CHEBI:136003 - levomethadone

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ChEBI Name levomethadone
ChEBI ID CHEBI:136003
Definition A 6-(dimethylamino)-4,4-diphenylheptan-3-one that has (R)-configuration. It is the active enantiomer of methadone and its hydrochloride salt is used to treat adults who are addicted to drugs such as heroin and morphine.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H27NO
Net Charge 0
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-/m1/s1
InChIKey USSIQXCVUWKGNF-QGZVFWFLSA-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): opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-opioid receptor.
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(s): antitussive
An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.
opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-opioid receptor.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing levomethadone (CHEBI:136003) has role μ-opioid receptor agonist (CHEBI:55322)
levomethadone (CHEBI:136003) has role antitussive (CHEBI:51177)
levomethadone (CHEBI:136003) has role NMDA receptor antagonist (CHEBI:60643)
levomethadone (CHEBI:136003) has role opioid analgesic (CHEBI:35482)
levomethadone (CHEBI:136003) is a 6-(dimethylamino)-4,4-diphenylheptan-3-one (CHEBI:167309)
levomethadone (CHEBI:136003) is enantiomer of dextromethadone (CHEBI:167308)
Incoming methadone (CHEBI:6807) has part levomethadone (CHEBI:136003)
dextromethadone (CHEBI:167308) is enantiomer of levomethadone (CHEBI:136003)
IUPAC Name
(6R)-6-(dimethylamino)-4,4-diphenylheptan-3-one
INNs Sources
levometadona WHO MedNet
lévométhadone WHO MedNet
levomethadone WHO MedNet
levomethadonum WHO MedNet
Synonyms Sources
(−)-(R)-6-(dimethylamino)-4,4-diphenyl-3-heptanone ChemIDplus
(−)-methadone ChemIDplus
(6R)-methadone ChemIDplus
(R)-(−)-methadone ChEBI
(R)-6-(dimethylamino)-4,4-diphenyl-3-heptanone ChemIDplus
(R)-methadone ChEBI
L-6-(dimethylamino)-4,4-diphenyl-3-heptanone ChemIDplus
l-methadone ChemIDplus
R-methadone ChEBI
Manual Xrefs Databases
20904 ChemSpider
4586 DrugCentral
D08121 KEGG DRUG
DB13515 DrugBank
Levomethadone Wikipedia
View more database links
Registry Numbers Types Sources
125-58-6 CAS Registry Number ChemIDplus
3213668 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
20308640 PubMed citation Europe PMC
21371149 PubMed citation Europe PMC
25669614 PubMed citation Europe PMC
27974484 PubMed citation Europe PMC
29393208 PubMed citation Europe PMC
29902789 PubMed citation Europe PMC
31842942 PubMed citation Europe PMC
32302325 PubMed citation Europe PMC
32586692 PubMed citation Europe PMC
32903474 PubMed citation Europe PMC
33345336 PubMed citation Europe PMC
33423953 PubMed citation Europe PMC
Last Modified
22 January 2021