Norcodeine

Norcodeine
Clinical data
ATC code
  • none
Legal status
Legal status
  • CA: Schedule I
  • DE: Anlage I (Authorized scientific use only)
Identifiers
IUPAC name
  • 3-Methoxy-6α-hydroxy-4,5α-epoxy-7,8-didehydromorphinan
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.006.718
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Chemical and physical data
FormulaC17H19NO3
Molar mass285.343 g·mol−1
3D model (JSmol)
SMILES
  • COC1=C2C3=C(C[C@@H]4[C@H]5[C@]3(CCN4)[C@@H](O2)[C@H](C=C5)O)C=C1
InChI
  • InChI=1S/C17H19NO3/c1-20-13-5-2-9-8-11-10-3-4-12(19)16-17(10,6-7-18-11)14(9)15(13)21-16/h2-5,10-12,16,18-19H,6-8H2,1H3/t10-,11+,12-,16-,17-/m0/s1 ☒N
  • Key:HKOIXWVRNLGFOR-KOFBORESSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Norcodeine is an opiate analogue that is the N-demethylated derivative of codeine. It has relatively little opioid activity in its own right,[1] but is formed as a metabolite of codeine following ingestion.[2]

Norcodeine is a Schedule I Narcotic controlled substance in the US with the ACSCN of 9309 and zero annual manufacturing quota. The salts in use are the acetate (free base conversion ratio 0.826), hydroiodide (0.662), hydrochloride (0.759), nitrate (0.819), platinichloride (0.582), and sulphate (0.744).[3]

See also

References

  1. ↑ Fraser HF, Isbell H, Vanhorn GD (June 1960). "Human pharmacology and addiction liability of norcodeine". The Journal of Pharmacology and Experimental Therapeutics. 129: 172–7. PMID 13824628.
  2. ↑ Posey BL, Kimble SN (1984). "High-performance liquid chromatographic study of codeine, norcodeine, and morphine as indicators of codeine ingestion". Journal of Analytical Toxicology. 8 (2): 68–74. doi:10.1093/jat/8.2.68. PMID 6716978.
  3. ↑ "Quotas - 2014". DEA Diversion Control Division.
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