Wikipedia

Ciramadol

Not to be confused with Cimaterol.

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]

Ciramadol
Clinical data
Other namesCiramadol, WY-15705
Routes of
administration		Oral
ATC code
  • none
Identifiers
  • 3-{(R)-Dimethylamino-[(1R,2R)-2-hydroxycyclohexyl]}methyl]phenol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H23NO2
Molar mass249.354 g·mol−1
3D model (JSmol)
  • OC1=CC=CC([C@@H]([C@H]2CCCC[C@H]2O)N(C)C)=C1
  • InChI=1S/C15H23NO2/c1-16(2)15(11-6-5-7-12(17)10-11)13-8-3-4-9-14(13)18/h5-7,10,13-15,17-18H,3-4,8-9H2,1-2H3/t13-,14 ,15-/m0/s1 checkY
  • Key:UVTLONZTPXCUPU-ZNMIVQPWSA-N checkY
  (verify)

Synthesis

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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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  1. ^ US 3928626, "Benzylamine Analgesics" 
  2. ^ Cochrane AD, Bell R, Sullivan JR, Shaw J (November 1979). "Ciramadol. A new analgesic". The Medical Journal of Australia. 2 (9): 501–2. doi:10.5694/j.1326-5377.1979.tb125803.x. PMID 522808.501-2&rft.date=1979-11&rft_id=info:doi/10.5694/j.1326-5377.1979.tb125803.x&rft_id=info:pmid/522808&rft.aulast=Cochrane&rft.aufirst=AD&rft.au=Bell, R&rft.au=Sullivan, JR&rft.au=Shaw, J&rfr_id=info:sid/en.wikipedia.org:Ciramadol" class="Z3988">
  3. ^ Preston KL, Bigelow GE, Liebson IA (March 1987). "Comparative evaluation of morphine, pentazocine and ciramadol in postaddicts". The Journal of Pharmacology and Experimental Therapeutics. 240 (3): 900–10. PMID 3559982.900-10&rft.date=1987-03&rft_id=info:pmid/3559982&rft.aulast=Preston&rft.aufirst=KL&rft.au=Bigelow, GE&rft.au=Liebson, IA&rfr_id=info:sid/en.wikipedia.org:Ciramadol" class="Z3988">
  4. ^ Romagnoli A, Keats AS (1986). "Low ceiling respiratory depression by ciramadol". International Journal of Clinical Pharmacology Research. 6 (6): 451–5. PMID 3100462.451-5&rft.date=1986&rft_id=info:pmid/3100462&rft.aulast=Romagnoli&rft.aufirst=A&rft.au=Keats, AS&rfr_id=info:sid/en.wikipedia.org:Ciramadol" class="Z3988">
  5. ^ Downing JW, Brock-Utne JG, Holloway AM (December 1983). "Ciramadol--a new synthetic analgesic. A double-blind comparison with oral codeine for postoperative pain relief". South African Medical Journal = Suid-Afrikaanse Tydskrif vir Geneeskunde. 64 (25): 978–82. PMID 6386386.978-82&rft.date=1983-12&rft_id=info:pmid/6386386&rft.aulast=Downing&rft.aufirst=JW&rft.au=Brock-Utne, JG&rft.au=Holloway, AM&rfr_id=info:sid/en.wikipedia.org:Ciramadol" class="Z3988">
  6. ^ Powell WF (November 1985). "A double-blind comparison of multiple intramuscular doses of ciramadol, morphine, and placebo for the treatment of postoperative pain". Anesthesia and Analgesia. 64 (11): 1101–7. doi:10.1213/00000539-198511000-00012. PMID 3901821.1101-7&rft.date=1985-11&rft_id=info:doi/10.1213/00000539-198511000-00012&rft_id=info:pmid/3901821&rft.aulast=Powell&rft.aufirst=WF&rft_id=https://dx.doi.org/10.1213%2F00000539-198511000-00012&rfr_id=info:sid/en.wikipedia.org:Ciramadol" class="Z3988">
  7. ^ Stambaugh JE, McAdams J (February 1987). "Comparison of the analgesic efficacy and safety oral ciramadol, codeine, and placebo in patients with chronic cancer pain". Journal of Clinical Pharmacology. 27 (2): 162–6. doi:10.1002/j.1552-4604.1987.tb02178.x. PMID 3680568. S2CID 21229861.162-6&rft.date=1987-02&rft_id=https://api.semanticscholar.org/CorpusID:21229861#id-name=S2CID&rft_id=info:pmid/3680568&rft_id=info:doi/10.1002/j.1552-4604.1987.tb02178.x&rft.aulast=Stambaugh&rft.aufirst=JE&rft.au=McAdams, J&rfr_id=info:sid/en.wikipedia.org:Ciramadol" class="Z3988">
  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, U.S. patent 3,928,626, U.S. patent 4,017,637 (1975 and 1977 to American Home Products Corporation).
  11. ^ John Patrick Yardley, Peter Byrom Russell, DE 2317183  (1986 to American Home Prod).
  12. ^ John P. Yardley & Peter B. Russell, U.S. patent 4,155,935 (1979 to Wyeth LLC).


 

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