5-Fluoro-AMT

5-Fluoro-AMT
Identifiers
IUPAC name
  • 1-(5-fluoro-1H-indol-3-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H13FN2
Molar mass192.237 g·mol−1
3D model (JSmol)
SMILES
  • Fc1cc2c(cc1)[nH]cc2CC(N)C
InChI
  • InChI=1S/C11H13FN2/c1-7(13)4-8-6-14-11-3-2-9(12)5-10(8)11/h2-3,5-7,14H,4,13H2,1H3 checkY
  • Key:CTGFDWBZMCPVED-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

5-Fluoro-α-methyltryptamine (5-Fluoro-αMT, 5F-AMT), also known as PAL-544,[1] is a putative stimulant, entactogen, and psychedelic tryptamine derivative related to α-methyltryptamine (αMT). It has been found to act as a well-balanced serotonin-norepinephrine-dopamine releasing agent,[1] a 5-HT2A receptor agonist,[2] and a potent and specific MAO-A inhibitor.[3][4] It produces a strong head-twitch response in mice, and this effect is known to correlate with psychedelic effects in humans,[5][6] which suggests that 5-fluoro-αMT could be an active psychedelic in humans, although it is not known to have been tested in humans and could be dangerous due to its strong inhibition of MAO-A.

See also

References

  1. 1 2 Banks ML, Bauer CT, Blough BE, Rothman RB, Partilla JS, Baumann MH, Negus SS (June 2014). "Abuse-related effects of dual dopamine/serotonin releasers with varying potency to release norepinephrine in male rats and rhesus monkeys". Experimental and Clinical Psychopharmacology. 22 (3): 274–284. doi:10.1037/a0036595. PMC 4067459. PMID 24796848.
  2. ↑ Chairungsrilerd N, Furukawa K, Tadano T, Kisara K, Ohizumi Y (March 1998). "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. 123 (5): 855–62. doi:10.1038/sj.bjp.0701695. PMC 1565246. PMID 9535013.
  3. ↑ Kinemuchi H, Arai Y (October 1986). "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. 54 (1): 125–8. doi:10.1016/0028-3908(91)90057-i. PMID 3797802. S2CID 34761939.
  4. ↑ Kim SK, Toyoshima Y, Arai Y, Kinemuchi H, Tadano T, Oyama K, et al. (April 1991). "Inhibition of monoamine oxidase by two substrate-analogues, with different preferences for 5-hydroxytryptamine neurons". Neuropharmacology. 30 (4): 329–35. doi:10.1016/0028-3908(91)90057-i. PMID 1852266. S2CID 34761939.
  5. ↑ Corne SJ, Pickering RW (1967). "A possible correlation between drug-induced hallucinations in man and a behavioural response in mice". Psychopharmacologia. 11 (1): 65–78. doi:10.1007/bf00401509. PMID 5302272. S2CID 3148623.
  6. ↑ Yamamoto T, Ueki S (January 1981). "The role of central serotonergic mechanisms on head-twitch and backward locomotion induced by hallucinogenic drugs". Pharmacology, Biochemistry, and Behavior. 14 (1): 89–95. doi:10.1016/0091-3057(81)90108-8. PMID 6258178. S2CID 45561708.

Further reading

  • Nakagawasai O, Arai Y, Satoh SE, Satoh N, Neda M, Hozumi M, et al. (January 2004). "Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives". Neurotoxicology. 25 (1–2): 223–32. doi:10.1016/S0161-813X(03)00101-3. PMID 14697897.
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