Dextromethadone
Dextromethadone (developmental code name REL-1017) is the (S)-enantiomer of methadone.[1] It acts as an N-methyl-D-aspartate receptor (NMDAR) antagonist.[2] The compound also has affinity for opioid receptors.[3] As of October 2019, dextromethadone is under development for the treatment of major depressive disorder.[1]
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| Other names | d-Methadone; 6S-Methadone; (+)-Methadone |
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| ECHA InfoCard | 100.164.915  |
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| Formula | C21H27NO |
| Molar mass | 309.453 g·mol−1 |
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There is now an asymmetric synthesis[4] available to prepare both dextromethadone (S-(+)-methadone) and levomethadone (R-(−)-methadone).[5]
| Compound | Affinities (Ki) | Ratios | |||||||
|---|---|---|---|---|---|---|---|---|---|
| MOR | DOR | KOR | SERT | NET | NMDAR | MOR:DOR:KOR | SERT:NET | ||
| Methadone | 1.7 nM | 435 nM | 405 nM | ND | ND | 2,500–8,300 nM | 1:256:238 | ND | |
| Dextromethadone | 19.7 nM | 960 nM | 1,370 nM | 992 nM | 12,700 nM | 2,600–7,400 nM | 1:49:70 | 1:13 | |
| Levomethadone | 0.945 nM | 371 nM | 1,860 nM | 14.1 nM | 702 nM | 2,800–3,400 nM | 1:393:1968 | 1:50 | |
| Sources: See template. | |||||||||
References
- https://adisinsight.springer.com/drugs/800038927
- Gorman AL, Elliott KJ, Inturrisi CE (14 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". Neuroscience Letters. 223 (1): 5–8. doi:10.1016/S0304-3940(97)13391-2. PMID 9058409.CS1 maint: uses authors parameter (link)
- Codd EE, Shank RP, Schupsky JJ, Raffa RB (September 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.
- 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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