N-Cyclopropyltryptamine

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).

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

The chemical synthesis of NcPT has been described. 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. 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.

See also

References

  1. 1 2 3 4 5 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. 1 2 3 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. 1 2 3 4 5 6 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.