Normethadone

Identification

Name
Normethadone
Accession Number
DB11609
Type
Small Molecule
Groups
Approved, Illicit
Description

Normethadone is used as an opioid antitussive in combination with Oxilofrine. It is marketed in Canada by Valeant under the tradename Cophylac.

Structure
Thumb
Synonyms
  • 6-dimethylamino-4,4-diphenyl-3-hexanone
  • Desmethylmethadone
  • Isomethadone I
External IDs
Hoechst 10582 / IDS-NN-007 / J5.915C / NSC-19598
Product Ingredients
IngredientUNIICASInChI Key
Normethadone hydrochlorideOIV53II16G847-84-7GYWUCVKLUKFJLC-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
CophylacNormethadone hydrochloride (10 mg) + Oxilofrine hydrochloride (20 mg)Solution / dropsOralValeant Canada Lp Valeant Canada S.E.C.1997-01-23Not applicableCanada
CophylacNormethadone hydrochloride (10 mg) + Oxilofrine hydrochloride (20 mg)Solution / dropsOralHoechst Canada Inc.1957-12-31Not applicableCanada
Cophylac DropsNormethadone hydrochloride (10 mg) + Oxilofrine hydrochloride (20 mg)Solution / dropsOralHoechst Roussel Canada Inc.1993-12-311999-08-11Canada
Categories
UNII
KR2L2A68XL
CAS number
467-85-6
Weight
Average: 295.426
Monoisotopic: 295.193614429
Chemical Formula
C20H25NO
InChI Key
WCJFBSYALHQBSK-UHFFFAOYSA-N
InChI
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
IUPAC Name
6-(dimethylamino)-4,4-diphenylhexan-3-one
SMILES
CCC(=O)C(CCN(C)C)(C1=CC=CC=C1)C1=CC=CC=C1

Pharmacology

Indication

For use in the treatment of cough when other less potent treatments have failed [Label].

Pharmacodynamics

Normethadone is an opioid which suppresses coughing by central and peripheral mechanisms [Label] [1].

Mechanism of action

Normethadone activates central opioid receptors in the medulla to supress the cough reflex [1]. It also likely activates peripheral opioid receptors to inhibit signalling by irritant receptors of the airway.

Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

The toxic effects of normethadone are similar to those of other opioids. It can produce respiratory depression, depression of central nervous system function, and constipation [Label].

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Normethadone.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Normethadone is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when 3,4-Methylenedioxyamphetamine is combined with Normethadone.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Normethadone.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Normethadone.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of serotonin syndrome can be increased when Normethadone is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Normethadone.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of serotonin syndrome can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Normethadone.
AcepromazineThe risk or severity of hypotension and central nervous system depression can be increased when Acepromazine is combined with Normethadone.
AceprometazineThe risk or severity of hypotension and central nervous system depression can be increased when Aceprometazine is combined with Normethadone.
Food Interactions
Not Available

References

General References
  1. Adcock JJ: Peripheral opioid receptors and the cough reflex. Respir Med. 1991 Jan;85 Suppl A:43-6. [PubMed:1852031]
External Links
KEGG Drug
D07384
PubChem Compound
10090
PubChem Substance
347828004
ChemSpider
9687
ChEBI
135242
ChEMBL
CHEMBL346331
Wikipedia
Normethadone
ATC Codes
R05DA06 — Normethadone
FDA label
Download (480 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Solution / dropsOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00737 mg/mLALOGPS
logP3.84ALOGPS
logP4.59ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)18.8ChemAxon
pKa (Strongest Basic)8.83ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity92.85 m3·mol-1ChemAxon
Polarizability34.67 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Aralkylamines / Gamma-amino ketones / Trialkylamines / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Diphenylmethane / Aralkylamine / Gamma-aminoketone / Ketone / Tertiary amine / Tertiary aliphatic amine / Carbonyl group / Organooxygen compound / Organonitrogen compound / Amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on June 24, 2016 16:29 / Updated on November 02, 2018 08:59