Isocarboxazid

Base Information

• Chemical Name: Isocarboxazid
• CAS No.: 59-63-2
• Molecular Formula: C12H13 N3 O2
• Molecular Weight: 231.254
• Hs Code.: 2934999090
• European Community (EC) Number: 200-438-4
• NSC Number: 169893
• UNII: 34237V843T
• DSSTox Substance ID: DTXSID4023171
• Nikkaji Number: J4.794E
• Wikipedia: Isocarboxazid
• Wikidata: Q409595
• NCI Thesaurus Code: C47573
• RXCUI: 6011
• Pharos Ligand ID: JSCDYC9VTP3K
• Metabolomics Workbench ID: 43455
• ChEMBL ID: CHEMBL1201168
• Mol file: 59-63-2.mol

Synonyms:Isocarboxazid

Chemical Property of Isocarboxazid

Chemical Property:

• Vapor Pressure: 1.97E-06mmHg at 25°C
• Melting Point: 98-1000C
• Refractive Index: 1.5290 (estimate)
• Boiling Point: 394.5°Cat760mmHg
• PKA: pKa 10.4 (Uncertain)
• Flash Point: 192.4°C
• PSA: 67.16000
• Density: 1.206g/cm³
• LogP: 2.19940
• Storage Temp.: -20°C Freezer
• Water Solubility.: 0.8g/L(25 oC)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 231.100776666
• Heavy Atom Count: 17
• Complexity: 254

Purity/Quality:

99%, ^*data from raw suppliers

Isocarboxazid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antidepressant Agents
• Canonical SMILES: CC1=CC(=NO1)C(=O)NNCC2=CC=CC=C2
• Recent ClinicalTrials: I2PETHV - Imidazoline2 Binding Site in Healthy Volunteers
• Uses: Isocarboxazid is a powerful MAO inhibitor. As with phenelzine, isocarboxazid is used for depressions that do not respond to other drugs. Monoamine oxidase inhibitor. Antidepressant
• Therapeutic Function: Antidepressant

Technology Process of Isocarboxazid

There total 5 articles about Isocarboxazid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

methyl 5-methylisoxazole-3-carboxylate (19788-35-3) + benzylhydrazine dihydrochloride (20570-96-1) → isocarboxazid (59-63-2)

Guidance literature:

With triethylamine; In n-heptane; at 35 ℃; Temperature;

Reference yield:

5-methyl-isoxazole-3-carboxylic acid benzylidenehydrazide (91397-11-4) → isocarboxazid (59-63-2)

Guidance literature:

With potassium borohydride; In methanol; water;

DOI:10.1021/jm50009a002

Reference yield:

5-methylisoxazole-3-carboxylic acid hydrazide (62438-03-3) → isocarboxazid (59-63-2)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol

2: KBH₄ / methanol; H₂O

With potassium borohydride; In methanol; ethanol; water;

DOI:10.1021/jm50009a002

upstream raw materials:

methyl 5-methylisoxazole-3-carboxylate

Benzylhydrazine

5-methyl-isoxazole-3-carboxylic acid benzylidenehydrazide

5-methylisoxazole-3-carboxylic acid hydrazide

Downstream raw materials:

Cyanoaceton

5-acetonyl-2-benzyl-4-hydroxy-1,2,3-triazole

N-benzyl-N,N'-bis-(5-methyl-isoxazole-3-carbonyl)-hydrazine

Refernces

• 1、 Kawase, Yasushi,Yamagishi, Takehiro,Kato, Jun-Ya,Kutsuma, Teruo,Kataoka, Tadashi,Iwakuma, Takeo,Yokomatsu, Tsutomu. "Reductive alkylation of hydrazine derivatives with α-picoline-borane and its applications to the syntheses of useful compounds related to active pharmaceutical ingredients". . p. 455 - 464. Retrieved 2014/03/21.
• 2、 GARDNER,WENIS,LEE. "Monoamine oxidase inhibitors. I. 1-Alkyl and 1-aralkyl-2-(picolinoyl and 5-methyl-3-isoxazolyl-carbonyl)hydrazines.". . p. 133 - 145. Retrieved 2007/10/04.