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DEIMDHPCA
Pharmaceutical compound From Wikipedia, the free encyclopedia
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DEIMDHPCA, also known as 3,5-seco-LSD, is an indole derivative and a "partial" or simplified ergoline which is closely related to the highly potent serotonergic psychedelic lysergic acid diethylamide (LSD).[1][2] 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.[1][2] This in turn renders the DEIMDHPCA molecule more flexible and makes it a partially rigid indolic phenethylamine-containing compound rather than an ergoline.[1][2] DEIMDHPCA is known to be a highly potent serotonin 5-HT2 receptor agonist similarly to LSD and to produce psychoplastogenic effects.[1]
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Pharmacology
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Like LSD, the drug is known to be a highly potent serotonin 5-HT2A and 5-HT2C receptor agonist in vitro.[1] Its affinities (IC50) 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 10 nM for the serotonin 5-HT2A receptor and in the range of 10–100 nM for the serotonin 5-HT2C receptor.[1] DEIMDHPCA was the most potent serotonin 5-HT2A receptor agonist of 27 evaluated ergoline-like compounds.[1] In line with its serotonin 5-HT2A receptor agonism, and similarly to LSD and other psychedelics,[3][4] DEIMDHPCA has been found to produce psychoplastogenic effects on neurite growth in vitro.[1]
Many serotonin 5-HT2A receptor agonists, for instance LSD, produce psychedelic effects in humans.[1][5][6][7] The publication that reported DEIMDHPCA specifically pertained to psychoplastogenic ergoline-like compounds with no or reduced hallucinogenic activity for potential therapeutic use.[1] 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.[1] As such, it remains unclear whether or not DEIMDHPCA could have psychedelic effects in humans.[1]
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History
DEIMDHPCA was first described in the literature by 2021.[1] It has been patented by Delix Therapeutics.[1]
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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[8][9] and NDTDI.[10][11][12] 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,[8][9] while NDTDI is the analogue of LSD in which only the carbon at position 9 has been removed to make a rigid tricyclic tryptamine.[10][11][12] N-DEAOP-NMT has been found to produce LSD-like effects in rodents,[8][9] while NDTDI has been encountered as a novel recreational and designer drug and made illegal in parts of Europe.[10][11]
The analogue of DEIMDHPCA without the ethyl groups on the amide has been described.[8][13] In addition, DEIMDHPCA's analogue without the amide ethyl groups and with a phenyl ring instead of the indole ring has been described.[8][13] Their activities were not reported.[8][13]
WXVL_BT0793LQ2118, an analogue of DEIMDHPCA lacking the N,N-diethyl-carboxamide moiety and with a fluorine at the 6-position, has been reported.[14][15] It was identified via in silico screening of 1.6 billion molecules for serotonin 5-HT2A receptor agonism with AlphaFold2.[14] Following identification, the drug was assessed and found to be a potent serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptor agonist.[14]
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