Clinical data | |
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Other names | Dextromethadone; d-Methadone; 6S-Methadone; (+)-Methadone |
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CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.164.915 |
Chemical and physical data | |
Formula | C21H27NO |
Molar mass | 309.453 g·mol−1 |
3D model (JSmol) | |
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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] Esmethadone is under development for the treatment of major depressive disorder.[4] As of August 2022, it is in phase 3 clinical trials for this indication.[4]
There is an asymmetric synthesis available to prepare both esmethadone (S-(+)-methadone) and levomethadone (R-(−)-methadone).[5][6]
Compound | Affinities (KiTooltip Inhibitor constant, in nM) | Ratios | ||||||
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MORTooltip μ-Opioid receptor | DORTooltip δ-Opioid receptor | KORTooltip κ-Opioid receptor | SERTTooltip Serotonin transporter | NETTooltip Norepinephrine transporter | NMDARTooltip N-Methyl-D-aspartate receptor | 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 |
https://seekingalpha.com/article/4679773?gt=007e6ed9bf2fefc2