Molecule ID: 30131

IUPAC Name: ethyl (1S,2R)-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate

Description: The molecule is an ethyl 2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate that has S configuration at the carbon bearing the phenyl group and R configuration at the carbon bearing the dimethylamino group. The opioid analgesic tilidine is the racemate comprising equimolar amounts of dextilidine and its enantiomer, ent-dextilidine. A prodrug, tilidine is converted by the liver to the active analgesic, nortilidine; virtually all of the opioid activity resides in the (1S,2R) isomer (i.e. the isomer derived from dextilidine). It has a role as an opioid analgesic and a prodrug. It is an enantiomer of an ent-dextilidine.

SMILES: CCOC(=O)[C@]1(c2ccccc2)CCC=C[C@H]1N(C)C

SELFIES: [C][C][O][C][=Branch1][C][=O][C@][Branch1][=Branch2][C][=C][C][=C][C][=C][Ring1][=Branch1][C][C][C][=C][C@H1][Ring1][N][N][Branch1][C][C][C]

InChI: InChI=1S/C17H23NO2/c1-4-20-16(19)17(14-10-6-5-7-11-14)13-9-8-12-15(17)18(2)3/h5-8,10-12,15H,4,9,13H2,1-3H3/t15-,17+/m1/s1

Molecular Properties:
- Polar Surface Area: 29.5 Ų
- LogP: 3.1