphetamine derivatives might be included by clandestine laboratories to enhance effects of the drug cocktail or because of a perception that MDA synthesis might be simpler than that of MDMA. Drug users and investigators examining possible brain neurotoxic effects of MDMA need to consider that ecstasy tablets can contain MDA and methamphetamine despite no demand for the drugs.
____ ___ __ _

Synthesis of methaqualone and its diphasic titration in pure and tablet forms
Soliman F.S.G.; Shafik R.M.; Elnenaey E.A.; J. Pharm. Sci. 67(3), 411-413 (1978)

Abstract
A one-step synthesis of methaqualone from N-acetylanthranilic acid and o-toluidine in the absence of a catalyst is described. A rapid diphasic titration procedure for its microestimation in pure and tablet forms is proposed. The data were compared with those obtained from nonaqueous titration methods.
____ ___ __ _

This article might be interesting, as they are preparing DMT and analogs by MeI alkylation of the correspinding tryptamines.

11C-labeling of indolealkylamine alkaloids and the comparative study of their tissue distributions
Takahashi T, Takahashi K, Ido T, Yanai K, Iwata R, Ishiwata K, Nozoe S., Int J Appl Radiat Isot. 36(12), 965-9 (1985)

Medline (PMID=3866749)



Abstract
Five indolealkylamines (N,N-dimethyltryptamine, N-methyltryptamine, bufotenine, O-methylbufotenine, N,N,N-trimethyltryptamine iodide) were labeled with 11C by use of 11CH3I. The labeled compounds were synthesized with a radiochemical yield of 2-50% (based on trapped 11CH3I) in 20-35 min with radiochemical purities of more than 92%. The tissue distributions of these labeled compounds were investigated in rats. In all cases, the accumulations in the liver, lung and small intestine were high. [11C]DMT and [11C]OMB also accumulated to a large extent in the brain, where their accumulation was retained. Brain uptake of three other radiopharmaceuticals was low. [11C]DMT is the radiopharmaceutical of choice for the study of the serotonin action mechanism in the brain, because it has the highest radiochemical yield and the highest brain uptake of these 11C-labeled compounds.
____ ___ __ _

GC-MS identification of amine-solvent condensation products formed during analysis of drugs of abuse
Clark, C R; DeRuiter, J; Noggle, F T, Journal Of Chromatographic Science, 30(10), 399-404 (1992)

Abstract
The use of methanol or ethanol as the injection solvent for the gas chromatographic-mass spectral (GC-MS) analysis of low molecular weight amine drugs of abuse results in the formation of additional components in the sample. Primary amines, such as amphetamine, 3,4-methylenedioxyamphetamine, and phenethylamine, yield imines upon injection as methanol or ethanol solutions. In methanol, the imine formed has a mass that is 12 mass units higher than the parent compound. In ethanol, the products formed have 26 additional mass units. Secondary amines appear to undergo methylation under similar conditions with methanol as the injection solvent. These products are absent from the analysis of equivalent amine samples dissolved in chloroform.


Nicodem

  • Guest
PCP/sigma receptor affinites of PCP homologues
« Reply #42 on: September 02, 2004, 12:56:00 PM »
Sigma compounds derived from phencyclidine: identification of PRE-084, a new, selective sigma ligand
TP Su, XZ Wu, EJ Cone, K Shukla, TM Gund, AL Dodge and DW Parish
J. Pharmacol. Exp. Ther. 259(2), (1991) 543-550. 

Medline (PMID=1658302)

 

A series of compounds derived from phencyclidine (PCP) was examined in the sigma receptor and PCP receptor binding assays. The derivatives included compounds containing methylene, ethylene or carboxyl ethylene insertion between the cycloalkyl ring and the amine group of PCP. Various phenyl substitutions, cycloalkyl rings and amines of these derivatives were also examined. The methylene and ethylene insertions decreased the compounds' potencies at PCP receptors, whereas they increased the potencies at sigma receptors. The carboxyl ethylene insertion produced compounds with negligible potencies at PCP receptors while possessing high potencies for sigma receptors. One derivative (PRE-084; 2-(4-morpholino)ethyl 1-phenylcyclohexane-1-carboxylate hydrochloride) had an IC50 of 44 nM in the sigma receptor assay, an IC50 of more than 100,000 nM for PCP receptors and an IC50 higher than 10,000 nM in a variety of other receptor systems. In general, compounds with hydroxy-substituted phenyl groups tended to have decreased potency at sigma receptors, whereas methylphenyl and chlorophenyl substitutions increased potencies. Reduction of cycloalkyl ring size decreased potencies for sigma receptors and quaternized amine groups invariably lowered the compound's potencies. Conformational analysis indicated that PRE-084 fitted onto a pharmacophore model for the sigma ligands. The study describes a new, highly selective ligand for the sigma receptor. The results of this study also confirm distinctly different structural requirements for binding to sigma and PCP receptors and provide a new structural consideration for synthesizing sigma-selective compounds.

I know that JPET papers can be downloaded, but this one is to old to be available. Also JPET online is down at the moment (!?) otherwise the abstract link would be 

http://jpet.aspetjournals.org/cgi/content/abstract/259/2/543

.




OK, I know...this time I ask nearly the impossible but anyway:
Nikolova M., Daleva L. Marinova V. Farmazia (Sofia) 19 (1969) 31.
and/or
Vasileva E., Natova L. Compt. Rend. Bulgaria 44 (1991) 37.
The papers are probably in Bulgarian but that is OK
Thanks


Kinetic

  • Guest
Bromination for starlight
« Reply #43 on: September 02, 2004, 01:18:00 PM »
I thought that the following ref. about bromination of anilines may be able to be adapted for other substrates such as methoxy or methylenedioxy benzenes

So did I. ;)  Here it is:

Mild and regioselective oxidative bromination of anilines using potassium bromide and sodium perborate
Didier Roche, Kapa Prasad,Oljan Repic and Thomas J. Blacklock
Tetrahedron Letters
, 41 (2000), 2083–2085

Abstract
The selective monobromination of various deactivated anilines using potassium bromide and sodium perborate as oxidant has been achieved. The use of ammonium molybdate as catalyst accelerates the rate of reaction but is not essential to obtain good yields and high selectivities.




Edit: This is reference 2(f) from the above paper:

Oxidative Bromination of Aromatic Amides using Sodium Perborate as Oxidant
James R. Hanson,* Simone Harpel, Inmaculada C. Rodriguez Medina and Dorian Rose
Journal of Chemistry Research (Synopsis)
2000, 432-433

Abstract
Sodium perborate in glacial acetic acid–acetic anhydride with potassium bromide and sodium tungstate as a catalyst, provides a novel system for the bromination of aromatic amides.


gsus

  • Guest
for Rhodium
« Reply #44 on: September 02, 2004, 10:18:00 PM »
Cadmium chloride–magnesium–water: a new system for regioselective transformation of conjugated nitroalkenes to ketocompounds
Manobjyoti Bordoloi, J. Chem. Soc. Chem. Commun., No. 11, 922-923 (1993)



Abstract
Reaction of 6-nitro-?5-steroids and nitroalkenes in tetrahydrofuran with CdCl2–Mg–H2O furnished 6-ketosteroids and ketocompounds, respectively, in good yield.


Captain_America

  • Guest
methyliodide from methanol various synths
« Reply #45 on: September 04, 2004, 03:27:00 AM »
HCl/Zn/iodine: de Postis; C.R.Hebd.Seances Acad.Sci.; 223; 1946; 82.

Mg/iodine:     Dangjan; Zh.Obshch.Khim.; 11; 617; Chem.Abstr.; 1941; 6925.

Al/Iodine:     Dangjan; Zh.Obshch.Khim.; 11; 1941; 1215; Chem.Abstr.; 1945; 4050.

Fe/Iodine:     Dangjan; Zh.Obshch.Khim.; 10; 1940; 1671; Chem.Zentralbl.; 112; I; 1941; 1930.



Rhodium

  • Guest
Organic Reactions Online
« Reply #46 on: September 04, 2004, 05:40:00 PM »
Anyone with access to Organic Reactions Online? They offer the first page of a whole lot of comprehensive review articles, just like the ones below...
The table of contents for the articles look really enticing, don't you think?  ;)



Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents
Ellen W. Baxter, Allen B. Reitz, Organic Reactions (2002), John Wiley and Sons, Inc.
DOI:

10.1002/0471264180.or059.01



Abstract
1.     Introduction
2.    Mechanism and Stereochemistry
3.    Scope and Limitations: The Reducing Agent
4.    Scope and Limitations: The Carbonyl Component
5.    Scope and Limitations: The Amine Component
6.    Intramolecular Reductive Aminations
7.    Side Reactions
8.    Failed Reactions
9.    Reductive Aminations on a Solid Support
10.    Tandem Reactions
11.    Comparison with Other Methods
12.    Experimental Conditions
13.   Experimental Procedures
14.   Tabular Survey
15.   Acknowledgments
   References


Keywords: organic reaction(s); organic synthesis; reaction(s); synthesis; reductive amination; condensation; alkylation; reductive alkylation; reduction; amination; carbonyl; amine; reducing agent(s); borohydride; borane; carbon-nitrogen bond(s); CN bond(s)

Abstract
Reductive amination is an important tool for synthetic organic chemists in the construction of carbon-nitrogen bonds. This reaction, also termed reductive alkylation, involves condensation of an aldehyde or ketone with an amine in the presence of a reducing agent. A wide variety of substrates can be used including aliphatic and aromatic aldehydes and ketones, and even benzophenones. A range of amines from ammonia to aromatic amines, including those with electron-withdrawing substituents, can be employed. For particularly sluggish reactions, such as those involving weakly electrophilic carbonyl groups, poorly nucleophilic amines, or sterically congested reactive centers, additives such as molecular sieves or Lewis acids are often useful.


This chapter focuses on those conditions in which the carbonyl component, amine, and reducing reagent react in the same vessel. This review is restricted to reductive aminations using borohydride and borane reducing agents. This chapter concentrates on reductive amination chemistry mediated by borohydride and other boron-containing reducing agents from 1971, the year when sodium cyanoborohydride was introduced, through the middle of 1999. In addition to reductive aminations of aldehyde and ketone substrates, reactions of related structures including acetals, aminals, ketals, carboxylic acids, nitriles, and dicarbonyls that form a nitrogen-containing ring are reviewed. Intramolecular processes in which the substrate contains both the carbonyl and amine moieties are described. The intramolecular variant is a useful method for preparing cyclic amines. All of the various boron-containing hydride sources in reductive aminations, including labeled metal hydrides, are reviewed. Instances of reductive aminations that failed are described. Applications of this method to a solid support in parallel synthesis in combinatorial chemistry as well as reductive aminations that proceed in tandem with a second reaction such as reductive lactamizations are discussed.


1. Introduction

Reductive amination is an important tool for synthetic organic chemists in the construction of carbon-nitrogen bonds. This reaction, also termed reductive alkylation, involves condensation of an aldehyde or ketone with an amine in the presence of a reducing agent as illustrated in Eq. 1. A wide variety of substrates
 


can be used including aliphatic aldehydes and ketones, aromatic aldehydes and ketones, and even benzophenones. Further, a range of amines from ammonia to aromatic amines, including those with electron-withdrawing substituents, can be employed. For particularly sluggish reactions, such as those involving weakly electrophilic carbonyl groups, poorly nucleophilic amines, or sterically congested reactive centers, additives such as molecular sieves or Lewis acids are often useful.

