Cilobamine

Cilobamine is a drug which acts as a norepinephrine-dopamine reuptake inhibitor (NDRI) and has stimulant and antidepressant effects.[1][2]

Cilobamine
Clinical data
ATC code
  • none
Identifiers
  • (2R,3R)-2-(3,4-Dichlorophenyl)-3-[(1-methylethyl)amino]bicyclo[2.2.2]octan-2-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC17H23Cl2NO
Molar mass328.28 g·mol−1
3D model (JSmol)
  • Clc1ccc(cc1Cl)[C@@]3(O)[C@H](NC(C)C)C2CCC3CC2

It can clearly be seen that the structure is based on dichloroisoprenaline that has been fused onto the bicycloalkane scaffold.

Synthesis
Patent:[3]

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

References
  1. 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.
  2. 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.
  3. DE2003744 idem Jules Freedman, U.S. Patent 3,651,142 (1970 to Colgate Palmolive Co).


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