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Methopholine has two [[enantiomer]]s, with the ''levo'' (R) enantiomer being the active form, around 3x the potency of codeine, and the (S) enantiomer being inactive.
Methopholine has two [[enantiomer]]s, 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Analogues where the 4'-chloro group has been replaced by other groups have also been tested, the fluoro derivative being slightly more potent than chloro, and the nitro derivative being most potent of all, with the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.<ref>{{ cite book | author = Casy, A. F.; Parfitt, R. Y. | title = Opioid Analgesics, Chemistry and Receptors | year = 1986 | publisher = Plenum Press | location = New York | page = 390 | isbn = 0-306-42130-5 | url = http://www.scribd.com/doc/58133814/Opioid-Analgesics-Chemistry-and-Receptors-1986-Opioid-Analgesics-Chemistry-and-Receptors-Alan-F-Casy-Robert-T-Parfitt-ISBN-0-306-42130-5 }}</ref><ref>{{ cite doi | 10.1002/hlca.19630460405 }}</ref>
Analogues where the 4'-chloro group has been replaced by other groups have also been tested, the fluoro derivative being slightly more potent than chloro, and the nitro derivative being most potent of all, with the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.<ref>{{ cite book | author = Casy, A. F.; Parfitt, R. Y. | title = Opioid Analgesics, Chemistry and Receptors | year = 1986 | publisher = Plenum Press | location = New York | page = 390 | isbn = 0-306-42130-5 | url = http://www.scribd.com/doc/58133814/Opioid-Analgesics-Chemistry-and-Receptors-1986-Opioid-Analgesics-Chemistry-and-Receptors-Alan-F-Casy-Robert-T-Parfitt-ISBN-0-306-42130-5 }}</ref><ref>{{ cite doi |10.1002/hlca.19630460405 }}</ref>
==Synthesis==
==Synthesis==
Starting material obtained from a [[Pictet–Spengler reaction]].
Starting material obtained from a [[Pictet–Spengler reaction]].

Revision as of 05:48, 9 September 2014

Metofoline
Clinical data
ATC code
  • none
Legal status
Legal status
  • In general: legal
Identifiers
  • 1-[2-(4-chlorophenyl)ethyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
CAS Number
  • 2154-02-1 checkY
    63937-57-5 (4'-nitromethopholine)
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H24ClNO2
Molar mass345.87 g/mol g·mol−1
3D model (JSmol)
  • ClC1=CC=C(CCC2C3=CC(OC)=C(OC)C=C3CCN2C)C=C1
  • 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 checkY
  • Key:YBCPYHQFUMNOJG-UHFFFAOYSA-N checkY
  (verify)

Methopholine is an opioid analgesic drug discovered in the 1950s by a team of Swiss researchers at Hoffmann-La Roche.[1]

4'-Nitromethopholine

Methopholine is an isoquinoline derivative which is not structurally related to most other opioids.[2] However, its structural similarity to papaverine is notable.

It has around the same efficacy as an analgesic as codeine, and was evaluated for the treatment of postoperative pain.[3][4][5] Methopholine tablets were marketed in the United States under the brand name of Versidyne,[6] 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.[7]

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.[8][9]

Synthesis

Starting material obtained from a Pictet–Spengler reaction.

Methopholine synthesis:[10]

References

  1. ^ US patent 3067203, "Tetrahydroisoquinoline Derivatives", issued 1962-12-04, assigned to Hoffmann-La Roche 
  2. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 186791 , please use {{cite journal}} with |pmid= 186791 instead.
  3. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 14475666 , please use {{cite journal}} with |pmid= 14475666 instead.
  4. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 14082642 , please use {{cite journal}} with |pmid= 14082642 instead.
  5. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 6057015 , please use {{cite journal}} with |pmid= 6057015 instead.
  6. ^ VERSIDYNE — ITS USE IN VASCULAR HEADACHE. ROBERT E. RYAN M.D., M.S., B.S. Assoc. Professor Otolaryngology. Headache: The Journal of Head and Face Pain Vol 2 Issue 4 pages 203–208 1963>
  7. ^ Federal Register, March 27, 1965 (30 FR 4083).
  8. ^ Casy, A. F.; Parfitt, R. Y. (1986). Opioid Analgesics, Chemistry and Receptors. New York: Plenum Press. p. 390. ISBN 0-306-42130-5.{{cite book}}: CS1 maint: multiple names: authors list (link)
  9. ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1002/hlca.19630460405 , please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1002/hlca.19630460405 instead.
  10. ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1002/hlca.19600430603, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1002/hlca.19600430603 instead.


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