THPC (drug)

Pharmaceutical compound From Wikipedia, the free encyclopedia

THPC, also known as 1-methyl-1,2,5,6-tetrahydropyridine-3-diethylcarboxamide, is a greatly simplified analogue of the psychedelic lysergamide lysergic acid diethylamide (LSD) in which only a modified version of the D ring (and its substitutions) remains.[1][2][3][4][5]

Other names1-Methyl-1,2,5,6-tetrahydropyridine-3-(N,N-diethylcarboxamide); 1-Methyl-1,2,5,6-tetrahydropyridine-3-diethylcarboxamide
ATC code
  • None
Quick facts Clinical data, Other names ...
THPC
Clinical data
Other names1-Methyl-1,2,5,6-tetrahydropyridine-3-(N,N-diethylcarboxamide); 1-Methyl-1,2,5,6-tetrahydropyridine-3-diethylcarboxamide
Drug classSerotonin antagonist; Serotonin 5-HT2A receptor antagonist; Hallucinogen antidote
ATC code
  • None
Identifiers
  • N,N-diethyl-1-methyl-3,6-dihydro-2H-pyridine-5-carboxamide
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H20N2O
Molar mass196.294 g·mol−1
3D model (JSmol)
  • CCN(CC)C(=O)C1=CCCN(C1)C
  • InChI=1S/C11H20N2O/c1-4-13(5-2)11(14)10-7-6-8-12(3)9-10/h7H,4-6,8-9H2,1-3H3
  • Key:QELRLWHVJBVJOI-UHFFFAOYSA-N
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THPC was assessed and produced no behavioral effects by itself in rodents.[1][2][4] However, the drug was reported to markedly potentiate the behavioral effects of mescaline and to inhibit the effects of LSD in rodents.[1][2][3][4] It was suggested that THPC might be clinically useful as a hallucinogen antagonist against LSD, for instance in the context of recreational LSD use.[5] In any case, findings of these studies were based on very small numbers of animals and have been limitedly or not replicated.[1][6]

Subsequent studies of THPC in several in vitro and in vivo systems have provided mixed results.[7] It has been found to strongly contract smooth muscle, but the mechanism of this action, such as α-adrenergic or histamine receptor activation, has not been determined, except that it was not reversed by serotonin antagonists.[2] In another study, THPC antagonized the contractions of sheep umbilical vasculature induced by serotonin, mescaline, and LSD, and it was concluded that THPC is a weak serotonin antagonist.[1][7][8] Accordingly, THPC was found to completely block LSD binding to receptors in synaptosomal membranes from rat forebrain.[7][9][10] However, THPC reportedly did not block serotonin binding in this preparation.[10] In any case, this binding site is said to have been later identified as the serotonin 5-HT2A receptor in 1979.[1] In other studies, THPC did not block various specific effects of mescaline and LSD.[1][7][6]

THPC was first described in the scientific literature by John Raymond Smythies and colleagues in 1970.[1][2][3][4][5] It was reviewed by David E. Nichols in his thesis in 1973[2] and by Steven A. Barker in 2025.[1] Along with other drugs like chlorpromazine, 2-bromo-LSD, and cinanserin, THPC was one of the first claimed antagonists of the behavioral effects of LSD to be identified.[1][9][11] Various analogues of THPC have also been synthesized and studied, including as serotonin antagonists.[1][5][6]

See also

References

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