Basic information
- CAS
54-92-2- Standard SMILES
CC(C)NNC(=O)c1ccncc1- InChIKey
NYMGNSNKLVNMIA-UHFFFAOYSA-N- Molecular formula
- C9H13N3O
- Average molar mass
- 179.22 g/mol
- Monoisotopic mass
- 179.10586205
Overview
Iproniazid is a member of pyridines and a carbohydrazide.
Names & identifiers
- Preferred name
- Iproniazid
- IUPAC
- N'-propan-2-ylpyridine-4-carbohydrazide
- English name
- iproniazid
- Molecular formula
- C9H13N3O
- Molecular weight
- 179.22
Names & synonyms
iproniazid54-92-2IprazidIproniazideEuphozidRivivolN'-isopropylpyridine-4-carbohydrazide4-Pyridinecarboxylic acid, 2-(1-methylethyl)hydrazideIproniazidaIproniazidumRo 2-45721-Isonicotinoyl-2-isopropylhydrazine
Show more names
Iproniazid>Iproniazid - Bio-X ?n’-isopropylisonicotinohydrazideN'-propan-2-ylpyridine-4-carbohydrazide
Isonicotinic acid 2-isopropylhydrazideD892HFI3XADTXSID5023168RefChem:148662DTXCID503168200-218-8N'-IsopropylisonicotinohydrazideMarsilid
Database identifiers
- CAS
54-92-2- PubChem CID
- 3748
- DTXSID
DTXSID5023168- ChEMBL
CHEMBL92401- ChEBI
CHEBI:5958- UNII
- D892HFI3XA
- EC Number
- 200-218-8
- Nikkaji
- J4.158K
Properties
Computed structural properties
- XLogP
- 0.4
- Topological polar surface area
- 54 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 164
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP0.33
Human DrugsPharmaceuticals
Melting Point161-161.5
Collision Cross Section131.31 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 112.5 · 112.5-113.5°
- Boiling point
- 311.75 °C · 311.75°C (rough estimate)
- Density
- 1.1305 · 1.1305 (rough estimate)
- refractive index
- 1.51 · 1.5100 (estimate)
- storage temp.
- -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Iproniazid
vMost-DILI-concern
8
Withdrawn
DOI:10.1016/j.drudis.2016.02.015
Safety data
- 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.
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302
- Precautionary statements
- P501-P270-P264-P301+P312+P330
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
PharmacodynamicsIproniazid is a monoamine oxidase inhibitor (MAOI) that was developed as the first anti-depressant.
MeSH Pharmacological Classification
Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems.
A chemically heterogeneous group of drugs that have in common the ability to block oxidative deamination of naturally occurring monoamines. (From Gilman, et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p414)
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
UsesIproniazid is a hydrazine based drug used as an antidepressant. Iproniazid acts as an irreversible and nonselective monoamine oxidase inhibitor.
Upstream & downstream products
Upstream raw materials
Suppliers
Related reactions
1 records
Compound notes
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