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Sulfur analogs of psychotomimetic agents. 2. Analogs of (2,5-dimethoxy-4-methylphenyl)- and of (2,5-dimethoxy-4-ethylphenyl)isopropylamine

Peyton Jacob, Alexander T. Shulgin

Journal of Medicinal Chemistry May 1, 1983 DOI: 10.1021/jm00359a021 (opens in new tab)

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AI-extracted from the abstract
Characteristics Pharmacological evaluation in man Peer reviewed
Population Humans
Keywords Isopropylamine Psychotomimetic Thio- Tetrahydrothiophene Potency Sulfur Mydriasis Stereochemistry Medicinal chemistry
Citations 18
Key points The 5-thio isomers of DOM and DOET are more potent psychotomimetic agents than the 2-thio isomers but are an order of magnitude less potent than the sulfur-free counterparts, and the dithio analogue of DOM lacks central activity at high doses.

Abstract

The two thio analogues of each of the well-known psychotomimetic drugs DOM [(2,5-dimethoxy-4-methylphenyl)isopropylamine] and DOET [(2,5-dimethoxy-4-ethylphenyl)isopropylamine] have been synthesized and pharmacologically evaluated in man. The 5-thio isomers are more potent as psychotomimetic agents than the 2-thio isomers but still represent a drop of an order of magnitude in potency from the sulfur-free counterparts. The dithio analogue of DOM was synthesized and found to be without central activity at a dosage of approximately 50 times the mean effective dose of DOM.

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