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

[H][C@@]12OC3=C4C(C[C@H]5NCC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3OC

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

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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 221 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 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

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

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.

Name

Type

Language

NORCODEINE

Official 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

IDS-NN-005(SECT.2)

Code

English

N-DEMETHYLCODEINE

Common Name

English

Code System Code Type Description

FDA UNII

32W9P3T4ML