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Details

Stereochemistry ACHIRAL
Molecular Formula C20H25NO
Molecular Weight 295.4186
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORMETHADONE

SMILES

CCC(=O)C(CCN(C)C)(C1=CC=CC=C1)C2=CC=CC=C2

InChI

InChIKey=WCJFBSYALHQBSK-UHFFFAOYSA-N
InChI=1S/C20H25NO/c1-4-19(22)20(15-16-21(2)3,17-11-7-5-8-12-17)18-13-9-6-10-14-18/h5-14H,4,15-16H2,1-3H3

HIDE SMILES / InChI

Description

Normethadone is a derivate of opioid analgetic methadone, used as component of antitussive drops in Canada. Illicit drug.

CNS Activity

CNS Active
4002

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Mu-type opioid receptor
61
Target ID: P33535|||Q64064
Gene ID: 25601.0
Gene Symbol: Oprm1
Target Organism: Rattus norvegicus (Rat)
Agonist
2752
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Cophylac

Approved Use

Cough
Doses

Doses

DosePopulationAdverse events​
100 mg single, oral
Overdose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6481543/
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/6481543/
Disc. AE: Hyporeflexia, Coma...
AEs leading to
discontinuation/dose reduction:
Hyporeflexia
Coma
Fever
Disseminated intravascular coagulation
Hepatocellular injury
Renal failure (grade 1)
Sources:
https://pubmed.ncbi.nlm.nih.gov/6481543/
15 drop 2 times / day multiple, oral
Recommended
Dose: 15 drop, 2 times / day
Route: oral
Route: multiple
Dose: 15 drop, 2 times / day
Sources:
https://pdf.hres.ca/dpd_pm/00045654.PDF
unhealthy, CHILD|ADOLESCENT|ADULT
Health Status: unhealthy
Age Group: CHILD|ADOLESCENT|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pdf.hres.ca/dpd_pm/00045654.PDF
Disc. AE: Opioid abuse, Opioid type dependence...
AEs leading to
discontinuation/dose reduction:
Opioid abuse
Opioid type dependence
Respiratory depression (grade 3-5)
Neonatal opioid withdrawal syndrome (grade 4)
Sources:
https://pdf.hres.ca/dpd_pm/00045654.PDF
AEs

AEs

AESignificanceDosePopulation
Coma Disc. AE
100 mg single, oral
Overdose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6481543/
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/6481543/
Disseminated intravascular coagulation Disc. AE
100 mg single, oral
Overdose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6481543/
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/6481543/
Fever Disc. AE
100 mg single, oral
Overdose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6481543/
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/6481543/
Hepatocellular injury Disc. AE
100 mg single, oral
Overdose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6481543/
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/6481543/
Hyporeflexia Disc. AE
100 mg single, oral
Overdose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6481543/
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/6481543/
Renal failure grade 1
Disc. AE
100 mg single, oral
Overdose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6481543/
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/6481543/
Opioid abuse Disc. AE
15 drop 2 times / day multiple, oral
Recommended
Dose: 15 drop, 2 times / day
Route: oral
Route: multiple
Dose: 15 drop, 2 times / day
Sources:
https://pdf.hres.ca/dpd_pm/00045654.PDF
unhealthy, CHILD|ADOLESCENT|ADULT
Health Status: unhealthy
Age Group: CHILD|ADOLESCENT|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pdf.hres.ca/dpd_pm/00045654.PDF
Opioid type dependence Disc. AE
15 drop 2 times / day multiple, oral
Recommended
Dose: 15 drop, 2 times / day
Route: oral
Route: multiple
Dose: 15 drop, 2 times / day
Sources:
https://pdf.hres.ca/dpd_pm/00045654.PDF
unhealthy, CHILD|ADOLESCENT|ADULT
Health Status: unhealthy
Age Group: CHILD|ADOLESCENT|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pdf.hres.ca/dpd_pm/00045654.PDF
Respiratory depression grade 3-5
Disc. AE
15 drop 2 times / day multiple, oral
Recommended
Dose: 15 drop, 2 times / day
Route: oral
Route: multiple
Dose: 15 drop, 2 times / day
Sources:
https://pdf.hres.ca/dpd_pm/00045654.PDF
unhealthy, CHILD|ADOLESCENT|ADULT
Health Status: unhealthy
Age Group: CHILD|ADOLESCENT|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pdf.hres.ca/dpd_pm/00045654.PDF
Neonatal opioid withdrawal syndrome grade 4
Disc. AE
15 drop 2 times / day multiple, oral
Recommended
Dose: 15 drop, 2 times / day
Route: oral
Route: multiple
Dose: 15 drop, 2 times / day
Sources:
https://pdf.hres.ca/dpd_pm/00045654.PDF
unhealthy, CHILD|ADOLESCENT|ADULT
Health Status: unhealthy
Age Group: CHILD|ADOLESCENT|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pdf.hres.ca/dpd_pm/00045654.PDF
PubMed

PubMed

TitleDatePubMed
Phenyl-substituted normethadones: synthesis and pharmacology.
1995 Mar
Simultaneous screening and quantification of 25 opioid drugs in post-mortem blood and urine by liquid chromatography-tandem mass spectrometry.
2009 Apr 15

