Levomethadone
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Levomethadone
Levomethadone
Levomethadone structure.svg
Levomethadone-xtal-1974-ball-and-stick.png
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral, IV, IM, SC, IT[1]
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityHigh[1]
Protein binding60-90%[1]
Elimination ~18 hours[1]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.120.592 Edit this at Wikidata
Chemical and physical data
FormulaC21H27NO
Molar mass309.445 g/mol g·mol-1
3D model (JSmol)

Levomethadone (INN; L-Polamidon, L-Polamivet, Levadone, Levothyl), or levamethadone, is a synthetic opioid analgesic and antitussive which is marketed in Europe and is used for pain management and in opioid maintenance therapy.[1][2][3] In addition to being used as a pharmaceutical drug itself, levomethadone, or R-(-)-methadone, is the active enantiomer of methadone,[2] having approximately 50x the potency of the S-(+)-enantiomer as well as greater ?-opioid receptor selectivity.[1][4] Accordingly, it is about twice as potent as methadone by weight and its effects are virtually identical in comparison.[5][6] In addition to its activity at the opioid receptors, levomethadone has been found to act as a weak competitive antagonist of the N-methyl-D-aspartate (NMDA) receptor complex[7] and as a potent noncompetitive antagonist of the ?3?4 nicotinic acetylcholine (nACh) receptor.[8]

There is now an asymmetric synthesis[9] available to prepare both levomethadone [R-(-)-methadone] and dextromethadone [S-(+)-methadone].[10]

The separation of the stereoisomers is one of the easier in organic chemistry and is described in the original patent. It involves "treatment of racemic methadone base with d-(+)-tartaric acid in an acetone/water mixture [which] precipitates almost solely the dextro-methadone levo-tartrate, and the more potent levo-methadone can easily be retrieved from the mother liquor in a high state of optical purity" [11]

Regulatory status

Levomethadone is listed under the Single Convention On Narcotic Drugs 1961 and is a Schedule II Narcotic controlled substance in the US as an isomer of methadone (ACSCN 9250) and is not listed separately, nor is dextromethadone.[12] It is similarly controlled under the German Betäubungsmittelgesetz and similar laws in practically every other country.

See also

References

  1. ^ a b c d e f Helmut Buschmann (20 December 2002). Analgesics: From Chemistry and Pharmacology to Clinical Application. Wiley-VCH. p. 196. ISBN 978-3-527-30403-5. Retrieved 2012.
  2. ^ a b F.. Macdonald (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1294. ISBN 978-0-412-46630-4. Retrieved 2012.
  3. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 605. ISBN 978-3-88763-075-1. Retrieved 2012.
  4. ^ Renate Förch; Holger Schönherr; A. Tobias A. Jenkins (11 August 2009). Surface Design: Applications in Bioscience and Nanotechnology. Wiley-VCH. p. 193. ISBN 978-3-527-40789-7. Retrieved 2012.
  5. ^ Eduardo Bruera; Sriram Yennurajalingam (16 August 2011). Oxford American Handbook of Hospice and Palliative Medicine. Oxford University Press. p. 43. ISBN 978-0-19-538015-6. Retrieved 2012.
  6. ^ Verthein U, Ullmann R, Lachmann A, et al. (November 2005). "The effects of racemic D,L-methadone and L-methadone in substituted patients--a randomized controlled study". Drug and Alcohol Dependence. 80 (2): 267-71. doi:10.1016/j.drugalcdep.2005.04.007. PMID 15916866.
  7. ^ Eric C. Strain; Maxine L. Stitzer (4 November 2005). The Treatment of Opioid Dependence. JHU Press. p. 63. ISBN 978-0-8018-8303-3. Retrieved 2012.
  8. ^ Xiao Y, Smith RD, Caruso FS, Kellar KJ (October 2001). "Blockade of rat alpha3beta4 nicotinic receptor function by methadone, its metabolites, and structural analogs". The Journal of Pharmacology and Experimental Therapeutics. 299 (1): 366-71. PMID 11561100.
  9. ^ 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.
  10. ^ US patent 6143933 
  11. ^ https://www.erowid.org/archive/rhodium/chemistry/methadone.html
  12. ^ http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html

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Levomethadone
 



 



 
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