Draft:Dimefadane
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| Clinical data | |
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| Other names | SK&F 1340, SKF 1340, NIH 7661, |
| Identifiers | |
| CAS Number | |
| PubChem CID | |
| Chemical and physical data | |
| Formula | C17H19N |
| Molar mass | 237.346 g·mol−1 |
| 3D model (JSmol) | |
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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[clarification needed], it is not known if this is opioidergic.[citation needed] It has SAR[clarification needed] that can be compared to tametraline. Klaus Bøgesø used dimefadane as the harbinger to Indatraline.[citation needed]
Synthesis
[edit]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).
References
[edit]- ^ Barltrop, J. A.; Acheson, R. M.; Philpott, P. G.; MacPhee, K. E.; Hunt, J. S. (1956). "570. Compounds of potential pharmacological interest. Part IV. Aryl and alkyl derivatives of 1-aminoindane". Journal of the Chemical Society (Resumed): 2928. doi:10.1039/JR9560002928.
- ^ Levshina, K.V. et al, Zh. Obshch. Khim., 1964,34, 3414; CA, 62, 3983f (synth)
- ^ Philpott, P. G.; Barltrop, J. A. (1956). "139. Compounds of potential pharmacological interest. Part 1. Acyl derivatives of 1-amino-3-phenylindane". Journal of the Chemical Society (Resumed): 691. doi:10.1039/jr9560000691.
- ^ Dr Helmer Richter, Dr Martin Schenck, DE951628 & DE946058 (1953 & 1956 both to Schering Ag).