dextromethadone (CHEBI:167308)

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ChEBI Name	dextromethadone

ChEBI ID	CHEBI:167308

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C21H27NO

Net Charge

Average Mass

309.453

Monoisotopic Mass

309.20926

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/t17-/m0/s1

InChIKey

USSIQXCVUWKGNF-KRWDZBQOSA-N

SMILES

CCC(=O)C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	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.

Application(s):	opioid analgesic A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.

ChEBI Ontology
Outgoing	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	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

Synonyms	Sources
(+)-(S)-6-(dimethylamino)-4,4-diphenyl-3-heptanone	ChEBI
(+)-methadone	ChemIDplus
(6S)-methadone	ChemIDplus
(S)-(+)-methadone	ChEBI
(S)-6-(dimethylamino)-4,4-diphenyl-3-heptanone	ChemIDplus
(S)-methadone	ChemIDplus
d-6-(dimethylamino)-4,4-diphenyl-3-heptanone	ChemIDplus
d-methadone	ChemIDplus
REL-1017	ChEBI
S-(+)-methadone	ChemIDplus
S-methadone	ChemIDplus

Last Modified

22 January 2021