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Experimental drugs
Esmethadone
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    Esmethadone

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    Esmethadone
    Dextromethadone structure.svg
    Clinical data
    Other names Dextromethadone; d-Methadone; 6S-Methadone; (+)-Methadone
    Identifiers
    • (6S)-6-(Dimethylamino)-4,4-diphenylheptan-3-one
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    ChEBI
    ECHA InfoCard 100.164.915
    Chemical and physical data
    Formula C21H27NO
    Molar mass 309.453 g·mol−1
    3D model (JSmol)
    • CCC(=O)C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2
    • 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

    Esmethadone (INN; 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. Unlike levomethadone, it has low affinity for opioid receptors and lacks significant respiratory depressant action and abuse liability. Esmethadone is under development for the treatment of major depressive disorder. As of August 2022, it is in phase 3 clinical trials for this indication.

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

    Receptor binding affinities of isomers of methadone
    Compound Affinities (Ki, in nM) Ratios
    MOR DOR KOR SERT NET NMDAR M:D:K SERT:NET
    Racemic methadone 1.7 435 405 1,400 259 2,500–8,300 1:256:238 1:5
    Dextromethadone 19.7 960 1,370 992 12,700 2,600–7,400 1:49:70 1:13
    Levomethadone 0.945 371 1,860 14.1 702 2,800–3,400 1:393:1968 1:50



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