Cilobamine is a drug which acts as a
norepinephrine-dopamine reuptake inhibitor (NDRI) and has
stimulant and
antidepressant
Antidepressants are a class of medication used to treat major depressive disorder, anxiety disorders, chronic pain conditions, and to help manage addictions. Common side-effects of antidepressants include dry mouth, weight gain, dizziness, heada ...
effects.
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
401222-79-4(3) with sodium hydride base gives reaction Methyl 3-oxobicyclo
.2.2ctane-2-carboxylate
0144-30-0(4). Treatment with
sodium nitrite
Sodium nitrite is an inorganic compound with the chemical formula NaNO2. It is a white to slightly yellowish crystalline powder that is very soluble in water and is hygroscopic. From an industrial perspective, it is the most important nitrit ...
introduces a isonitroso group adjacent to the ketone, giving 3-Hydroxyiminobicyclo
.2.2ctan-2-one
CID:131066320(5). Addition of the aryl Grignard reagent, and reduction of the oxime give
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
Antidepressants
Chloroarenes
Stimulants
Norepinephrine–dopamine reuptake inhibitors
Phenylethanolamines
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