Compound

Norbuprenorphine

Original Wikipedia articleen.wikipedia.org/wiki/Norbuprenorphine revision used (24 October 2026)

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Part of the metabolic pathway of Buprenorphine. See the timeline on the metabolic highway.

Overview

Norbuprenorphine is a major active metabolite of the opioid modulator buprenorphine. It is a μ-opioid, δ-opioid, and nociceptin receptor full agonist, and a κ-opioid receptor partial agonist. In rats, unlike buprenorphine, norbuprenorphine produces marked respiratory depression but with very little antinociceptive effect. In explanation of these properties, norbuprenorphine has been found to be a high affinity P-glycoprotein substrate, and in accordance, shows very limited blood-brain-barrier penetration.[1][2][3] WP

Chemistry

Formula: C25H35NO4 PC
CAS number: 78715-23-8 PC
Molar mass (g/mol): 413.5 PC
IUPAC name (computed by PubChem): (1S,2S,6R,14R,15R,16R)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol PC
SMILES: C[C@]([C@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN[C@@H]3CC6=C5C(=C(C=C6)O)O4)OC)(C(C)(C)C)O PC
InChIKey: YOYLLRBMGQRFTN-IOMBULRVSA-N PC
PubChem CID: 114976

Harm reduction information

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Sources

Journal / agency Yassen A, Kan J, Olofsen E, Suidgeest E, Dahan A, Danhof M. Pharmacokinetic-pharmacodynamic modeling of the respiratory depressant effect of norbuprenorphine in rats. The Journal of Pharmacology and Experimental Therapeutics. May 2007. doi:10.1124/jpet.106.115972 · PMID 17283225
Journal / agency Huang P, Kehner GB, Cowan A, Liu-Chen LY. Comparison of pharmacological activities of buprenorphine and norbuprenorphine: norbuprenorphine is a potent opioid agonist. The Journal of Pharmacology and Experimental Therapeutics. May 2001. doi:10.1016/S0022-3565(24)29586-0 · PMID 11303059
Journal / agency Brown SM, Campbell SD, Crafford A, Regina KJ, Holtzman MJ, Kharasch ED. P-glycoprotein is a major determinant of norbuprenorphine brain exposure and antinociception. J. Pharmacol. Exp. Ther. October 2012. doi:10.1124/jpet.112.193433 · PMID 22739506 · PMC3464040

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