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Details

Stereochemistry ACHIRAL
Molecular Formula C6H3N2O5.Na
Molecular Weight 206.0882
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM 2,4-DINITROPHENOLATE

SMILES

[Na+].[O-]C1=CC=C(C=C1[N+]([O-])=O)[N+]([O-])=O

InChI

InChIKey=JMOHQJVXBQAVNW-UHFFFAOYSA-M
InChI=1S/C6H4N2O5.Na/c9-6-2-1-4(7(10)11)3-5(6)8(12)13;/h1-3,9H;/q;+1/p-1

HIDE SMILES / InChI

Description

2,4-dinitrophenol (DNP) is a FDA-banned weight-loss agent and EPA-regulated environmental toxicant, traditionally used in research labs as an uncoupler of OXPHOS. Although not licensed for human consumption, DNP and DNP crystal form are used by bodybuilders and extreme dieters for their fat burning properties through inhibiting efficient energy (ATP) production in cells. Through uncoupling mitochondrial oxidative phosphorylation by facilitating proton transport across the mitochondrial membrane, DNP leads to rapid consumption of energy without generating ATP and consequently, to increased fat metabolism. However, the weight-loss effect comes with serious, and in some cases potentially fatal, adverse side effects, namely hyperthermia (the leading cause of fatality with acute DNP toxicity) and cardiac arrest, but also diaphoresis, tachycardia, tachypnea, skin toxicity, Fourier’s gangrene and cataracts with low dose chronic exposure. The proposed mechanism of DNP induced toxicity suggests the activation of ATP-sensitive K+ channels.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
The amounts ingested and length of exposure in 2,4-dinitrophenol (DNP)-related illnesses and deaths range between (1 to 46 mg/kg/day and 3 to 46 mg/kg/day, respectively).
Route of Administration: Oral
In Vitro Use Guide
2,4-dinitrophenol (DNP, 50 uM) and isoproterenol (0.1 uM) failed to produce a transient vasodilatory response and caused a significant diastolic pressure increase in Kir6.2(-/-) hearts.