Chemistry:N-Cyclopropyltryptamine
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| Other names | NcPT |
| Drug class | Monoamine oxidase inhibitor (MAOI) |
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| Formula | C13H16N2 |
| Molar mass | 200.285 g·mol−1 |
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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
- ↑ 1.0 1.1 1.2 1.3 1.4 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml. "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."
- ↑ 2.0 2.1 2.2 "Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens". Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. New York: Raven Press. 1984. pp. 95–142. ISBN 978-0-89004-990-7. OCLC 10324237. https://bitnest.netfirms.com/external/Books/HallucinogensNBCP95. "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."
- ↑ 3.0 3.1 3.2 3.3 3.4 3.5 "N-cyclopropyltryptamines, potent monoamine oxidase inhibitors". Journal of Medicinal Chemistry 18 (4): 437–438. April 1975. doi:10.1021/jm00238a025. PMID 1079054.
- ↑ "Mechanism of inactivation of mitochondrial monoamine oxidase by N-cyclopropyl-N-arylalkyl amines". Journal of the American Chemical Society 102 (2): 884–886. 1980. doi:10.1021/ja00522a093. ISSN 0002-7863. Bibcode: 1980JAChS.102..884S.
- ↑ "[Substances inhibiting monoamine oxidase. II. Inhibition of bovine plasma amine oxidase by N-cyclopropyltryptamines]" (in Italian). Il Farmaco; Edizione Scientifica 38 (6): 425–428. June 1983. PMID 6575920.
- ↑ "[Monoamine oxidase inhibitors. I. Synthesis of N-cyclopropyltryptamines]" (in Italian). Il Farmaco; Edizione Scientifica 35 (9): 785–790. September 1980. PMID 6935082.
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