Levomethadone
Basic information
- CAS
125-58-6- Standard SMILES
CCC(=O)C(C[C@@H](C)N(C)C)(c1ccccc1)c1ccccc1- InChIKey
USSIQXCVUWKGNF-QGZVFWFLSA-N- Molecular formula
- C21H27NO
- Average molar mass
- 309.4 g/mol
- Monoisotopic mass
- 309.20926449
Overview
Levomethadone is 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. It has a role as an opioid analgesic, an antitussive, a mu-opioid receptor agonist and a NMDA receptor antagonist. It is an enantiomer of a dextromethadone.
Names & identifiers
- Preferred name
- Levomethadone
- IUPAC
- (6R)-6-(dimethylamino)-4,4-diphenylheptan-3-one
- English name
- R(-)-methadone hydrochloride opioid agon IST
- Molecular formula
- C21H27NO
- Molecular weight
- 309.45
Names & synonyms
Levomethadonel-MethadoneLevothyl(-)-Methadonel-Polamivet(R)-Methadone(6R)-MethadoneLevometadonaLevadone125-58-6(6R)-6-(dimethylamino)-4,4-diphenylheptan-3-oneD-(-)-Methadone
Show more names
(-)-DiaminoneLaevomethadon4-diphenyl-6-(dimethylamino)-l-3-heptanon4-diphenyl-6-(dimethylamino)-(r)-3-hetpanon
LevomethadonumR-(-)-MethadoneLevomethadone [INN]METHADONE, L-Levometadona [INN-Spanish]Levomethadonum [INN-Latin]6Y75Z4E8NS(R)-6-(Dimethylamino)-4,4-diphenyl-3-heptanone
Database identifiers
- CAS
125-58-6- PubChem CID
- 22267
- DTXSID
DTXSID701016376- ChEMBL
CHEMBL159659- ChEBI
CHEBI:136003- UNII
- 6Y75Z4E8NS
- EC Number
- 603-081-6
- Nikkaji
- J56.319F
Properties
Computed structural properties
- XLogP
- 3.9
- Topological polar surface area
- 20.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 7
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 346
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Human DrugsPharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Melting point
- 99 °C · 99°C
- Boiling point
- 449.71 °C · 449.71°C (rough estimate)
- Density
- 1.035 · 1.0350 (rough estimate)
- refractive index
- 1.5614 · 1.5614 (estimate)
- pka
- 9.048 · 9.048±0.50(predicted)
- FDA UNII
- 6 Y75Z4E8NS · 6Y75Z4E8NS
- ATC code
- 7 BC05 · N07BC05
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 300 · H300-H412-H336
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (95.1%): Toxic if swallowed [Danger Acute toxicity, oral]
P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationREACH registered substance: (6R)-6-(dimethylamino)-4,4-diphenylheptan-3-one (EC: 603-081-6)
Hazard Classes and CategoriesAcute Tox. 3 (95.1%)
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Hazard statements
- H300-H412-H336
- REACH Registrations
- Active
- Precautionary statements
- P264-P270-P301+P310-P321-P330-P405-P501-P273-P501-P261-P271-P304+P340-P312-P403+P233-P405-P501
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Uses & manufacturing
UsesUse (kg) in Switzerland (2009): >75
Use ClassificationPharmaceuticals
Additional notes
DefinitionChEBI: Levomethadone is 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. It has a role as an antitussive, an opioid analgesic, a mu-opioid receptor agonist and a NMDA receptor antagonist. It is an enantiomer of a dextromethadone.
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