Noroxycodone

Noroxycodone
Clinical data
Dependence; liability	High (same oxycodone)
Identifiers
	IUPAC name (4R,4aS,7aR,12bS)-4a-Hydroxy-9-methoxy-1,2,3,4,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one;
CAS Number	57664-96-7;
PubChem CID	5489120;
ChemSpider	4590081;
UNII	95Q949779D;
CompTox Dashboard (EPA)	DTXSID60973261 ;
ECHA InfoCard	100.055.334
Chemical and physical data
Formula	C17H19NO4
Molar mass	301.342 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=C2C3=C(C[C@@H]4[C@]5([C@]3(CCN4)[C@@H](O2)C(=O)CC5)O)C=C1;
	InChI InChI=1S/C17H19NO4/c1-21-11-3-2-9-8-12-17(20)5-4-10(19)15-16(17,6-7-18-12)13(9)14(11)22-15/h2-3,12,15,18,20H,4-8H2,1H3/t12-,15+,16+,17-/m1/s1; Key:RIKMCJUNPCRFMW-ISWURRPUSA-N;

Noroxycodone is the major metabolite of the opioid analgesic oxycodone. It is formed from oxycodone in the liver via N-demethylation predominantly by CYP3A4. Noroxycodone binds to and activates the μ-opioid receptor (MOR) similarly to oxycodone, although with one-third of the affinity of oxycodone and 5- to 10-fold lower activational potency. However, although a potent MOR agonist, noroxycodone poorly crosses the blood-brain-barrier into the central nervous system, and for this reason, is only minimally analgesic in comparison.

Clinical data

Dependence liability	High (same oxycodone)
Identifiers
IUPAC name (4R,4aS,7aR,12bS)-4a-Hydroxy-9-methoxy-1,2,3,4,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one
CAS Number	57664-96-7
PubChem CID	5489120
ChemSpider	4590081
UNII	95Q949779D
CompTox Dashboard (EPA)	DTXSID60973261
ECHA InfoCard	100.055.334
Chemical and physical data
Formula	C₁₇H₁₉NO₄
Molar mass	301.342 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COC1=C2C3=C(C[C@@H]4[C@]5([C@]3(CCN4)[C@@H](O2)C(=O)CC5)O)C=C1
InChI InChI=1S/C17H19NO4/c1-21-11-3-2-9-8-12-17(20)5-4-10(19)15-16(17,6-7-18-12)13(9)14(11)22-15/h2-3,12,15,18,20H,4-8H2,1H3/t12-,15+,16+,17-/m1/s1 Key:RIKMCJUNPCRFMW-ISWURRPUSA-N