Archives of Journal Articles

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Article(s) on electrolytic synthesis of phenylacetone in 80% yield using a benzyl hydroxypentanoic (valeric) acid..
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GENERATION OF CATIONIC CARBON BY ANODIC OXIDATION OF CARBOXYLIC ACIDS
E. J. Corey, N. L. Bauld, R. T. La Londe, J. Casanova, and E. T. Kaiser
J. Am. Chem. SOC., 82, 2645(1960)
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The Formation of Carbonium Ions by Oxidative Decarboxylation of Carboxylic Acids with Lead Tetraacetate
Corey, E. J., and Casanova, J., Jr.
J. Am. Chem. SOC., 85,165 (1963)
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The Synthesis of Pentacyclosqualene (8,8?-Cycloönocerene) and the ?- and ?-Onoceradienes
Corey, E. J., and Sauers,R.R.
J . Am. Chem. Soc., 81,1739 (1959).
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C?-C? Cleavage of a ?-Hydroxy Acid by Electrolytic Oxidation
Corey, E. J., and Sauers, R. R.
J. Am. Chem. SOC., 81,1743 (1959)
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Biochemical and Behavioral Characterization of Novel Methylphenidate Analogs
M. M. SCHWERI, H. M. DEUTSCH, A.T. MASSEY,1 AND S. G. HOLTZMAN
J Pharmacol Exp Ther 2002, vol.301 pg.527-35

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Abstract
As part of a project to develop treatment agents for cocaine
abuse, ( )-threo-methylphenidate (TMP) and 11 analogs were
characterized biochemically and behaviorally to assess their
potential as anti-cocaine medications. The compounds contained
aryl and/or nitrogen substitutions, and/or replacement of
the ester function by an alcohol or ether. All of the analogs,
except for the N-methyl-substituted compounds, showed increased
inhibitory potency against 3H-( )-2- -carbomethoxy-
3- -(4-fluorophenyl)tropane 1,5-naphthalenedisulfonate
([3H]WIN 35,428) ([3H]WIN) binding to the dopamine transporter,
compared with TMP. In general, parallel results were
obtained for inhibition of [3H]dopamine ([3H]DA) uptake. Although
compounds with N-substitutions were proportionally
less potent at blocking DA uptake than WIN binding (compared
with the unsubstituted compounds), one such compound that
was 6-fold more potent against [3H]WIN binding than [3H]DA
uptake did not attenuate inhibition by cocaine of synaptosomal
[3H]DA transport. The compounds were significantly less potent
in displacing [3H]citalopram binding from the serotonin transporter.
In cocaine discrimination studies in rats, all but two of
the analogs (both N-substituted) completely generalized with
the cocaine stimulus. Robust positive correlations were observed
between potency in the drug discrimination assay and
activity at the dopamine transporter, but not the serotonin
transporter. When tested for their ability to alter cocaine discrimination,
four of the analogs (three of which had Nsubstitutions
and shallow dose-response curves as cocaine
substitutes) actually enhanced cocaine discrimination, often at
combined doses of cocaine and test compound that were
inactive when given separately. Taken together, the results
suggest that TMP analogs may have potential as substitution
therapies for the treatment of cocaine abuse.

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Schiff bases. I. Thermal decarboxylation of alpha-amino-acids in the presence of ketones.
Al-Sayyab AF, Lawson A.
J Chem Soc [Perkin 1]. 1968;4:406-10.

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Abstract
A number of Schiff bases derived from a-amino-acids and hydroxy-substituted aromatic ketones have been prepared. Their infrared spectra suggest that their relative stability to hydrolysis as compared with those from ketones with no hydroxy-groups is due to hydrogen bonding.
The thermal decomposition of a-amino-acids in the presence of ketones, followed by hydrolysis produces the amines corresponding to the amino-acids or the ketones (transamination) or both, depending on the nature of the amino-acid and the ketone used and also on the method of hydrolysis. In the case of amino-acids with a quaternary a-carbon atom, transamination is the principal reaction.
The preparation of tyramine, tryptamine. and histamine in good yield from the corresponding amino-acids is described.

NOTE thanks to shib for finding this citation needed for an on going discussion over at the "other stimulant "forum......

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Mechanism of base-catalyzed reactions in phase-transfer systems with poly(ethylene glycols) as catalysts. The isomerization of allylanisole
Ronny Neumann and Yoel Sasson
J. Org. Chem. 49, p 3448-3451, (1984)
Comment: Isomerization of allylanisole to anethole using KOH with PEG as a PTC. Probably works to convert any allylbenzene to propenylbenzne.

