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Cilobamine is a drug which acts as a norepinephrine-dopamine reuptake inhibitor (NDRI) and has
An intramolecular
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).
stimulant
Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and inv ...
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, hea ...
effects.
It can clearly be seen that the structure is based on dichloroisoprenaline
Dichloroisoprenaline (DCI), also known as dichloroisoproterenol, was the first beta blocker ever to be developed. It is non-selective for the β1-adrenergic and β2-adrenergic receptors. DCI has low potency and acts as a partial agonist/antagoni ...
that has been fused onto the bicycloalkane scaffold.
Synthesis
An intramolecular Dieckmann cyclization
The Dieckmann condensation is the intramolecular chemical reaction of diesters with base to give β-keto esters. It is named after the German chemist Walter Dieckmann (1869–1925). The equivalent intermolecular reaction is the Claisen condensat ...
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 nitrite ...
introduces a isonitroso group adjacent to the ketone, giving 3-Hydroxyiminobicyclo .2.2ctan-2-oneCID: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
Fencamfamin ( INN), also known as fencamfamine or by the brand names Glucoenergan and Reactivan, is a stimulant which was developed by Merck in the 1960s.
Medical uses
Fencamfamin is still used, though rarely, for treating depressive day-time fa ...
* Manifaxine
Manifaxine (developmental code name GW-320,659) is a norepinephrine–dopamine reuptake inhibitor developed by GlaxoSmithKline through structural modification of radafaxine, an isomer of hydroxybupropion and one of the active metabolites of bup ...
References
Antidepressants Chloroarenes Stimulants Norepinephrine–dopamine reuptake inhibitors Phenylethanolamines {{nervous-system-drug-stub