Cilobamine
Chemical compound
- none
- (2R,3R)-2-(3,4-Dichlorophenyl)-3-[(1-methylethyl)amino]bicyclo[2.2.2]octan-2-ol
- 69429-84-1
- 299379
- 8557262
- 067U1T4S30
- ChEMBL2106470
- Interactive image
- Clc1ccc(cc1Cl)[C@@]3(O)[C@H](NC(C)C)C2CCC3CC2
Cilobamine is a drug which acts as a norepinephrine-dopamine reuptake inhibitor (NDRI) and has stimulant and antidepressant effects.[1][2]
It can clearly be seen that the structure is based on dichloroisoprenaline that has been fused onto the bicycloalkane scaffold.
Synthesis
An intramolecular Dieckmann cyclization on methyl 4-(2-methoxy-2-oxoethyl)cyclohexanecarboxylate [1401222-79-4] (3) with sodium hydride base gives reaction Methyl 3-oxobicyclo[2.2.2]octane-2-carboxylate [30144-30-0] (4). Treatment with sodium nitrite introduces an isonitroso group adjacent to the ketone, giving 3-Hydroxyiminobicyclo[2.2.2]octan-2-one, CID:131066320 (5). Addition of the aryl Grignard reagent, and reduction of the oxime gives CID:154108204 (6). A reductive amination of the primary amino group with acetone then completed the synthesis of cilobamine (7).
See also
- Fencamfamine
- Manifaxine
References
- ^ Leeson GA, Shaath ZA, Biedenbach SA, Yarrington JT, Okerholm RA (April 1984). "Dose related induction of the drug metabolizing enzymes of rat liver by cilobamine". Fundamental and Applied Toxicology. 4 (2 Pt 1): 261–9. doi:10.1016/0272-0590(84)90127-1. PMID 6724198.
- ^ Wager S, Quitkin F, Stewart J, McGrath P, Harrison W, Markowitz J, Tricamo E (1988). "Cilobamine in the treatment of atypical depression". Human Psychopharmacology: Clinical and Experimental. 3 (3): 201–205. doi:10.1002/hup.470030308. S2CID 145253439.
- ^ DE2003744 idem Jules Freedman, U.S. patent 3,651,142 (1970 to Colgate Palmolive Co).
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