Sample Use Guides

In Vivo Use Guide
Cophylac (normethadone HCl 10 mg and p-hydroxyephedrine HCl 20 mg): 15 drops twice daily
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
HOECHST-10582
Preferred Name English
NORMETHADONE
INN   MI   WHO-DD  
INN  
Official Name English
1,1-DIPHENYL-1-(2-DIMETHYLAMINOETHYL)-2-BUTANONE
Systematic Name English
NORMETHADONE [MI]
Common Name English
normethadone [INN]
Common Name English
6-DIMETHYLAMINO-4,4-DIPHENYL-3-HEXANONE
Systematic Name English
MEPIDON
Common Name English
ISOMETHADONE I
Common Name English
HOECHST 10582
Code English
IDS-NN-007
Code English
J5.915C
Code English
NSC-19598
Code English
Normethadone [WHO-DD]
Common Name English
EUCOPON
Common Name English
Classification Tree Code System Code
DEA NO. 9635
Created by admin on Mon Mar 31 18:31:07 GMT 2025 , Edited by admin on Mon Mar 31 18:31:07 GMT 2025
WHO-ATC R05DA06
Created by admin on Mon Mar 31 18:31:07 GMT 2025 , Edited by admin on Mon Mar 31 18:31:07 GMT 2025
NCI_THESAURUS C67413
Created by admin on Mon Mar 31 18:31:08 GMT 2025 , Edited by admin on Mon Mar 31 18:31:08 GMT 2025
WHO-VATC QR05DA06
Created by admin on Mon Mar 31 18:31:07 GMT 2025 , Edited by admin on Mon Mar 31 18:31:07 GMT 2025
Code System Code Type Description
RXCUI
32009
Created by admin on Mon Mar 31 18:31:08 GMT 2025 , Edited by admin on Mon Mar 31 18:31:08 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID6057748
Created by admin on Mon Mar 31 18:31:08 GMT 2025 , Edited by admin on Mon Mar 31 18:31:08 GMT 2025
PRIMARY
NCI_THESAURUS
C76843
Created by admin on Mon Mar 31 18:31:07 GMT 2025 , Edited by admin on Mon Mar 31 18:31:07 GMT 2025
PRIMARY
WIKIPEDIA
NORMETHADONE
Created by admin on Mon Mar 31 18:31:08 GMT 2025 , Edited by admin on Mon Mar 31 18:31:08 GMT 2025
PRIMARY Normethadone (INN, BAN; brand names Cophylac, Dacartil, Eucopon, Mepidon, Noramidone, Normedon, and others), also known as desmethylmethadone or phenyldimazone, is a synthetic opioid analgesic and antitussive agent.Normethadone is listed under the Single Convention on Narcotic Drugs 1961 and is an Schedule I Narcotic controlled substance in the United States, with a DEA ACSCN of 9635 and an annual manufacturing quota of 2 grams.
DRUG CENTRAL
1969
Created by admin on Mon Mar 31 18:31:08 GMT 2025 , Edited by admin on Mon Mar 31 18:31:08 GMT 2025
PRIMARY
FDA UNII
KR2L2A68XL
Created by admin on Mon Mar 31 18:31:08 GMT 2025 , Edited by admin on Mon Mar 31 18:31:08 GMT 2025
PRIMARY
NSC
19598
Created by admin on Mon Mar 31 18:31:08 GMT 2025 , Edited by admin on Mon Mar 31 18:31:08 GMT 2025
PRIMARY
INN
467
Created by admin on Mon Mar 31 18:31:07 GMT 2025 , Edited by admin on Mon Mar 31 18:31:07 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-401-1
Created by admin on Mon Mar 31 18:31:08 GMT 2025 , Edited by admin on Mon Mar 31 18:31:08 GMT 2025
PRIMARY
EVMPD
SUB09376MIG
Created by admin on Mon Mar 31 18:31:07 GMT 2025 , Edited by admin on Mon Mar 31 18:31:07 GMT 2025
PRIMARY
MERCK INDEX
m8068
Created by admin on Mon Mar 31 18:31:08 GMT 2025 , Edited by admin on Mon Mar 31 18:31:08 GMT 2025
PRIMARY Merck Index
CAS
467-85-6
Created by admin on Mon Mar 31 18:31:07 GMT 2025 , Edited by admin on Mon Mar 31 18:31:07 GMT 2025
PRIMARY
SMS_ID
100000083620
Created by admin on Mon Mar 31 18:31:08 GMT 2025 , Edited by admin on Mon Mar 31 18:31:08 GMT 2025
PRIMARY
PUBCHEM
10090
Created by admin on Mon Mar 31 18:31:08 GMT 2025 , Edited by admin on Mon Mar 31 18:31:08 GMT 2025
PRIMARY
DRUG BANK
DB11609
Created by admin on Mon Mar 31 18:31:08 GMT 2025 , Edited by admin on Mon Mar 31 18:31:08 GMT 2025
PRIMARY
MESH
C005845
Created by admin on Mon Mar 31 18:31:07 GMT 2025 , Edited by admin on Mon Mar 31 18:31:07 GMT 2025
PRIMARY
ChEMBL
CHEMBL346331
Created by admin on Mon Mar 31 18:31:08 GMT 2025 , Edited by admin on Mon Mar 31 18:31:08 GMT 2025
PRIMARY
ACTIVE MOIETY
Structure of NORMETHADONE
PARENT (SALT/SOLVATE)
Structure of NORMETHADONE OXALATE
PARENT (SALT/SOLVATE)
Structure of NORMETHADONE HYDROCHLORIDE
PARENT (SALT/SOLVATE)
Structure of NORMETHADONE HYDROBROMIDE
SALT/SOLVATE (PARENT)
Structure of NORMETHADONE PICRATE
NIH
NCATS
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