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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H27NO
Molecular Weight 309.4452
Optical Activity ( - )
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
3913
Curator's Comment: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/006134s040s041lbl.pdf

Originator

Approval Year

Unknown
139594
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
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 Fri Dec 15 18:03:48 GMT 2023
Edited
by admin
on Fri Dec 15 18:03:48 GMT 2023
Record UNII
6Y75Z4E8NS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVOMETHADONE
INN   WHO-DD  
INN  
Official 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
LEVOTHYL
Brand 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 Fri Dec 15 18:03:48 GMT 2023 , Edited by admin on Fri Dec 15 18:03:48 GMT 2023
WHO-VATC QN07BC05
Created by admin on Fri Dec 15 18:03:48 GMT 2023 , Edited by admin on Fri Dec 15 18:03:48 GMT 2023
Code System Code Type Description
CAS
3861-94-7
Created by admin on Fri Dec 15 18:03:48 GMT 2023 , Edited by admin on Fri Dec 15 18:03:48 GMT 2023
SUPERSEDED
CAS
52310-03-9
Created by admin on Fri Dec 15 18:03:48 GMT 2023 , Edited by admin on Fri Dec 15 18:03:48 GMT 2023
SUPERSEDED
CHEBI
136003
Created by admin on Fri Dec 15 18:03:48 GMT 2023 , Edited by admin on Fri Dec 15 18:03:48 GMT 2023
PRIMARY
WIKIPEDIA
Levomethadone
Created by admin on Fri Dec 15 18:03:48 GMT 2023 , Edited by admin on Fri Dec 15 18:03:48 GMT 2023
PRIMARY
NCI_THESAURUS
C166969
Created by admin on Fri Dec 15 18:03:48 GMT 2023 , Edited by admin on Fri Dec 15 18:03:48 GMT 2023
PRIMARY
DRUG CENTRAL
4586
Created by admin on Fri Dec 15 18:03:48 GMT 2023 , Edited by admin on Fri Dec 15 18:03:48 GMT 2023
PRIMARY
EVMPD
SUB08477MIG
Created by admin on Fri Dec 15 18:03:48 GMT 2023 , Edited by admin on Fri Dec 15 18:03:48 GMT 2023
PRIMARY
PUBCHEM
22267
Created by admin on Fri Dec 15 18:03:48 GMT 2023 , Edited by admin on Fri Dec 15 18:03:48 GMT 2023
PRIMARY
RXCUI
236913
Created by admin on Fri Dec 15 18:03:48 GMT 2023 , Edited by admin on Fri Dec 15 18:03:48 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB13515
Created by admin on Fri Dec 15 18:03:48 GMT 2023 , Edited by admin on Fri Dec 15 18:03:48 GMT 2023
PRIMARY
CAS
125-58-6
Created by admin on Fri Dec 15 18:03:48 GMT 2023 , Edited by admin on Fri Dec 15 18:03:48 GMT 2023
PRIMARY
SMS_ID
100000082297
Created by admin on Fri Dec 15 18:03:48 GMT 2023 , Edited by admin on Fri Dec 15 18:03:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID70101637
Created by admin on Fri Dec 15 18:03:48 GMT 2023 , Edited by admin on Fri Dec 15 18:03:48 GMT 2023
PRIMARY
ChEMBL
CHEMBL159659
Created by admin on Fri Dec 15 18:03:48 GMT 2023 , Edited by admin on Fri Dec 15 18:03:48 GMT 2023
PRIMARY
INN
5002
Created by admin on Fri Dec 15 18:03:48 GMT 2023 , Edited by admin on Fri Dec 15 18:03:48 GMT 2023
PRIMARY
FDA UNII
6Y75Z4E8NS
Created by admin on Fri Dec 15 18:03:48 GMT 2023 , Edited by admin on Fri Dec 15 18:03:48 GMT 2023
PRIMARY
Related Record Type Details
Structure of LEVOMETHADONE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of METHADONE
RACEMATE -> ACTIVE ENANTIOMER
approximately 50x the potency of the S-(+)-enantiomer as well as greater μ-opioid receptor selectivity
Structure of ESMETHADONE
ENANTIOMER -> ENANTIOMER
OCT-2
TRANSPORTER -> INHIBITOR
Related Record Type Details
Structure of LEVOMETHADONE
ACTIVE MOIETY
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