4′-Fluorococaine

4′-Fluorococaine
Legal status
Legal status	UK: Under Psychoactive Substances Act; US: Schedule II;
Identifiers
	IUPAC name methyl (1R,2R,3S,5S)-3-(4-fluorobenzoyloxy)-8-methyl-8-azabicyclo[3.2.1] octane-2-carboxylate;
CAS Number	134507-62-3;
PubChem CID	126112;
ChemSpider	112124 ;
UNII	6045353J3C;
CompTox Dashboard (EPA)	DTXSID10928640 ;
Chemical and physical data
Formula	C17H20FNO4
Molar mass	321.348 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)C3=CC=C(C=C3)F)C(=O)OC;
	InChI InChI=1S/C17H20FNO4/c1-19-12-7-8-13(19)15(17(21)22-2)14(9-12)23-16(20)10-3-5-11(18)6-4-10/h3-6,12-15H,7-9H2,1-2H3/t12-,13-,14-,15+/m0/s1 ; Key:JRPRINGETIYVSV-ZQDZILKHSA-N ;
	(verify)

4′-Fluorococaine is a tropane derivative drug which is a synthetic analogue of cocaine. Unlike related compounds such as the corresponding 4′-fluorophenyltropane derivative CFT and the 2′-hydroxy analogue salicylmethylecgonine, 4′-fluorococaine has only around the same potency as cocaine as an inhibitor of dopamine reuptake, but conversely it is a much stronger serotonin reuptake inhibitor than cocaine, resulting in a significantly altered pharmacological profile in animal studies.^[1]

References

^ Gatley SJ, Yu DW, Fowler JS, MacGregor RR, Schlyer DJ, Dewey SL, et al. (March 1994). "Studies with differentially labeled [11C]cocaine, [11C]norcocaine, [11C]benzoylecgonine, and [11C]- and 4'-[18F]fluorococaine to probe the extent to which [11C]cocaine metabolites contribute to PET images of the baboon brain". Journal of Neurochemistry. 62 (3): 1154–62. doi:10.1046/j.1471-4159.1994.62031154.x. PMID 8113802. S2CID 25854431.

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[1] Gatley SJ, Yu DW, Fowler JS, MacGregor RR, Schlyer DJ, Dewey SL, et al. (March 1994). "Studies with differentially labeled [11C]cocaine, [11C]norcocaine, [11C]benzoylecgonine, and [11C]- and 4'-[18F]fluorococaine to probe the extent to which [11C]cocaine metabolites contribute to PET images of the baboon brain". Journal of Neurochemistry. 62 (3): 1154–62. doi:10.1046/j.1471-4159.1994.62031154.x. PMID 8113802. S2CID 25854431.

[1]

Legal status

Legal status	UK: Under Psychoactive Substances Act US: Schedule II
Identifiers
IUPAC name methyl (1R,2R,3S,5S)-3-(4-fluorobenzoyloxy)-8-methyl-8-azabicyclo[3.2.1] octane-2-carboxylate
CAS Number	134507-62-3
PubChem CID	126112
ChemSpider	112124^Y
UNII	6045353J3C
CompTox Dashboard (EPA)	DTXSID10928640
Chemical and physical data
Formula	C₁₇H₂₀FNO₄
Molar mass	321.348 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)C3=CC=C(C=C3)F)C(=O)OC
InChI InChI=1S/C17H20FNO4/c1-19-12-7-8-13(19)15(17(21)22-2)14(9-12)23-16(20)10-3-5-11(18)6-4-10/h3-6,12-15H,7-9H2,1-2H3/t12-,13-,14-,15+/m0/s1^Y Key:JRPRINGETIYVSV-ZQDZILKHSA-N^Y
(verify)

4′-Fluorococaine

See also

References