J.Org.Chem. 1984, 49, 3448-3451

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Lipase-catalysed preparation of optically active .gamma.-butyrolactones in organic solvents
Gutman,Arie.; Zuobi, Kheir.; Bravdo, Tamar.
J. ORG. CHEM., Vol. 55, No. 11, 3546-3552 (1990)

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Oxidation of hydrazines with benzeneseleninic acid and anhydride
Thomas G. Back, Scott Collins, and Russell G. Kerr
J. ORG. CHEM., Vol. 46, No. 8, 1564-1570 (1981)

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CONVERSION OF OLEFINS INTO [cyclic ester comprised of 4 hydrocarbons]
BROWN, S. P.;BAL, BALKRISHNA, S.;PINNICK, H. W.
TETRAHEDRON LETTERS, Vol. 22, Issue 49 , 1981, Pages 4891-4894

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b-Phenylethylamines, Indolines and Isoquinolones via Hydroamination of
Styrenes by Microwave Irradiation
Julio A. Seijas,* M. Pilar Vázquez-Tato,* M. Montserrat Martínez
[red]Synlett 2001 No. 6, 875–877[/red]
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Abstract:
Microwave irradiation promotes hydroamination of styrenes.
This method can be used as a direct way of producing different
kinds of bioactive compounds: open chain compounds like
ß-phenylethylamines or cyclized products like indolines or isoquinolones.
Key words: amination, domino reaction, indoline, isoquinolone,
microwave heating, nucleophilic addition, phenethylamine

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Unique Spirocyclopiperazinium Salt I: Synthesis and Structure–Activity Relationship of Spirocyclopiperazinium Salts as Analgesics
Feng-Li Gao, Xin Wang, Hong-Mei Zhang, Tie-Ming Cheng and Run-Tao Li,
Bioorganic & Medicinal Chemistry Letters. 13(9), 1535–1537 (2003)
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DOI: 10.1016/S0960-894X(03)00177-X

Abstract:
Based on the structure of compound 3, two series of spirocyclopiperazinium derivatives 7a–n and 10a–h were synthesized and evaluated for their in vivo analgesic and sedative activities. Compounds 7f and 10c were discovered to exhibit excellent analgesic activity. Structure–activity relationships revealed that anion of the quaternary salt affected the analgesic and sedative activity significantly; the allyl group is a most effective group among the compounds 7a–n; the electron-released substitute on the aromatic ring is favorable to increase the analgesic activity.

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Unique Spirocyclopiperazinium Salt. Part 2: Synthesis and Structure–Activity Relationship of Dispirocyclopiperazinium Salts as Analgesics
Xin Wang, Feng-Li Gao, Hong-Bin Piao, Tie-Ming Cheng and Run-Tao Li,
Bioorganic & Medicinal Chemistry Letters. 13(10), 1729–1732 (2003)
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DOI: 10.1016/S0960-894X(03)00213-0

Abstract:
Three series of spirocyclopiperazinium derivatives 5a–d, 6a–f and 17a–d were synthesized and evaluated for their in vivo analgesic activities. Compounds 5a, 17a and 17b exhibited excellent analgesic activity. Two important structure–activity relationships were observed from this study: (1) the quaternary ammonium functionality is a critical pharmacophore for analgesic activity; (2) it is important to adjust the lipophilic property of compounds to improve analgesic activity.

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Silica Chloride (SiO2-Cl), a New Heterogeneous Reagent, for the Selective and Efficient Conversion of Benzylic Alcohols to Their Corresponding Chlorides and Iodides.
Habib Firouzabadi A1, Naser Iranpoor A1, Babak Karimi A1, Hassan Hazarkhani
Synthetic Communications, Volume 33, Number 21, pgs. 3671-3677, 2003
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DOI: 10.1081/SCC-120025175

Abstract: Structurally different benzylic alcohols were efficiently converted to their corresponding chlorides by silica chloride (SiO2-Cl) in CHCl3 at room temperature. Silica chloride is also able to convert benzylic alcohols to their iodides in the presence of NaI in a mixture of CH3CN/CHCl3 in excellent yields.

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Recent advances in the chemistry and biochemistry of cannabis
Raphael Mechoulam, Neil K. McCallum, and Sumner Burstein,
Chemical Reviews. 76(1), pp 75 - 112 (1976)
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QSAR studies on psychotomimetic phenylalkylamines
Mamta Thakur, Abhilash Thakurb and Padmakar V. Khadikarc,
Bioorganic & Medicinal Chemistry. 12, 825–831 (2004)
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DOI: 10.1016/j.bmc.2003.10.027

Abstract:
Quantitative Structure–Activity Relationship (QSAR) studies on a series of psychotomimetic phenylalkylamines have been made using a combination of Minimum Topological Difference (MTD) method and topological methodology. The topological indices used being a pool of distance-based topological indices. The regression analyses have shown that excellent results are obtained in multiparametric model containing MTD parameters, topological indices in that quantum chemical parameters has to be introduced. The predictive power of the proposed model is discussed on the basis of cross-validation parameters.

