N-Phenethylnormorphine

N-Phenethylnormorphine is an opioid analgesic drug derived from morphine by replacing the N-methyl group with β-phenethyl.^[1] It is around eight to fourteen times more potent than morphine as a result of this modification,^[2] in contrast to most other N-substituted derivatives of morphine, which are substantially less active, or act as antagonists.^[3] Binding studies have helped to explain the increased potency of N-phenethylnormorphine, showing that the phenethyl group extends out to reach an additional binding point deeper inside the μ-opioid receptor cleft, analogous to the binding of the phenethyl group on fentanyl.^[4][5]

PubChem CID

• 46908217

ChemSpider

• 34254115 ^Y

ChEMBL

• ChEMBL3275472

CompTox Dashboard (EPA)

• DTXSID101018229

Quick facts Identifiers, PubChem CID ...

N-Phenethylnormorphine

Identifiers
IUPAC name 3,6-dihydroxy-7,8-didehydro-4,5α-epoxy-17-(2-phenylethyl)morphinan
PubChem CID	46908217
ChemSpider	34254115 Y
ChEMBL	ChEMBL3275472
CompTox Dashboard (EPA)	DTXSID101018229
Chemical and physical data
Formula	C24H25NO3
Molar mass	375.468 g·mol−1
3D model (JSmol)	Interactive image
SMILES c1ccc(cc1)CCN2CC[C@]34c5c6ccc(c5O[C@H]3[C@H](C=C[C@H]4[C@H]2C6)O)O
InChI InChI=1S/C24H25NO3/c26-19-8-6-16-14-18-17-7-9-20(27)23-24(17,21(16)22(19)28-23)11-13-25(18)12-10-15-4-2-1-3-5-15/h1-9,17-18,20,23,26-27H,10-14H2/t17-,18+,20-,23-,24-/m0/s1 Key:BXKJGGVENHTVBF-JFDOVZFRSA-N
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