DEMPDHPCA
Pharmaceutical compound
From Wikipedia, the free encyclopedia
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 (LSD).[1][2][3] 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.[1][2][3]
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| Other names | "Compound 160a"; des-B-des-C-LSD; dides-B,C-LSD; 1-Deaza-2,3,4-trinor-LSD |
| Drug class | Serotonin 5-HT2 receptor agonist; Simplified/partial LSD analogue |
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| Formula | C17H24N2O |
| Molar mass | 272.392 g·mol−1 |
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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.[1] However, the drug has not been tested in humans.[1] DEMPDHPCA is much less potent than LSD in rodents, which was active at a dose of 0.16 μmol/kg by intraperitoneal injection, whereas DEMPDHPCA was active at doses of 10 to 35 μmol/kg (63- to 219-fold less potent).[1] On the other hand, DEMPDHPCA was more potent than dimethyltryptamine (DMT) and is more potent than mescaline.[1]
Like LSD, the drug has been found to act as a potent serotonin 5-HT2A and 5-HT2C receptor agonist in vitro.[2] The affinities (IC50) of the more active enantiomer are in the ranges of 10–100 nM for the serotonin 5-HT2A receptor and 100–1,000 nM for the serotonin 5-HT2C receptor, while its activational potencies (EC50) are less than 100 nM for the serotonin 5-HT2A receptor and in the range of 10–100 nM for the serotonin 5-HT2C receptor.[2] The more active enantiomer of DEIMDHPCA was among the most potent serotonin 5-HT2A receptor agonists of 27 evaluated ergoline-like compounds.[2]
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.[1] The former two were less potent than DEMPDHPCA, whereas the latter was slightly more potent.[1] Another derivative, DEMPDHPCA-2C-D, was attempted to be synthesized by David E. Nichols in his PhD thesis.[4] It is the derivative with 4-methyl and 2,5-dimethoxy substitutions on the phenyl ring.[4] These DEMPDHPCA derivatives are cyclized phenethylamine analogues of various psychedelic- and/or stimulant-related phenethylamines and amphetamines including para-methoxyamphetamine (PMA), mescaline (M), 1-naphthylaminopropane (1-NAP), and 2C-D.[1][4]
History
DEMPDHPCA was first described in the scientific literature by Mangner in 1978.[1] It was subsequently patented in 2021 by David E. Olson and colleagues and the patent was assigned to Delix Therapeutics.[2]