Nialamide

Chemical Properties

White, crystalline powder. Low solubility in water; good solubility in slightly acid solution. It is stable in crystalline form, suspension, and solution.

Originator

Niamid,Pfizer,US,1959

Uses

MAO inhibitor

Uses

Nialamide is a nonselective monoamine oxidase (MAO) inhibitor that is used as an antidepressant.

Definition

ChEBI: 3-[[oxo(pyridin-4-yl)methyl]hydrazo]-N-(phenylmethyl)propanamide is an organooxygen compound and an organonitrogen compound. It is functionally related to a beta-amino acid.

Manufacturing Process

Methyl acrylate, 28.0 g (0.4 mol) was added dropwise during one hour to a solution containing 54.8 g (0.4 mol) of isonicotinic acid hydrazide (isoniazid) and 10 ml of glacial acetic acid in 400 ml of tertiary butyl alcohol. The resulting solution then was heated for 18 hours on a steam bath. Concentration of the reaction mixture to 100 ml yielded 13.0 g of unreacted isonicotinic acid hydrazide. The filtrate was concentrated to a thick syrup which was triturated with anhydrous ether and recrystallized from isopropyl alcohol; MP 87°C to 88.5°C. Elemental analysis of the product gave 1- isonicotinyl-2-(β-carbomethoxyethyl)hydrazine.
A slurry of 7.5 g (0.034 mol) of 1-isonicotinyl-2-(carbomethoxyethyl)- hydrazine and 5 ml of benzylamine is heated with stirring at 130°C for three hours. The cooled mass is then recrystallized from ethyl acetate to yield white needles melting at 151.1°C to 152.1°C.

brand name

Nialamid;Niamidal;Niamide;Niaquital;Niaquitil;Novazid;Nuredal;Psyco-retard;Surgexl.

Therapeutic Function

Antidepressant

World Health Organization (WHO)

Nialamide, 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 nialamide remains available in several countries.

General Description

Nialamide is an antidepressant drug and its effect on β-adrenergic receptor-adenylate cyclase system of rat pineal gland has been studied. Antidepressant action of the combination of nialamide and 5-hydroxytryptophan has been evaluated.

Hazard

Toxic in overdose.

Biological Activity

Non-selective MAO-A/B inhibitor.

Safety Profile

Poison by intravenous andintraperitoneal routes. Moderately toxic by ingestion.Mutation data reported. Experimental reproductiveeffects. An antidepressant. When heated to decompositionit emits toxic fumes of NOx.