Compound: isocarboxazid
SMILES: O=C(NNCc1ccccc1)c2noc(c2)C
InChIKey: XKFPYPQQHFEXRZ-UHFFFAOYSA-N
Synonyms: isocarboxazid, 59-63-2, Isocarboxazide, Enerzer, Marplan, Isocarbonazid, Isocarbossazide, N'-benzyl-5-methyl-1,2-oxazole-3-carbohydrazide, Isocarboxazida, Ro 5-0831, Isocarboxazidum, 5-Methyl-3-isoxazolecarboxylic acid 2-benzylhydrazide, 3-Isoxazolecarboxylic acid, 5-methyl-, 2-(phenylmethyl)hydrazide, DTXSID4023171, NSC-169893, RO-5-0831, NSC169893, DTXCID003171, 34237V843T, 4-27-00-03999 (Beilstein Handbook Reference), Isocarboxacid, RefChem:57807, N06AF01, 200-438-4, Benazide, N'-Benzyl-5-methylisoxazole-3-carbohydrazide, Isocarboxyzid, Marplon, Maraplan, Isocarbossazide [DCIT], BMIH, Isocarboxazide [INN-French], Isocarboxazidum [INN-Latin], Isocarboxazida [INN-Spanish], Ro 5-0831/1, N'-Benzyl N-methyl-5-isoxazolecarboxylhydrazide-3, NSC 169893, Isocarboxazid (INN), 1-Benzyl-2-(5-methyl-3-isoxazolylcarbonyl)hydrazine, MLS003106729, 3-Isoxazolecarboxylic acid, 5-methyl-, 2-benzylhydrazide, CAS-59-63-2, NCGC00016267-01, ISOCARBOXAZID [INN], N'-benzyl-5-methyl-isoxazole-3-carbohydrazide, SMR001233334, Marplan (TN), Isocarboxazid (1.0 mg/mL in Acetonitrile), CCRIS 9178, SR-01000841192, EINECS 200-438-4, BRN 0201295, 1-Benzyl-2-(5-methyl-3-isoxazolyl-carbonyl)hydrazine, 59-63-2 (free base), Isocarboxazid [USP:INN:BAN], UNII-34237V843T, MFCD00865409, Isocarboxazid (ICD), Isocarboxazid (Standard), Prestwick0_000795, Prestwick1_000795, Prestwick2_000795, Prestwick3_000795, ISOCARBOXAZID [MI], SCHEMBL49562, BSPBio_000930, MLS002154005, ISOCARBOXAZID [MART.], 5-methyl-N'-(phenylmethyl)isoxazole-3-carbohydrazide, SPBio_002869, ISOCARBOXAZID [USP-RS], ISOCARBOXAZID [WHO-DD], BPBio1_001024, GTPL7204, orb1302759, CHEMBL1201168, WLN: T5NOJ C1 EVMM1R, CHEBI:93635, BDBM163692, GLXC-02865, HMS1570O12, HMS2097O12, HMS2230E11, HMS3369G18, HMS3714O12, HMS3887K05, HMS6018D22, ISOCARBOXAZID [ORANGE BOOK], MSK10880, Tox21_110336, EBC-10021, HY-13929R, AKOS016003091, CCG-220795, DB01247, Isocarboxazid (1 mg/mL in Acetonitrile), NCGC00016267-02, NCGC00016267-03, NCGC00016267-06, AC-24841, DA-64526, HY-13929, MS-23317, AB00513923, CS-0008613, NS00007049, 3-Isoxazolecarboxylic acid, 2-benzylhydrazide, N?-Benzyl-5-methylisoxazole-3-carbohydrazide, D02580, G12701, N'-Benzyl-5-methyl-3-isoxazolecarbohydrazide #, EN300-12578055, Q409595, SR-01000841192-2, SR-01000841192-3, 3-Isoxazolecarboxylic acid, 2-(phenylmethyl)hydrazide, 5-methyl-N'-(phenylmethyl)-3-isoxazolecarbohydrazide, BRD-K93332168-001-03-2, BRD-K93332168-001-10-7, BRD-K93332168-001-11-5, Z2044793215, Isocarboxazid 5-methyl-3-isoxazole-carboxylic acid 2-benzylhydrazide, AldrichCPR
Theoretical properties:
molecular_formula: C12H13N3O2
molecular_weight: 231.25 g/mol
exact_mass: 231.100776666 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 4
heavy_atom_count: 17
topological_polar_surface_area: 67.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
boiling_point: 394.5ºC at 760 mmHg
melting_point: 105-106 °C
solubility: Very slightly soluble in hot water
Descriptions:
pubchem: 5-methyl-N'-(phenylmethyl)-3-isoxazolecarbohydrazide is a member of benzenes.
chembl: ISOCARBOXAZID is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Isocarboxazid, sold under the brand name Marplan among others, is a non-selective irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class used as an antidepressant. Along with phenelzine and tranylcypromine, it is one of only three classical MAOIs still available for clinical use in the treatment of psychiatric disorders in the United States, though it is not as commonly employed in comparison to the others.
Isocarboxazid is primarily used to treat mood and anxiety disorders. It has also been investigated in the treatment of schizophrenia, Parkinson's disease, and other dementia-related disorders. 
Isocarboxazid, as well as other MAOIs, increase the levels of the monoamine neurotransmitters serotonin, dopamine, norepinephrine, epinephrine, melatonin, and phenethylamine in the brain.
Classical MAOIs, including isocarboxazid, are used only rarely due to prominent food and drug interactions and have been largely superseded by newer antidepressants such as the selective serotonin reuptake inhibitors (SSRIs). The cause of the interactions is because MAOIs inhibit the metabolism of dietary amines (e.g., tyramine) and the monoamine neurotransmitters. In combination with other drugs that increase the levels of the monoamine neurotransmitters such as the SSRIs, or with certain foods high in dietary amines such as aged cheeses, MAOIs can produce dangerous elevations of monoamine neurotransmitters resulting in potentially life-threatening syndromes such as hypertensive crisis and serotonin syndrome.