Английская Википедия:Ciramadol

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Шаблон:Short description Шаблон:Distinguish Шаблон:Drugbox

Ciramadol (WY-15,705) is an opioid analgesic that was developed in the late 1970s[1] and is related to phencyclidine, tramadol, tapentadol and venlafaxine.[2] It is a mixed agonist-antagonist for the μ-opioid receptor with relatively low abuse potential[3] and a ceiling on respiratory depression[4] which makes it a relatively safe drug. It has a slightly higher potency and effectiveness as an analgesic than codeine,[5] but is weaker than morphine.[6] Other side effects include sedation and nausea but these are generally less severe than with other similar drugs.[7]

Synthesis

Файл:Ciramadolsynthesis.svg
Ciramadol synthesis:[8][9] Patents:[10][11][12]

The Claisen-Schmidt condensation between 3-(methoxymethoxy)benzaldehyde [13709-05-2] (1) and cyclohexanone (2) afforded CID:54364197 (3). Michael addition of dimethylamine leads the aminoketone, i.e. 2-[dimethylamino-[3-(methoxymethoxy)phenyl]methyl]cyclohexan-1-one, CID21518320. Reduction of the ketone proceeds stereospecifically to afford the cis aminoalcohol [51356-58-2] (4). Mild hydrolysis of the product gives the free phenol ciramadol (5).

See also

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References

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Шаблон:Analgesics Шаблон:Opioidergics


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Партнерские ресурсы
Криптовалюты
Магазины
Хостинг
Разное

  1. ↑ Шаблон:Cite patent
  2. ↑ Шаблон:Cite journal
  3. ↑ Шаблон:Cite journal
  4. ↑ Шаблон:Cite journal
  5. ↑ Шаблон:Cite journal
  6. ↑ Шаблон:Cite journal
  7. ↑ Шаблон:Cite journal
  8. ↑ Yardley, J. P.; Fletcher, H.; Russell, P. B. (1978). "A potent benzylamine analgesic:(−)cis-2(α-dimethylamino-m-hydroxybenzyl)cyclohexanol". Experientia 34(9): 1124–1125. doi:10.1007/BF01922905.
  9. ↑ Paton, D.M.; Castaner, J.; Ciramadol. Drugs Fut 1980, 5, 6, 283.
  10. ↑ Peter B Russell, John P Yardley, Шаблон:US patent, Шаблон:US patent (1975 and 1977 to American Home Products Corporation).
  11. ↑ John Patrick Yardley, Peter Byrom Russell, Шаблон:Cite patent (1986 to American Home Prod).
  12. ↑ John P. Yardley & Peter B. Russell, Шаблон:US patent (1979 to Wyeth LLC).
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