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For other uses, see THPC.
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
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

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]

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

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References

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  1. ^ a b c d e f g h i j k Barker SA (November 2025). "Simple Analogs of the LSD D-Ring: A Consideration of Structure-Activity Relationships and Their Potential as Therapeutics". ACS Chemical Neuroscience. 16 (22): 4309–4314. doi:10.1021/acschemneuro.5c00695. PMC 12636032. PMID 41190572.
  2. ^ a b c d e f Nichols DE (May 1973). Potential Psychotomimetics: Bromomethoxyamphetamines and Structural Congeners of Lysergic Acid (Thesis). University of Iowa. pp. 15–18. OCLC 1194694085.
  3. ^ a b c Brimblecombe RW, Pinder RM (1975). "Mechanisms of Action of Hallucinogenic Agents". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 217–267. ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M.
  4. ^ a b c d Smythies JR, Beaton J, Benington F, Morin RD (May 1970). "Behavioural effects of some derivatives of amphetamine and LSD and their significance". Nature. 226 (5246): 644–645. Bibcode:1970Natur.226..644S. doi:10.1038/226644a0. PMID 5444927.
  5. ^ a b c d Smythies JR, Beaton JM, Benington F, Morin RD (February 1972). "The design of some new compounds to block psychotomimetic drugs". European Journal of Pharmacology. 17 (2): 270–272. doi:10.1016/0014-2999(72)90168-9. PMID 5026401.
  6. ^ a b c Kovacic B, Wang Lu LJ, Ruffing D, Domino EF (January 1978). "Interactions of partial LSD analogs with behavioral disrupting effects of LSD and DMT in the rat". European Journal of Pharmacology. 47 (1): 37–44. doi:10.1016/0014-2999(78)90371-0. PMID 271075.
  7. ^ a b c d Mangner TJ, University of Michigan (1978). Potential Psychotomimetic Antagonists. N,n -diethyl-1-methyl-3-aryl-1, 2, 5, 6-tetrahydropyridine-5-carboxamides (Thesis). University of Michigan. doi:10.7302/11268. hdl:2027.42/180879. Archived from the original on 24 December 2025.
  8. ^ Dyer DC, Benington F, Morin RD (October 1975). "Antagonism of d-lysergic acid diethylamide and mescaline by 1-methyl-1, 2, 5, 6-tetrahydropyridine-N, N-diethyl-carboxamide (THPC)". Archives Internationales de Pharmacodynamie et de Therapie. 217 (2): 197–200. PMID 127560.
  9. ^ a b Christian ST, McClain LD, Morin RD, Benington F (August 1975). "Blockage of LSD binding at its high affinity site on synaptosomal membranes by 1-methyl-1,2,5,6-tetrahydropyridine-N,N-diethyl- carboxamide". Experientia. 31 (8): 910–911. doi:10.1007/BF02358845. PMID 125655.
  10. ^ a b Smythies JR, Bradley RJ, Linton PH (1975). "Meeting report: Biochemical aspects of schizophrenia. Alabama, April 1975". Psychoneuroendocrinology. 1 (2): 199–201. doi:10.1016/0306-4530(75)90011-6. PMID 1087034.
  11. ^ Panu AM (1980). Synthesis and Characterization of 1-Methyl-4-Substituted-3-Piperidine-Carboxylic Acid N, N-Diethyamide (Masters thesis). University of Alabama in Birmingham.
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