cilobamine cilobamine cilobamine is a drug which acts as a norepinephrine-dopamine reuptake inhibitor (ndri) and has stimulant and antidepressant effects. cilobamineclinical dataatc codenoneidentifiers iupac name (2r,3r)-2-(3,4-dichlorophenyl)-3-bicyclooctan-2-ol cas number69429-84-1pubchem cid299379chemspider8557262unii067u1t4s30chemblchembl2106470chemical and physical dataformulac17h23cl2nomolar mass328.28 g·mol−13d model (jsmol)interactive image smiles clc1ccc(cc1cl)3(o)(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: an intramolecular dieckmann cyclization on methyl 4-(2-methoxy-2-oxoethyl)cyclohexanecarboxylate (3) with sodium hydride base gives reaction methyl 3-oxobicyclooctane-2-carboxylate (4). treatment with sodium nitrite introduces a isonitroso group adjacent to the ketone, giving 3-hydroxyiminobicyclooctan-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).