DEIMDHPCA

DEIMDHPCA is an indole derivative and a "partial" or simplified ergoline which is closely related to the highly potent serotonergic psychedelic lysergic acid diethylamide (LSD). It is specifically the analogue of LSD in which one of LSD's carbon atoms in the ergoline ring system, the carbon at position 4, has been removed. This in turn renders the DEIMDHPCA molecule more flexible and makes it a partially rigid indolic phenethylamine-containing compound rather than an ergoline. DEIMDHPCA is known to be a highly potent serotonin 5-HT₂ receptor agonist similarly to LSD and to produce psychoplastogenic effects.

Pharmacology

Like LSD, the drug is known to be a highly potent serotonin 5-HT_2A and 5-HT_2C receptor agonist in vitro. Its affinities (IC₅₀Tooltip half-maximal inhibitory concentration) are in the ranges of 10–100 nM for the serotonin 5-HT_2A receptor and 100–1,000 nM for the serotonin 5-HT_2C receptor, while its activational potencies (EC₅₀Tooltip half-maximal effective concentration) are less than 10 nM for the serotonin 5-HT_2A receptor and in the range of 10–100 nM for the serotonin 5-HT_2C receptor. DEIMDHPCA was the most potent serotonin 5-HT_2A receptor agonist of 27 evaluated ergoline-like compounds. In line with its serotonin 5-HT_2A receptor agonism, and similarly to LSD and other psychedelics, DEIMDHPCA has been found to produce psychoplastogenic effects on neurite growth in vitro.

Many serotonin 5-HT_2A receptor agonists, for instance LSD, produce psychedelic effects in humans. The publication that reported DEIMDHPCA specifically pertained to psychoplastogenic ergoline-like compounds with no or reduced hallucinogenic activity for potential therapeutic use. However, the hallucinogenic-related properties of DEIMDHPCA and the other reported compounds, for instance their effects in the head-twitch response (HTR) assay, were not individually described. As such, it remains unclear whether or not DEIMDHPCA could have psychedelic effects in humans.

History

DEIMDHPCA was first described in the literature by 2021. It has been patented by Delix Therapeutics.

Related compounds

Other related compounds in which one or more other carbons have been removed from the LSD's ergoline ring system to produce simplified and less-rigid phenethylamines and tryptamines include N-DEAOP-NMT and NDTDI. N-DEAOP-NMT is the analogue of LSD in which the carbon atoms at positions 9 and 10 of the ergoline ring system have been removed to make a fully non-rigid tryptamine, while NDTDI is the analogue of LSD in which only the carbon at position 9 has been removed to make a rigid tricyclic tryptamine. N-DEAOP-NMT has been found to produce LSD-like effects in rodents, while NDTDI has been encountered as a novel recreational and designer drug and made illegal in parts of Europe.

The analogue of DEIMDHPCA without the ethyl groups on the amide has been described. In addition, DEIMDHPCA's analogue without the amide ethyl groups and with a phenyl ring instead of the indole ring has been described. Their activities were not reported.

WXVL_BT0793LQ2118, an analogue of DEIMDHPCA lacking the N,N-diethyl-carboxamide moiety and with a fluorine at the 6-position, has been reported. It was identified via in silico screening of 1.6 billion molecules for serotonin 5-HT_2A receptor agonism with AlphaFold2. Following identification, the drug was assessed and found to be a potent serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptor agonist.