U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H27NO.ClH
Molecular Weight 345.906
Optical Activity ( - )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOMETHADONE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=FJQXCDYVZAHXNS-UNTBIKODSA-N
InChI=1S/C21H27NO.ClH/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;1H/t17-;/m1./s1

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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 17:57:05 GMT 2025
Edited
by admin
on Mon Mar 31 17:57:05 GMT 2025
Record UNII
V57LC776C0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHADONE L-FORM HYDROCHLORIDE
MI  
Preferred Name English
LEVOMETHADONE HYDROCHLORIDE
EP   MART.   WHO-DD  
Common Name English
LEVOMETHADONE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
L-6-DIMETHYLAMINO-4,4-DIPHENYL-3-HEPTANONE HYDROCHLORIDE
Common Name English
3-HEPTANONE, 6-(DIMETHYLAMINO)-4,4-DIPHENYL-, HYDROCHLORIDE (1:1), (6R)-
Systematic Name English
LEVOMETHADONE HCL
Common Name English
LEVOMETHADONE HYDROCHLORIDE [MART.]
Common Name English
L-POLAMIDON HYDROCHLORIDE
Common Name English
Levomethadone hydrochloride [WHO-DD]
Common Name English
D-(-)-METHADONE HYDROCHLORIDE
Common Name English
(6R)-6-(DIMETHYLAMINO)-4,4-DIPHENYLHEPTAN-3-ONE HYDROCHLORIDE
Systematic Name English
METHADONE L-FORM HYDROCHLORIDE [MI]
Common Name English
L-METHADONE HYDROCHLORIDE
Common Name English
Code System Code Type Description
CAS
5967-73-7
Created by admin on Mon Mar 31 17:57:05 GMT 2025 , Edited by admin on Mon Mar 31 17:57:05 GMT 2025
PRIMARY
ECHA (EC/EINECS)
227-756-6
Created by admin on Mon Mar 31 17:57:05 GMT 2025 , Edited by admin on Mon Mar 31 17:57:05 GMT 2025
PRIMARY
EVMPD
SUB30942
Created by admin on Mon Mar 31 17:57:05 GMT 2025 , Edited by admin on Mon Mar 31 17:57:05 GMT 2025
PRIMARY
SMS_ID
100000115569
Created by admin on Mon Mar 31 17:57:05 GMT 2025 , Edited by admin on Mon Mar 31 17:57:05 GMT 2025
PRIMARY
FDA UNII
V57LC776C0
Created by admin on Mon Mar 31 17:57:05 GMT 2025 , Edited by admin on Mon Mar 31 17:57:05 GMT 2025
PRIMARY
EPA CompTox
DTXSID30975070
Created by admin on Mon Mar 31 17:57:05 GMT 2025 , Edited by admin on Mon Mar 31 17:57:05 GMT 2025
PRIMARY
MERCK INDEX
m7286
Created by admin on Mon Mar 31 17:57:05 GMT 2025 , Edited by admin on Mon Mar 31 17:57:05 GMT 2025
PRIMARY Merck Index
PUBCHEM
22266
Created by admin on Mon Mar 31 17:57:05 GMT 2025 , Edited by admin on Mon Mar 31 17:57:05 GMT 2025
PRIMARY
RXCUI
236914
Created by admin on Mon Mar 31 17:57:05 GMT 2025 , Edited by admin on Mon Mar 31 17:57:05 GMT 2025
PRIMARY RxNorm
Related Record Type Details
Structure of LEVOMETHADONE
PARENT -> SALT/SOLVATE
Structure of METHADONE HYDROCHLORIDE
RACEMATE -> ENANTIOMER
Related Record Type Details
Structure of DIDIAVALO
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of ESMETHADONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of DIPHENYLACETONITRILE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of ISODIDIAVALO
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of ISOMETHADONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of TOSYLGLUTAMIC ACID
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966