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| Clinical data | |
|---|---|
| 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 nameREL-1017), also known asdextromethadone, is the (S)-enantiomer ofmethadone. It acts as anN-methyl-D-aspartate receptor (NMDAR)antagonist, among other actions.[1] Unlikelevomethadone, it has lowaffinity foropioid receptors and lacks significant respiratory depressant action and abuse liability.[2][3] Esmethadone was under development for the treatment ofmajor depressive disorder.[4] As of December 2024,phase 3clinical trials for this indication were discontinued due to the potential of eye disorders, mitochondrial disorders, neuropathic pain and Rett syndrome.[4]
There is anasymmetric synthesis available to prepare both esmethadone (S-(+)-methadone) and levomethadone (R-(−)-methadone).[5][6]
| Compound | Affinities (KiTooltip Inhibitor constant, innM) | Ratios | ||||||
|---|---|---|---|---|---|---|---|---|
| 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 | |
| Racemicmethadone | 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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https://seekingalpha.com/article/4679773?gt=007e6ed9bf2fefc2