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CHEBI:167308 - dextromethadone

Default Structure
ChEBI IDCHEBI:167308
ChEBI Namedextromethadone
Stars
DefinitionA 6-(dimethylamino)-4,4-diphenylheptan-3-one that has (S)-configuration. It is the less active enantiomer of methadone and has very little activity on opioid receptors and mainly responsible for the inhibition of hERG K+ channels and thus for cardiac toxicity. The drug is currently under clinical development for the treatment of major depressive disorder.
Last Modified22 January 2021
SubmitterAdnan
DownloadsMolfile
FormulaC21H27NO
Net Charge0
Average Mass309.453
Monoisotopic Mass309.20926
SMILESCCC(=O)C(C[C@H](C)N(C)C)(c1ccccc1)c1ccccc1
InChIInChI=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/t17-/m0/s1
InChIKeyUSSIQXCVUWKGNF-KRWDZBQOSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
NMDA receptor antagonist  Any substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs.
opioid analgesic  A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
Applications:
antidepressant  Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
opioid analgesic  A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
ChEBI Ontology
Outgoing Relation(s)
dextromethadone (CHEBI:167308) has role antidepressant (CHEBI:35469)
dextromethadone (CHEBI:167308) has role NMDA receptor antagonist (CHEBI:60643)
dextromethadone (CHEBI:167308) has role opioid analgesic (CHEBI:35482)
dextromethadone (CHEBI:167308) is a 6-(dimethylamino)-4,4-diphenylheptan-3-one (CHEBI:167309)
dextromethadone (CHEBI:167308) is enantiomer of levomethadone (CHEBI:136003)
Incoming Relation(s)
methadone (CHEBI:6807) has part dextromethadone (CHEBI:167308)
levomethadone (CHEBI:136003) is enantiomer of dextromethadone (CHEBI:167308)
IUPAC Name 
(6S)-6-(dimethylamino)-4,4-diphenylheptan-3-one
INNs  Source
esmetadonaWHO MedNet
esmethadoneWHO MedNet
Synonyms  Source
(6S)-methadoneChemIDplus
DextromethadoneChEMBL
d-6-(dimethylamino)-4,4-diphenyl-3-heptanoneChemIDplus
d-methadoneChemIDplus
esmethadoneChEMBL
(+)-(S)-6-(dimethylamino)-4,4-diphenyl-3-heptanoneChEBI
Manual XrefsDatabases
559067ChemSpider
DB15198DrugBank
DextromethadoneWikipedia
Registry NumbersSources
Reaxys:3213667Reaxys
CAS:5653-80-5ChemIDplus
Citations