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Norbuprenorphine-3-glucuronide

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Chemical compound

Pharmaceutical compound

Norbuprenorphine-3-glucuronide
Clinical data

ATC code	None
Identifiers
IUPAC name (5β,7β)-7-[(2R)-2-Hydroxy-3,3-dimethyl-2-butanyl]-6-methoxy-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-yl (5ξ)-β-D-lyxo-hexopyranosiduronic acid
CAS Number	469887-29-4
PubChemCID	46782577
ChemSpider	35517741
UNII	YPZ2R0PR50
ECHA InfoCard	100.230.712
Chemical and physical data
Formula	C₃₁H₄₃NO₁₀
Molar mass	589.682 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[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O)O)O4)OC)(C(C)(C)C)O
InChI InChI=1S/C31H43NO10/c1-27(2,3)28(4,38)16-13-29-8-9-31(16,39-5)26-30(29)10-11-32-17(29)12-14-6-7-15(22(42-26)18(14)30)40-25-21(35)19(33)20(34)23(41-25)24(36)37/h6-7,16-17,19-21,23,25-26,32-35,38H,8-13H2,1-5H3,(H,36,37)/t16-,17-,19+,20+,21-,23+,25-,26-,28+,29-,30+,31-/m1/s1 Key:OOLGGESLZHGXGC-TXYLTYGDSA-N

Norbuprenorphine-3-glucuronide (N3G) is a majoractive metabolite of theopioid modulator buprenorphine.^[1] It hasaffinity for theκ-opioid receptor (K_i = 300 nM) and thenociceptin receptor (K_i = 18 μM), but not for theμ- orδ-opioid receptors.^[1] Whether N3G acts as anagonist orantagonist of each of the former two respective sites has yet to be determined.^[2] In animals, N3G has been found to producesedation, decreasedlocomotion, and a small amount ofantinociception, properties which are consistent with the effects of κ-opioid receptor agonists.^[1] In addition, N3G has been found to reducetidal volume but notrespiratory rate.^[1] Unlikenorbuprenorphine, but similarly to buprenorphine andbuprenorphine-3-glucuronide, N3G is not asubstrate forP-glycoprotein.^[2] However, due to its highlyhydrophilic nature, N3G nonetheless passes theblood-brain-barrier in only very small amounts.^[2]