2,4-dinitrophenol

Also known as 2,4-DNP, Dinitrophenol, DNP

2,4-Dinitrophenol (2,4-DNP or simply DNP) is an organic compound with the formula . It occurs as yellow crystals or platelets. It has been used in explosives manufacturing and as a pesticide and herbicide.

Chemical data

Formula: C6H4N2O5
Molecular weight: 184.11 g/mol
IUPAC name: 2,4-dinitrophenol
SMILES: C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])O
InChIKey: UFBJCMHMOXMLKC-UHFFFAOYSA-N
XLogP: 1.7
Polar surface area: 112 Å²
H-bond donors: 1
H-bond acceptors: 5
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 2
Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 184.012
Image: 2,4-Dinitrophenol.jpg
Has use: dye

Show 4 more facts

melting point: 107
chemical formula: C₆H₄N₂O₅
Commons category: 2,4-Dinitrophenol
canonical SMILES: C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])O

Sources (4)

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Encyclopedic overview

14 sections

Contents

Chemical properties
Uses
Industrial
In humans
Biochemistry
Mechanism of action
Pharmacokinetics
Adverse effects
Overdose
History
As a pollutant
Legal status
References
External links

In humans, DNP causes dose-dependent mitochondrial uncoupling, causing the rapid loss of ATP as heat and leading to uncontrolled hyperthermia—up to —and death in case of overdose. Researchers noticed its effect on raising the basal metabolic rate in accidental exposure and developed it as one of the first weight loss drugs in the early twentieth century. DNP was banned from human use by the end of the 1930s due to its risk of death and toxic side effects. DNP continues to be used after its ban and experienced a resurgence in popularity after it became available on the Internet.

Excerpted from Wikipedia’s “2,4-dinitrophenol” article, available under the CC BY-SA 4.0 licence.