Profadol
Introduction '''Profadol''' (CI-572) is an opioid analgesic which was developed in the 1960s by Parke-Davis. It acts as a mixed agonist-antagonist of the μ-opioid receptor. The analgetic potency is about the same as of pethidine (meperidine), the antagonistic effect is 1/50 of nalorphine.
Synthesis Synthesis: Patents:The Knoevenagel condensation between 3'-Methoxybutyrophenone 21550-06-1 and Ethyl cyanoacetate gives ('''1'''). Conjugate addition of cyanide gives ('''2'''). Hydrolysis of both nitrile groups, saponification of the ester and decarboxylation gives the diacid,  CID:164137621 ('''3'''). Imide formation occurs upon treatment with methylamine giving 3-(3-Methoxyphenyl)-1-methyl-3-propylpyrrolidine-2,5-dione,  CID:163444474 ('''4'''). Reduction of the imide by lithium aluminium hydride gave 1505-32-429369-01-5 ('''5'''). Demethylation completed the synthesis of Profadol ('''6''').
See also * Bromadol* C-8813* Ciramadol* Faxeladol* Prodilidine* Tapentadol* Tramadol
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