Ciramadol Explained

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

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

• Bromadol
• C-8813
• Faxeladol
• Profadol
• Tapentadol
• Tramadol

Notes and References

1. US . 3928626 . Benzylamine Analgesics .
2. Cochrane AD, Bell R, Sullivan JR, Shaw J . Ciramadol. A new analgesic . The Medical Journal of Australia . 2 . 9 . 501–2 . November 1979 . 522808 . 10.5694/j.1326-5377.1979.tb125803.x.
3. Preston KL, Bigelow GE, Liebson IA . Comparative evaluation of morphine, pentazocine and ciramadol in postaddicts . The Journal of Pharmacology and Experimental Therapeutics . 240 . 3 . 900–10 . March 1987 . 3559982 .
4. Romagnoli A, Keats AS . Low ceiling respiratory depression by ciramadol . International Journal of Clinical Pharmacology Research . 6 . 6 . 451–5 . 1986 . 3100462 .
5. Downing JW, Brock-Utne JG, Holloway AM . 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 . December 1983 . 6359486 .
6. Powell WF . A double-blind comparison of multiple intramuscular doses of ciramadol, morphine, and placebo for the treatment of postoperative pain. . Anesthesia and Analgesia . November 1985 . 64 . 11 . 1101–7 . 10.1213/00000539-198511000-00012 . 3901821 .
7. Stambaugh JE, McAdams J . 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 . February 1987 . 3680568 . 10.1002/j.1552-4604.1987.tb02178.x . 21229861 .