Chemistry:4-Fluoro-DMT

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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).[1][2][3][4] 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.[1][2] It has been encountered online as a novel designer drug, with claimed mild entactogen-like effects.[4]

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.[4] It was described as being like a lighter version of MDMA and being like an LSD or psilocybin afterglow.[4] However, there was also said to be a slight feeling of "psychedelic dissociation".[4] The drug is said to be active at doses of 10 to 30 mg sublingually and 15 mg by inhalation.[4] Its onset is said to be 40 minutes and its duration is said to be 2 to 3 hours.[4]

Interactions

Pharmacology

Pharmacodynamics

4-Fluoro-DMT's affinity (Ki) for the serotonin 5-HT1A receptor was 135 nM.[1] This can be compared to psilocin's affinity of 378 nM and serotonin's affinity of 1.7 nM.[1] 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.[2] Its activational potencies (EC50) and efficacies (Emax) 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.[2] 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).[2][4] 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.[2] 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%).[2]

4-F-DMT produced partial generalization (0–56%) to LSD in animal drug discrimination tests, but this was not statistically significant and an ED50 was not calculated.[1] It also failed to substitute for DOI in drug discrimination tests (10–33%).[1] Conversely, psilocin produced full generalization at much lower doses.[1] Hence, 4-F-DMT may not be hallucinogenic in humans.[1] 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.[2]

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.[2]

Synthesis

The chemical synthesis of 4-fluoro-DMT has been described.[3][2]

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.[3][4] It was encountered online as a novel designer drug in 2025.[4]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 "Synthesis and pharmacological evaluation of fluorinated hallucinogenic tryptamine analogs and thienopyrrole bioisosteres of N,N-dimethyltryptamine". August 1997. https://docs.lib.purdue.edu/dissertations/AAI9818919/. 
  2. ↑ 2.00 2.01 2.02 2.03 2.04 2.05 2.06 2.07 2.08 2.09 "SAR of psilocybin analogs: discovery of a selective 5-HT 2C agonist". Bioorganic & Medicinal Chemistry Letters 15 (20): 4555–4559. October 2005. doi:10.1016/j.bmcl.2005.06.104. PMID 16061378. 
  3. ↑ 3.0 3.1 3.2 "4-Fluoroindole and Derivatives". Israel Journal of Chemistry 2 (1): 25–28. 1964. doi:10.1002/ijch.196400006. ISSN 0021-2148. 
  4. ↑ 4.00 4.01 4.02 4.03 4.04 4.05 4.06 4.07 4.08 4.09 "4-F-DMT (4F-DMT)" (in ru). https://aipsin.com/newsubstance/1795/. 
  5. ↑ Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml. 
  6. ↑ "Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines". Journal of Medicinal Chemistry 43 (24): 4701–4710. November 2000. doi:10.1021/jm000339w. PMID 11101361. 



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