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Structure-Activity Correlations for Psychotomimetics. 1. Phenylalkylamines: Electronic, Volume, and Hydrophobicity Parameters
Brian W. Clare,
J. Med. Chem. 33(2), 687-702 (1990)
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Abstract:
CNDO/Z calculations have been performed on a series of alkyl, alkoxy, and alkylthio derivatives of phenethylamine and phenylisopropylamine. The results of these, of van der Waals volume calculations, and of Hansch type hydrophobicity calculations were correlated with psychotomimetic activity by chemometric methods. Eight parameters, involving seven chemical descriptors, were found to be highly significant. Directional hydrophobicity and volume effects were found, which suggests that steric and hydrophobic interactions in the neighborhood of the receptor site are important. A puzzling but strong interaction effect between meta and para substituents was noted. Electrunic terms may be explicable in terms of formation of charge-transfer complexes by accepting, rather than by donating, charge, as has been believed in the past. A charge effect indicates that a charge or dipole is influential at the binding site, or alternatively, a specific reactivity at the meta position is involved.

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Quasi-atomistic Receptor Surrogates for the 5-HT2A Receptor: A 3D-QSAR Study on Hallucinogenic Substances
Meike Schulze-Alexandru, Karl-Artur Kovar and Angelo Vedani,
Quant. Struct.-Act. Relat. 18, 548-560 (1999)
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Abstract:
The 5-HT2A receptor is known to act as the biological target for a series of hallucinogenic substances including substituted phenylalkylamines, tryptamines and LSD. A prerequisite for a hallucinogenic effect is an agonistic binding mode to the high-affinity state of the receptor. Attempts to establish a quantitative structure-activity relationship for such compounds are typically based on homology models or 3D-QSAR. In this paper, we describe a surrogate for the 5-HT2A receptor derived by means of quasi-atomistic receptor modeling (software Quasar), a more recently developed 3D-QSAR technique. This approach allows for the simulation of local induced phenomena. The QSARs are established based on a family of receptor-surface models, generated by a genetic algorithm combined with cross-validation. The surrogate for the 5-HT2A receptor yielded a cross-validated q2 of 0.954 for the 23 compounds de®ning the training set. A series of 7 test compounds was then used to validate the model, resulting in a RMS deviation of 0.40 kcal/mol. The largest individual deviation was 0.61 kcal/mol, corresponding to an uncertainty of a factor 2.7 in the binding affnity. A scramble test with negative outcome demonstrates the sensitivity of the model with respect to the biological data. Subsequently, the surrogate was used to estimate the activity of a series of 53 hypothetical congeneric compounds, some of which are predicted to be close in activity to LSD.

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Structure-Activity Relationships of One-ring Psychotomimetics
Shulgin,Sargent, Naranjo
Nature (1969), vol.221, pg.537

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Chromatographic and mass spectral studies on regioisomeric and mass equivalent derivatives related to the methylenedioxyphenethylamines
Laura Annikki Aalberg, PhD.
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Chromatographic and Spectroscopic Methods of Identification for the Side-Chain Regioisomers of 3,4-Methylenedioxyphenethylamines Related to MDEA, MDMMA, and MBDB
Aalberg L.1; DeRuiter J.1; Noggle F.T.2; Sippola E.3; Clark C.R.1
Journal of Chromatographic Science, May/June 2003, vol. 41, no. 5, pp. 227-233(7)

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Abstract

Three regioisomeric 3,4-methylenedioxyphenethylamines having the same molecular weight and major mass spectral fragments of equivalent mass have been reported as components of clandestine drug samples in recent years. These drugs of abuse are 3,4-methylenedioxy-N-ethylamphetamine, 3,4-methylenedioxy-N,N-dimethylamphetamine, and N-methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine. These three compounds are a subset of a total of ten regioisomeric 3,4-methylenedioxyphenethylamines of molecular weight 207, yielding regioisomeric fragment ions of equivalent mass (m/z 72 and 135/136) in the electron impact mass spectrum. The specific identification of one of these compounds in a forensic drug sample depends upon the analyst's ability to eliminate the other regioisomers as possible interfering or coeluting substances. This paper reports the synthesis, mass spectral characterization, and chromatographic analysis of these ten unique regioisomers. The ten regioisomeric methylenedioxyphenethylamines are synthesized from commercially available precursor chemicals. The electron impact mass spectra of these regioisomers show some variation in the relative intensity of the major ions with only one or two minor ions that might be considered side-chain specific fragments. Thus, the ultimate identification of any one of these amines with the elimination of the other nine regioisomeric substances depends heavily upon chromatographic methods. Chromatographic separation of these ten uniquely regioisomeric amines is studied using gas chromatographic temperature program optimization