Structure via PubChem · Public domain (PubChem)
nialamide
Sign in to saveAlso known as BEIH, N-isonicotinyl hydrazide, N-benzyl-beta-(isonicotinylhydrazino)propionamide, N-benzyl-beta-(isonicotinoylhydrazine)propionamide, 2-[2-(benzylcarbamoyl)ethyl]hydrazide, isonicotinic acid, N-[2-(benzylcarbamyl)ethylamino]isonicotinamide, 2-[2-(benzylcarbamoyl)ethyl]hydrazide isonicotinic acid, 2-(2-(benzylcarbamyl)ethyl)hydrazide isonicotinic acid
Nialamide (Niamid, Niamide, Nuredal, Surgex) is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class that was used as an antidepressant. It was withdrawn by Pfizer several decades ago due to the risk of hepatotoxicity.
Chemical data
- Formula
- C16H18N4O2
- Molecular weight
- 298.34 g/mol
- IUPAC name
- N-benzyl-3-[2-(pyridine-4-carbonyl)hydrazinyl]propanamide
- SMILES
- C1=CC=C(C=C1)CNC(=O)CCNNC(=O)C2=CC=NC=C2
- InChIKey
- NOIIUHRQUVNIDD-UHFFFAOYSA-N
- XLogP
- 0.9
- Polar surface area
- 83.1 Ų
- H-bond donors
- 3
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- Indications
- major depressive disorder
via ChEMBL · EBI
Research
1,644 papers- NIALAMIDE IN CHILDREN.Indian pediatrics · 1964
- [Nialamide in gastroenterology].Revista de la Facultad de Medicina, Universidad Nacional de Colombia · 1961
- Intravenous use of nialamide in depression.Psychosomatics · 1961
- [Pyrexia following nialamide].Dapim refuiim. Folia medica · 1968
- On the role of central nervous system catecholamines and 5-hydroxytryptamine in the nialamide-induced behavioural syndrome.British journal of pharmacology · 1972
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 298.142976
- Has use
- medication
Show 8 more facts
- chemical formula
- C₁₆H₁₈N₄O₂
- World Health Organisation international non-proprietary name
- nialamide
- isomeric SMILES
- C1=CC=C(C=C1)C/N=C(/CCNNC(=O)C2=CC=NC=C2)\O
- canonical SMILES
- C1=CC=C(C=C1)CNC(=O)CCNNC(=O)C2=CC=NC=C2
- defined daily dose
- 0.1
- subject has role
- monoamine oxidase inhibitor
- has characteristic
- bitterness
- Commons category
- Nialamide
Sources (6)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Nialamide (Niamid, Niamide, Nuredal, Surgex) is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class that was used as an antidepressant. It was withdrawn by Pfizer several decades ago due to the risk of hepatotoxicity.
Side effects include agitation and insomnia, less frequently dry mouth, dizziness, blurred vision, and hypomania, and rarely leukopenia and hepatitis. As with other MAOIs, a hypertensive crisis can be triggered by co-ingestion of tyramine. It is metabolized into isoniazid, an anti-tuberculosis agent, and so is contraindicated in patients with tuberculosis. The recommended dosage range is 75 to 200 mg per day, with maintenance doses as low as 12.5 mg every other day.
Excerpted from Wikipedia’s “nialamide” article, available under the CC BY-SA 4.0 licence.