59-63-2 Usage
Description
ISOCARBOXAZID (200 MG) is a potent monoamine oxidase (MAO) inhibitor, primarily used as an antidepressant for treating depressions that do not respond to other medications. It is a pale yellow solid and is known by the brand name Marplan.
Uses
Used in Pharmaceutical Industry:
ISOCARBOXAZID (200 MG) is used as an antidepressant for treating depressions that do not respond to other drugs. It functions as a monoamine oxidase inhibitor, which helps in increasing the levels of certain neurotransmitters in the brain, thereby alleviating depressive symptoms.
Used in Antidepressant Applications:
ISOCARBOXAZID (200 MG) is used as a powerful MAO inhibitor for patients suffering from depression. It is particularly effective in cases where other antidepressants have failed to provide relief. The drug works by inhibiting the activity of monoamine oxidase enzymes, which are responsible for breaking down neurotransmitters such as serotonin, norepinephrine, and dopamine. By blocking this enzyme, ISOCARBOXAZID (200 MG) increases the levels of these neurotransmitters, leading to an improvement in mood and a reduction in depressive symptoms.
Originator
Marplan,Roche,US,1959
Manufacturing Process
800 g of benzaldehyde was added to a hot solution (75°C) of 7 liters of
ethanol containing 720 g of 5-methyl-2-isoxazole carboxylic acid hydrazide.
The solution was stirred for ten minutes at which time the product began to
crystallize. On cooling at 4°C for 14 hours, the solid was filtered off under
vacuum and the solid filter cake was washed twice using 250 ml of ice cold
ethanol for each washing. The lbenzylidene-2-(5-methyl-3-isoxazolylcarbonyl)
hydrazine was recrystallized from ethanol, MP 199°C to 200°C.115 g of 1-benzylidene-2-(5-methyl-3-isoxazolylcarbonyl)hydrazine was added
portionwise over the period of an hour to 5 liters of anhydrous ether
containing 18.5 g of lithium aluminum hydride. The reaction mixture was
stirred for four hours and permitted to stand overnight. The excess lithium
aluminum hydride was decomposed with 250 ml of ethyl acetate and 150 ml
of water was added to decompose the complex. The solid was separated by
filtration and the ether layer was concentrated to about 500 mi. 200 ml of
benzene was added to dehydrate the solution. Concentration was continued
until a solid remained. The 1-benzyl-2-(5-methyl-3-isoxazolylcarbonyl)
hydrazine was recrystallized from methanol, MP 105°C to 106°C.
Therapeutic Function
Antidepressant
World Health Organization (WHO)
Isocarboxazid, a monoamine oxidase inhibitor (MAOI), was
introduced in 1959 for the treatment of depressive illness. Subsequently concern
regarding potentially serious interactions between MAOIs and foods containing
tyramine inspired much restrictive regulatory action. However, MAOIs still retain a
place in the treatment of serious depressive illness although there is no
international consensus on which compounds should be preferred. Thus
isocarboxazid remains available in several countries and is cited in the British
National Formulary as a relatively safe example of this class of compound.
Synthesis
Isocarboxazid, 2-benzylhydrazid-5-methyl-3-isoxazolecarboxylate (7.2.6),
can be synthesized from acetylacetone, which on nitrosation with nitrous acid gives 5-
methyl-isoxazol-3-carboxylic acid (7.2.2). Esterification of this product gives the ethyl
ester of 5-methyl-isoxazol-3-carboxylic acid (7.2.3). The synthesized ester (7.2.3) is further reacted with benzylhydrazine, to give isocarboxazide (7.2.6), or with hydrazine,
which forms 5-methyl-isoxazol-3-carboxylic acid hydrazide (7.2.4). Reacting the latter
with benzaldehyde gives hydrazone (7.2.5), which is further reduced to the isocarboxazide
(7.2.6) [46,47].
Check Digit Verification of cas no
The CAS Registry Mumber 59-63-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 9 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 59-63:
(4*5)+(3*9)+(2*6)+(1*3)=62
62 % 10 = 2
So 59-63-2 is a valid CAS Registry Number.
InChI:InChI=1/C12H13N3O2/c1-9-7-11(15-17-9)12(16)14-13-8-10-5-3-2-4-6-10/h2-7,13H,8H2,1H3,(H,14,16)
59-63-2Relevant articles and documents
PROCESS FOR THE PREPARATION OF ISOCARBOXAZID
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Page/Page column 10; 11; 12, (2017/02/28)
This invention relates to a novel chemical process for the synthesis of N'-benzyl-5- methylisoxazole-3-carbohydrazide (Isocarboxazid) which comprises reacting 5-methyl-3- isoxazole carboxylic acid ester with benzylhydrazine or a salt thereof in an aprotic organic solvent and in the presence of an organic base.
The Boulton-Katritzky rearrangement of isocarboxazid
Van Arnum, Susan D.,Niemczykapi, Henry J.
experimental part, p. 909 - 913 (2010/01/11)
(Chemical Equation Presented) Isocarboxazid rearranges on heating to 5-acetonyl-2-benzyl-4-hydroxy-1,2,3-triazole in DMF at 150°C, in the ionic liquid, [bmin]HSO4- at 100°C or as a melt at 105°C. This is the first reported example of the Boulton-Katritzky rearrangement of an acyl hydrazide.