Reductive aminations have been reviewed on numerous occasions, (1-17) and this chapter focuses on those conditions in which the carbonyl component, amine, and reducing agent react in the same vessel. The reduction of a preformed, isolated species such as an imine or oxime is not covered. This review is also restricted to reductive aminations using borohydride and borane reducing agents. Reactions carried out with other metal hydrides or inorganic reducing agents in addition to catalytic hydrogenations, Leuckart conditions, and enzymatic reductive aminations are not included. A review summarizing reductive alkylation of proteins has been published recently, (18) and these substrates are not covered here. This chapter concentrates on reductive amination chemistry mediated by borohydride and other boron-containing reducing agents from 1971, the year when sodium cyanoborohydride was introduced by Borch and coworkers, (19) through the middle of 1999. Although we have been as inclusive as possible, there are almost certainly additional references that we inadvertently missed. We apologize in advance to those authors who do not see their own contributions cited here.

In addition to reductive aminations of aldehyde and ketone substrates, we review reactions of related structures including acetals, aminals, ketals, carboxylic acids, and nitriles as well as dicarbonyl substrates that form a nitrogen-containing ring. Intramolecular processes in which the substrate contains both the carbonyl and amine moieties are described. In these reactions, one of the components is typically masked, and reductive amination occurs upon deprotection. The intramolecular variant is a useful method for preparing cyclic amines.

While sodium cyanoborohydride is the best known hydride reagent for reductive alkylations, sodium borohydride is often used as well. (20) Sodium triacetoxyborohydride is now widely used because it is nontoxic and generally does not reduce the carbonyl group prior to imine formation. (21) Amine boranes such as borane-pyridine are also employed in reductive aminations. (22) We review all of the various boron-containing hydride sources in reductive aminations in this chapter, including labeled metal hydrides such as sodium cyanoborodeuteride.

Instances where reductive aminations fail are described, including cases when reaction is not observed and also where side products appear, such as alcohols and bis-alkylated amines.

Finally, we discuss the application of this method to a solid support in parallel synthesis and combinatorial chemistry as well as reductive aminations that proceed in tandem with a second reaction such as in reductive lactamizations.

The Tabular Survey at the end of the chapter includes thousands of specific reactions and applications for reductive aminations, including sections on aldehydes, ketones, dicarbonyl substrates, tricarbonyl substrates, carboxylic acids, nitriles, intramolecular reductive aminations, reductive lactamizations, and Michael-type additions and reductive aminations.





Dioxirane Epoxidation of Alkenes
Waldemar Adam, Chantu R. Saha-Möller, Cong-Gui Zhao
Organic Reactions (2002) John Wiley & Sons, Inc.
DOI:

10.1002/0471264180.or061.02



   Abstract
1.    Introduction
2.    Mechanism
3.    Scope and Limitations
4.    Comparison with Other Methods
5.    Experimental Conditions
6.    Experimental Procedures
7.    Tabular Survey
8.    Acknowledgments
   References


Keywords: dioxirane; epoxidation; alkenes; unfunctionalized alkenes; electron-rich; electron poor; electron donor; electron acceptor; chemoselectivity; regioselectivity; diastereoselectivity; entioselectivity; scope; limitations; oxidation; solvents; temperature; neutral conditions; basic conditions; homogeneous media; comparison of methods; experimental conditions; experimental procedures; tabular survey

Abstract
An ideal oxidant should be highly reactive, selective, and environmentally benign. It should transform a broad range of substrates with diverse functional groups, preferably under catalytic conditions, and be readily generated from commercially available and economical starting materials. Of course, such an ideal oxidant has not yet been invented; however, the dioxiranes, which have risen to prominence during the past few decades, appear to fulfill these requirements in many respects. These three membered ring cyclic peroxides are very efficient in oxygen transfer, yet very mild toward the substrate and product. They exhibit chemo-, regio-, diastereo-, and enantioselectivities, act catalytically, and can be readily prepared from a suitable ketone (for example, acetone) and potassium monoperoxysulfate ( 2KHSO5 · K2SO4 · Caroate®, Oxone®, or Curox®), which are low-cost commercial bulk chemicals. Throughout the text KHSO5 is used to specify this oxygen source, rather than refer to one of the commercial trade names.


Isolated dioxiranes (as solutions in the parent ketones) perform oxidation under strictly neutral conditions so that many elusive oxyfunctionalized products have been successfully prepared in this way for the first time. Epoxidations, heteroatom oxidations, and X-H insertions constitute the most investigated oxidations by dioxiranes. An overview of these transformations is displayed in a rosette scheme. These preparatively useful oxidations have been extensively reviewed during the last decade in view of their importance in synthetic chemistry.

This chapter deals mainly with the epoxidation of carbon-carbon double bonds [ bonds in simple alkenes and with these electron donors (ED), electron acceptors (EA), and with both ED and EA] with either isolated or in situ generated dioxiranes. In view of the vast amount of material on alkene oxidation, the epoxidation of the double bonds in cumulenes (allenes, acetylenes) and arenes is covered in a separate chapter, together with the oxidation of heteroatom functionalities (nonbonding electron pairs), X-H insertions ( bonds) and transition-metal complexes.


jsorex

  • Guest
For Rhodium: The adulteration of drugs
« Reply #47 on: September 06, 2004, 11:36:00 PM »
For Rhodium:

The adulteration of drugs: What dealers do to illicit drugs, and what they think is done to them
Coomber, Ross, Addiction Research 5(4),  297-306 (1997)



Abstract
The notion that street drugs have been adulterated/diluted by dangerous substances such as Vim, Ajax, ground glass, brick dust and even rat poison is common. Moreover, it is a practice believed to be true by those involved with the researching of drug issues, the treatment and rehabilitation of drug users, the policing of drug users and the educating of drug users (R. Coomber, 1996) as well as by the users themselves. This paper shows, through survey of 31 admitted or convicted drug dealers, that it is also thought to happen and be perpetrated by those who are deemed to be responsible for such adulteration/dilution: the dealers themselves. This, however, does not accord with the forensic evidence, or, as are the concerns of this paper with the practice or experience of individual drug dealers. This paper suggests, on the evidence of interviews with drug dealers at different levels of the drug distribution chain that less adulteration/dilution actually occurs than previously thought and that when it does happen "on the street" it is of relatively benign character.


Captain_America

  • Guest
wanted
« Reply #48 on: September 09, 2004, 11:58:00 AM »
I. The preparation of ethyl bromide
Alfred Holt, J. Chem. Soc., Trans., 109, 1-2 (1916)
DOI:

10.1039/CT9160900001



CLXIV. The preparation of ethyl bromide
Frank Edwin Weston, J. Chem. Soc., Trans., 107, 1489-1490 (1915)
DOI:

10.1039/CT9150701489


lugh

  • Guest
Organic Reactions Articles Sans Tables
« Reply #49 on: September 10, 2004, 03:06:00 AM »
As far as the articles mentioned in

Post 529553

(Rhodium: "Organic Reactions Online", Novel Discourse)
as said in a recent unanswered PM, the first article sans tables was provided long ago and can be found at:

https://www.thevespiary.org/rhodium/Rhodium/djvu/boros.djvu



The second article sans tables:



There's little doubt that Organic Reactions articles are among the most comprehensive available anywhere, but the tabular surveys are in an incredibly inefficient and wasteful format, averaging five entries per page  ::)  There are almost six hundred pages of tables in the first article, and almost two hundred in the second, a practical impossiblity to retrieve manually  :(


Lego

  • Guest
Science of Synthesis
« Reply #50 on: September 10, 2004, 09:33:00 PM »
Anybody with access to Science of Synthesis?

http://www.thieme-chemistry.com/thieme-chemistry/sos/info/electronic/index.shtml




The following chapter (Benzofurans, Indoles) would bee great for Lego:

http://www.thieme-chemistry.com/thieme-chemistry/sos/info/include/pdf/toc.vol10.pdf





Thanks!


gsus

  • Guest
some retrievals
« Reply #51 on: September 11, 2004, 07:50:00 AM »
for Rhodium

Synthesis of deuterio-l-amphetamine, d1 sulfate
Foreman RL, Siegel FP, Mrtek RG.
J Pharm Sci. 1969 Feb;58(2):189-92.



--------

The Synthesis of a New Homologue of Mescaline
Hey, P.
Quarterly Journal of Pharmacy and Pharmacology, Vol. 20, 129-134 (1947)



--------

Use of MDA (the Love Drug) and methamphetamine in Toronto by unsuspecting users of Ecstasy (MDMA)
Kalasinsky, KS; Hugel, J; Kish, SJ
J. Forensic Sci., Vol. 49, No. 5, 1106-1112 (2004)



--------

Synthesis of methaqualone and its diphasic titration in pure and tablet forms
Soliman F.S.G., Shafik R.M., Elnenaey E.A.
J. Pharm. Sci. 67(3), 411-413 (1978)

Abstract
A one-step synthesis of methaqualone from N-acetylanthranilic acid and o-toluidine in the absence of a catalyst is described. A rapid diphasic titration procedure for its microestimation in pure and tablet forms is proposed. The data were compared with those obtained from nonaqueous titration methods.



--------

11C-labeling of indolealkylamine alkaloids and the comparative study of their tissue distributions
Takahashi T, Takahashi K, Ido T, Yanai K, Iwata R, Ishiwata K, Nozoe S.
Int J Appl Radiat Isot. 36(12), 965-9 (1985)

Abstract
Five indolealkylamines (N,N-dimethyltryptamine, N-methyltryptamine, bufotenine, O-methylbufotenine, N,N,N-trimethyltryptamine iodide) were labeled with 11C by use of 11CH3I. The labeled compounds were synthesized with a radiochemical yield of 2-50% (based on trapped 11CH3I) in 20-35 min with radiochemical purities of more than 92%. The tissue distributions of these labeled compounds were investigated in rats. In all cases, the accumulations in the liver, lung and small intestine were high. [11C]DMT and [11C]OMB also accumulated to a large extent in the brain, where their accumulation was retained. Brain uptake of three other radiopharmaceuticals was low. [11C]DMT is the radiopharmaceutical of choice for the study of the serotonin action mechanism in the brain, because it has the highest radiochemical yield and the highest brain uptake of these 11C-labeled compounds.



