Journal of Medicinal Chemistry
May 1, 1982
David E. Nichols, David Harley Lloyd, Andrew J. Hoffman et al.
178 citations
The enantiomers of 3,4-(methylenedioxy)amphetamine (MDA), p-methoxyamphetamine (PMA), and N-Me-MDA (MDMA), along with their alpha, alpha-dimethylated derivatives, were evaluated for an effect on the release of [3H]serotonin from rat whole brain synaptosomes. The amphetamine isomers were all potent in inducing the release of [3H]serotonin at bath concentrations of 1 and 10 micrometers but were...
Journal of Medicinal Chemistry
May 1, 1982
James N. Jacob, David E. Nichols
6 citations
The hallucinogen analogue trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine was modified by adding a 3-methyl group, either cis or trans with respect to the amino group. These two isomeric cyclopropyl ring-methylated compounds were then tested for activity in the mouse ear-scratch assay and for a contractile effect in the rat fundus preparation. Neither compound was found to possess...
Journal of Medicinal Chemistry
April 1, 1979
David E. Nichols, Ronald W. Woodard, Bruce A. Hathaway et al.
16 citations
An hallucinogen analogue, trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine (DMCPA), was resolved into ints two enantiomers by fractional crystallization of salts with d- or l-O,O-dibenzoyltartaric acid. A comparison of the ORD and CD curves of the N-5-bromosalicylidene derivatives of trans-2-phenylcyclopropylamine of known absolute configuration and of the title compound established the...
Brain Research Bulletin
May 1, 1977
David E. Nichols, William Pfister, G.k.w. Yim et al.
10 citations
An examination of the effects of S-(-) and R-(+) 2-amino-1,2,3,4-tetrahydronaphthalene (2-AT) on mouse spontaneous activity and rabbit EEG has shown that the S-(-) enantiomer shows selective central effects similar to those of hallucinogens like mescaline. A stereochemical analysis of these results indicates that the structural relationship between mescaline, or other phenethylamine type...
Journal of Medicinal Chemistry
February 1, 1977
David E. Nichols, Donald C. Dyer
23 citations
Replacement of the 4-methoxy of mescaline with higher alkyl homologues or with bromine led to increased activity at serotonin receptors in a sheep umbilical artery preparation. This activity appears correlated with lipophilicity, as measured by 1-octanol-water partition coefficients, but drops off when the 4-substituent is about five atoms in length. It is suggested that 3,4,5-trisubhe...
Journal of Medicinal Chemistry
February 1, 1975
Charles F. Barfknecht, David E. Nichols, William J. Dunn
42 citations
In an attempt to relate the hallucinogenic potencies in man of some biologically important amphetamines and phenethylamines, the 1-octanol-water partition coefficients for 11 amphetamines were determined. Using these values and published Hansch pi constants, the log P for 17 additional amines was estimated. It was found that lipophilicity, as measured by the log of the partition coefficient,...