iproniazid Chemical Properties

Melting point:

112.5-113.5°

Boiling point:

311.75°C (rough estimate)

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)

form 

Solid

color 

Pale Beige

CAS DataBase Reference

54-92-2

Safety Information

HS Code 

2933399990

Toxicity

An isopropyl derivative of isoniazid that was found to have mood-elevating effects in tuberculosis patients. It was later found to be a monoamine oxidase (MAO) inhibitor and, although not currently approved for clinical use as an antidepressant due to its propensity to cause liver damage it led to the development of other MAO inhibitors currently in use. In addition to hepatotoxic effects, iproniazid is a hypotensive agent and can cause potentially hazardous reactions with other drugs and amine-rich foods.

iproniazid Usage And Synthesis

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.

Definition

ChEBI: Iproniazid is a carbohydrazide and a member of pyridines.

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.

iproniazid(54-92-2)Related Product Information

• Thionyl chloride
• 2-Chloropropane
• 2-[[(3aS,4R,6S,6aR)-4-[7-[[(1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl]amino]-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-6-yl]oxy]ethanol
• METHYL ISOINDOLINE-5-CARBOXYLATE HYDROCHLORIDE
• tert-Butyl isonicotinate
• Phenelzine
• Sulpiride
• PENTAZOCINE
• Carbamazepine
• ISOCARBOXAZID (200 MG)
• Clozapine
• Procaine hydrochloride
• LONICERAE JAPONICAE FLOS
• Moclobemide
• Chlorpromazine
• IPRONIAZID PHOSPHATE
• iproniazid
• N-(6,7-DIMETHOXY-1-(4-METHOXYPHENYL)-3-OXO-3,4-DIHYDROISOQUINOLIN-2(1H)-YL)ISONICOTINAMIDE