5-F-AMT

drugbox
IUPAC_name = 1-(5-fluoro-1H-indol-3-yl)propan-2-amine


width = 140
CAS_number = 712-08-3
ATC_prefix =
ATC_suffix =
PubChem = 12834
C=11 | H=13 | F=1 | N=2
molecular_weight = 192.233 g/mol
smiles =
melting_point =
melting_high =
bioavailability =
protein_bound =
metabolism =
elimination_half-life =
excretion =
pregnancy_AU =
pregnancy_US =
pregnancy_category =
legal_AU =
legal_CA =
legal_UK =
legal_US =
legal_status =
routes_of_administration =

5-Fluoro-alphamethyltryptamine (5-F-α-MT) is a tryptamine derivative. It is similar in structure to hallucinogenic tryptamines such as AMT and 5-MeO-AMT.

5-F-α-MT has been found to act as a potent and selective MAO-A inhibitor, [Kinemuchi H, Arai Y. Selective inhibition of monoamine oxidase A and B by two substrate-analogues, 5-fluoro-alpha-methyltryptamine and p-chloro-beta-methylphenethylamine. "Research Communications in Chemical Pathology and Pharmacology". 1986 Oct;54(1):125-8.] [Kim SK, Toyoshima Y, Arai Y, Kinemuchi H, Tadano T, Oyama K, Satoh N, Kisara K. Inhibition of monoamine oxidase by two substrate-analogues, with different preferences for 5-hydroxytryptamine neurons. "Neuropharmacology". 1991 Apr;30(4):329-35.] and also as a 5HT_2A receptor agonist. [Chairungsrilerd N, Furukawa K, Tadano T, Kisara K, Ohizumi Y. Effect of gamma-mangostin through the inhibition of 5-hydroxy-tryptamine2A receptors in 5-fluoro-alpha-methyltryptamine-induced head-twitch responses of mice. "British Journal of Pharmacology. 1998 Mar;123(5):855-62.] It produces a strong head-twitch response in mice, and this effect is known to correlate with hallucinogenic effects in humans, [Corne SJ, Pickering RW. A possible correlation between drug inducedhallucinations in man and a behavioral response in mice. "Psychopharmacologia" 1967, 11, 65-78.] [Yamamoto T, Ueki S. The role of central serotonergic mechanisms on head-twitch and backward locomotion induced by hallucinogenic drugs. "Pharmacology, Biochemistry and Behaviour". 1981, 14, 89-95.] which suggests that 5-F-α-MT would be an active hallucinogen in humans, although it is not known to have been tested in humans and could potentially be dangerous due to its strong MAO-A inhibition effects.

References