--------

for Ganesha

Evaluation of 3,4-Methylenedioxyamphetamine (MDA) as an Adjunct to Psychotherapy
C. Naranjo, A.T. Shulgin, and T. Sargent
Med. Pharmacol. exp. 17, 359-364 (1967)



--------

for Nicodem

Sigma compounds derived from phencyclidine: identification of PRE-084, a new, selective sigma ligand
TP Su, XZ Wu, EJ Cone, K Shukla, TM Gund, AL Dodge and DW Parish
J. Pharmacol. Exp. Ther. 259(2), 543-550 (1991)

Abstract
A series of compounds derived from phencyclidine (PCP) was examined in the sigma receptor and PCP receptor binding assays. The derivatives included compounds containing methylene, ethylene or carboxyl ethylene insertion between the cycloalkyl ring and the amine group of PCP. Various phenyl substitutions, cycloalkyl rings and amines of these derivatives were also examined. The methylene and ethylene insertions decreased the compounds' potencies at PCP receptors, whereas they increased the potencies at sigma receptors. The carboxyl ethylene insertion produced compounds with negligible potencies at PCP receptors while possessing high potencies for sigma receptors. One derivative (PRE-084; 2-(4-morpholino)ethyl 1-phenylcyclohexane-1-carboxylate hydrochloride) had an IC50 of 44 nM in the sigma receptor assay, an IC50 of more than 100,000 nM for PCP receptors and an IC50 higher than 10,000 nM in a variety of other receptor systems. In general, compounds with hydroxy-substituted phenyl groups tended to have decreased potency at sigma receptors, whereas methylphenyl and chlorophenyl substitutions increased potencies. Reduction of cycloalkyl ring size decreased potencies for sigma receptors and quaternized amine groups invariably lowered the compound's potencies. Conformational analysis indicated that PRE-084 fitted onto a pharmacophore model for the sigma ligands. The study describes a new, highly selective ligand for the sigma receptor. The results of this study also confirm distinctly different structural requirements for binding to sigma and PCP receptors and provide a new structural consideration for synthesizing sigma-selective compounds.




gsus

  • Guest
retrievals and a comment for longimanus
« Reply #52 on: September 12, 2004, 02:55:00 AM »
The Biochemical Bases of Psychoses (or; the Serotonin Hypothesis about Mental Diseases)
D.W. Woolley

comment first. not sure what you want to know, longimanus, and the comments on these two are a little scattered and short. so to sum up - 2-methyl-3-ethyl-5-nitroindole was given to humans in a single trial. these were hypertensive patients (number not stated) and in 10g/day oral doses they experienced "severe depression". studies on mice and dogs went well for a few months, but then a few of the mice began to freak out, and were very prone to noise-induced convulsions. there is a reference to another article by the author, which sadly gives absolutely no further details on the human research, except that it was not published.

medmain, where the above cpd. has its O's replaced with methyls, was not tested in man at the time of publication. this is because mice given 200mg/kg had violent seizures followed by temporary stupor. there isn't much else but some receptor studies.


--------

for Rhodium

Behavioural Effects of 4-Alkyl-2,5-Dimethoxyamphetamines
RD Morin, JR Smythies, Experientia 31, 93-95 (1975)



--------

Rapid TLC identification test for khat (Catha edulis)
T. Lehmann , S. Geisshüsler and R. Brenneisen
Forensic Science International 45(1-2), 47-51 (1990)

Abstract
A rapid and sensitive method for identification of Catha edulis (khat) basing on a simple extraction and TLC separation is described. The test is specific for the main khatamines cathinone and norpseudoephedrine.



--------

Synthesis of deuterium labelled drugs of abuse for use as internal standards in quantification by selected ion monitoring. I.
Methamphetamine: 2,5-dimethoxy-4-methylamphetamine (DOM); phencyclidine (PCP); and methaqualone

Fentiman A.F. Jr.; Foltz R.L., J. Label. Compounds Radiopharm. 12(1), 69-78 (1976)

Abstract
Four deuterium labelled compounds were prepared for use as internal standards in the quantification of methamphetamine, DOM, PCP, and methaqualone at low levels in body fluids by selected ion monitoring. The need for standards containing more than three deuterium atoms per molecule and having high isotopic purity is discussed.




Bubbleplate

  • Guest
Wanted : LSD References
« Reply #53 on: September 14, 2004, 02:48:00 AM »
I am in immediate need of following:

Cerny, A. and Semonsky, M. Coll. Czech. Chem. Commun. 27, 1585-1590 (1962)

Chemical Abstracts 75, 77110 (1971)

Cerny, A. and Semonsky, M. Coll. Czech. Chem. Commun. 34, 694-698 (1968)

Semonsky, M.; Zikan V,; Beran, M.; "Preparing D-Lysergic and Iso-Lysergic Acid or Mixtures thereof" Chemical Abstracts 68: 36323w 1968

Czech Patent 123,689

Thanks in advance!

lugh

  • Guest
Already Retrieved
« Reply #54 on: September 14, 2004, 02:36:00 PM »
Nitroaliphatic Compounds - Ideal Intermediates in Organic Synthesis?
Dieter Seebach, Ernest W. Colvin, Friedrich Lehr, Thomas Weller, Chimia 33, 1-18 (1979)



That article was retrieved long ago after another bee's request  ;)


Kinetic

  • Guest
Methyl iodide syntheses
« Reply #55 on: September 16, 2004, 10:43:00 PM »
For Captain_America

Unfortunately the details are pretty sparse in the two articles I managed to retrieve:

Reaction of a halogen and magnesium with alcohols and complex esters. V. Reaction of iodine and magnesium with alcohols
M. T. Dangyan
Chemical Abstracts
1941, 6925




Reaction of iodine and aluminium with ethers and alcohols
M. T. Dangyan
Chemical Abstracts
1941, 4050


Captain_America

  • Guest
more wanted refs
« Reply #56 on: September 17, 2004, 01:02:00 PM »
EDIT: Good work gsus!  :)

Levulinic acid in organic synthesis
B V Timokhin, V A Baransky, G D Eliseeva

Russ. Chem. Rev. 68(1), 73-84 (1999)

(http://www.turpion.org/php/paper.phtml?journal_id=rc&paper_id=381)

Abstract
Data concerning the methods of synthesis, chemical transformations and application of levulinic acid are analysed and generalised. The wide synthetic potential of levulinic acid, particularly as a key compound in the synthesis of various heterocyclic systems, saturated and unsaturated ketones and diketones, difficultly accessible acids and other compounds is demonstrated. The accessibility of levulinic acid from hexose-containing wood-processing and agricultural wastes is noted. The bibliography includes 260 references.
____ ___ __ _

Methyl Iodide from methanol, various synths:
HCl/Zn/iodine: de Postis; C.R.Hebd.Seances Acad.Sci.; 223; 1946; 82.
Mg/iodine:     Dangjan; Zh.Obshch.Khim.; 11; 617; Chem.Abstr.; 1941; 6925. [Retrieved]
Al/Iodine:     Dangjan; Zh.Obshch.Khim.; 11; 1941; 1215; Chem.Abstr.; 1945; 4050. [Retrieved]
Fe/Iodine:     Dangjan; Zh.Obshch.Khim.; 10; 1940; 1671; Chem.Zentralbl.; 112; I; 1941; 1930.

____ ___ __ _

Ok, these are according to Ott when they injected their victimes against their will with huge amounts of psychoactive compounds, some ppl nearly died.

Effect of some indolealkylamines on man
Turner, W.J and S. Merlis
Archives of Neurology and Psychiatry 81, 121-129 (1959)


Lego

  • Guest
Friedel-Crafts alkylation of indoles & other stuff
« Reply #57 on: September 18, 2004, 12:32:00 AM »
Anybody with access to Science of Synthesis?

http://www.thieme-chemistry.com/thieme-chemistry/sos/info/electronic/index.shtml



The following chapter (Benzo[b]furans, Indoles) would bee great for Lego:

http://www.thieme-chemistry.com/thieme-chemistry/sos/info/include/pdf/toc.vol10.pdf





Synthesis and characterization of melatonin
Yang, Jian-wu; Cao, Hui-lan
Huaxue Yanjiu, 14(4), 42-44 (2003) [Journal  written in Chinese]
 
Abstract
The title compd. was prepd. by a four-step reaction route with indole as a main starting material.  Indole was hydroxylated in methanol to give 5-hydroxyindole in 71% yield.  5-Hydroxyindole reacted with 2-chloroethylamine in Et acetate to give serotonin in 73% yield, and serotonin reacted with di-Me sulfate in toluene to give 5-methoxytryptamine in 78% yield, and  5-methoxytryptamine was acetylated to give the title compd. in 80% yield.




indole_amine

  • Guest
wanted
« Reply #58 on: September 18, 2004, 03:38:00 AM »
Phase Transfer Catalysis in the Production of Pharmaceuticals
L. Lindblom, M. Elander
Pharmaceutical Tech. 1980 (4), 59

In this article, they synthesize different lysergic acid based pharmaceutic drugs using PTC.

Unfortunately I don't know the page, just title, author and issue/year - maybe someone is also interested in this one and can check his library - mine doesn't have such old issues...


The following articles on N-alkylation look highly interesting, but unfortunately I have no access to Green Chem. ... Maybe someone else has? (purchase is 13$ each; but unfortunately I am a VERY poor bee...)


Direct mono-N-alkylation of amines in ionic liquids: chemoselectivity and reactivity
(Cinzia Chiappe and Daniela Pieraccini, Green Chem., 2003, 5 (2), (193-197))

"A simple method for the N-alkylation of primary amines was developed using ionic liquids as solvent in order to prepare secondary amines selectively. In ionic liquids overalkylation of the initially produced secondary amines is in general markedly reduced. Various amines, alkyl halides and sulfonates were examined. The observed selectivities between mono- and dialkylation are typically on the order of 91, or higher. Only in the cases of allyl or benzyl bromides does the reaction give the corresponding tertiary amines exclusively. The relative nucleofugality of chloride, bromide, iodide and tosylate with several primary amines was also evaluated, as well as the effect of caesium hydroxide."




Aqueous N-alkylation of amines using alkyl halides: direct generation of tertiary amines under microwave irradiation
(Yuhong Ju and Rajender S. Varma; Green Chem., 2004, 6 (4), (219-221))

"Direct formation of tertiary amines viaN-alkylation of amines by alkyl halides occurs in aqueous media under microwave irradiation. This greener alternative is also a useful and powerful method to construct C–N bond without using any transition metal catalysts."



If someone could get at least the latter article, this would be very cool! (imagine: DET from tryptamine and EtBr in water, in every microwave oven  ;D )(TIA)

indole_amine


jsorex

  • Guest
for indole_amine, Catalytic enantioselective...
« Reply #59 on: September 18, 2004, 06:04:00 PM »
for indole_amine,

Catalytic enantioselective addition to imines
Kobayashi, Shu, Ishitani, Haruro
Chemical Reviews. Easton: May 1999. Vol. 99, Iss. 5; p. 1069 (26 pages)




Nicodem

  • Guest
“Tryptazolamines” and their pharmacology
« Reply #60 on: September 19, 2004, 02:14:00 PM »
Sorry if I don’t have the titles and abstracts, but I would very much appreciate if anybee would find and post these papers on various aza analogues of DMT and AMT based on the benzimidazol and benzotriazol indole isosteres.

