methadone   

GtoPdb Ligand ID: 5458

Synonyms: (±)-methadone | dl-methadone | Dolophine HCL® | methadone HCl | Methadose®
methadone is an approved drug (FDA (1947, prior history not available))
Compound class: Synthetic organic
Comment: The approved drug methadone is a racemic mixture of two enantiomers; (S)-methadone and (R)-methadone. The structure shown here does not specify stereochemistry and represents the mixture.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 20.31
Molecular weight 309.21
XLogP 4.59
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCC(=O)C(c1ccccc1)(c1ccccc1)CC(N(C)C)C
Isomeric SMILES CCC(=O)C(c1ccccc1)(c1ccccc1)CC(N(C)C)C
InChI InChI=1S/C21H27NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3
InChI Key USSIQXCVUWKGNF-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1947, prior history not available))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
6-(dimethylamino)-4,4-diphenylheptan-3-one
International Nonproprietary Names
INN number INN
788 methadone
Synonyms
(±)-methadone | dl-methadone | Dolophine HCL® | methadone HCl | Methadose®
Comments
The approved drug methadone is a racemic mixture of two enantiomers; (S)-methadone and (R)-methadone. The structure shown here does not specify stereochemistry and represents the mixture.
Database Links
CAS Registry No. 76-99-3
ChEBI CHEBI:6807
ChEMBL Ligand CHEMBL651
DrugBank Ligand DB00333
DrugCentral Ligand 1728
GtoPdb PubChem SID 178102108
PubChem CID 4095
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Wikipedia Methadone