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
3D model (JSmol)
UNII
  • 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 checkY
    Key: WYMBHLXUDPDGQJ-BRJGLHKUSA-N checkY
  • 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
  • CN1CC[C@]23[C@@H]4[C@H](C=C[C@]2([C@H]1CC5=C3C(=C(C=C5)OC)O4)O)O
Properties
C18H21NO4
Molar mass 315.4 g/mol
Hazards
GHS labelling:
GHS08: Health hazard GHS07: Exclamation mark
Danger
H302, H317, H332, H334
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).

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]

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

14-Hydroxycodeine is a hazardous 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

  1. ^ a b Meshulam, Haim; Lavie, David (1980-01-01). "The alkaloidal constituents of Papaver bracteatum arya II". Phytochemistry. 19 (12): 2633–2635. Bibcode:1980PChem..19.2633M. doi:10.1016/S0031-9422(00)83934-5. ISSN 0031-9422.
  2. ^ a b PubChem. "14-Hydroxycodeine". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-12-07.
  3. ^ a b Kunz, 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. Bibcode:1985ApEnM..50..831K. doi:10.1128/aem.50.4.831-836.1985. ISSN 0099-2240. PMC 291756. PMID 3936418.
  4. ^ 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". Journal of the American Chemical Society. 127 (20): 7286–7287. Bibcode:2005JAChS.127.7286Z. doi:10.1021/ja051682z. ISSN 0002-7863. PMID 15898757.
  5. ^ 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". Journal of the American Chemical Society. 127 (20): 7286–7287. Bibcode:2005JAChS.127.7286Z. doi:10.1021/ja051682z. ISSN 0002-7863. PMID 15898757.

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