14-Hydroxycodeine

14-Hydroxycodeine.svg skin-invert-image Morphinan-6,14-diol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6alpha)- (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 correct chemspider YPZPXTZKBNWUTF-QMVVXIJUSA-N correct chemspider 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 correct chemspider WYMBHLXUDPDGQJ-BRJGLHKUSA-N changed ?? 4829-46-3 changed ?? (HCl) correct FDA 332OI8E5Z4 14261327 CN1CC[C@]23[C@@H]4[C@H](C=C[C@]2([C@H]1CC5=C3C(=C(C=C5)OC)O4)O)O 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 correct kegg 18 21 1 4 315.4 g/mol 08 07 Danger 302 317 332 334 P233 P260 P261 P264 P270 P271 P272 P280 P284 P301+P317 P302+P352 P304+P340 P317 P321 P330 P333+P317 P342+P316 P362+P364 P403 P501 14-Hydroxycodeine also known as hydroxycodeine, is an toxic opioid, and also an alkaloidMeshulam Haim Lavie David 1980-01-01 The alkaloidal constituents of Papaver bracteatum arya II https://www.sciencedirect.com/science/article/pii/S0031942200839345 Phytochemistry 19 12 2633–2635 10.1016/S0031-9422(00)83934-5 1980PChem..19.2633M 0031-9422 subscription PubChem 14-Hydroxycodeine https://pubchem.ncbi.nlm.nih.gov/compound/14261327 2025-12-07 pubchem.ncbi.nlm.nih.gov en an organic compound that is a minor natural product found in some plantsKunz D. A. Reddy G. S. Vatvars A. 1985 Identification of transformation products arising from bacterial oxidation of codeine by Streptomyces griseus Applied and Environmental Microbiology 50 4 831–836 10.1128/aem.50.4.831-836.1985 0099-2240 291756 3936418 1985ApEnM..50..831K and is an important intermediate in the synthesis of potent opioid analgesicsZhang Qibo Rich Joseph O. Cotterill Ian C. Pantaleone David P. Michels Peter C. 2005-05-25 14-Hydroxylation of opiates: catalytic direct autoxidation of codeinone to 14-hydroxycodeinone Journal of the American Chemical Society 127 20 7286–7287 10.1021/ja051682z 0002-7863 15898757 2005JAChS.127.7286Z such as oxycodone and other 14-hydroxylated opiate drugs. It is not used as a standalone drug and has no medical use.Zhang Qibo Rich Joseph O. Cotterill Ian C. Pantaleone David P. Michels Peter C. 2005-05-25 14-Hydroxylation of Opiates: Catalytic Direct Autoxidation of Codeinone to 14-Hydroxycodeinone https://doi.org/10.1021/ja051682z Journal of the American Chemical Society 127 20 7286–7287 10.1021/ja051682z 15898757 2005JAChS.127.7286Z 0002-7863 subscription 14-Hydroxycodeine is an alkaloid component of the plant Papaver bracteatum. 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. Toxicity 14-Hydroxycodeine is a toxic substance, acute toxic substance upon ingestion and inhalation, causes skin sensitization (contact dermatitis) and subsequent hypersensitivity to specific substances and severe allergic reactions. Possesses acute toxicity when inhaled or may cause allergy or asthma symptoms or breathing difficulties if inhaled. Chemistry 14-Hydroxycodeine is an N-methyl-14-hydroxy derivative of codeine, where hydroxylation occurs at the carbon atom in position 14 of the morphinan skeleton. References Category:Opioids Category:Heterocyclic compounds with 5 rings Category:Secondary alcohols Category:Methoxy compounds Category:Hydroxyarenes