On benzimidazol-ethylamine derivatives:

Pharm. Chem. J. (Engl.Transl.); 10(9); 1976; 1184-1187. [English]
or 
Khim. Farm. Zh.; 10(9); 1976; 51-55.
  [Russian] [Retrieved]

I already have enough papers on the chemistry and synthesis of these compounds, but if anybee knows of any other info on their pharmacology please PM me. Thank you very much. :)


Earlier Requests:

OK, I know...this time I ask nearly the impossible but anyway:
Nikolova M., Daleva L. Marinova V. Farmazia (Sofia) 19 (1969) 31.
and/or
Vasileva E., Natova L. Compt. Rend. Bulgaria 44 (1991) 37.
The papers are probably in Bulgarian but that is OK
Thanks


moo

  • Guest
Here you go
« Reply #61 on: September 20, 2004, 03:01:00 PM »
For Organikum:

Decarboxylation Studies: I
R.Davis and H.P.Schultz
J.Org.Chem., 27, 854 (1962)



This request refers to:

Post 514619

(psyloxy: "Propiophenon from PhCOOH / PrOOH / Fe - 72%", Chemistry Discourse)



Rhodium

  • Guest
Four refs for three bees
« Reply #62 on: September 20, 2004, 11:15:00 PM »
For Psyloxy:
The Bromination of Phenolic Methyl Ethers with Hydrogen Bromide using Sodium Tungstate and Hydrogen Peroxide as Oxidant
Paul Bezodis, James R. Hanson and Philippe Petit

J. Chem. Research (S) 334-335 (1996)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/bromination.h2o2-tungstate.pdf)

Abstract
Sodium tungstate has been found to be an effective catalyst for the nuclear bromination of some aromatic methyl ethers using hydrogen bromide in glacial acetic acid and hydrogen peroxide as the oxidant.


For Lego:
Direct Synthesis of Molecular Self-Complexes in the Indole Series
A. N. Kost, M. A. Yurovskaya, A. S. Vyazgin, and A. Z. Afanas'ev
Chem. Heterocycl. Comp. (Engl. Transl.) 921-925 (1980)
Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1222-1226 (1980)



Abstract
A method for the alkylation of 3-unsubstituted indoles by means of 1-(?-haloalkyl)pyridinium salts via the Friedel-Crafts reaction with the aid of complex catalysts, viz. complexes of zinc, tin and titanium chlorides with pyridine, was developed. On the basis of a study of the electronic spectra of the resulting 1-(3-indolylalkyl)pyridinium salts it was shown that they are molecular self-complexes. The stabilities of the molecular self-complexes were investigated as a function of the length of the alkyl chain and the character of the substituents in the indole ring.
____ ___ __ _

Friedel-Crafts alkylation of indoles
Budylin, V. A.; Ermolenko, M. S.; Kost, A. N.
Khimiya Geterotsiklicheskikh Soedinenii  No. 7,  921-924 (1978)


 
Abstract
Indoles I (R = H, Me; R1 = Bu, MeCHEt, Me2CHCH2, Me3C, PhCMeEt) were prepd. in 30-85% yield by alkylation of the resp. indole with R1X (X = Cl, Br) in the presence of ZnCl2-dipyridine zinc chloride.  The activity of the halides increased in the order: primary, secondary, tertiary.  Alkyl bromides were more reactive than alkyl chlorides.


For josef_k:

One of your wanted refs - Chem. Heterocycl. Compd. 21(12) 1327 - is incorrect and does not point to an article of interest, the other article you wanted follows here:

Synthesis, Molecular Structure, and Absolute Configuration of 1-?-Phenylethyl-3-(2-Cyanoethyl)-4-Piperidone
G. V. Grishina, et al., Chem. Heterocycl. Compd. 21(12), 1362 (198?)




cattleprodder

  • Guest
I ran across this tonight online while reading
« Reply #63 on: September 21, 2004, 06:31:00 AM »
I ran across this tonight online while reading another study.  The following sentence was the second to the last line of the Discussion section of that study:  "Olefins may be converted to primary amines...by reaction with mercury (II) nitrate in acetonitrile (see footnote number 10)."  The final sentence added that the addition would follow Markovnikov's rule which is what we want in the cases of MDA, 3,4-DMA, MMDA and TMA from their respective olefinic precursors.  Namely, safrole, 4-methoxlated eugenol, myristicin and elemicin in that order.

Footnote #10:  H.C. Brown and J.T. Kurek, _J. Am. Chem. Soc._, 91, 5647 (1969).

Thanks. 

(This article seems too good to be true, but let's hope not.)

Rhodium

  • Guest
Aminomercuration
« Reply #64 on: September 21, 2004, 06:09:00 PM »
cattleprodder: That article is already at my page, linked at the end of

https://www.thevespiary.org/rhodium/Rhodium/chemistry/aminomercuration.html


A related procedure is described in

https://www.thevespiary.org/rhodium/Rhodium/chemistry/allylamination.html




lugh

  • Guest
Requested Articles
« Reply #65 on: September 22, 2004, 02:36:00 AM »
In addtion to Rhodium's page, cattleprodder could have found the article's experimental and some other well known bee's posts concerning it in

Post 100234 (missing)

(Osmium: "Solvomercuration-demercuration", Chemistry Discourse)
 ;D


For Captain_America:
Concearning theories of indoles in schizophrenigenesis
Turner, W.J et al., American Journal of Psychiatry 112, 466-467 (1955)


The prior article was included since it was on the same page for the edification
of those that have more confidence in modern medicine than is warranted  ::)

____ ___ __ _

For Potter:
A Simple Method for the Removal of Phenolic Hydroxy-groups
W. Lonsky, et al., J. Chem. Soc. Perkin. Trans. 1975, Part 1, ?2, 169-170

(Vanillin -> 3-MeO-Benzaldehyde)


azole

  • Guest
retrieved refs.
« Reply #66 on: September 22, 2004, 06:17:00 PM »
For Lego:
Zhurnal Organicheskoi Khimii 1(11), 1973-1976 (1965)
See

Post 532695

(azole: "R2N(CH2)3MgCl + HC(OEt)3 : previous work", Tryptamine Chemistry)
.


For Bubbleplate:

Ergot Alkaloids. XXXIII.
Epimerization of the Simpler Amides of D-Lysergic, D-Isolysergic and 1-Methyl-D-lysergic Acids

Cerný and M. Semonský
Coll. Czech. Chem. Commun.
, 34, 694-698 (1969).


   Quaternary ammonium hydroxides, methylates and phenolates and strongly basic anion exchangers in the OH- form were applied to achieve partial isomerization of the simpler amides of D-lysergic, D-isolysergic and 1-methyl-D-lysergic acids at the centre of symmetry C(8) of the molecule. Their effect was compared with that of potassium hydroxide.

Mutterkornalkaloide XIX.
Über die Verwendung von N, N'-Carbonyldiimidazol zur Synthese der D-Lysergsäure-, D-Dihydrolysergsäure(I)- und 1-Methyl-D-dihydrolysergsäure(I)amide

Cerný and M. Semonský
Coll. Czech. Chem. Commun.
, 27,  1585-1592 (1962).


   Substituted amides of D-lysergic, D-dihydrolysergic and 1-methyl-D-dihydrolysergic acids were synthesized in good yields from the corresponding acids and primary and secondary amines with the help of N, N'-carbonyldiimidazole. Successful application of N, N'-carbonyldiimidazole is accounted for the reactivity of the acids and the stability of the intermediate acylated imidazoles.


For Nicodem:

Synthesis and Muscarinic Receptor Binding Profiles of Antagonist Benzotriazole derivatives
B. Cappello, G. Greco, E. Novellino, E. Perissutti, V. Santagada, C. Silipo, A. Vittoria, R. Di Carlo, R. Meli, and G. Muccioli
Il Farmaco
, 48(7), 907-918 (1993).


Abstract
A series of benzotriazole derivatives were synthesized and tested in order to determine their activities for muscarinic receptor subtypes (M1, M2 and M3).Binding affinities were measured as K1 values by competition against <3H>-N-methylscopolamine in rat cortex, atria and ileum. Pharmacological in vitro tests were performed on isolated tissue preparations (rabbit vas deferens, guinea pig atria and ileum); the compounds showed antimuscarinic activity. The synthesized ligands were characterized by moderate activity; however, some of them displayed interesting selectivity profiles (M2/M1 and M2/M3); particularly, the selectivity exhibited by the benzotriazole derivative 14b was quite similar to that observed for AF-DX 116, a typical M2 specific antagonist.


Studio di alcuni derivati del nucleo benzotriazolico
R. Calvino, V. Mortarini, A. Serafino
Il Farmaco, Ed. Sci.
, 35(3), 240-247 (1980).



Derivati amminoalchilici del benzotriazolo. Nota II.
F. Sparatore, F. Pagani
Il Farmaco, Ed. Sci.
, 20(4), 248-258 (1965).



Derivati amminoalchilici del benzotriazolo.
F. Sparatore, F. Pagani
Il Farmaco, Ed. Sci.
, 17(6), 414-429 (1962).



Synthesis and Investigation of Some Derivatives of Benzimidazole. VII. Phenothiazine Derivatives of Benzimidazole.
N. A. Mukhina, V. M. Pechenina, L. P. Grebenshchikova, V. M. Kurilenko, L. S. Rogova, T. M. Vysokovskii
Khim. Farm. Zh.
, 10(9), 51-55 (1976).
(journal written in Russian)


Rhodium

  • Guest
Wanted ones
« Reply #67 on: September 24, 2004, 06:29:00 PM »
Isolation, Analysis, and Synthesis of Ephedrine and its Derivatives
Gazaliev, A. N.; Zhurinov, M. Zh.; Fazylov, S. D.; Balitskii, S. N.
Chem.Nat.Compd.(Engl.Transl.), 25(3), 261-271 (1989)

Abstract
A review is given of methods for the isolation, quantitative determination, and modification of the ephedrine alkaloids, and advances in this field of natural compound chemistry.
____ ___ __ _

A protocol for the evaluation of new psychoactive drugs in man.
Shulgin AT, Shulgin LA, Jacob P 3rd., Methods Find Exp Clin Pharmacol. 8(5), 313-20 (1986)

Medline (PMID=3724306)



Abstract
A protocol is presented that has proven effective in the determination, in man, of the psychotomimetic potency and qualitative nature of action of a new drug. It involves a minimum of animal screening, but relies heavily upon the use of experienced human subjects. This procedure has been successful in the discovery of over 200 novel CNS-active agents.
____ ___ __ _

Seizure And Analysis Of A Clandestine Methylphenidate Laboratory
Abercrombie Jt; Journal Of The Forensic Science Society 28(2), 121-122 (1988)
____ ___ __ _

Analysis Of 1-(3,4-Methylenedioxyphenyl)-1-Ethanamines - Homologs Of 3,4-Methylenedioxyamphetamines
Noggle Ft, Clark Cr, Deruiter J; Journal Of Liquid Chromatography 12 (3): 431-444 1989 (EJ KTH)
____ ___ __ _

[Synthesis of radiolabeled amphetamine derivatives]
RS Varma & GW Kabalka
J. Labelled Comp Radiopharm., 23, 1244 (1986)


gsus

  • Guest
for Rhodium
« Reply #68 on: September 25, 2004, 01:28:00 AM »
A protocol for the evaluation of new psychoactive drugs in man.
Shulgin AT, Shulgin LA, Jacob P 3rd., Meth and Find Exptl Clin Pharmacol. 8(5), 313-20 (1986)

Abstract
A protocol is presented that has proven effective in the determination, in man, of the psychotomimetic potency and qualitative nature of action of a new drug. It involves a minimum of animal screening, but relies heavily upon the use of experienced human subjects. This procedure has been successful in the discovery of over 200 novel CNS-active agents.



