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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
Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications.
1998 Mar
Involvement of CYP3A4, CYP2C8, and CYP2D6 in the metabolism of (R)- and (S)-methadone in vitro.
2003 Jun
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007 Jan
[Methadone and levomethadone - dosage and side effects].
2014 Mar
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
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
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
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 BANK
DB13515
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
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
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