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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H27NO
Molecular Weight 309.446
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)(c1ccccc1)c2ccccc2

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 309.446
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

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

Approval Year

PubMed

PubMed

TitleDatePubMed
Involvement of CYP3A4, CYP2C8, and CYP2D6 in the metabolism of (R)- and (S)-methadone in vitro.
2003 Jun
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 02:10:45 UTC 2021
Edited
by admin
on Sat Jun 26 02:10:45 UTC 2021
Record UNII
6Y75Z4E8NS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVOMETHADONE
INN   WHO-DD  
INN  
Official 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
(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
POLAMIVET
Brand Name English
LEVOMETHADONE [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC N07BC05
Created by admin on Sat Jun 26 02:10:45 UTC 2021 , Edited by admin on Sat Jun 26 02:10:45 UTC 2021
WHO-VATC QN07BC05
Created by admin on Sat Jun 26 02:10:45 UTC 2021 , Edited by admin on Sat Jun 26 02:10:45 UTC 2021
Code System Code Type Description
CAS
3861-94-7
Created by admin on Sat Jun 26 02:10:45 UTC 2021 , Edited by admin on Sat Jun 26 02:10:45 UTC 2021
SUPERSEDED
CAS
52310-03-9
Created by admin on Sat Jun 26 02:10:45 UTC 2021 , Edited by admin on Sat Jun 26 02:10:45 UTC 2021
SUPERSEDED
WIKIPEDIA
Levomethadone
Created by admin on Sat Jun 26 02:10:45 UTC 2021 , Edited by admin on Sat Jun 26 02:10:45 UTC 2021
PRIMARY
NCI_THESAURUS
C166969
Created by admin on Sat Jun 26 02:10:45 UTC 2021 , Edited by admin on Sat Jun 26 02:10:45 UTC 2021
PRIMARY
DRUG CENTRAL
4586
Created by admin on Sat Jun 26 02:10:45 UTC 2021 , Edited by admin on Sat Jun 26 02:10:45 UTC 2021
PRIMARY
EVMPD
SUB08477MIG
Created by admin on Sat Jun 26 02:10:45 UTC 2021 , Edited by admin on Sat Jun 26 02:10:45 UTC 2021
PRIMARY
PUBCHEM
22267
Created by admin on Sat Jun 26 02:10:45 UTC 2021 , Edited by admin on Sat Jun 26 02:10:45 UTC 2021
PRIMARY
RXCUI
236913
Created by admin on Sat Jun 26 02:10:45 UTC 2021 , Edited by admin on Sat Jun 26 02:10:45 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB13515
Created by admin on Sat Jun 26 02:10:45 UTC 2021 , Edited by admin on Sat Jun 26 02:10:45 UTC 2021
PRIMARY
CAS
125-58-6
Created by admin on Sat Jun 26 02:10:45 UTC 2021 , Edited by admin on Sat Jun 26 02:10:45 UTC 2021
PRIMARY
ChEMBL
CHEMBL159659
Created by admin on Sat Jun 26 02:10:45 UTC 2021 , Edited by admin on Sat Jun 26 02:10:45 UTC 2021
PRIMARY
INN
5002
Created by admin on Sat Jun 26 02:10:45 UTC 2021 , Edited by admin on Sat Jun 26 02:10:45 UTC 2021
PRIMARY
FDA UNII
6Y75Z4E8NS
Created by admin on Sat Jun 26 02:10:45 UTC 2021 , Edited by admin on Sat Jun 26 02:10:45 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
RACEMATE -> ACTIVE ENANTIOMER
approximately 50x the potency of the S-(+)-enantiomer as well as greater ?-opioid receptor selectivity
TRANSPORTER -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY