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6-Fluoro-DMT

Chemical compound From Wikipedia, the free encyclopedia

6-Fluoro-DMT, also known as 6-fluoro-N,N-dimethyltryptamine, is a serotonin receptor modulator and possible psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT).[1][2]

Other names6-Fluoro-N,N-dimethyltryptamine; 6-Fluoro-DMT; 6-F-DMT; 6F-DMT
ATC code
  • None
Quick facts Clinical data, Other names ...
6-Fluoro-DMT
Clinical data
Other names6-Fluoro-N,N-dimethyltryptamine; 6-Fluoro-DMT; 6-F-DMT; 6F-DMT
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Possible psychedelic drug or hallucinogen
ATC code
  • None
Identifiers
  • 2-(6-fluoro-1H-indol-3-yl)-N,N-dimethyl-ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC12H15FN2
Molar mass206.264 g·mol−1
3D model (JSmol)
  • CN(CCC1=CNC2=C1C=CC(F)=C2)C
  • InChI=1S/C12H15FN2/c1-15(2)6-5-9-8-14-12-7-10(13)3-4-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3 checkY
  • Key:DZXZPVGWRZCXDH-UHFFFAOYSA-N checkY
  (verify)
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Use and effects

6-Fluoro-DMT was not included nor mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved).[3] However, he did briefly discuss it in an early literature review, but its properties and effects in humans were not described.[1]

The closely related compound 6-fluoro-DET has been found to be inactive in terms of psychedelic-type effects both in animals and humans.[4][5][6][3][7] Relatedly, it has been claimed that 6-fluoro-DMT is inactive as a psychedelic similarly to 6-fluoro-DET, though it is unclear whether this claim was based on actual testing or on extrapolation from 6-fluoro-DET and theoretical notions.[8] In the 1960s, it had been theorized by Stephen Szára and colleagues that psychedelic tryptamines were prodrugs that required 6-hydroxylation to become hallucinogenic, but this theory was later found to be incorrect.[9][10][11][12]

Indeed, the related compound 6-fluoro-AMT is known to be robustly active as a psychedelic.[13][14] Additionally, 6-fluoro-DMT robustly induces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[15][16] Likewise, HBL20016 (5-MeS-6-F-DMT), the 5-methylthio derivative of 6-fluoro-DMT, robustly produces the head-twitch response in rodents as well.[17][18]

Pharmacology

Pharmacodynamics

More information Target, Affinity (Ki, nM) ...
6-Fluoro-DMT activities
TargetAffinity (Ki, nM)
5-HT1A693–865 (Ki)
IA (EC50Tooltip half-maximal effective concentration)
5-HT1B218
5-HT1D55
5-HT1E461
5-HT1FND
5-HT2A511–866 (Ki)
41–16,830 (EC50)
74% (EmaxTooltip maximal efficacy)
5-HT2B30
5-HT2C674 (Ki)
1.252–5.816 (EC50)
105–131% (Emax)
5-HT3>10,000
5-HT4ND
5-HT5A961
5-HT626
5-HT741
α1A173
α1B>10,000
α1DND
α2A>10,000
α2B260
α2C149
β1>10,000
β2>10,000
β3ND
D1547
D2610
D3867
D41,454
D56,291
H147
H2925
H3, H4>10,000
M1–M5>10,000
I1898
σ16,892
σ27,128
TAAR1Tooltip Trace amine-associated receptor 1ND
SERTTooltip Serotonin transporter145 (Ki)
NETTooltip Norepinephrine transporter>10,000 (Ki)
DATTooltip Dopamine transporter>10,000 (Ki)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [19][2][15][16]
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6-Fluoro-DMT is known to possess varying affinities for serotonin receptors, adrenergic receptors, dopamine receptors, histamine receptors, the imidazoline I1 receptor, sigma receptors, and the serotonin transporter (SERT).[2] It has been found to be a potent partial agonist of the serotonin 5-HT2A receptor and a potent full agonist of the serotonin 5-HT2C receptor.[2] In another study however, it showed affinity for the serotonin 5-HT1A and 5-HT2A receptors but was inactive as a serotonin 5-HT1A receptor agonist and showed low potency as a serotonin 5-HT2A receptor agonist.[15][16] On the other hand, it was only about 3-fold less potent than dimethyltryptamine (DMT) as a serotonin 5-HT2A receptor agonist in this study.[16] 6-Fluoro-DMT was less active than DMT in producing effects in early animal studies.[1][20] It robustly induces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, with maximal efficacy greater than that of psilocin or 5-MeO-DMT but less than that of DMT.[15][16]

Chemistry

History

6-Fluoro-DMT was first described in the scientific literature by at least 1966.[1][20][8]

See also

References

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