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
IUPAC name (2R,3R)-2-(3,4-Dichlorophenyl)-3-[(1-methylethyl)amino]bicyclo[2.2.2]octan-2-ol
CAS Number	69429-84-1
PubChem CID	299379
ChemSpider	8557262
UNII	067U1T4S30
ChEMBL	ChEMBL2106470
Chemical and physical data
Formula	C17H23Cl2NO
Molar mass	328.28 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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 (3) with sodium hydride base provides methyl 3-oxobicyclo[2.2.2]octane-2-carboxylate (4). Treatment with sodium nitrite introduces an isonitroso group adjacent to the ketone, giving 3-Hydroxyiminobicyclo[2.2.2]octan-2-one (5). Addition of the aryl Grignard reagent, and reduction of the oxime gives (6). A reductive amination of the primary amino group with acetone then completes the synthesis of cilobamine (7).

See also

• Fencamfamine
• Manifaxine