Nortilidine

Nortilidine
Identifiers
	IUPAC name ethyl (1R,2S)-2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylate;
CAS Number	38677-94-0;
PubChem CID	162321;
ChemSpider	142535;
UNII	7145G6817J;
ChEBI	CHEBI:77839 ;
ChEMBL	ChEMBL1614654;
CompTox Dashboard (EPA)	DTXSID10191256 ;
Chemical and physical data
Formula	C16H21NO2
Molar mass	259.3434 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCOC(=O)[C@]1(CCC=C[C@@H]1NC)C2=CC=CC=C2;
	InChI InChI=1S/C16H21NO2/c1-3-19-15(18)16(13-9-5-4-6-10-13)12-8-7-11-14(16)17-2/h4-7,9-11,14,17H,3,8,12H2,1-2H3/t14-,16+/m0/s1; Key:PDJZPNKVLDWEKI-GOEBONIOSA-N;

Nortilidine^[1] is the major active metabolite of tilidine. It is formed from tilidine by demethylation in the liver. The racemate has opioid analgesic effects roughly equivalent in potency to that of morphine^[2] but virtually all of the opioid activity resides in the (1S,2R) isomer.^[3] The (1R,2S) isomer has NMDA antagonist activity. The drug also acts as a dopamine reuptake inhibitor.^[4] The reversed-ester of nortilidine is also known^[5] which has almost identical properties to nortilidine.^[6]

References

^ US Patent 3792080 - Process for Substituted Cyclohexenes its Products
^ J Clin Pharmacol. 2002 Nov ;42 (11):1257-61 - Sequential first-pass metabolism of nortilidine: the active metabolite of the synthetic opioid drug tilidine
^ Opiates: George R. Lenz page 439, Table 9-30 (78)
^ Schifano, Fabrizio; Orsolini, Laura; Duccio Papanti, G.; Corkery, John M. (2015). "Novel psychoactive substances of interest for psychiatry". World Psychiatry. 14 (1): 15–26. doi:10.1002/wps.20174. ISSN 1723-8617. PMC 4329884.
^ US Patent 4291059 - Cycloaromatic compounds, analgesic Properties thereof and Method of use thereof as analgesic
^ Personal Communication with Derek P. Reynolds

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[1] US Patent 3792080 - Process for Substituted Cyclohexenes its Products

[2] J Clin Pharmacol. 2002 Nov ;42 (11):1257-61 - Sequential first-pass metabolism of nortilidine: the active metabolite of the synthetic opioid drug tilidine

[3] Opiates: George R. Lenz page 439, Table 9-30 (78)

[SchifanoOrsolini2015-4] Schifano, Fabrizio; Orsolini, Laura; Duccio Papanti, G.; Corkery, John M. (2015). "Novel psychoactive substances of interest for psychiatry". World Psychiatry. 14 (1): 15–26. doi:10.1002/wps.20174. ISSN 1723-8617. PMC 4329884.

[5] US Patent 4291059 - Cycloaromatic compounds, analgesic Properties thereof and Method of use thereof as analgesic

[6] Personal Communication with Derek P. Reynolds

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See also

References