--------

Synthesis of High Specific Activity 1 2 3 I-Labeled N-Isopropyl p-Iodoamphetamine via Organoborane Chemistry
RS Varma & GW Kabalka
J. Labelled Comp Radiopharm., 23, 1244-1245 (1986)




Rhodium

  • Guest
Forensic Articles
« Reply #69 on: September 27, 2004, 06:38:00 PM »
Impurities in illicit amphetamine
Huizer H, Theeuwen AB, Verweij AM, Sinnema A, van der Toorn JM.
J. Forensic. Sci Soc. 21(3), 225-32 (1981)
____ ___ __ _

Isolation, Analysis, and Synthesis of Ephedrine and its Derivatives
Gazaliev, A. N.; Zhurinov, M. Zh.; Fazylov, S. D.; Balitskii, S. N.
Chem.Nat.Compd.(Engl.Transl.), 25(3), 261-271 (1989)

Abstract
A review is given of methods for the isolation, quantitative determination, and modification of the ephedrine alkaloids, and advances in this field of natural compound chemistry.
____ ___ __ _

Seizure And Analysis Of A Clandestine Methylphenidate Laboratory
Abercrombie Jt; Journal Of The Forensic Science Society 28(2), 121-122 (1988)
____ ___ __ _

Analysis Of 1-(3,4-Methylenedioxyphenyl)-1-Ethanamines - Homologs Of 3,4-Methylenedioxyamphetamines
Noggle Ft, Clark Cr, Deruiter J; Journal Of Liquid Chromatography 12 (3): 431-444 1989
____ ___ __ _

[Synthesis of BDB]
Azafonov, N. E.; Sedishev, I. P.; Zhulin, V. M.
Bull.Acad.Sci.USSR Div.Chem.Sci.(Engl.Transl.) 39, 4.1, 738-741 (1990)
[Translation of Izv.Akad.Nauk SSSR Ser.Khim. 4, 829-832 (1990)]
____ ___ __ _

[Synthesis of BDB]
Solbach, M.; Guendisch, D.; Wuellner, U.; Blocher, A.; Kovar, K.-A.; Machulla, H.-J.
J.Labelled Compd.Radiopharm. 40, 522-524 (1997)
____ ___ __ _

[N-Methylation by Reduction of N-COOEt Carbamates]
Marshall, F. J. and McMahon, R. E.
J.Labelled Compd.Radiopharm. 6, 261 (1970)
____ ___ __ _

Structure-Activity-Relationships Of MDMA and Related-Compounds - A New Class Of Psychoactive-Drugs
Nichols DE, Oberlender R,
Ann. N. Y. Acad. Sci, 600, 613-625 (1990)


Rhodium

  • Guest
For Indole_Amine:
« Reply #70 on: September 27, 2004, 08:47:00 PM »
Indole_Amine: ChemInform is not a journal, it is a collection of abstracts pointing to other recent publications. Here are some of the publications your ChemInform abstracts are pointing to:


Reductive aminations of carbonyl compounds with borohydride and borane reducing agents
Baxter, E. W.; Reitz, A. B.
Org. React. (N.Y.), 59, 1-714 (2002)
Excerpts posted in

Post 533416

(Rhodium: "Org. React. 59: Reductive amination w/ BH3 & MBH4", Novel Discourse)

____ ___ __ _

Enantioselective Borohydride Reduction Catalyzed by Optically Active Cobalt Complexes
Tohru Yamada,Takushi Nagata, Kiyoaki D. Sugi, Kiyotaka Yorozu, Taketo Ikeno, Yuhki Ohtsuka, Daichi Miyazaki, Teruaki Mukaiyama
Chemistry - A European Journal, 9(18), 4485-4509 (2003)
Posted in

Post 533407

(Rhodium: "Reductions with modified borohydride reagents", Novel Discourse)

____ ___ __ _

Sodium Borohydride-Iodine, an Efficient Reagent for Reductive Amination of Aromatic Aldehydes
Ira Saxena, Ruli Borah, Jadab C. Sarma
Indian Journal of Chemistry Sect. B, 41(9), 1970-1971 (2002)
Already posted in

Post 436354

(Rhodium: "Archive of  "Wanted References" Volume 1", Novel Discourse)

____ ___ __ _

Chemoselective and stereoselective reductions with modified borohydride reagents
Guy Windey, Karl Seper, John H. Yamamoto, PharmaChem, 15-18 (2002)
Posted in

Post 533407

(Rhodium: "Reductions with modified borohydride reagents", Novel Discourse)

____ ___ __ _

This is not the particular book review you asked for, but maybe the following suits you just as as well?

Review: Reductions by the Alumino- and Borohydrides in Organic Synthesis, 2nd edition (by Jacqueline Seyden-Penne)
Hoye, R. C. J. Chem. Educ. 76, 33 (1999)

This book focuses entirely on the aluminohydride and borohydride reducing agents. It condenses a large body of information into a valuable user-friendly resource for synthetic organic chemists. The author states that "This second edition has been broadly updated, but it is no longer exhaustive. As in the previous edition, the examples are selected in order to cover problems that are frequently encountered in synthesis."

The first chapter (13 pages) gives an excellent summary of the approximately two dozen most widely used aluminohydride and borohydride reagents. Information is presented on the main applications of each reagent and its solubility characteristics, stability, and handling requirements. Cross-references are liberally given to subsequent chapters where more complete reactivity profiles and examples are found. Chapters two through five (155 pages) detail reduction of the main functional groups by these reagents.

Chapter two covers reductions of carbon-heteroatom single bonds (C-Hal, C-O, C-N, C-P). Reagents capable of effecting a desired single-bond cleavage are described, as are mechanistic considerations of the process. Chemoselectivity and regioselectivity are duly noted.

Chapter three is concerned with reduction of double bonds (C=C, C=O, C=N) and is by far the largest chapter in the book. Reduction of carbon-oxygen double bonds is organized by functional group. The examples for aldehydes and ketones illustrate the potential for selectivity in the presence of other functional groups; the control of stereoselectivity, including a discussion of the factors favoring the Felkin-Ahn or Houk models; a survey of enantioselective reducing agents, particularly those developed in recent years; and the influence of neighboring substituents on stereoselectivity as the result of chelation control. These concerns and further consideration of conditions for partial reduction are given for carboxylic acid derivatives. Similar examples are included for reduction of carbon-nitrogen double bonds.

Carbon-carbon and carbon-nitrogen triple bonds, both isolated and conjugated, are treated in Chapter four. The examples illustrate the potential for chemo-, regio-, and stereoselectivity. Chapter five addresses the reduction of "other derivatives", including nitro and nitroso derivatives, azides, organometallics, sulfides (sulfoxides, sulfones, and amine oxides), phosphine oxides and phosphates, silyl derivatives, and boron reagents. Seyden-Penne concludes with a large table (11 pages) that "shows at a glance" the various methods by which major functional groups can be obtained by hydride reduction with cross references to the appropriate sections of the text.

This book is a thorough and dense compilation of experimental results and observations that highlight selectivity at every level as well as experimental practicality. The 10-page index appears to be well organized and the referencing is extensive (more than 1000 references in 33 pages). Given the prevalent role of hydride reduction reactions in organic synthesis, many practitioners will want to have ready access to this book, and it is a must for all science libraries.
____ ___ __ _
latest addition (09-27-04): Edit: Yet another Review:

Review: Reductions by the Alumino- and Borohydrides in Organic Synthesis (by J. Seyden-Penne)
K. Smith, Appl. Organometal. Chem. 12, 881 (1998)

This book is an update from the first edition, which was published in 1991. In the first edition there was an attempt at comprehensive coverage of the topic, but in the second edition any such attempt has been forced to be abandoned. Nevertheless, this second edition is packed with information, cites around 1200 references, and provides a very useful source for anyone contemplating a complex hydride reduction.

The book is organized into five chapters, followed by 11 pages of synoptic tables, then the references and a subject index.

Chapter 1 introduces the most commonly used reagents, indicates their stability and solubility characteristics and briefly describes their main applications. Chapters 2–5 present the reduction of the main functional groups, with reference to features of selectivity and compatibility.
Chapter 2 deals with cleavage of carbon–heteroatom single bonds (halides, sulphonates, epoxides, alcohols, ethers, ammonium salts etc).
Chapter 3, the largest chapter with over 100 pages, deals with reduction of double bonds (other than C=C bonds). The bulk of the chapter (85 pages) concerns reductions of carbonyl compounds, including sections on different kinds of carbonyl compounds, asymmetric reductions and regioselectivity of the reduction of a,b-unsaturated derivatives. The chapter also covers imines, enamines, nitrogen heterocycles and oximes/hydrazones.
Chapter 4 deals with reduction of triple bonds and Chapter 5 with other derivatives (nitro compounds, azides, organometallics, and sulphur, phosphorus, silicon and boron compounds).

The entry point for many will be the synoptic tables. Here it is possible to look up a class of compound and choose a precursor substrate; the table will provide a list of reagents for the transformation and section references indicating where the reactions are discussed. The appropriate sections in Chapters 2–5 will provide the detailed discussion of those reactions and Chapter 1 will give an outline of the characteristics of the chosen reagent. Thus, the book is ideal for identifying the most useful references for any given reduction.

Because it is so densely packed with information, the text is somewhat difficult to read. This is almost unavoidable if the coverage is to remain so full and the book so short (220 pages), and the difficulty is easily outweighed by the value of the work as a source of reference and information.

This book is an imperative purchase for all chemical libraries and for any individuals who make regular use of complex hydride reductions.
____ ___ __ _

Reductions by the Alumino- and Borohydrides in Organic Synthesis, 2nd Edition
Jacqueline Seyden-Penne
ISBN: 0-471-19036-5, 224 pages (1997)
Published by

John Wiley & Sons

(http://www.wiley.com/WileyCDA/WileyTitle/productCd-0471190365.html)

   
Table of Contents
  • Description and Characteristics of the Main Reagents
  • Cleavage of the Carbon-Heteroatom Single Bond
  • Reduction of Double Bonds
  • Reduction of Triple Bonds
  • Other Derivatives
  • Synoptic Tables
  • References
  • Index
A complete guide to selection and use of the best reagents for a wide range of transformations

This book is the updated and expanded Second Edition of Jacqueline Seyden-Penne's practical guide to selection of reducing reagents in organic synthesis. It is an indispensable working resource for organic synthetic chemists—the only reference focusing exclusively on aluminohydrides and borohydrides and their derivatives.

Simple to use, it is organized according to specific reductions so that chemists can more easily match the best reagent to a given transformation. Throughout, Dr. Seyden-Penne emphasizes four crucial categories: compatibility, possibilities for partial reduction, the regio- and stereoselectivity of reductions that are altered or controlled by neighboring groups, and asymmetric reductions.

