dextromethadone (CHEBI:167308)

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CHEBI:167308 - dextromethadone

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ChEBI ID	CHEBI:167308
ChEBI Name	dextromethadone
Stars
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.
Last Modified	22 January 2021
Submitter	Adnan
Downloads	Molfile

Formula	C21H27NO
Net Charge	0
Average Mass	309.453
Monoisotopic Mass	309.20926
SMILES	CCC(=O)C(C[C@H](C)N(C)C)(c1ccccc1)c1ccccc1
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

Wikipedia

Roles Classification

Chemical Role:	Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:	opioid analgesic A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood. 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.
Application:	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 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

Synonyms	Source
(+)-methadone	ChemIDplus
(S)-6-(dimethylamino)-4,4-diphenyl-3-heptanone	ChemIDplus
(6S)-methadone	ChemIDplus
d-6-(dimethylamino)-4,4-diphenyl-3-heptanone	ChemIDplus
d-methadone	ChemIDplus
(S)-methadone	ChemIDplus

Manual Xrefs	Databases
DB15198	DrugBank
Dextromethadone	Wikipedia
559067	ChemSpider

Registry Numbers	Sources
Reaxys:3213667	Reaxys
CAS:5653-80-5	ChemIDplus

Citations