NORCODEINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H19NO3
Molecular Weight	285.3377
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C2C[C@H]3NCC[C@@]45[C@@H](OC1=C24)[C@@H](O)C=C[C@@H]35

InChI

InChIKey=HKOIXWVRNLGFOR-KOFBORESSA-N

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

HIDE SMILES / InChI

Molecular Formula	C17H19NO3
Molecular Weight	285.3377
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22285504 | https://www.ncbi.nlm.nih.gov/pubmed/338517 | https://www.pharmgkb.org/pathway/PA146123006 | https://www.ncbi.nlm.nih.gov/pubmed/6716978

Norcodeine is the N-demethylated derivative of codeine. It has relatively little opioid activity in its own right, but is formed as a metabolite of codeine following ingestion. Codeine and its other major metabolites codeine-6-glucuronide and norcodeine have weak affinity to opioid μ-receptors.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu opioid receptor 231 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8818573 \| https://www.pharmgkb.org/pathway/PA146123006 \| https://www.ncbi.nlm.nih.gov/pubmed/22285504	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
High-performance liquid chromatographic study of codeine, norcodeine, and morphine as indicators of codeine ingestion.	1984-03-01	6716978
Methadone maintenance and narcotic blocking drugs. Appendix.	1977-10	338517
Human pharmacology and addiction liability of norcodeine.	1960-06	13824628

Patents

Sample Use Guides

In Vivo Use Guide

In a "cross-over” test, norcodeine (75 mg/80 kg) was given to 9 nontolerant subjects. Using a balanced cross-over plan, 5 nontolerant subjects received, in a 30-hour period, five doses of norcodeine in one experiment and five doses of codeine in another, the successive doses of both drugs being 75, 50, 50, 75 and 75 mg/80 kg.

Route of Administration: Oral

In Vitro Use Guide

Norcodeine (50 uM) was incubated with 5 mM to 100 mM of ethanol and the metabolism of both norethylmorphine and norcodeine was found to be inhibited by ethanol in a concentration-dependent manner.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:40:28 GMT 2025` Edited by `admin` on `Mon Mar 31 18:40:28 GMT 2025`
Record UNII	32W9P3T4ML
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NORCODEINE

Official Name

English

IDS-NN-005(SECT.2)

Preferred Name

English

N-DESMETHYLCODEINE

Common Name

English

CODEINE HYDROCHLORIDE DIHYDRATE IMPURITY H [EP IMPURITY]

Common Name

English

3-O-METHYLNORMORPHINE

Common Name

English

MORPHINAN-6-OL, 7,8-DIDEHYDRO-4,5-EPOXY-3-METHOXY-, (5.ALPHA.,6.ALPHA.)-

Systematic Name

English

CODEINE MONOHYDRATE IMPURITY H [EP IMPURITY]

Common Name

English

CODEINE PHOSPHATE HEMIHYDRATE IMPURITY H [EP IMPURITY]

Common Name

English

NORCODEINE [MI]

Common Name

English

norcodeine [INN]

Common Name

English

NORMORPHINE 3-METHYL ETHER

Common Name

English

N-DEMETHYLCODEINE

Common Name

English

Code System Code Type Description

FDA UNII

32W9P3T4ML