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N-Cyclopropyltryptamine (NcPT) is a monoamine oxidase inhibitor (MAOI) of the tryptamine family related to N-methyltryptamine (NMT).[1][2][3]

It is a potent MAOI, with greater activity than pargyline (56–67% inhibition at 100 nM versus 41% inhibition at 100 nM, respectively).[3][4][1] The drug markedly potentiates the behavioral effects of 5-hydroxytryptophan (5-HTP) in rodents.[3] In addition, it produces tremors, hypolocomotion, motor incoordination, and vasodilation in rodents.[3] NcPT has also been reported to have antihyperglycemic activity.[1] The drug has not been assessed in terms of psychedelic-related behavioral effects.[2]

The chemical synthesis of NcPT has been described.[1] Some notable derivatives of NcPT include 5-MeO-NcPT, 7-MeO-NcPT, 5,6-DiMeO-NcPT, and 6,7-DiMeO-NcPT, which showed MAOI activity similarly to NcPT.[1][2][3][5][6] Some other derivatives include the psychedelic designer drugs N-methyl-N-cyclopropyltryptamine (McPT), 4-HO-McPT, and 4-AcO-McPT.

NcPT was first described in the scientific literature by 1975.[3]

See also

References

  1. ^ a b c d e Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. “Another provocative mono-alkyl analogue of DMT is N-cyclopropyltryptamine, made from indole-3-oxalylchloride and benzyl cyclopropylamine with eventual hydrogenolysis of the benzyl group; mp 180–182. This compound, as with the 5-methoxy (5-MeO-NCPT) and the 7-methoxy (7-MeO-NCPT) counterparts, is a potent monoamine-oxidase inhibitor, and it has also been reported to have hypoglycemic activity.”
  2. ^ a b c Nichols DE, Glennon RA (1984). “Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens”. In Jacobs BL (ed.). Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. New York: Raven Press. pp. 95–142. ISBN 978-0-89004-990-7. OCLC 10324237. N-Cyclopropyltryptamine and its 5-methoxy (248), 7-methoxy (248), 5,6-dimethoxy (34), and 6,7-dimethoxy (34) derivatives have been reported to be inhibitors of MAO, but none of these agents has been evaluated for behavioral activity.
  3. ^ a b c d e f Winn M, Horrom BW, Rasmussen RR, Chappell EB, Plotnikoff NP (April 1975). “N-cyclopropyltryptamines, potent monoamine oxidase inhibitors”. Journal of Medicinal Chemistry. 18 (4): 437–438. doi:10.1021/jm00238a025. PMID 1079054.
  4. ^ Silverman RB, Hoffman SJ (1980). “Mechanism of inactivation of mitochondrial monoamine oxidase by N-cyclopropyl-N-arylalkyl amines”. Journal of the American Chemical Society. 102 (2): 884–886. Bibcode:1980JAChS.102..884S. doi:10.1021/ja00522a093. ISSN 0002-7863.
  5. ^ Chimenti F, Casanova MC, Zagarese V, Turin P, Sabatini S (June 1983). “[Substances inhibiting monoamine oxidase. II. Inhibition of bovine plasma amine oxidase by N-cyclopropyltryptamines]”. Il Farmaco; Edizione Scientifica (in Italian). 38 (6): 425–428. PMID 6575920.
  6. ^ Chimenti F, Casanova MC, Turini P, Sabatini S (September 1980). “[Monoamine oxidase inhibitors. I. Synthesis of N-cyclopropyltryptamines]”. Il Farmaco; Edizione Scientifica (in Italian). 35 (9): 785–790. PMID 6935082.