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
Chemical and physical data
Formula	C24H27NO2
Molar mass	361.485 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 Key:JZVQXSYNZPVRTQ-FPRSRYDQSA-N
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See also

• 14-Cinnamoyloxycodeinone
• 14-Phenylpropoxymetopon
• 7-PET
• N-Phenethyl-14-ethoxymetopon
• N-Phenethylnormorphine
• RAM-378
• Ro4-1539

References

1. Casy AF, Parfitt RY. Opioid analgesics, chemistry and receptors. 1986, Plenum Press, New York. pp 37-38. ISBN 0-306-42130-5