Norcodeine

Norcodeine
Clinical data
Dependence; liability	High
ATC code	none;
Legal status
Legal status	BR: Class A2 (Narcotic drugs); 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 ;
PubChem CID	9925873;
ChemSpider	8101508 ;
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 ; Key:HKOIXWVRNLGFOR-KOFBORESSA-N ;
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Norcodeine is an opiate analogue that is the N-demethylated derivative of codeine. It has relatively little opioid activity in its own right,^[2] but is formed as a metabolite of codeine following ingestion.^[3]

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).^[4]

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-03.
^ 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.
^ 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.
^ "Quotas - 2014". DEA Diversion Control Division.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-03.

[2] 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.

[pmid6716978-3] 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.

[4] "Quotas - 2014". DEA Diversion Control Division.

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Clinical data

Dependence liability	High
ATC code	none
Legal status
Legal status	BR: Class A2 (Narcotic drugs)^[1] 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
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