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'''Methopholine''' is an ] ] drug discovered in the 1950s by a team of Swiss researchers at Hoffmann-La Roche<ref>US Patent 3067203 - Tetrahydroisoquinoline Derivatives</ref>. '''Methopholine''' is an ] ] drug discovered in the 1950s by a team of Swiss researchers at Hoffmann-La Roche<ref>{{ cite patent | country = US | status = patent | number = 3067203 | title = Tetrahydroisoquinoline Derivatives | assign1 = Hoffmann-La Roche }}</ref>.


Methopholine is an ] derivative which is not structurally related to most other opioids.<ref>Feinberg AP, Creese I, Snyder SH. The opiate receptor: a model explaining structure-activity relationships of opiate agonists and antagonists. ''Proceedings of the National Academy of Sciences U S A''. 1976 Nov;73(11):4215-9.</ref> It has around the same efficacy as an analgesic as ], and was evaluated for the treatment of postoperative pain.<ref>Moore J, Foldes FF, Davidson GM. An evaluation of the efficacy of methopholine for the relief of postoperative pain. ''American Journal of Medical Sciences''. 1962 Sep;244:337-43.</ref><ref>Cass LJ, Frederik WS. Methopholine, A New Analgesic Agent. ''American Journal of Medical Sciences''. 1963 Nov;246:550-7.</ref><ref>Sciorelli G. Plasma levels and renal excretion of unchanged methopholine in man. ''Experientia''. 1967 Nov 15;23(11):934-6.</ref> Methopholine tablets were marketed in the United States under the brand name of Versidyne, but the drug was withdrawn from the market in 1965 due to the occurrence of ] side-effects and the discovery that it could produce corneal opacities in dogs.<ref>''Federal Register'', March 27, 1965 (30 FR 4083).</ref> Methopholine is an ] derivative which is not structurally related to most other opioids.<ref>Feinberg AP, Creese I, Snyder SH. The opiate receptor: a model explaining structure-activity relationships of opiate agonists and antagonists. ''Proceedings of the National Academy of Sciences U S A''. 1976 Nov;73(11):4215-9.</ref> It has around the same efficacy as an analgesic as ], and was evaluated for the treatment of postoperative pain.<ref>Moore J, Foldes FF, Davidson GM. An evaluation of the efficacy of methopholine for the relief of postoperative pain. ''American Journal of Medical Sciences''. 1962 Sep;244:337-43.</ref><ref>Cass LJ, Frederik WS. Methopholine, A New Analgesic Agent. ''American Journal of Medical Sciences''. 1963 Nov;246:550-7.</ref><ref>Sciorelli G. Plasma levels and renal excretion of unchanged methopholine in man. ''Experientia''. 1967 Nov 15;23(11):934-6.</ref> Methopholine tablets were marketed in the United States under the brand name of Versidyne, but the drug was withdrawn from the market in 1965 due to the occurrence of ] side-effects and the discovery that it could produce corneal opacities in dogs.<ref>''Federal Register'', March 27, 1965 (30 FR 4083).</ref>

Revision as of 12:10, 15 December 2011

Pharmaceutical compound
Metofoline
Clinical data
ATC code
  • none
Legal status
Legal status
  • In general: legal
Identifiers
IUPAC name
  • 1--6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H24ClNO2
Molar mass345.87 g/mol g·mol
3D model (JSmol)
SMILES
  • Clc1ccc(cc1)CCC3c2c(cc(OC)c(OC)c2)CCN3C
InChI
  • InChI=1S/C20H24ClNO2/c1-22-11-10-15-12-19(23-2)20(24-3)13-17(15)18(22)9-6-14-4-7-16(21)8-5-14/h4-5,7-8,12-13,18H,6,9-11H2,1-3H3
  • Key:YBCPYHQFUMNOJG-UHFFFAOYSA-N
  (verify)

Methopholine is an opioid analgesic drug discovered in the 1950s by a team of Swiss researchers at Hoffmann-La Roche.

Methopholine is an isoquinoline derivative which is not structurally related to most other opioids. It has around the same efficacy as an analgesic as codeine, and was evaluated for the treatment of postoperative pain. Methopholine tablets were marketed in the United States under the brand name of Versidyne, but the drug was withdrawn from the market in 1965 due to the occurrence of ophthalmic side-effects and the discovery that it could produce corneal opacities in dogs.

Methopholine has two enantiomers, with the levo (R) enantiomer being the active form, around 3x the potency of codeine, and the (S) enantiomer being inactive. Analogues where the 4'-chloro group has been replaced by other groups have also been tested, the fluoro derivative being slightly more potent than chloro, and the nitro derivative being most potent of all, with the racemic 4'-nitromethopholine being around 20x the potency of codeine.

4'-Nitromethopholine

References

  1. US patent 3067203, "Tetrahydroisoquinoline Derivatives", assigned to Hoffmann-La Roche 
  2. Feinberg AP, Creese I, Snyder SH. The opiate receptor: a model explaining structure-activity relationships of opiate agonists and antagonists. Proceedings of the National Academy of Sciences U S A. 1976 Nov;73(11):4215-9.
  3. Moore J, Foldes FF, Davidson GM. An evaluation of the efficacy of methopholine for the relief of postoperative pain. American Journal of Medical Sciences. 1962 Sep;244:337-43.
  4. Cass LJ, Frederik WS. Methopholine, A New Analgesic Agent. American Journal of Medical Sciences. 1963 Nov;246:550-7.
  5. Sciorelli G. Plasma levels and renal excretion of unchanged methopholine in man. Experientia. 1967 Nov 15;23(11):934-6.
  6. Federal Register, March 27, 1965 (30 FR 4083).
  7. Casy AF, Parfitt RY. Opioid analgesics, chemistry and receptors. 1986, Plenum Press, New York. p 390. ISBN 0306421305
  8. Walter M, Besendorf H, Schnider O. Synthesen in der Isochinolinreihe Substituierte 1--1,2,3,4-tetrahydro-isochinoline. Helvetica Chimica Acta. 1963;46(4):1127-1131.
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