Extremely well-referenced, Reductions by the Alumino- and Borohydrides in Organic Synthesis provides the most up-to-date, detailed coverage of:
  • Successful techniques for performing highly selective reductions
  • Chemo-, regio-, stereo-, and enantioselective reductions of both simple and complex compounds
  • Best methods for obtaining the main functional groups by hydridereduction, provided in quick-reference tabular form
  • New and more selective reagents developed within the last five years
  • Experimental conditions, including solvent and temperature, and yields for most cases described.



java

  • Guest
Wanted: articles in Reduction of OH with RP/I
« Reply #71 on: September 30, 2004, 07:23:00 PM »
In folowing a lead from an old post from Labrat as to the use of RP/I in the reduction of OH , nitrites , halogens to the alkane......as in the use of primary amino alcohols...java

Reagents for Organic Synthesis Vol.1, 449, 1967 [Retrieved]

Survey of Organic Synthesis Vol.7, pg.332& pg.7, 1970


gsus

  • Guest
Fieser and Fieser for java
« Reply #72 on: September 30, 2004, 10:54:00 PM »
Reagents for Organic Synthesis Vol.1, 449, 1967




gsus

  • Guest
retrievals
« Reply #73 on: October 02, 2004, 10:18:00 AM »
mentioned in the Vitus Verdegast post above:


Analgesic Activity Profile of a-Allylphenethylamine HCl (Aletamine)
I. Shemano, J.T. Hitchens, S. Goldstein, J.M. Beiler
Arch. int. Pharmacodyn., 172, 251-259 (1968)



--------

for 7is

Improved pharmacological activity via pro-drug modification: comparative pharmacokinetics of sodium gamma-hydroxybutyrate and gamma-butyrolactone
Lettieri J, Fung H-L, Research Communications in Chemical Pathology and Pharmacology 22(1), 107-118 (1978)

Abstract
Although gamma-butyrolactone (GBL) rapidly converts to gamma-hydroxybutyrate (GHB) in vivo, the lactone gave significantly more prolonged hypnotic effects than GHB when equimolar doses were compared both parenterally and orally in rats. Plasma drug concentrations were higher after GBL administration through both routes, consistent with the observed differences in the pharmacological activity of these two compounds. Oral GBL was absorbed much faster than oral GHB, with the dual effects of decreasing potential first-pass metabolism and elevating plasma drug concentrations to the region where capacity-limited elimination is operative. Parenteral GBL produced a slower initial drug plasma clearance than parenteral GHB. In spite of the rapid metabolism of GBL to GHB, the apparent tissue distribution of these two compounds may be different.



--------

for Rhodium

The Cocaine Diastereoisomers
Allen AC, Cooper DA, Kiser WO, Cottrell RC
J. Forensic Sci. 26(1), 12-26 (1981)

Abstract
In the past, it has been argued in court, from a theoretical basis, that the techniques available to the forensic chemist would differentiate the “cocaines.” This work has moved that argument from the realm of the theoretical into that of experimental fact. The techniques of infrared spectroscopy (IR), nuclear magnetic resonance (NMR), and mass spectrometry (MS) will unequivocally identify the racemic cocaine diastereoisomer. In addition, this work shows that the enantiomeric form of cocaine can be assigned by crystal tests, IR, and melting point techniques. The pure enantiomers of allococaine and pseudoallococaine were not isolated. This does not create a problem because the techniques of NMR and MS, as performed in this study, will not differentiate enantiomers. Therefore, the logical sequence of first identifying the diastereoisomer (via IR, MNR, or MS) and then determining the chirality by crystal tests, IR, melting points, or optical rotation measurements is valid.



--------

Identification of Some Chemical Analogues and Positional Isomers of Methaqualone
Dal Cason TA, Angelos SA, Washington O
J. Forensic Sci. 26(4), 793-833 (1981)

Abstract
The drug 2-methyl-3-ortho-tolyl-4-quinazolinone (methaqualone) and 15 chemical analogues and positional isomers were synthesized and identified by spectroscopic techniques. The series of analogues studied includes the compounds formed through substitution of hydrogen or halogen atoms in place of the methyl group of the 3-tolyl substituent in methaqualone. Additionally, the substituent's positional orientation of ortho, meta, or para is considered. Infrared, nuclear magnetic resonance, and mass spectra of the compounds are distinctive, and reference spectra are provided. Gas-liquid and thin-layer chromatographic systems for analysis of the compounds as well as melting point and ultraviolet data are discussed.



--------

The Characterization of Some 3,4-Methylenedioxyphenylisopropylamine (MDA) Analogs
Dal Cason TA, J. Forensic Sci. 34, 928–961 (1989)

Abstract
The seizure in 1986 of a large-scale clandestine laboratory producing both the N-ethyl and the N,N-dimethyl analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine [MDA]) and the recent identification of N-hydroxy MDA hydrochloride (HCl) indicate an interest by illegal laboratory operators in the synthesis of noncontrolled MDA analogs. Currently, identification of these new analogs may be hampered due to lack of available standards or reference data or both. This potential problem prompted the synthesis of the following N-substituted MDA analogs: N-methyl, N-ethyl, N-propyl, N-isopropyl, N-hydroxy, and N,N-dimethyl MDA. Each compound was prepared by reductive amination of 3,4-methylene-dioxyphenyl-2-propanone (MDP-2-P) using the appropriate amine hydrochloride and sodium cyanoborohydride. In addition, the acetyl derivatives of MDA, N-hydroxy MDA, and MDP-2-P oxime are reported. Spectral and chromatographic data are presented for each of the compounds synthesized.



--------

A Fatality Involving U4Euh
FT Davis and ME Brewster
J. Forensic Sci. 33, 549-553 (1988)

Abstract
A fatality following ingestion of diazepam and 4,5-dihydro-4-methyl-5-phenyl-2-oxazolamine, a cyclic derivative of phenylpropanolamine known as U4EuH or 4-methyl aminorex, is described. Solid dosage samples of U4EuH were analyzed using gas chromatography, ultraviolet and infrared spectroscopy, nuclear magnetic resonance, and mass spectrometry. Physiological fluids were analyzed quantitatively by gas chromatography and qualitatively by gas chromatography-mass spectrometry. Concentrations of 4,5-dihydro-4-methyl-5-phenyl-2-oxazolamine were: in blood 21.3 mg/L; in urine 12.3 mg/L. Diazepam concentration in blood was 0.8 mg/L.




fogged

  • Guest
For Rhodium
« Reply #74 on: October 04, 2004, 08:59:00 AM »
Methamphetamine synthesis via reductive alkylation hydrogenolysis of phenyl-2-propanone with N-benzylmethylamine
Harry F. Skinner, Forensic Sci. Int. 60(3), 155-162 (1993)
DOI:

10.1016/0379-0738(93)90234-2





Abstract
Methamphetamine was synthesized by reductive alkylation hydrogenolysis of phenyl-2-propanone with N-benzylmethylamine. The expected product N-benzylmethamphetamine, once formed, undergoes hydrogenolysis to methamphetamine and toluene. The progress of the reaction, the intermediates formed during the reaction, and the products were analyzed by gas chromatography and mass spectrometry.
____ ___ __ _

Spectral distinction between cis- and trans-4-methylaminorex
A. W. By , B. A. Dawson , B. A. Lodge and W-W. Sy, Forensic Sci. Int. 43(1), 83-91 (1989)
DOI:

10.1016/0379-0738(89)90124-2





Abstract
The recent identification of the anorectic agent 4-methylaminorex (2-amino-4-methyl-5-phenyl-2-oxazoline) as a police exhibit in Canada led to the need to synthesize a reference standard specimen. Since this substance can occur as cis and trans isomers, both had to be prepared and characterized spectrally. cis-4-Methylaminorex was made from the erythro amino alcohol norephedrine (phenylpropanolamine), while the trans compound was made from the threo diastereoisomer norpseudoephedrine, in both cases by the treatment of the substrate with cyanogen bromide in a methanolic solution of sodium acetate. In this paper, the 13C- and 1H-NMR, infrared (IR), mass (MS) and ultraviolet (UV) spectra are reported, together with a commentary on the distinguishing features noted between the sets of spectra.

Nicodem

  • Guest
For Ganesha
« Reply #75 on: October 04, 2004, 02:04:00 PM »

Medicinal chemistry and structure-activity relationships of hallucinogens.
Nichols, D.E., and Glennon, R.A.
In: Jacobs, B.L., ed. Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. New York: Raven Press, 1984. pp. 95-142.








indole_amine

  • Guest
for Barium...
« Reply #76 on: October 04, 2004, 09:48:00 PM »
Retrieved:

Catalytic debenzylation. The effect of substitution on the strength of the O-benzyl and N-benzyl linkages
(R. Baltzly and J. Buck)
J. Am. Chem. Soc. Vol 65 (1943) pages 1984-1992





effects of amines on O-benzyl group hydrogenolysis
(C. Bronislav and R. Bartsch)
J. Org. Chem. 49 (1984) 4076-4078





indole_amine

gsus

  • Guest
for Rhodium
« Reply #77 on: October 09, 2004, 03:15:00 AM »
Structure-Activity-Relationships Of MDMA and Related-Compounds - A New Class Of Psychoactive-Drugs
Nichols DE, Oberlender R,
Ann. N. Y. Acad. Sci, 600, 613-625 (1990)




Organikum

  • Guest
Azeotropes of 1-chloro-2-propanone
« Reply #78 on: October 13, 2004, 11:01:00 AM »
Referring to this post:

Post 535431

(lugh: "Purification of Chloroacetone", Chemistry Discourse)


this article would be needed for the wanted information:

Lecat, Ann Soc Sci Bruxelles 4 21-7 (1927); Cent II, 226, (1927)

Either the whole article or the azeotrope and other data on chloroacetone from the article.

regards
ORG


lugh

  • Guest
For Embezzler: Electrosynthesis of 1,4 Butanediol
« Reply #79 on: October 14, 2004, 02:13:00 AM »
Butler, A. L.; Peters, D. G.
Synthesis of 1,4-Butanediol by Catalytic Reduction of 2-Bromo- and 2-Iodoethanol with Homogeneous-Phase Nickel(I) Salen Electrogenerated at Carbon and Mercury Cathodes
J. Electrochem. Soc. 144, 4212–4217 (1997)




;)


java

  • Guest
Reference on Hydrogenation of Alcohols
« Reply #80 on: October 14, 2004, 05:26:00 AM »
This is a reference on hydrogenation of alcohols..........it may apply to amino alcohols, not sure....java

Bull. Chem. Soc. Japan (1960) Vol 33, Pg 1356


In following a lead from an old post from Labrat as to the use of RP/I in the reduction of OH , nitrites , halogens to the alkane......as in the use of primary amino alcohols:

Survey of Organic Synthesis Vol.7, pg.332& pg.7, 1970


lugh

  • Guest
Already Uploaded
« Reply #81 on: October 16, 2004, 02:02:00 AM »

Trans. Roy. Soc. Can. (3) 23, Sect. 3, 77 (1929) [C. A. 24, 586 (1930)
Clark and Streight




If you had used the search engine, you would have found it in

Post 523897

(lugh: "Chlorination Methods", Stimulants)  ;)




Rhodium

  • Guest
Chimica Oggi & Borohydride/PTC Reductions
« Reply #82 on: October 18, 2004, 05:09:00 AM »
Chimica Oggi has ISSN 0392-839X and it's found at

http://www.teknoscienze.com/co_profile.htm


They do not respond to any inquiries concerning reprints though. Can anyone here get these articles?

