Dimefadane
Analgesic
From Wikipedia, the free encyclopedia
Dimefadane is an analgesic agent with about the same activity as codeine, but without any of the GI side effects.[citation needed] Although it does not adhere to the classical morphine rule (structure includes a tertiary amine, phenyl ring and quaternary carbon), it is not known if this is opioidergic.[citation needed] It has structure activity relationships that can be compared to tametraline. Klaus Bøgesø used dimefadane as the harbinger to Indatraline.[citation needed]
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| Other names | SK&F 1340, SKF 1340, NIH 7661, |
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| Formula | C17H19N |
| Molar mass | 237.346 g·mol−1 |
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Synthesis
Synthesis:[1][2] Cyclic Normethadone derivative:[3] Patents:[4]
The Friedel-Crafts reaction between cinnamic acid [140-10-3] (1) and benzene in the presence of a Lewis acid catalyst gives 3,3-diphenylpropionic acid [606-83-7] (2). The cyclization of this gives 3-phenyl-1-indanone [16618-72-7] (3). Heating with ammonium formate (Leuckart reaction) gives 3-phenyl-1-indanamine, PC22346445 (4). Although reduction of the oxime would also work, perhaps there is differences in the proficiency between the different methods. Heating with formaldehyde and formic acid (Eschweiler-Clark reaction) then produces dimefadane (5).