2,4-Dinitrophenol

2,4-Dinitrophenol
Chemical structure (top) and sample of pure compound (bottom)
Clinical data
Routes of
administration
Oral
Drug classUncoupling agents
Legal status
Legal status
  • Banned for human consumption in many countries
Pharmacokinetic data
MetabolismNitro reduction
Elimination half-lifeUnknown
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.080 Edit this at Wikidata
Chemical and physical data
FormulaC6H4N2O5
Molar mass184.107 g·mol−1
3D model (JSmol)
  • O=[N+]([O-])c1cc(ccc1O)[N+]([O-])=O
  • InChI=1S/C6H4N2O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H checkY
  • Key:UFBJCMHMOXMLKC-UHFFFAOYSA-N checkY

2,4-Dinitrophenol (2,4-DNP or simply DNP) is an organic compound with the formula HOC6H3(NO2)2. It has been used in explosives manufacturing and as a pesticide and herbicide.

In humans, DNP causes dose-dependent mitochondrial uncoupling, causing the rapid loss of ATP as heat and leading to uncontrolled hyperthermia—up to 44 °C (111 °F)—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.