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Normethadone

HCID 10090
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
467-85-6
Standard SMILES
CCC(=O)C(CCN(C)C)(c1ccccc1)c1ccccc1
InChIKey
WCJFBSYALHQBSK-UHFFFAOYSA-N
Molecular formula
C20H25NO
Average molar mass
295.4 g/mol
Monoisotopic mass
295.19361442

Overview

Normethadone is a diarylmethane.

Names & identifiers

Preferred name
Normethadone
IUPAC
6-(dimethylamino)-4,4-diphenylhexan-3-one
English name
normethadone
Molecular formula
C20H25NO
Molecular weight
295.42

Names & synonyms

NormethadoneMepidonIsomethadone IEucoponPhenyldimazoneHoechst 10582NormetadonaNormethadonumNormetadone6-Dimethylamino-4,4-diphenyl-3-hexanone467-85-6KR2L2A68XL
Show more names
Hoechst 10,582WCJFBSYALHQBSK-UHFFFAOYSA-N6-(Dimethylamino)-4,4-diphenyl-3-hexanone3-Hexanone, 6-(dimethylamino)-4,4-diphenyl-
6-(dimethylamino)-4,4-diphenylhexan-3-oneHOECHST-10582NSC-19598IDS-NN-007DTXSID6057748J5.915CDTXCID7031537nor-methadone

Database identifiers

CAS
467-85-6
PubChem CID
10090
DTXSID
DTXSID6057748
ChEMBL
CHEMBL346331
ChEBI
CHEBI:135242
UNII
KR2L2A68XL
EC Number
207-401-1
Nikkaji
J5.915C

Properties

Computed structural properties

XLogP
3.5
Topological polar surface area
20.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
7
Heavy atoms
22
Formal charge
0
Complexity
320

Experimental & physicochemical properties

Drugs · 4 items

DEA NFLIS-Drug Category -> Narcotic Analgesics

DEA Schedule I Controlled Substance -> Opiates

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

Pharmaceuticals -> Listed in ZINC15

LogP4.15
Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Melting point
25 °C · <25 °C
Boiling point
3 · bp3 164-167°
Density
1.0389 · 1.0389 (rough estimate)
refractive index
1.5614 · 1.5614 (estimate)
pka
6 · pKa 6.00(50% aq EtOH) (Uncertain)
FDA UNII
2 L2A68XL · KR2L2A68XL
ATC code
5 DA06 · R05DA06

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Regulatory InformationDEA schedule I controlled substance

Chemistry & industry

Pharmacology

ATC Code · 2 items

R - Respiratory system

QR - Respiratory system

PharmacodynamicsNormethadone is an opioid which suppresses coughing by central and peripheral mechanisms.
Mechanism of ActionNormethadone activates central opioid receptors in the medulla to supress the cough reflex. It also likely activates peripheral opioid receptors to inhibit signalling by irritant receptors of the airway.
MeSH Pharmacological Classification · 2 items

Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS.

Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.

Upstream & downstream products

Upstream raw materials

Sodium amideMagnesiumBromoethaneDiphenylacetonitrile

Additional notes

DefinitionChEBI: Normethadone is a diarylmethane.

Related reactions

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Compound notes

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