Merits of sodium borohydride reductions under phase transfer catalysis. Part I.    
Yadav, Vasanti G.; Yadav, G. D.; Vyas, J. R.
Chimica Oggi (Chemistry Today) 18(6), 39-44 (2000)
____ ___ __ _

Merits of sodium borohydride reductions under phase transfer catalysis. Part II.    
Yadav, Vasanti G.; Yadav, G. D.; Vyas, J. R.
Chimica Oggi (Chemistry Today) 18(7/8), 39-43 (2000)
____ ___ __ _

The reactivity of gamma-hydroxybutyric acid (GHB) and gamma-butyrolactone (GBL) in alcoholic solutions
Hennessy SA, Moane SM, McDermott SD, Journal of Forensic Sciences, Vol. 49(6), [10 pages] (2004)
DOI:

10.1520/JFS2003340



Abstract
In this work the stability of GBL (gamma-butyrolactone) and GHB (gamma-hydroxybutyric acid) in alcoholic media was studied. Under acidic conditions the GBL will react with ethanol or methanol to give the corresponding ethyl and methyl esters of GHB. It can be seen that ester formation is dependent on the type of alcohol, the alcohol content of the solution, and the pH of the solution. Under the same conditions it was shown that GHB does not give rise directly to the corresponding ester when merely in the presence of an alcohol; however the ester will be formed if the conditions are present for conversion of GHB to GBL followed by subsequent reaction with alcohol. In alcoholic beverage samples spiked with GBL the expected conversion to GHB occurred, and the formation of the ethyl ester of GHB was also seen in some samples. Wine samples were analyzed for the presence of the ethyl ester of GHB, and the effect of adding GHB/GBL to hot beverages was studied.


fogged

  • Guest
For Lego:
« Reply #83 on: October 18, 2004, 06:46:00 AM »
For Lego:

Conversion of ?-Amino Acids into Nitriles by Oxidative Decarboxylation with Trichloroisocyanuric Acid
Gene A. Hiegel, Justin C. Lewis, Jason W. Bae
Synth. Comm., 2004, 34(19), 3449-3453



Abstract:
Trichloroisocyanuric acid oxidation of ?-amino acids in water or methanol in the presence of pyridine produces nitriles with one less carbon in good yields and of high purity.

Stalin

  • Guest
amphetamine impurities
« Reply #84 on: October 19, 2004, 10:35:00 AM »
As requested in

Post 217986

(Rhodium: "Wanted references", Novel Discourse)


AM van der Ark et al. Weakly Basic Impurities in Illicit Amphetamine




Daphuk_up

  • Guest
MoS2 Hydrogenation
« Reply #85 on: October 19, 2004, 08:36:00 PM »
If someone could dig this one up, would be appreciated greatly.  :)

Cawley and Hall, J. Soc. Chem. Ind. (London), 62, 116 (1943)

It is an article concerning the hydrogenation of thiophene to tetrahydrothiophene utilizing Molybdenum Disulfide.  Concurrently, any other articles dealing with MoS2 as a hydrogenation catalyst would be most helpful.  TIA.


psychokitty

  • Guest
Here are the three Green Chemistry articles
« Reply #86 on: October 22, 2004, 06:31:00 PM »
High atomic yield bromine-less benzylic bromination
Ramon Mestres* and Jesús Palenzuela
Green Chemistry, 2002, 4, 314–316

A two-phase mixture (sodium bromide, aqueous hydrogen peroxide/carbon tetrachloride or chloroform) under visible light provides a simple and convenient system for benzylic bromination of toluenes. A high atomic yield for bromine atoms is attained. Substitution of the chlorinated solvents by other more environmentally benign organic solvents has been attempted and good results are obtained for methyl pivalate.



Aqueous N-alkylation of amines using alkyl halides: direct generation of tertiary amines under microwave irradiation
Yuhong Ju and Rajender S. Varma
Green Chemistry , 2 0 0 4 , 6 , 2 1 9 – 2 2 1

Direct formation of tertiary amines via N-alkylation of amines by alkyl halides occurs in aqueous media under microwave irradiation. This greener alternative is also a useful and powerful method to construct C–N bond without using any transition metal catalysts.



Direct mono-N-alkylation of amines in ionic liquids: chemoselectivity and reactivity
Cinzia Chiappe* and Daniela Pieraccini
Green Chemistry, 2003, 5, 193–197

A simple method for the N-alkylation of primary amines was developed using ionic liquids as solvent in order to prepare secondary amines selectively. In ionic liquids overalkylation of the initially produced secondary amines is in general markedly reduced. Various amines, alkyl halides and sulfonates were examined. The observed selectivities between mono- and dialkylation are typically on the order of 9+1, or higher. Only in the cases of allyl or benzyl bromides does the reaction give the corresponding tertiary amines exclusively. The relative nucleofugality of chloride, bromide, iodide and tosylate with several primary amines was also evaluated, as well as the effect of caesium hydroxide.


Captain_America

  • Guest
oxoacetic acid
« Reply #87 on: October 23, 2004, 08:41:00 AM »
From oxalic acid w/ zinc/sulfuric:

Church; J.Chem.Soc.; 16; 1863; 302; Justus Liebigs Ann. Chem.; 130; 1864; 50.


From oxalic w/ Mg powder:

Benedict; Chem. Zentralbl.; 80; I; 1909; 1645.


From EtOH w/ nitric acid:

Boettinger; Arch.Pharm. (Weinheim Ger.); 232; 1894; 65.

Debus; Justus Liebigs Ann. Chem.; 100; 1856; 5; J.Chem.Soc.; 85; 1904; 1392.

indole_amine

  • Guest
"J.Chem.Soc." ?
« Reply #88 on: October 23, 2004, 06:45:00 PM »
Dear Capn, I really would like to help you, but:

are you sure about the journal titles? I have access to 17(!) online journals all carring "journal","chemical" and "society" in their titles (including the famous "Journal of the Serbian Chemical Society", so if anyone needs anything related to serbic chemistry, let me know...  ;D ) - but none of them is called "Journal of (the) Chemical Society" alone...

And the assumption that it might perhaps be JACS was qickly proven wrong by the fact that there exists no "JACS vol.16 p.302" ...  :(

If there exists a journal being really abbreviated with J.Chem.Soc., I would like to know it of course, to avoid such misapprehension next time then...

indole_amine

roger2003

  • Guest
J. Chem. Soc.
« Reply #89 on: October 23, 2004, 07:15:00 PM »

indole_amine

  • Guest
request
« Reply #90 on: October 24, 2004, 11:45:00 AM »
Roger2003: thx for clarifying this,it seems I sadly don't have access to this journal...




And also no access to the following, maybe anyone else has:

A.E. Chichibabin, Zh. Russ. Fiz. Khim. O-va. 37, p.1229 (1905)
(Syntheses of pyridine and derivatives)

TIA,

indole_amine

Captain_America

  • Guest
2,5-dimethoxy-4-bromoacetophenone
« Reply #91 on: October 24, 2004, 05:30:00 PM »
Bates, M. A.; Sammes, P. G.; Thomson, G. A. Synthesis of the
C-glycoside fragment of nogalamycin and some nogalamycin
precursors. J. Chem. Soc., Perkin Trans. 1 1988, 3037-3045.

hypo

  • Guest
J. Chem. Soc., Perkin Trans. 1 1988, 3037-3045
« Reply #92 on: October 25, 2004, 04:53:00 AM »


(what's that good for? DOET?)


Captain_America

  • Guest
Thanks hypo, not DOET, but possibly active CAT
« Reply #93 on: October 25, 2004, 07:12:00 AM »
Thanks hypo, not DOET, but possibly active CAT analogues of 2C-X;

Post 537566

(Captain_America: "bromination + Delephine from the above paper", Novel Discourse)
For DOET it's better to make 2,5-dimethoxyacetophenone, clemmensen and since a vilsmeyer give wierd results on this substrate a bit more OTC, indirect formylation would bee preferred;

Patent US4190583


gsus

  • Guest
for Captain America
« Reply #94 on: October 26, 2004, 02:13:00 AM »
Ueber einige Oxydationsproducte des Alkohols
H. Debus
Ann. 100, 1-19 (1856)



Ueber einige Umwandlungen der Oxalsäure
A.H. Church
Ann. 130, 48-53 (1864)



the microfilm and microfiche readers are hooked up to computers. unfortunately JCS of that era is on microcard.


this message was approved by JACS 16(1), 302 and


azole

  • Guest
retrieved...
« Reply #95 on: October 26, 2004, 09:43:00 AM »
For Captain_America:

Note on some Metamorphoses of Oxalic Acid
A. H. Church
J. Chem. Soc., 1863, 16, 301-304.



Contributions to the History of Glyoxylic Acid
H. Debus
J. Chem. Soc., 1904, 85, 1382-1403.



Zur Darstellung der Glyoxylsäure
C. Boettinger
Arch. Pharm., 1894, 232, 65-69.




For java:

Hydrogenation and Hydrogenolysis. IV. Catalytic Reductions of Cinnamyl Alcohols and 3-Phenylpropargyl Alcohol
S. Nishimura, T. Onoda and A. Nakamura
Bull. Chem. Soc. Japan, 1960, 33, 1356-1359.


java

  • Guest
Vapor Phase Dehydrationof Alcohols
« Reply #96 on: October 26, 2004, 03:00:00 PM »
Would like to read these two articles , to facilitate my understanding of dehydration of primary alcohols in wanting to avoid re-arrangement. I'm trying to reduce Phenyalaninol to the alkene which will then be reduced to the alkane via catalytic hydrogenation....java



In dehydration of alcohols, if the alcohol can be evaporated, vapor phase elimination over AL2O3 is an excellent method since side reactions are greatly reduced



.......as per March's 5th ed. pg.1327, Dehydration of Alcohols

Journal für praktische Chemie 1964, 4(25), 160 and 184




archivist

  • Guest
World Market for Rye Ergot
« Reply #97 on: October 28, 2004, 04:39:00 AM »
The following is an e-Book, not journal article, however this seemes like the most appropriate place to post my request.  For the paltry fee of $795.00, Amazon.com will let you download "The World Market for Rye Ergot Alkaloids, Their Derivatives, and Salts Thereof: A 2004 Global Trade Perspective" as a pdf. 

"This report was created for strategic planners, international executives and import/export managers who are concerned with the market for rye ergot alkaloids, their derivatives, and salts thereof...On the demand side, exporters and strategic planners approaching the world market face a number of questions. Which countries are supplying rye ergot alkaloids, their derivatives, and salts thereof? What is the dollar value of these imports? How much do the imports of rye ergot alkaloids, their derivatives, and salts thereof vary from one country to another? Do exporters serving the world market have similar market shares across the importing countries? Which countries supply the most exports of rye ergot alkaloids, their derivatives, and salts thereof? Which countries are buying their exports? What is the value of these exports and which countries are the largest buyers?"

