DEMPDHPCA

DEMPDHPCA, also known as dides-B,''C''-LSD or 1-deaza-2,3,4-trinor-LSD, is a serotonin 5-HT₂ receptor agonist and a cyclized phenethylamine and simplified or partial ergoline that is structurally related to the serotonergic psychedelic lysergic acid diethylamide. It is the analogue of LSD in which the carbon and nitrogen atoms at positions 1 through 4 of the ergoline ring system have been removed.

Pharmacology

Pharmacodynamics

DEMPDHPCA produces gross behavioral effects very similar to those of psychedelics like LSD in rodents and has been assumed to act as a hallucinogen likewise. However, the drug has not been tested in humans. DEMPDHPCA is much less potent than LSD in rodents, which was active at a dose of 0.16μmol/kg by intraperitoneal injection, whereas DEMPDHPCA was active at doses of 10 to 35μmol/kg. On the other hand, DEMPDHPCA was more potent than dimethyltryptamine and is more potent than mescaline.
Like LSD, the drug has been found to act as a potent serotonin 5-HT_2A and 5-HT_2C receptor agonist in vitro. The affinities of the more active enantiomer are in the ranges of 10–100nM for the serotonin 5-HT_2A receptor and 100–1,000nM for the serotonin 5-HT_2C receptor, while its activational potencies are less than 100nM for the serotonin 5-HT_2A receptor and in the range of 10–100nM for the serotonin 5-HT_2C receptor. The more active enantiomer of DEIMDHPCA was among the most potent serotonin 5-HT_2A receptor agonists of 27evaluated ergoline-like compounds.

Chemistry

Derivatives

A few derivatives of DEMPDHPCA have also been studied and found to produce similar effects and/or amphetamine-like in animals, including the derivatives with 4-methoxy- and 3,4,5-trimethoxy- substitutions on the phenyl ring and the derivative with the phenyl ring replaced with a 1-naphthalene ring. The former two were less potent than DEMPDHPCA, whereas the latter was slightly more potent. Another derivative, DEMPDHPCA-2C-D, was attempted to be synthesized by David E. Nichols in his PhD thesis. It is the derivative with 4-methyl and 2,5-dimethoxy substitutions on the phenyl ring. These DEMPDHPCA derivatives are cyclized phenethylamine analogues of various psychedelic- and/or stimulant-related phenethylamines and amphetamines including para-methoxyamphetamine, mescaline, 1-naphthylaminopropane, and 2C-D.

History

DEMPDHPCA was first described in the scientific literature by Mangner in 1978. It was subsequently patented in 2021 by David E. Olson and colleagues and the patent was assigned to Delix Therapeutics.