Desocodeine

Last updated
Desocodeine
Desocodeine.svg
Names
IUPAC name
3-Methoxy-17-methyl-4,5α-epoxymorphinan
Systematic IUPAC name
(4R,4aR,7aS,12bS)-9-Methoxy-3-methyl-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinoline
Other names
Dihydrodeoxycodeine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C18H23NO2/c1-19-9-8-18-12-4-3-5-15(18)21-17-14(20-2)7-6-11(16(17)18)10-13(12)19/h6-7,12-13,15H,3-5,8-10H2,1-2H3/t12-,13+,15-,18+/m0/s1
    Key: ZJWPQUSUXBOTPF-SCGCMHLBSA-N
  • InChI=1/C18H23NO2/c1-19-9-8-18-12-4-3-5-15(18)21-17-14(20-2)7-6-11(16(17)18)10-13(12)19/h6-7,12-13,15H,3-5,8-10H2,1-2H3/t12-,13+,15-,18+/m0/s1
    Key: ZJWPQUSUXBOTPF-SCGCMHLBBV
  • O(c2c1O[C@@H]5[C@@]34c1c(cc2)C[C@@H](N(CC3)C)[C@@H]4CCC5)C
Properties
C18H23NO2
Molar mass 285.387 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Desocodeine is a potent semi-synthetic opioid which is the penultimate intermediate in the manufacture of desomorphine from codeine. [1] [2] Desocodeine is a potent analgesic, being as potent as morphine. It is partially metabolized into desomorphine, among others, after parenteral and oral administration. [3] [4]

Since 1936, desocodeine has been classified in the US as a Schedule I controlled substance under the Controlled Substances Act, indicating that the FDA has determined that there are no legal medicinal uses for it. [5]

In Canada, desocodeine is classified as a Schedule I drug under the Controlled Drugs and Substances Act.


Synthesis of desomorphine from codeine Synthesis of Desomorphine from Codein.svg
Synthesis of desomorphine from codeine

References

  1. ↑ PubChem. "Desocodeine". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-11-15.
  2. ↑ "Desocodeine | C18H23NO2 | ChemSpider". www.chemspider.com. Retrieved 2022-11-15.
  3. ↑ Eddy NB (1 November 1935). "STUDIES OF MORPHINE, CODEINE AND THEIR DERIVATIVES X. DESOXYMORPHINE-C, DESOXYCODEINE-C AND THEIR HYDROGENATED DERIVATIVES". Journal of Pharmacology and Experimental Therapeutics. 55 (1): 257–267. S2CID   93217792.
  4. ↑ Himmelsbach Clifton K (1939). "STUDIES OF CERTAIN ADDICTION CHARACTERISTICS OF (a) DIHYDROMORPHINE ("PARAMORPHAN"), (b) DIHYDRODESOXYMORPHINE-D ("DESOMORPHINE"), (c) DIHYDRODESOXYCODEINE-D ("DESOCODEINE"), AND (d) METHYLDIHYDROMORPHINONE ("METOPON")". Journal of Pharmacology and Experimental Therapeutics. 67: 239–249. S2CID   102042333.
  5. ↑ "DEA Diversion Control Division". Archived from the original on 4 March 2016. Retrieved 4 May 2015.



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