Esmethadone

Esmethadone (INNTooltip International Nonproprietary Name; developmental code name REL-1017), also known as dextromethadone, is the (S)-enantiomer of methadone. It acts as an N-methyl-D-aspartate receptor (NMDAR) antagonist, among other actions.^[1] Unlike levomethadone, it has low affinity for opioid receptors and lacks significant respiratory depressant action and abuse liability.^[2][3]

Other namesDextromethadone; d-Methadone; S-Methadone; (+)-Methadone

CAS Number

• 5653-80-5

PubChem CID

• 643985

ChemSpider

• 559067

Quick facts Clinical data, Other names ...

Esmethadone

Clinical data
Other names	Dextromethadone; d-Methadone; S-Methadone; (+)-Methadone
Identifiers
IUPAC name (6S)-6-(Dimethylamino)-4,4-diphenylheptan-3-one
CAS Number	5653-80-5
PubChem CID	643985
ChemSpider	559067
UNII	S95RZH8AMH
ChEBI	CHEBI:167308
CompTox Dashboard (EPA)	DTXSID501045751
ECHA InfoCard	100.164.915
Chemical and physical data
Formula	C21H27NO
Molar mass	309.453 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCC(=O)C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2
InChI 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-/m0/s1 Key:USSIQXCVUWKGNF-KRWDZBQOSA-N

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Esmethadone has been under development for major depressive disorder.^[4]

There is an asymmetric synthesis available to prepare both esmethadone (S-(+)-methadone) and levomethadone (R-(−)-methadone).^[5][6]