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| Clinical data | |
|---|---|
| Other names | Dextromethadone; d-Methadone; 6S-Methadone; (+)-Methadone |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
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| UNII | |
| ChEBI | |
| 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 (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.[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 (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 |
References
- ^ a b Gorman AL, Elliott KJ, Inturrisi CE (February 1997). "The d- and l-isomers of methadone bind to the non-competitive site on the N-methyl-D-aspartate (NMDA) receptor in rat forebrain and spinal cord". Neurosci. Lett. 223 (1): 5–8. doi:10.1016/S0304-3940(97)13391-2. PMID 9058409.
- ^ "METHADONE" (PDF). Drug & Chemical Evaluation Section. Drug Enforcement Agency. Retrieved 14 November 2020.
- ^ a b Codd EE, Shank RP, Schupsky JJ, Raffa RB (1995). "Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception". J. Pharmacol. Exp. Ther. 274 (3): 1263–70. PMID 7562497.
- ^ a b "Dextromethadone - Cornell University/Relmada Therapeutics - AdisInsight".
- ^ Hull JD, Scheinmann F, Turner NJ (March 2003). "Synthesis of optically active methadones, LAAM and bufuralol by lipase-catalysed acylations". Tetrahedron: Asymmetry. 14 (5): 567–576. doi:10.1016/S0957-4166(03)00019-3.
- ^ US patent 6143933
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This page was last edited on 22 March 2024, at 03:09