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 ;
CompTox Dashboard (EPA)	DTXSID30376407 ;
Chemical and physical data
Formula	C12H15FN2
Molar mass	206.259 g/mol 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 ;
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5-Fluoro-N,N-dimethyltryptamine (5-fluoro-DMT) is a tryptamine derivative related to compounds such as 5-bromo-DMT and 5-MeO-DMT. 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.^[1]^[2]

References

^ Blair, JB; Kurrasch-Orbaugh, D; Marona-Lewicka, D; Cumbay, MG; Watts, VJ; Barker, EL; Nichols, DE (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 (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.

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[1] Blair, JB; Kurrasch-Orbaugh, D; Marona-Lewicka, D; Cumbay, MG; Watts, VJ; Barker, EL; Nichols, DE (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.

[2] Rabin, RA; Regina, M; Doat, M; Winter, JC (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.

[1]

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See also

References