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Caroxazone (Surodil, Timostenil) is an
Synthesis starts by
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 ...
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 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 antidepressants, espe ...
(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 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 deamination of amines, s ...
and MAO-B
Monoamine oxidase B, also known as MAOB, 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. ...
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 involves the conversion of a carbonyl group to an amine via an intermediate imine. The carbonyl group is most commonly a ketone or an aldehyde. It is considered ...
of salicylaldehyde
Salicylic aldehyde (2-hydroxybenzaldehyde) is the organic compound with the formula (C7 H6 O2) C6H4CHO-2-OH. Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. This colorless oil ...
and glycinamide
Glycinamide is a 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 the organic chemical compound with the formula COCl2. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. Phosgene is a valued and important industrial building block, espe ...
and NaHCO3.
See also
* Paraxazone, anisomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers.
Iso ...
of Caroxazone
References
{{Monoamine metabolism modulators Benzoxazines Carbamates