Nortilidine

Nortilidine
Identifiers
	IUPAC name ethyl (1R,2S)-2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylate;
CAS Number	38677-94-0;
ChEMBL	ChEMBL1614654;
CompTox Dashboard (EPA)	DTXSID10191256 ;
Chemical and physical data
Formula	H21NO2
Molar mass	259.3434 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCOC([C@@]1(C2=CC=CC=C2)CCC=C[C@@H]1NC)=O;
	InChI 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+/m1/s1; Key:InChIKey=PDJZPNKVLDWEKI-ZBFHGGJFSA-N;

Nortilidine^[1] is the active metabolite of the drug 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 (1R,2S) isomer^[3]. The (1S,2R) isomer has NMDA antagonist activity. The drug also acts as a dopamine reuptake inhibitor.

References

^ US Patent 3792080 - Process for Substituted Cyclohexenes & it's 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)

[1] US Patent 3792080 - Process for Substituted Cyclohexenes & it's 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)

[1]

[2]

[3]

See also

References