N-Phenethylnordesomorphine

N-Phenethylnordesomorphine is an opiate analgesic drug derived from desomorphine by replacing the N-methyl group with β-phenethyl. Since desomorphine is already around eight times more potent than morphine, the additional boost in binding affinity produced by using the larger phenethyl group makes N-phenethylnordesomorphine a highly potent analgesic drug, some 85x more potent than morphine,[1] and a similar strength to the closely related morphinan derivative phenomorphan.

N-Phenethylnordesomorphine

Identifiers
IUPAC name 3-hydroxy-4,5α-epoxy-17-(2-phenylethyl)morphinan
ChemSpider	26231038 Y
Chemical and physical data
Formula	C24H27NO2
Molar mass	361.477 g/mol g·mol−1
3D model (JSmol)	Interactive image
SMILES [H][C@@]12[C@]3(CCN4CCC5=CC=CC=C5)C6=C(O2)C(O)=CC=C6C[C@@H]4[C@]3([H])CCC1
InChI InChI=1S/C24H27NO2/c26-20-10-9-17-15-19-18-7-4-8-21-24(18,22(17)23(20)27-21)12-14-25(19)13-11-16-5-2-1-3-6-16/h1-3,5-6,9-10,18-19,21,26H,4,7-8,11-15H2/t18-,19+,21-,24+/m0/s1 Y Key:JZVQXSYNZPVRTQ-FPRSRYDQSA-N Y
(verify)