(On the off chance) Any beeshave access to this file?

indole_amine

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wanted
« Reply #98 on: October 29, 2004, 03:49:00 AM »
1) Indian J. Chem. B 1978, 16, 465
(Andrews, M. J.; Pillai, C. N.)

2) Synthesis 1981, 640
(Ayyanger, N. R.; Lugade, A. G.; Nikrad, P. V.; Sharma, V. K.)

Would be nice if anyone could get these...


indole_amine

jsorex

  • Guest
Neuropsychopharmacology, 2004, 29, 1782-1789
« Reply #99 on: October 31, 2004, 10:22:00 AM »
for lego:

Inactivation of 5-HT2C Receptors Potentiates Consequences of Serotonin Reuptake Blockade
Thomas I F H Cremers, Marco Giorgetti, Fokko J Bosker, Sandra Hogg, Jørn Arnt, Arne Mørk, Gerard Honig, Klaus-Peter Bøgesø, Ben H C Westerink, Hans den Boer, Hkan V Wikstrom and Laurence H Tecott
Neuropsychopharmacology, 2004, 29, 1782-1789



Abstract: The enhancement of central serotonin system function underlies the therapeutic effects of selective serotonin reuptake inhibitors (SSRIs), which have become the most commonly used class of antidepressant agents. However, many individuals experience depressive episodes that are resistant to SSRI treatment. Homeostatic mechanisms that limit the extent to which SSRIs enhance serotonergic neurotransmission have been implicated in this phenomenon. Here, we report a novel strategy for enhancing the efficacy of SSRIs. Using in vivo microdialysis methods in rats, the nonselective 5-HT2 receptor antagonist ketanserin was observed to produce a robust augmentation of citalopram-, fluoxetine-, and sertraline-induced elevations of hippocampal extracellular serotonin levels. Similar effects were also observed in cortex. The potentiation of SSRI-induced increases in hippocampal serotonin levels was reproduced by the 5-HT2C receptor-selective antagonists SB 242084 and RS 102221, but not by the 5-HT2A receptor-selective antagonist MDL 100 907. Although 5-HT2C receptor antagonists augmented the actions of SSRIs, they had no effect on extracellular serotonin levels or tail suspension responses when administered alone. These results were in strong accord with independent findings using a line of 5-HT2C receptor-null mutant mice. Although this mutation did not affect baseline extracellular serotonin levels or tail suspension test (TST) behavior, it enhanced fluoxetine effects on serotonin levels and immobility in the TST. These findings reveal an unanticipated pharmacological action of 5-HT2C receptors that warrants consideration in the development of novel strategies for the treatment of depression.


java

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Journal Ref. for Indole_amine
« Reply #100 on: November 01, 2004, 08:55:00 AM »
Zirconium Borohydride Piperazine Complex: An Efficient, Air and Thermally Stable Reducing Agent
M. Tajbakhsh, M. M. Lakouraj, F. Shirini, S. Habibzadeh, A. Nikdoost
Tetrahedron Lett. 45 (2004) 16, 3295-3299


Rhodium

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Recent GHB Publications
« Reply #101 on: November 01, 2004, 10:20:00 AM »
The following are listed at

http://www.ingenta.com/isis/browsing/TOC/ingenta%3B?issue=pubinfobike%3A//adis/txr/2004/00000023/00000001



Symposium on ?-Hydroxybutyrate (GHB): The Clinical Toxicology of GHB – an Introduction
Toxicological Reviews, 23(1), 1 (2004)
 
?-Hydroxybutyric Acid: Neurobiology and Toxicology of a Recreational Drug
C. Guin Ting Wong; Katherine F.Y. Chan; K. Michael Gibson; O. Carter Snead III
Toxicological Reviews, 23(1), 3-20 (2004)
 
?-Butyrolactone and 1,4-Butanediol: Abused Analogues of ?-Hydroxybutyrate
Robert B. Palmer,
Toxicological Reviews, 23(1), 21-31 (2004)
 
?-Hydroxybutyrate: Bridging the Clinical-Analytical Gap
Cynthia L. Morris-Kukoski,
Toxicological Reviews, 23(1), 33-43 (2004)

The ?-Hydroxybutyrate Withdrawal Syndrome
Asim F. Tarabar; Lewis S. Nelson
Toxicological Reviews, 23(1), 45-49 (2004)



Chimica Oggi has ISSN 0392-839X and it's found at

http://www.teknoscienze.com/co_profile.htm


They do not respond to any inquiries concerning reprints though. Can anyone here get these articles?

Merits of sodium borohydride reductions under phase transfer catalysis. Part I.    
Yadav, Vasanti G.; Yadav, G. D.; Vyas, J. R.
Chimica Oggi (Chemistry Today) 18(6), 39-44 (2000)
____ ___ __ _

Merits of sodium borohydride reductions under phase transfer catalysis. Part II.    
Yadav, Vasanti G.; Yadav, G. D.; Vyas, J. R.
Chimica Oggi (Chemistry Today) 18(7/8), 39-43 (2000)
____ ___ __ _

The reactivity of gamma-hydroxybutyric acid (GHB) and gamma-butyrolactone (GBL) in alcoholic solutions
Hennessy SA, Moane SM, McDermott SD, Journal of Forensic Sciences, Vol. 49(6), [10 pages] (2004)
DOI:

10.1520/JFS2003340



Abstract
In this work the stability of GBL (gamma-butyrolactone) and GHB (gamma-hydroxybutyric acid) in alcoholic media was studied. Under acidic conditions the GBL will react with ethanol or methanol to give the corresponding ethyl and methyl esters of GHB. It can be seen that ester formation is dependent on the type of alcohol, the alcohol content of the solution, and the pH of the solution. Under the same conditions it was shown that GHB does not give rise directly to the corresponding ester when merely in the presence of an alcohol; however the ester will be formed if the conditions are present for conversion of GHB to GBL followed by subsequent reaction with alcohol. In alcoholic beverage samples spiked with GBL the expected conversion to GHB occurred, and the formation of the ethyl ester of GHB was also seen in some samples. Wine samples were analyzed for the presence of the ethyl ester of GHB, and the effect of adding GHB/GBL to hot beverages was studied.


fogged

  • Guest
For Rhodium and Java
« Reply #102 on: November 01, 2004, 03:34:00 PM »
For Java:

Zirconium Borohydride Piperazine Complex: An Efficient, Air and Thermally Stable Reducing Agent
M. Tajbakhsh, M. M. Lakouraj, F. Shirini, S. Habibzadeh, A. Nikdoost
Tetrahedron Lett. 45 (2004) 16, 3295-3299




For Rhodium:

Use of GHB Compounds by HIV-Positive Individuals
Alvaro Camacho, Scott Matthews, Joel Dimsdale
American Journal on Addictions 13(2), 120 (2004)



Abstract
Gamma hydroxybutyrate (GHB) has been used by body-builders to enhance performance and by young adults in rave parties. Warnings have been posted about its addictive potential. The use of these dietary compounds is currently banned by the Food and Drug Administration, but they are widely available through the Internet and in certain communities. The purpose of the study was to examine the use of these compounds by HIV-positive individuals and to investigate their knowledge of the addictive potential of GHB and its related dietary compounds. One hundred HIV-positive individuals from the UCSD outpatient HIV clinic responded to an anonymous survey that inquired about their knowledge, use, and effects produced by GHB containing dietary compounds. The most common reported dietary compound beside GHB was Growth Hormone Release Extract (GHRE). Fifty-two percent of individuals reported using at least one GHB containing dietary compound. Gay subjects reported the highest use of GHB compounds (76.9%; p???0.001). The most common effect reported by users was increased energy (71%). Only 24% of the total responders knew about GHB's addictive potential. Among reported users of GHB containing compounds, fourteen (27%) knew about its addictive potential and nine (17%) knew that the compound is illegal. This study shows that HIV-positive gay individuals attending our clinic are using GHB compounds. Reported GHB users have limited knowledge about its addictive potential and serious adverse effects. More controlled studies are needed to evaluate long-term effects of dietary compounds containing GHB, especially among HIV-positive individuals who are actively receiving antiretroviral treatment.

____ ___ __ _

Gamma-Hydroxybutyric Acid: Patterns of Use, Effects and Withdrawal
Karen Miotto, Jack Darakjian, Janice Basch, Shanna Murray, Jennifer Zogg, Richard Rawson
American Journal on Addictions 10(3), 232-241 (2001)



Abstract
Gamma-hydroxybutyric acid (GHB) is gaining popularity as a drug of abuse. Reports of toxicity and lethality associated with GHB use have increased. This survey study was designed to identify patterns of GHB use, its effects, and withdrawal syndrome. A survey inquiring about the effects of GHB was administered to 42 users. The results showed that GHB was used to increased feelings of euphoria, relaxation, and sexuality. Adverse effects occurred more frequently in daily users and polydrug users than in occasional GHB users. Loss of consciousness was reported by 66%, overdose by 28%, and amnesia by 13% of participants during GHB use and by 45% after GHB use. Three daily users developed a withdrawal syndrome that presented with anxiety, agitation, tremor, and delirium. Participants described GHB intoxication as having similarities to sedative-hypnotic or alcohol intoxication. Regular use has been shown to produce tolerance and dependence. Participants dependent on GHB reported using multiple daily doses around the clock. High frequency users appeared at the greatest risk for developing withdrawal delirium and psychosis after abrupt discontinuation of GHB use.

Osmium

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ASTM G5-94 (1999)e1; Standard Reference Test...
« Reply #103 on: November 02, 2004, 01:00:00 AM »
ASTM G5-94 (1999)e1; Standard Reference Test Method for Making Potentiostatic and Potentiodynamic Anodic Polarization Measurements

ASTM G3-89 (1999); Standard practise for Conventions Applicable to Electrochemical Measurements in Corrosion Testing


Captain_America

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Leminger
« Reply #104 on: November 02, 2004, 11:58:00 AM »
a ref from Karel's translation; Chemicky Prumysl 22, 553 (1972)

Leminger, O.: Polish Pat. PV 3870z (May 25, 1971)

I can't find it on esp@cenet, there are two patents from him that have nothing to do w/ phenetylamines, he seems to have several research interests.

(Karel's voice:) This is Part 1* of Leminger's series "The Chemistry of Alkoxylated Phenethylamines".   It contains a preparation of syringaldehyde by Reimer-Tiemann formylation of 2,6-dimethoxyphenol (33% yield), etherification
of that and other phenols with alkyl iodides (67-81%) and condensation of the resulting benzaldehydes with
nitromethane in ethanolic KOH (55-67%).


*: Leminger, O.: Chem. Prum. 22, 496 (1972)
Could possibly this part be made available too?


gsus

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ASTM Section 3, v.03.02
« Reply #105 on: November 04, 2004, 10:03:00 PM »
ASTM G5-94 (1999)e1; Standard Reference Test Method for Making Potentiostatic and Potentiodynamic Anodic Polarization Measurements

ASTM G3-89 (1999); Standard practise for Conventions Applicable to Electrochemical Measurements in Corrosion Testing