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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H27NO
Molecular Weight 309.4452
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOMETHADONE

SMILES

CCC(=O)C(C[C@@H](C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2

InChI

InChIKey=USSIQXCVUWKGNF-QGZVFWFLSA-N
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

HIDE SMILES / InChI
Molecular Formula C21H27NO
Molecular Weight 309.4452
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Sources: Helmut Buschmann (20 December 2002). Analgesics: From Chemistry and Pharmacology to Clinical Application. Wiley-VCH. p. 196. ISBN 978-3-527-30403-5. | F.. Macdonald (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1294. ISBN 978-0-412-46630-4.
Curator's Comment: see METHADONE

levomethadone, or R-(−)-methadone, is the active enantiomer of methadone; having approximately 50x the potency of the S-(+)-enantiomer as well as greater μ-opioid receptor selectivity.

CNS Activity

CNS Active
4002
Curator's Comment: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/006134s040s041lbl.pdf

Originator

Approval Year

Unknown
149124
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
[Methadone and levomethadone - dosage and side effects].
2014-03
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007-01
Involvement of CYP3A4, CYP2C8, and CYP2D6 in the metabolism of (R)- and (S)-methadone in vitro.
2003-06
Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications.
1998-03
Patents

Patents

20030175214
3
US20040242617A1
3
US20080221141A1
3
US20090163451A1
3
WO2002000197A1
3

Sample Use Guides

In Vivo Use Guide
Curator's Comment: see METHADONE
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Curator's Comment: see METHADONE
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:01:44 GMT 2025
Edited
by admin
on Mon Mar 31 19:01:44 GMT 2025
Record UNII
6Y75Z4E8NS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVOMETHADONE
INN   WHO-DD  
INN  
Official Name English
LEVOTHYL
Preferred Name English
LEVADONE
Common Name English
L-POLAMIVET
Common Name English
(6R)-6-(DIMETHYLAMINO)-4,4-DIPHENYL-3-HEPTANONE
Systematic Name English
D-(-)-METHADONE
Common Name English
(R)-METHADONE
Common Name English
R-(-)-METHADONE
Common Name English
METHADONE, L-
Common Name English
(6R)-METHADONE
Common Name English
HEPTANONE, 6-(DIMETHYLAMINO)-4,4-DIPHENYL-, L-
Common Name English
(-)-METHADONE
Common Name English
(-)-(R)-6-(DIMETHYLAMINO)-4,4-DIPHENYL-3-HEPTANONE
Systematic Name English
3-HEPTANONE, 6-(DIMETHYLAMINO)-4,4-DIPHENYL-, (R)-
Systematic Name English
3-HEPTANONE, 6-(DIMETHYLAMINO)-4,4-DIPHENYL-, (6R)-
Systematic Name English
L-METHADONE
Common Name English
Levomethadone [WHO-DD]
Common Name English
levomethadone [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC N07BC05
Created by admin on Mon Mar 31 19:01:44 GMT 2025 , Edited by admin on Mon Mar 31 19:01:44 GMT 2025
WHO-VATC QN07BC05
Created by admin on Mon Mar 31 19:01:44 GMT 2025 , Edited by admin on Mon Mar 31 19:01:44 GMT 2025
Code System Code Type Description
CAS
3861-94-7
Created by admin on Mon Mar 31 19:01:44 GMT 2025 , Edited by admin on Mon Mar 31 19:01:44 GMT 2025
SUPERSEDED
CAS
52310-03-9
Created by admin on Mon Mar 31 19:01:44 GMT 2025 , Edited by admin on Mon Mar 31 19:01:44 GMT 2025
SUPERSEDED
CHEBI
136003
Created by admin on Mon Mar 31 19:01:44 GMT 2025 , Edited by admin on Mon Mar 31 19:01:44 GMT 2025
PRIMARY
WIKIPEDIA
Levomethadone
Created by admin on Mon Mar 31 19:01:44 GMT 2025 , Edited by admin on Mon Mar 31 19:01:44 GMT 2025
PRIMARY
NCI_THESAURUS
C166969
Created by admin on Mon Mar 31 19:01:44 GMT 2025 , Edited by admin on Mon Mar 31 19:01:44 GMT 2025
PRIMARY
DRUG CENTRAL
4586
Created by admin on Mon Mar 31 19:01:44 GMT 2025 , Edited by admin on Mon Mar 31 19:01:44 GMT 2025
PRIMARY
EVMPD
SUB08477MIG
Created by admin on Mon Mar 31 19:01:44 GMT 2025 , Edited by admin on Mon Mar 31 19:01:44 GMT 2025
PRIMARY
PUBCHEM
22267
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PRIMARY
RXCUI
236913
Created by admin on Mon Mar 31 19:01:44 GMT 2025 , Edited by admin on Mon Mar 31 19:01:44 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID701016376
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PRIMARY
DRUG BANK
DB13515
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PRIMARY
CAS
125-58-6
Created by admin on Mon Mar 31 19:01:44 GMT 2025 , Edited by admin on Mon Mar 31 19:01:44 GMT 2025
PRIMARY
SMS_ID
100000082297
Created by admin on Mon Mar 31 19:01:44 GMT 2025 , Edited by admin on Mon Mar 31 19:01:44 GMT 2025
PRIMARY
ChEMBL
CHEMBL159659
Created by admin on Mon Mar 31 19:01:44 GMT 2025 , Edited by admin on Mon Mar 31 19:01:44 GMT 2025
PRIMARY
INN
5002
Created by admin on Mon Mar 31 19:01:44 GMT 2025 , Edited by admin on Mon Mar 31 19:01:44 GMT 2025
PRIMARY
FDA UNII
6Y75Z4E8NS
Created by admin on Mon Mar 31 19:01:44 GMT 2025 , Edited by admin on Mon Mar 31 19:01:44 GMT 2025
PRIMARY
Related Record Type Details
CYTOCHROME P450 2C8
METABOLIC ENZYME -> SUBSTRATE
CYP2C8 contribution to the metabolism was smaller than that of CYP3A4.
Structure of LEVOMETHADONE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
CYP2C8 contribution to the metabolism was smaller than that of CYP3A4.
MAJOR
OCT-2
TRANSPORTER -> INHIBITOR
Structure of METHADONE
RACEMATE -> ACTIVE ENANTIOMER
Structure of ESMETHADONE
ENANTIOMER -> ENANTIOMER
MU-TYPE OPIOID RECEPTOR
TARGET -> AGONIST
Male, Wistar rats
Ki
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
MINOR
Related Record Type Details
Structure of DESMETHYLLEVOMETHADONE
METABOLITE -> PARENT
Related Record Type Details
Structure of LEVOMETHADONE
ACTIVE MOIETY
NIH
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