5-Fluoro-DMT explained
| Verifiedfields: | changed |
| Watchedfields: | changed |
| Verifiedrevid: | 477224355 |
| Iupac Name: | 2-(5-fluoro-1H-indol-3-yl)-N,N-dimethylethanamine |
| Width: | 200px |
| Cas Number: | 22120-36-1 |
| Pubchem: | 2762738 |
| Chemspiderid: | 2043436 |
| Chembl: | 1630729 |
| C: | 12 |
| H: | 15 |
| F: | 1 |
| N: | 2 |
| Smiles: | CN(C)CCC1=CNC2=C1C=C(C=C2)F |
| Stdinchi: | 1S/C12H15FN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3 |
| Stdinchikey: | BXYDWQABVPBLBU-UHFFFAOYSA-N |
5-Fluoro-N,N-dimethyltryptamine (5-fluoro-DMT, 5F-DMT) is a tryptamine derivative related to compounds such as 5-bromo-DMT and 5-MeO-DMT.[1] It produces a robust head-twitch response in mice, and hence is a putative serotonergic psychedelic.[2] Fluorination of psychedelic tryptamines either reduces or has little effect on 5-HT2A/C receptor affinity or intrinsic activity, although 6-fluoro-DET is inactive as a psychedelic despite acting as a 5-HT2A agonist (cf. lisuride), while 4-fluoro-5-methoxy-DMT is a much stronger agonist at 5-HT1A than 5-HT2A.[3] [4]
See also
Notes and References
- Chen CY, Senanayake CH, Bill TJ, Larsen RD, Verhoeven TR, Reider PJ . Improved Fischer indole reaction for the preparation of N, N-dimethyltryptamines: Synthesis of L-695,894, a potent 5-HT1D receptor agonist. . The Journal of Organic Chemistry . July 1994 . 59 . 13 . 3738–3741 . 10.1021/jo00092a046 .
- Duan W, Cao D, Wang S, Cheng J . Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants . Chem Rev . 124 . 1 . 124–163 . January 2024 . 38033123 . 10.1021/acs.chemrev.3c00375 .
- Blair JB, Kurrasch-Orbaugh D, Marona-Lewicka D, Cumbay MG, Watts VJ, Barker EL, Nichols DE . Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines . Journal of Medicinal Chemistry . 43 . 24 . 4701–10 . November 2000 . 11101361 . 10.1021/jm000339w .
- Rabin RA, Regina M, Doat M, Winter JC . 5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens . Pharmacology, Biochemistry, and Behavior . 72 . 1–2 . 29–37 . May 2002 . 11900766 . 10.1016/S0091-3057(01)00720-1 . 6480715 .
