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Caroxazone (Surodil, Timostenil) is an
Synthesis starts by
antidepressant
Antidepressants are a class of medications used to treat major depressive disorder, anxiety disorders, chronic pain, and addiction.
Common side effects of antidepressants include Xerostomia, dry mouth, weight gain, dizziness, headaches, akathi ...
which was formerly used for the treatment of depression but is now no longer marketed. It acts as a reversible monoamine oxidase inhibitor
Monoamine oxidase inhibitors (MAOIs) are a drug class, class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressa ...
(RIMA
Rima, also known as Rima the Jungle Girl, is the fictional heroine of W. H. Hudson's 1904 novel '' Green Mansions: A Romance of the Tropical Forest''. In it, Rima, a primitive girl of the shrinking rain forest of South America, meets Abel, a pol ...
) of both MAO-A
Monoamine oxidase A, also known as MAO-A, is an enzyme ( E.C. 1.4.3.4) that in humans is encoded by the ''MAOA'' gene. This gene is one of two neighboring gene family members that encode mitochondrial enzymes which catalyze the oxidative deamin ...
and MAO-B
Monoamine oxidase B (MAO-B) is an enzyme that in humans is encoded by the ''MAOB'' gene.
The protein encoded by this gene belongs to the flavin monoamine oxidase family. It is an enzyme located in the outer mitochondrial membrane. It catalyze ...
subtypes, with five-fold preference for the latter.
Synthesis
Synthesis starts by reductive amination
Reductive amination (also known as reductive alkylation) is a form of amination that converts a carbonyl group to an amine via an intermediate imine. The carbonyl group is most commonly a ketone or an aldehyde. It is a common method to make amine ...
of salicylaldehyde
Salicylic aldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula . Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. This colorless oily liquid has a bitter almo ...
and glycinamide
Glycinamide is an organic compound with the molecular formula H2NCH2C(O)NH2. It is the amide derivative of the amino acid glycine. It is a water-soluble, white solid. Amino acid amides, such as glycinamide are prepared by treating the amino acid ...
to give 3. The synthesis is completed by reaction with phosgene
Phosgene is an organic chemical compound with the formula . It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. It can be thought of chemically as the double acyl chloride analog of ...
and NaHCO3.
See also
*Paraxazone
Paraxazone is an antidepressant. It acts as a reversible inhibitor of the enzyme monoamine oxidase
Monoamine oxidases (MAO) () are a family of enzymes that catalyze the oxidation of monoamines, employing oxygen to clip off their amine gr ...
, an isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...
of Caroxazone
References
{{Monoamine metabolism modulators Benzoxazines Carbamates