Wanted references

[fallen_Angel]

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]

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]

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]

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]

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]

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]

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

<sub>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)</sub>

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

   <sub>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</sub>

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]

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]

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]

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]

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]

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]

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]

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]

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]

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]

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]

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]

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   )(TIA)

_{indole_amine}

[jsorex]

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)