54-92-2

Basic information

• Product Name: iproniazid
• Synonyms: iproniazid;IPRAZID;N'-propan-2-ylpyridine-4-carbohydrazide;N'-Isopropylpyridine-4-Carbohydrazide
• CAS NO: 54-92-2
• Molecular Formula: C₉H₁₃N₃O
• Molecular Weight: 179.222
• EINECS: 200-218-8
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals
• Mol File: 54-92-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 112.5-113.5°
• Boiling Point: 311.75°C (rough estimate)
• Appearance: /
• Density: 1.1305 (rough estimate)
• Refractive Index: 1.5100 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 11.28±0.23(Predicted)
• CAS DataBase Reference: iproniazid(CAS DataBase Reference)
• NIST Chemistry Reference: iproniazid(54-92-2)
• EPA Substance Registry System: iproniazid(54-92-2)

Safety Data

• Hazardous Substances Data: 54-92-2(Hazardous Substances Data)

Usage

Originator

Marsilid,Roche,US,1952

Uses

Iproniazid is a hydrazine based drug used as an antidepressant. Iproniazid acts as an irreversible and nonselective monoamine oxidase inhibitor.

Manufacturing Process

A mixture of 40 g of isonicotinyl hydrazine and 600 cc of acetone was heated on a steam bath until solution was complete. Upon cooling the reaction mixture, 1-isonicotinyl-2-isopropylidene hydrazine precipitated in the form of white needles; MP 161°C to 161.5°C.A solution of 20 g of 1-isonicotinyl-2-isopropylidene hydrazine in 150 cc of methanol was reduced with hydrogen at room temperature and 50 psi using 300 mg of platinum black as a catalyst.

Brand name

Euphozid;Ipropran;Isotamine;Laniazid;Marsilid;Nydrazid;P-1-n forte;Pms isoniazid;Rifamate;Rimactane;Rimifon;Ro 7-1554;Teebaconin;Triniad;Uniad.

Therapeutic Function

Antidepressant, Monoamine oxidase inhibitor

World Health Organization (WHO)

Iproniazid, a monoamine oxidase inhibitor (MAOI), was introduced in 1952 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 iproniazid remains available in several countries.

Purification Methods

Crystallise it from *benzene or *benzene /pet ether and dry it in a vacuum. It is soluble in H2O and EtOH. [Fox & Gibas J Org Chem 18 994 1953.] The dihydrochloride has m 227-228o (from EtOH). [Beilstein 22 III/IV 551.] It is an antidepressant.

InChI:InChI=1S/C9H13N3O/c1-7(2)11-12-9(13)8-3-5-10-6-4-8/h3-7,11H,1-2H3,(H,12,13)

Upstream product

• 54-85-3 isoniazid 
• 4813-04-1 isonicotinic acid isopropylidenehydrazide 
• 75-26-3 isopropyl bromide 
• 75-30-9 2-iodo-propane 

Downstream Products

• 14229-03-9 3-isopropyl-5-pyridin-4-yl-3H-[1,3,4]oxadiazole-2-thione 

Relevant articles and documents

Discovery of a novel series of indolyl hydrazide derivatives as diacylglycerol acyltransferase-1 inhibitors

A novel series of hydrazide derivatives were synthesized as potential diacylglycerol acyltransferase (DGAT) inhibitors. Among them, compounds 8u and 8v exhibited selective and potent DGAT-1 inhibitory activities. In addition, compound 8u dose-dependently inhibited triglyceride synthesis in HepG2 cell lines. Furthermore, treatment with compound 8u for an oral lipid tolerance test showed a significant decrease in plasma triglyceride levels compared with vehicle-treated control animals, indicating delayed absorption of triglyceride after an acute lipid challenge.

Some recently synthesised tuberculostatic 4-substituted oxadiazolones and oxadiazol-thiones. VI.

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