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
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
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
Sample Use Guides
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