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).
Use and effects 6-Fluoro-DMT was not included nor mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved). However, he did briefly discuss it in an early literature review, but its properties and effects in humans were not described.
The closely related compound 6-fluoro-DET has been found to be inactive in terms of psychedelic-type effects both in animals and humans. 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. 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.
Indeed, the related compound 6-fluoro-AMT is known to be robustly active as a psychedelic. Additionally, 6-fluoro-DMT robustly induces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. 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.
Pharmacology Pharmacodynamics + Target Affinity (Ki, nM) 5-HT1A 693–865 (Ki) () 5-HT1B 218 5-HT1D 55 5-HT1E 461 5-HT1F 5-HT2A 511–866 (Ki)41–16,830 ()74% () 5-HT2B 30 5-HT2C 674 (Ki)1.252–5.816 ()105–131% () 5-HT3 >10,000 5-HT4 5-HT5A 961 5-HT6 26 5-HT7 41 α1A 173 α1B >10,000 α1D α2A >10,000 α2B 260 α2C 149 β1 >10,000 β2 >10,000 β3 D1 547 D2 610 D3 867 D4 1,454 D5 6,291 H1 47 H2 925 H3, H4 >10,000 M1–M5 >10,000 I1 898 σ1 6,892 σ2 7,128 145 (Ki) >10,000 (Ki) >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:
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). 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. 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. 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. 6-Fluoro-DMT was less active than DMT in producing effects in early animal studies. 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.
Chemistry Analogues Analogues of 6-fluoro-DMT include 6-fluorotryptamine, dimethyltryptamine (DMT), 4-fluoro-DMT, 5-fluoro-DMT, 5-fluoro-AMT, 5-bromo-DMT, 5-chloro-DMT, bretisilocin (5-fluoro-MET), 6-fluoro-AMT, 6-fluoro-DET, 6-methyl-DMT, 6-MeO-DMT, 6-hydroxy-DMT, and HBL20016 (5-MeS-6-F-DMT), among others.
History 6-Fluoro-DMT was first described in the scientific literature by at least 1966.
See also Substituted tryptamine Non-hallucinogenic 5-HT2A receptor agonist
References
External links 6-Fluoro-DMT - Isomer Design