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N-Cyclopropyltryptamine

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

Last revised
Jun 6, 2026
Read time
≈ 2 min
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Wikipedia ↗
N-Cyclopropyltryptamine
Clinical data
Other namesNcPT
Drug classMonoamine oxidase inhibitor (MAOI)
ATC code
  • None
Identifiers
  • N-[2-(1H-indol-3-yl)ethyl]cyclopropanamine
PubChem CID
ChemSpider
Chemical and physical data
FormulaC13H16N2
Molar mass200.285 g·mol−1
3D model (JSmol)
  • C1CC1NCCC2=CNC3=CC=CC=C32
  • InChI=1S/C13H16N2/c1-2-4-13-12(3-1)10(9-15-13)7-8-14-11-5-6-11/h1-4,9,11,14-15H,5-8H2
  • Key:VYIORSRXNBGASE-UHFFFAOYSA-N

N-Cyclopropyltryptamine (NcPT) is a monoamine oxidase inhibitor (MAOI) of the tryptamine family related to N-methyltryptamine (NMT).123

It is a potent MAOI, with greater activity than pargyline (56–67% inhibition at 100 nM versus 41% inhibition at 100 nM, respectively).341 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.12356 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

See also

References

References

  1. 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. 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. 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.
External links