Norcodeine

{{Short description|Chemical compound}}

{{Distinguish|Norco (medication)}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 412253910

| IUPAC_name = 3-Methoxy-6α-hydroxy-4,5α-epoxy-7,8-didehydromorphinan

| image = Norcodeine.svg

| image_class = skin-invert-image

| width = 180

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_BR = A2

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-03 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_CA = Schedule I

| legal_UK =

| legal_US =

| legal_DE = Anlage I

| dependency_liability = High

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 467-15-2

| ATC_prefix = none

| ATC_suffix =

| PubChem = 9925873

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 8101508

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 32W9P3T4ML

| C = 17

| H = 19

| N = 1

| O = 3

| synonyms =

| smiles = COC1=C2C3=C(C[C@@H]4[C@H]5[C@]3(CCN4)[C@@H](O2)[C@H](C=C5)O)C=C1

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = HKOIXWVRNLGFOR-KOFBORESSA-N

}}

Norcodeine is an opiate analogue that is the N-demethylated derivative of codeine. It has relatively little opioid activity in its own right,{{cite journal | vauthors = Fraser HF, Isbell H, Vanhorn GD | title = Human pharmacology and addiction liability of norcodeine | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 129 | pages = 172–7 | date = June 1960 | pmid = 13824628 }} but is formed as a metabolite of codeine following ingestion.{{cite journal | vauthors = Posey BL, Kimble SN | title = High-performance liquid chromatographic study of codeine, norcodeine, and morphine as indicators of codeine ingestion | journal = Journal of Analytical Toxicology | volume = 8 | issue = 2 | pages = 68–74 | date = 1984 | pmid = 6716978 | doi = 10.1093/jat/8.2.68 }}

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).{{Cite web | title = Quotas - 2014 | url=http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm | work = DEA Diversion Control Division }}