14-Hydroxycodeine

14-Hydroxycodeine
Names
	Systematic IUPAC name (4R,4aS,7S,7aR,12bS)-9-methoxy-3-methyl-1,2,4,7,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7-diol
	Other names Morphinan-6,14-diol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6alpha)-
Identifiers
CAS Number	4829-46-3 ;
3D model (JSmol)	Interactive image;
PubChem CID	14261327;
UNII	332OI8E5Z4 ;
CompTox Dashboard (EPA)	DTXSID50197474 ;
	InChI InChI=1S/C18H21NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-6,11,13,16,20-21H,7-9H2,1-2H3/t11-,13+,16-,17-,18+/m0/s1 Key: WYMBHLXUDPDGQJ-BRJGLHKUSA-N ; InChI=1S/C18H21NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-6,11,13,16,20-21H,7-9H2,1-2H3/t11-,13+,16-,17-,18+/m0/s1 Key: YPZPXTZKBNWUTF-QMVVXIJUSA-N;
	SMILES CN1CC[C@]23[C@@H]4[C@H](C=C[C@]2([C@H]1CC5=C3C(=C(C=C5)OC)O4)O)O;
Properties
Chemical formula	C18H21NO4
Molar mass	315.4 g/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H317, H332, H334
Precautionary statements	P233, P260, P264, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P317, P321, P330, P333+P317, P342+P316, P362+P364, P403, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

14-Hydroxycodeine also known as hydroxycodeine, is an toxic opioid, and also an alkaloid^[1]^[2] an organic compound that is a minor natural product found in some plants and bacteria^[3] and is an important intermediate in the synthesis of potent opioid analgesics^[4] such as oxycodone and other 14-hydroxylated opiate drugs. It is not used as a standalone drug and has no medical use.^[5] 14-Hydroxycodeine is an alkaloid component of the plant Papaver bracteatum.^[1]^[2]

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Transformations occurring during bacterial oxidation of codeine by Streptomyces griseus: 14-hydroxycodeine and norcodeine were rigorously identified as products arising from codeine oxidation by Streptomyces griseus.^[3]

Toxicity