5-Fluoro-DMT

5-Fluoro-DMT
Identifiers
	IUPAC name 2-(5-fluoro-1H-indol-3-yl)-N,N-dimethylethanamine;
CAS Number	22120-36-1 ;
PubChem CID	2762738;
ChemSpider	2043436 ;
ChEMBL	ChEMBL1630729;
CompTox Dashboard (EPA)	DTXSID30376407 ;
Chemical and physical data
Formula	C12H15FN2
Molar mass	206.264 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C)CCC1=CNC2=C1C=C(C=C2)F;
	InChI InChI=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 ; Key:BXYDWQABVPBLBU-UHFFFAOYSA-N ;
	(what is this?) (verify)

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-HT_2A/C receptor affinity or intrinsic activity, although 6-fluoro-DET is inactive as a psychedelic despite acting as a 5-HT_2A agonist (cf. lisuride), while 4-fluoro-5-methoxy-DMT is a much stronger agonist at 5-HT_1A than 5-HT_2A.^[3]^[4]

References

^ Chen CY, Senanayake CH, Bill TJ, Larsen RD, Verhoeven TR, Reider PJ (July 1994). "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. 59 (13): 3738–3741. doi:10.1021/jo00092a046.
^ Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chem Rev. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID 38033123.
^ Blair JB, Kurrasch-Orbaugh D, Marona-Lewicka D, Cumbay MG, Watts VJ, Barker EL, Nichols DE (November 2000). "Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines". Journal of Medicinal Chemistry. 43 (24): 4701–10. doi:10.1021/jm000339w. PMID 11101361.
^ Rabin RA, Regina M, Doat M, Winter JC (May 2002). "5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens". Pharmacology, Biochemistry, and Behavior. 72 (1–2): 29–37. doi:10.1016/S0091-3057(01)00720-1. PMID 11900766. S2CID 6480715.

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[1] Chen CY, Senanayake CH, Bill TJ, Larsen RD, Verhoeven TR, Reider PJ (July 1994). "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. 59 (13): 3738–3741. doi:10.1021/jo00092a046.

[DuanCaoWang2024-2] Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chem Rev. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID 38033123.

[3] Blair JB, Kurrasch-Orbaugh D, Marona-Lewicka D, Cumbay MG, Watts VJ, Barker EL, Nichols DE (November 2000). "Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines". Journal of Medicinal Chemistry. 43 (24): 4701–10. doi:10.1021/jm000339w. PMID 11101361.

[4] Rabin RA, Regina M, Doat M, Winter JC (May 2002). "5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens". Pharmacology, Biochemistry, and Behavior. 72 (1–2): 29–37. doi:10.1016/S0091-3057(01)00720-1. PMID 11900766. S2CID 6480715.

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Identifiers

IUPAC name 2-(5-fluoro-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number	22120-36-1^Y
PubChem CID	2762738
ChemSpider	2043436^Y
ChEMBL	ChEMBL1630729
CompTox Dashboard (EPA)	DTXSID30376407
Chemical and physical data
Formula	C₁₂H₁₅FN₂
Molar mass	206.264 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN(C)CCC1=CNC2=C1C=C(C=C2)F
InChI InChI=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^Y Key:BXYDWQABVPBLBU-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

5-Fluoro-DMT

See also

References