6-Fluoro-DMT

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

6-Fluoro-DMT

Clinical data
Other names	6-Fluoro-N,N-dimethyltryptamine; 6-Fluoro-DMT; 6-F-DMT; 6F-DMT
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code	None
Identifiers
IUPAC name 2-(6-fluoro-1H-indol-3-yl)-N,N-dimethyl-ethanamine
CAS Number	1511-31-5 Y
PubChem CID	121013343
ChemSpider	26286731 Y
UNII	J4CZH8D9EN
Chemical and physical data
Formula	C12H15FN2
Molar mass	206.264 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN(CCC1=CNC2=C1C=CC(F)=C2)C
InChI 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 Y Key:DZXZPVGWRZCXDH-UHFFFAOYSA-N Y
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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]

Pharmacology

Pharmacodynamics

6-Fluoro-DMT activities

Target	Affinity (Ki, nM)
5-HT1A	693–865 (Ki) IA (EC50Tooltip half-maximal effective concentration)
5-HT1B	218
5-HT1D	55
5-HT1E	461
5-HT1F	ND
5-HT2A	511–866 (Ki) 41–16,830 (EC50) 74% (EmaxTooltip maximal efficacy)
5-HT2B	30
5-HT2C	674 (Ki) 1.252–5.816 (EC50) 105–131% (Emax)
5-HT3	>10,000
5-HT4	ND
5-HT5A	961
5-HT6	26
5-HT7	41
α1A	173
α1B	>10,000
α1D	ND
α2A	>10,000
α2B	260
α2C	149
β1	>10,000
β2	>10,000
β3	ND
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
TAAR1Tooltip Trace amine-associated receptor 1	ND
SERTTooltip Serotonin transporter	145 (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: [15][2][16][17]

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-HT_2A receptor and a potent full agonist of the serotonin 5-HT_2C receptor.^[2] In another study however, it showed affinity for the serotonin 5-HT_1A and 5-HT_2A receptors but was inactive as a serotonin 5-HT_1A receptor agonist and showed low potency as a serotonin 5-HT_2A receptor agonist.^[16][17] On the other hand, it was only about 3-fold less potent than dimethyltryptamine (DMT) as a serotonin 5-HT_2A receptor agonist in this study.^[17] 6-Fluoro-DMT is less active than dimethyltryptamine (DMT) in producing effects in animal studies.^[1][18]

Chemistry

Analogues

Analogues of 6-fluoro-DMT include 4-fluoro-DMT, 5-fluoro-DMT, 5-fluoro-AMT, 5-bromo-DMT, 5-chloro-DMT, bretisilocin (5-fluoro-MET), 6-fluoro-AMT, and 6-fluoro-DET, among others.

History

6-Fluoro-DMT was first described in the scientific literature by at least 1966.^[1][18][8]

See also

• Substituted tryptamine
• Non-hallucinogenic 5-HT_2A receptor agonist