4-Fluoro-DMT

Clinical data
Other names	4-Fluoro-N,N-dimethyltryptamine; 4-F-DMT; 4F-DMT
Routes of administration	Sublingual,inhalation[1]
Drug class	Serotonin5-HT2C receptoragonist;Psychoactive drug;Entactogen
ATC code	None
Pharmacokinetic data
Onset of action	40 minutes[1]
Duration of action	2–3 hours[1]
Identifiers
IUPAC name 2-(4-fluoro-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number	1644-64-0
PubChemCID	11492162
ChemSpider	9666968
UNII	A2FA8F63VS
ChEMBL	ChEMBL197646
Chemical and physical data
Formula	C12H15FN2
Molar mass	206.264 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN(C)CCC1=CNC2=C1C(=CC=C2)F
InChI 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 (or4-F-DMT), also known as4-fluoro-N,N-dimethyltryptamine, is aserotonin receptor agonist of thetryptamine family and a closeanalogue ofpsilocin (4-HO-DMT) anddimethyltryptamine (DMT).^[2][3][4][1] It is a modestlyselectiveserotonin5-HT_2C receptorfull agonist and doesn't appear to producepsychedelic-like effects in animals but instead producesantiobsessional-like effects.^[2][3] It has been encountered online as a noveldesigner drug, with claimed mildentactogen-like effects.^[1]

According to an unverified onlineanecdotal report, 4-fluoro-DMT is said to produce mildentactogen-like effects, such as enhancedsociability,empathy, and communication and a feeling of peace, with few or nopsychedelic effects.^[1] It was described as being like a lighter version ofMDMA and being like anLSD orpsilocybinafterglow.^[1] However, there was also said to be a slight feeling of "psychedelicdissociation".^[1] The drug is said to be active at doses of 10 to 30 mgsublingually and 15 mg byinhalation.^[1] Itsonset is said to be 40 minutes and itsduration is said to be 2 to 3 hours.^[1]

4-Fluoro-DMT'saffinity (K_i) for theserotonin5-HT_1A receptor was 135 nM.^[2] This can be compared topsilocin's affinity of 378 nM and serotonin's affinity of 1.7 nM.^[2] In another study, 4-F-DMT showed affinities (K_i) of 335 nM for the serotonin5-HT_2A receptor, 8.39 nM for the serotonin5-HT_2B receptor, and 82–84 nM for the serotonin5-HT_2C receptor.^[3] Itsactivationalpotencies (EC₅₀Tooltip half-maximal effective concentration) andefficacies (E_maxTooltip maximal efficacy) were 949 nM (49%) at the serotonin 5-HT_2A receptor, 1,180 nM (38%) at the serotonin 5-HT_2B receptor, and 99 nM (93%) at the serotonin 5-HT_2C receptor.^[3] 4-F-DMT showed dramatically less potentEC₅₀ values at the serotonin 5-HT_2A and 5-HT_2B receptors compared to psilocin (40- and 20-fold less potent), whereas its potency was less markedly reduced at the serotonin 5-HT_2C receptor (about 3-fold less potent).[3]^[1] Hence, whereas psilocin is a balanced agonist of the serotonin5-HT₂ receptors, 4-F-DMT is aselective serotonin 5-HT_2C receptor agonist with about 10-fold preference for activation of this receptor over the serotonin 5-HT_2A and 5-HT_2B receptors.^[3] Moreover, whereas psilocin was apartial agonist of the serotonin 5-HT_2C receptor (E_max = 51%), 4-F-DMT had higher efficacy and was afull agonist (E_max = 93%).[3]

4-F-DMT produced partial generalization (0–56%) toLSD in animaldrug discrimination tests, but this was notstatistically significant and anED₅₀Tooltip median effective dose was not calculated.^[2] It also failed to substitute forDOI in drug discrimination tests (10–33%).^[2] Conversely, psilocin produced full generalization at much lower doses.^[2] Hence, 4-F-DMT may not behallucinogenic in humans.^[2] On the other hand, the drug wasdose-dependently and strongly active in producingantiobsessional-like effects in ananimal model ofobsessive–compulsive disorder (OCD) (specifically inhibition of serotonin-inducedscratching behavior), an effect that it is thought may be mediated by serotonin 5-HT_2C receptor agonism.^[3]

4-F-DMT is morelipophilic than psilocin (4-HO-DMT) due to lacking itshydrophilichydroxyl group, and hence 4-F-DMT might cross theblood–brain barrier more readily than psilocin.^[3]

Thechemical synthesis of 4-fluoro-DMT has been described.^[4][3]

Analogues of 4-F-DMT includedimethyltryptamine (DMT),psilocin (4-HO-DMT),4-methyl-DMT, and4-MeO-DMT, among others.^[5]Derivatives of 4-F-DMT such as4-fluoro-5-methoxy-DMT (4-F-5-MeO-DMT) have also beensynthesized and studied.^[6]

4-F-DMT was firstsynthesized and described in thescientific literature by 1964.^[4][1] It was encountered online as a noveldesigner drug in 2025.^[1]

• Substituted tryptamine
• 5-Fluoro-DMT
• 6-Fluoro-DMT
• 4-F-5-MeO-DMT
• 4-F-5-MeO-pyr-T

• 4-Fluoro-DMT - Isomer Design
• 4F-DMT - an interesting "social enhancer"? (effects report) - r/researchchemicals - Reddit

• Drugs not assigned an ATC code
• 5-HT2A agonists
• 5-HT2B agonists
• 5-HT2C agonists
• Designer drugs
• N,N-Dialkyltryptamines
• Dimethylamino compounds
• Fluoroarenes
• Psychoactive drugs
• Serotonin receptor agonists

• CS1 Russian-language sources (ru)
• Articles with short description
• Short description matches Wikidata
• Chemical pages without DrugBank identifier
• Articles without KEGG source
• Drugs with no legal status
• Articles containing unverified chemical infoboxes