Cannabaceae

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Esmethadone
Clinical data
Other namesDextromethadone; d-Methadone; 6S-Methadone; (+)-Methadone
Identifiers
  • (6S)-6-(Dimethylamino)-4,4-diphenylheptan-3-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.164.915 Edit this at Wikidata
Chemical and physical data
FormulaC21H27NO
Molar mass309.453 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 (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]

Receptor binding affinities of isomers of methadone[3][1]
Compound Affinities (KiTooltip Inhibitor constant, in nM) 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
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[edit]

  1. ^ 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.
  2. ^ "METHADONE" (PDF). Drug & Chemical Evaluation Section. Drug Enforcement Agency. Retrieved 14 November 2020.
  3. ^ 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.
  4. ^ a b "Dextromethadone - Cornell University/Relmada Therapeutics - AdisInsight".
  5. ^ 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.
  6. ^ US patent 6143933 


https://seekingalpha.com/article/4679773?gt=007e6ed9bf2fefc2

source: https://en.wikipedia.org/wiki/Dextromethadone

One thought on “Cannabaceae”

  1. Well, that’s interesting to know that Psilotum nudum are known as whisk ferns. Psilotum nudum is the commoner species of the two. While the P. flaccidum is a rare species and is found in the tropical islands. Both the species are usually epiphytic in habit and grow upon tree ferns. These species may also be terrestrial and grow in humus or in the crevices of the rocks.
    View the detailed Guide of Psilotum nudum: Detailed Study Of Psilotum Nudum (Whisk Fern), Classification, Anatomy, Reproduction

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