Norcodeine

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

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	467-15-2^Y
PubChem CID	9925873
ChemSpider	8101508^N
UNII	32W9P3T4ML
CompTox Dashboard (EPA)	DTXSID8046327
ECHA InfoCard	100.006.718
Chemical and physical data
Formula	C17H19NO3
Molar mass	285.343 g·mol^−1
3D model (JSmol)	Interactive image
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
^NY (what is this?)  (verify)

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

• Nalodeine

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.