4-Fluoro-DMT

4-Fluoro-DMT
Clinical data
Other names4-Fluoro-N,N-dimethyltryptamine; 4-F-DMT; 4F-DMT
Routes of
administration		Sublingual, inhalation[1]
Drug classSerotonin 5-HT2C receptor agonist; Psychoactive drug; Entactogen
ATC code
  • None
Pharmacokinetic data
Onset of action40 minutes[1]
Duration of action2–3 hours[1]
Identifiers
  • 2-(4-fluoro-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC12H15FN2
Molar mass206.264 g·mol−1
3D model (JSmol)
  • CN(C)CCC1=CNC2=C1C(=CC=C2)F
  • InChI=1S/C12H15FN2/c1-15(2)7-6-9-8-14-11-5-3-4-10(13)12(9)11/h3-5,8,14H,6-7H2,1-2H3
  • Key:ISJZKVWGUWBUFG-UHFFFAOYSA-N

4-Fluoro-DMT (or 4-F-DMT), also known as 4-fluoro-N,N-dimethyltryptamine, is a serotonin receptor agonist of the tryptamine family and a close analogue of psilocin (4-HO-DMT) and dimethyltryptamine (DMT).[2][3][4][1] It is a modestly selective serotonin 5-HT2C receptor full agonist and doesn't appear to produce psychedelic-like effects in animals but instead produces antiobsessional-like effects.[2][3] It has been encountered online as a novel designer drug, with claimed mild entactogen-like effects.[1]

Use and effects

According to an unverified online anecdotal report, 4-fluoro-DMT is said to produce mild entactogen-like effects, such as enhanced sociability, empathy, and communication and a feeling of peace, with few or no psychedelic effects.[1] It was described as being like a lighter version of MDMA and being like an LSD or psilocybin afterglow.[1] However, there was also said to be a slight feeling of "psychedelic dissociation".[1] The drug is said to be active at doses of 10 to 30 mg sublingually and 15 mg by inhalation.[1] Its onset is said to be 40 minutes and its duration is said to be 2 to 3 hours.[1]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

4-Fluoro-DMT's affinity (Ki) for the serotonin 5-HT1A receptor was 135 nM.[2] This can be compared to psilocin's affinity of 378 nM and serotonin's affinity of 1.7 nM.[2] In another study, 4-F-DMT showed affinities (Ki) of 335 nM for the serotonin 5-HT2A receptor, 8.39 nM for the serotonin 5-HT2B receptor, and 82–84 nM for the serotonin 5-HT2C receptor.[3] Its activational potencies (EC50Tooltip half-maximal effective concentration) and efficacies (EmaxTooltip maximal efficacy) were 949 nM (49%) at the serotonin 5-HT2A receptor, 1,180 nM (38%) at the serotonin 5-HT2B receptor, and 99 nM (93%) at the serotonin 5-HT2C receptor.[3] 4-F-DMT showed dramatically less potent EC50 values at the serotonin 5-HT2A and 5-HT2B receptors compared to psilocin (40- and 20-fold less potent), whereas its potency was less markedly reduced at the serotonin 5-HT2C receptor (about 3-fold less potent).[3][1] Hence, whereas psilocin is a balanced agonist of the serotonin 5-HT2 receptors, 4-F-DMT is a selective serotonin 5-HT2C receptor agonist with about 10-fold preference for activation of this receptor over the serotonin 5-HT2A and 5-HT2B receptors.[3] Moreover, whereas psilocin was a partial agonist of the serotonin 5-HT2C receptor (Emax = 51%), 4-F-DMT had higher efficacy and was a full agonist (Emax = 93%).[3]

4-F-DMT produced partial generalization (0–56%) to LSD in animal drug discrimination tests, but this was not statistically significant and an ED50Tooltip median effective dose was not calculated.[2] It also failed to substitute for DOI in drug discrimination tests (10–33%).[2] Conversely, psilocin produced full generalization at much lower doses.[2] Hence, 4-F-DMT may not be hallucinogenic in humans.[2] On the other hand, the drug was dose-dependently and strongly active in producing antiobsessional-like effects in an animal model of obsessive–compulsive disorder (OCD) (specifically inhibition of serotonin-induced scratching behavior), an effect that it is thought may be mediated by serotonin 5-HT2C receptor agonism.[3]

Chemistry

Properties

4-F-DMT is more lipophilic than psilocin (4-HO-DMT) due to lacking its hydrophilic hydroxyl group, and hence 4-F-DMT might cross the blood–brain barrier more readily than psilocin.[3]

Synthesis

The chemical synthesis of 4-fluoro-DMT has been described.[4][3]

Analogues

Analogues of 4-F-DMT include dimethyltryptamine (DMT), psilocin (4-HO-DMT), 4-methyl-DMT, and 4-MeO-DMT, among others.[5] Derivatives of 4-F-DMT such as 4-fluoro-5-methoxy-DMT (4-F-5-MeO-DMT) have also been synthesized and studied.[6]

History

4-F-DMT was first synthesized and described in the scientific literature by 1964.[4][1] It was encountered online as a novel designer drug in 2025.[1]

See also

References

  1. ^ a b c d e f g h i j k l m "4-F-DMT (4F-DMT)". АИПСИН (in Russian). Retrieved 1 January 2026.
  2. ^ a b c d e f g h Blair JB (August 1997). "Synthesis and pharmacological evaluation of fluorinated hallucinogenic tryptamine analogs and thienopyrrole bioisosteres of N,N-dimethyltryptamine". Purdue e-Pubs. Retrieved 20 March 2025.
  3. ^ a b c d e f g h i j Sard H, Kumaran G, Morency C, Roth BL, Toth BA, He P, et al. (October 2005). "SAR of psilocybin analogs: discovery of a selective 5-HT 2C agonist". Bioorganic & Medicinal Chemistry Letters. 15 (20): 4555–4559. doi:10.1016/j.bmcl.2005.06.104. PMID 16061378.
  4. ^ a b c Bentov M, Pelchowicz Z, Levy A (1964). "4-Fluoroindole and Derivatives". Israel Journal of Chemistry. 2 (1): 25–28. doi:10.1002/ijch.196400006. ISSN 0021-2148.
  5. ^ Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  6. ^ Blair JB, Kurrasch-Orbaugh D, Marona-Lewicka D, Cumbay MG, Watts VJ, Barker EL, et al. (November 2000). "Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines". Journal of Medicinal Chemistry. 43 (24): 4701–4710. doi:10.1021/jm000339w. PMID 11101361.
allikas: https://en.wikipedia.org/wiki/4-Fluoro-DMT