6-Fluoro-AMT

6-Fluoro-AMT
Clinical data
Other names6-Fluoro-AMT; 6-Fluoro-αMT; 6F-AMT; 6F-αMT; 6-F-AMT; 6-F-αMT
Identifiers
IUPAC name
  • 1-(6-fluoro-1H-indol-3-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H13FN2
Molar mass192.237 g·mol−1
3D model (JSmol)
SMILES
  • NC(C)CC1=CNC2=CC(F)=CC=C21
InChI
  • InChI=1S/C11H13FN2/c1-7(13)4-8-6-14-11-5-9(12)2-3-10(8)11/h2-3,5-7,14H,4,13H2,1H3
  • Key:XYJYWUUXCUJXAI-UHFFFAOYSA-N

6-Fluoro-α-methyltryptamine (6-fluoro-AMT, 6F-AMT) is a tryptamine derivative related to compounds such as α-methyltryptamine (AMT) and 5-MeO-AMT which has been sold as a designer drug.[1][2]

Animal tests showed the drug to be somewhat less potent in terms of pharmacological activity than AMT or 5-fluoro-AMT.[3] It produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[4][5][6] Its IC50Tooltip half-maximal inhibitory concentration for monoamine oxidase A (MAO-A) inhibition is 580 to 1,800 nM, compared to 180 to 450 nM for 5-fluoro-AMT and 380 nM for AMT.[5][7][8]

6-Fluoro-AMT was allegedly manufactured and sold from the laboratory operated by Leonard Pickard and Gordon Todd Skinner, who described 6-fluoro-AMT as "a beast".[1] In interviews, Skinner stated that he first began to experiment with 6-fluoro-AMT in the early 1980s by giving it to high school friends.[2] Their experiences made him cautious about the appropriate doses, which he said ranged from 25 to 75 mg (Skinner weighed about 250 lbs at the time of his own bioassay).[2] Skinner said that 6-fluoro-AMT is a long-lasting psychedelic with more time distortion and that it was enhanced by combination with ALD-52.[2]

See also

References

  1. 1 2 Morris H (2010). "Life is a Cosmic Giggle on the Breath of the Universe. A Tour of Gordon Todd Skinner's Subterranean LSD Palace". Vice Magazine. Archived from the original on 2014-10-13. Retrieved 2017-08-23.
  2. 1 2 3 4 "Unusual Analogues: Drugs Used by Gordon Todd Skinner". thislandpress.com. This Land Press. Retrieved 8 April 2016.
  3. ↑ Kalir A, Szara S (November 1963). "Synthesis and Pharmacological Activity of Fluorinated Tryptamine Derivatives". Journal of Medicinal Chemistry. 6 (6): 716–719. doi:10.1021/jm00342a019. PMID 14184932.
  4. ↑ Halberstadt AL, Geyer MA (2018). "Effect of Hallucinogens on Unconditioned Behavior". Behavioral Neurobiology of Psychedelic Drugs. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 159–199. doi:10.1007/7854_2016_466. ISBN 978-3-662-55878-2. PMC 5787039. PMID 28224459.
  5. 1 2 Nakagawasai O, Arai Y, Satoh SE, Satoh N, Neda M, Hozumi M, Oka R, Hiraga H, Tadano T (January 2004). "Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives". Neurotoxicology. 25 (1–2): 223–232. Bibcode:2004NeuTx..25..223N. doi:10.1016/S0161-813X(03)00101-3. PMID 14697897.
  6. ↑ Tadano T, Neda M, Hozumi M, Yonezawa A, Arai Y, Fujita T, Kinemuchi H, Kisara K (February 1995). "alpha-Methylated tryptamine derivatives induce a 5-HT receptor-mediated head-twitch response in mice". Neuropharmacology. 34 (2): 229–234. doi:10.1016/0028-3908(94)00119-d. PMID 7617148.
  7. ↑ Wagmann L, Brandt SD, Kavanagh PV, Maurer HH, Meyer MR (April 2017). "In vitro monoamine oxidase inhibition potential of alpha-methyltryptamine analog new psychoactive substances for assessing possible toxic risks" (PDF). Toxicol Lett. 272: 84–93. doi:10.1016/j.toxlet.2017.03.007. PMID 28302559.
  8. ↑ "Advantageous tryptamine compositions for mental disorders or enhancement". Google Patents. 20 September 2021. Retrieved 8 December 2024.
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