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Biomedical subjects

A T Shulgin

Publications and source records attributed to A T Shulgin.

At least 55 records · Page 3Linked to original sources
PubMed1977

Monomethylthio analogues of 1-(2,4,5-trimethoxyphenyl)-2-aminopropane.

Regiospecific syntheses of the three monomethylthio analogues of 1-(2,4,5-trimethoxyphenyl)-2-aminopropane are described. The three isomeric amines were evaluated for potential psychotomimetic potency using the rabbit hyperthermia assay. Enantiomeric compositions and time-concentration curves in rat brains were determined following intraperitoneal administration of each compound. The biological data are contrasted with the corresponding results obtained with the potent human psychotogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM).

DOM 2,5-Dimethoxy-4-Methylamphetamine↗
PubMed1977

Synthesis and body distribution of several iodine-131 labeled centrally acting drugs.

1-(4-iodo-2,5-dimethoxyphenyl)-2-aminopropane (3B), 4-iodo-2,5-dimethoxyphenylethylamine (3A), and 1-(4-iodo-2,5, dimethoxyhenyl)-2-aminobutane (3C) have been synthesized with 131I. Labeled iodine monochloride reacts with the appropriately substituted phthalimide at the aromatic 4 position, and the phthalic acid group is removed with hydrazine. Body distribution was measured in rats; the most prominent difference between the three compounds was a much greater concentration in the lung with 3b than with 3a or 3c. gamma-Ray scintigraphs of 3a-c in rats and of 3b in a dog indicate an uptake by the brain similar to that of the bromine analogue of 3b (DOB) in humans. [82Br]-DOB has been suggested as a potential brain scanning agent for nuclear medicine; 3b would have the advantage over DOB of providing the superior gamma-ray imaging properties of 131I or 123I.

Animals↗
PubMed1976

Sulfur analogs of psychotomimetic amines.

The syntheses and physical properties are described for 2,5-dimethoxy-4-methylthiophenylethylamine and 2,5-dimethoxy-4-methylthiophenylisopropylamine. The latter compound is the sulfur analog of the psychotomimetic phenylisopropylamines 2,4,5-trimethoxyphenylisopropylamine and 2,5-dimethoxy-4-methylphenylisopropylamine wherein the methylthio group replaces a methoxy group or a methyl group, respectively. This compound is predicted to be about 30 times as active as mescaline.

Hallucinogens↗
PubMed1976

Quantitative measurement of demethylation of 14C-methoxyl labeled DMPEA and TMA-2 in rats.

Some reports have suggested that methylation and demethylation of compounds related to 6-hydroxydopamine may be involved in endogenous mental disorder. We report the synthesis of 3,4-dimethoxyphenethylamine (DMPEA) and 2,4,5-trimethoxyphenylisopropylamine (TMA-2) with each methoxyl group separately labeled with 14C. The rate and percent demethylation of these two compounds, with five labeled positions, were determined in the rat. The results suggest that TMA-2 might be metabolized to a hydroquinone in vivo; a similar metabolic intermediate of the psychoactive compound DOM is known to give rise in vitro to an indole.

Amphetamines↗
PubMed1975

Psychotomimetic phenylisopropylamines. 5. 4-Alkyl-2,5-dimethoxyphenylisopropylamines.

A homologous series of 4-alkyl-2,5-dimethoxyphenylisopropylamines (alkyl = H through n-C5H11 and t-C4H9) was synthesized and compared with mescaline as serotonin agonists in a sheep umbilical preparation. The three-carbon homolog 6d was found to be the most potent of the straight-chain series in accordance with its observed psychotomimetic effectiveness in man.

Animals↗
PubMed1975

Centrally active phenethylamines.

The two-carbon homologs of two potent psychotomimetic agents are described. Unlike the parent isopropylamine compounds (4-methyl-2,5-dimethoxyamphetamine, DOM, STP; and 4-bromo-2,5-dimethoxyamphetamine, PBR, 4-BR) these phenethylamines lead to an intoxication state which is, in normal subjects, of short duration and of greatly increased sensory enhancement, but which does not superimpose hallucinogenesis. These two phenethylamines, 4-methyl-2,5-dimethoxyphenethylamine (II) and 4-bromo-2,5-dimethoxyphenethylamine (III), are active in man at oral levels of 0.1 to 0.2 mg/Kg, approximately one tenth the potency of their three-carbon counterparts.

Adult↗