Norbuprenorphine

Norbuprenorphine
Clinical data
ATC code	None;
Identifiers
	IUPAC name (5α,6β,14β,18R)-18-[(1S)-1-hydroxy-1,2,2-trimethylpropyl]-6-methoxy-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-ol;
CAS Number	78715-23-8;
PubChem CID	114976;
ChemSpider	102911;
UNII	7E53B4O073;
CompTox Dashboard (EPA)	DTXSID60891436 ;
ECHA InfoCard	100.208.387
Chemical and physical data
Formula	C25H35NO4
Molar mass	413.558 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]([C@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN[C@@H]3Cc6c5c(c(cc6)O)O4)OC)(C(C)(C)C)O;
	InChI InChI=1S/C25H35NO4/c1-21(2,3)22(4,28)16-13-23-8-9-25(16,29-5)20-24(23)10-11-26-17(23)12-14-6-7-15(27)19(30-20)18(14)24/h6-7,16-17,20,26-28H,8-13H2,1-5H3/t16-,17-,20-,22+,23-,24+,25-/m1/s1; Key:YOYLLRBMGQRFTN-IOMBULRVSA-N;

Norbuprenorphine is a major active metabolite of the opioid modulator buprenorphine. It is a μ-opioid, δ-opioid, and nociceptin receptor full agonist,^[1]^[2] and a κ-opioid receptor partial agonist.^[2] In rats, unlike buprenorphine, norbuprenorphine produces marked respiratory depression but with very little antinociceptive effect.^[3] 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.^[3]

References

^ Yassen A, Kan J, Olofsen E, Suidgeest E, Dahan A, Danhof M (May 2007). "Pharmacokinetic-pharmacodynamic modeling of the respiratory depressant effect of norbuprenorphine in rats". The Journal of Pharmacology and Experimental Therapeutics. 321 (2): 598–607. doi:10.1124/jpet.106.115972. PMID 17283225. S2CID 11921738.
^ ^a ^b Huang P, Kehner GB, Cowan A, Liu-Chen LY (May 2001). "Comparison of pharmacological activities of buprenorphine and norbuprenorphine: norbuprenorphine is a potent opioid agonist". The Journal of Pharmacology and Experimental Therapeutics. 297 (2): 688–95. PMID 11303059.
^ ^a ^b Brown SM, Campbell SD, Crafford A, Regina KJ, Holtzman MJ, Kharasch ED (October 2012). "P-glycoprotein is a major determinant of norbuprenorphine brain exposure and antinociception". J. Pharmacol. Exp. Ther. 343 (1): 53–61. doi:10.1124/jpet.112.193433. PMC 3464040. PMID 22739506.

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Clinical data

ATC code	None
Identifiers
IUPAC name (5α,6β,14β,18R)-18-[(1S)-1-hydroxy-1,2,2-trimethylpropyl]-6-methoxy-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-ol
CAS Number	78715-23-8
PubChem CID	114976
ChemSpider	102911
UNII	7E53B4O073
CompTox Dashboard (EPA)	DTXSID60891436
ECHA InfoCard	100.208.387
Chemical and physical data
Formula	C₂₅H₃₅NO₄
Molar mass	413.558 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@]([C@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN[C@@H]3Cc6c5c(c(cc6)O)O4)OC)(C(C)(C)C)O
InChI InChI=1S/C25H35NO4/c1-21(2,3)22(4,28)16-13-23-8-9-25(16,29-5)20-24(23)10-11-26-17(23)12-14-6-7-15(27)19(30-20)18(14)24/h6-7,16-17,20,26-28H,8-13H2,1-5H3/t16-,17-,20-,22+,23-,24+,25-/m1/s1 Key:YOYLLRBMGQRFTN-IOMBULRVSA-N