2,4-DNP
2,4-Dinitrophenol (2,4-DNP or simply DNP) is an organic compound with the formula HOC6H3(NO2). It is a yellow, crystalline solid that has a sweet, musty odor. It sublimates, is volatile with steam, and is soluble in most organic solvents as well as aqueous alkaline solutions. When in a dry form, it is a high explosive and has an instantaneous explosion hazard.
2,4-Dinitrophenol (2,4-DNP or simply DNP) is an organic compound with the formula HOC6H3(NO2). It is a yellow, crystalline solid that has a sweet, musty odor. It sublimates, is volatile with steam, and is soluble in most organic solvents as well as aqueous alkaline solutions. When in a dry form, it is a high explosive and has an instantaneous explosion hazard. It is a precursor to other chemicals and is biochemically active, uncoupling oxidative phosphorylation from the electron transport chain in cells with mitochondria, by allowing hydrogen cations to pass from the intermembrane space into the mitochondrial matrix. Oxidative phosphorylation is a highly regulated step in aerobic respiration that is inhibited, among other factors, by normal cellular levels of ATP.
Uses
Although DNP is widely considered too dangerous for clinical use, its mechanism of action remains under investigation as a potential approach for treating obesity. As of 2015, research is being conducted on uncoupling proteins naturally found in humans.
Biochemistry
In living cells, DNP acts as a proton ionophore, an agent that can shuttle protons (hydrogen cations) across biological membranes. It dissipates the proton gradient across the mitochondria membranes, collapsing the proton motive force that the cell uses to produce most of its ATP chemical energy. Instead of producing ATP, the energy of the proton gradient is lost as heat.
Mechanism of action
DNP acts as a protonophore, allowing protons to leak across the inner mitochondrial membrane and thus bypass ATP synthase. This makes ATP energy production less efficient. In effect, part of the energy that is normally produced from cellular respiration is wasted as heat. The inefficiency is proportional to the dose of DNP that is taken. As the dose increases and energy production is made more inefficient, metabolic rate increases (and more fat is burned) in order to compensate for the inefficiency and to meet energy demands. DNP is probably the best known agent for uncoupling oxidative phosphorylation. The phosphorylation of adenosine diphosphate (ADP) by ATP synthase gets disconnected or uncoupled from oxidation.
Dinitrophenol uncouples oxidative phosphorylation, causes release of calcium from mitochondrial stores and prevents calcium re-uptake. This leads to free intracellular calcium and causes muscle contraction and hyperthermia. Dantrolene inhibits calcium release from the sarcoplasmic reticulum which reduces intracellular calcium. The resulting muscle relaxation allows heat dissipation. There is little risk to dantrolene administration. Since dantrolene may be effective in reducing hyperthermia caused by agents that inhibit oxidative phosphorylation, early administration may improve outcome.
Pharmacokinetics
Information about pharmacokinetics of DNP in humans is limited. The ATSDR's Toxicological Profile for Dinitrophenols remarks that DNP elimination appears to be rapid except when liver function is impaired. The NEJM remarks that DNP appears to be eliminated in around three to four days, except possibly when the liver and kidneys are damaged. Other papers give a wide array of possible half-lives, ranging from 3 hours to 5–14 days, while still other, more recent papers maintain that the half-life in humans is unknown.
Clinical data
|
Product Name |
2,4-Dinitrophenol |
|
CAS |
51-28-5 |
|
Molar mass |
184.107 |
|
MF |
C6H4N2O5 |
|
Purity |
Above 98% |
|
Apprarance |
Yellow Tablet |
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What is the mechanism of action of 2,4-DNP?
The mechanism of action of 2,4-dinitrophenol (2,4-DNP) is related to its effect on cellular energy production, specifically on the process of oxidative phosphorylation in the mitochondria, which are the energy-producing organelles within cells.
In normal cellular respiration, the mitochondria generate adenosine triphosphate (ATP), the molecule that carries energy for cellular functions. This process involves the electron transport chain (ETC), a series of protein complexes that transfer electrons from one molecule to another, ultimately leading to the pumping of protons (H+) across the mitochondrial inner membrane. This creates an electrochemical gradient, and as protons flow back into the mitochondrial matrix through ATP synthase, it drives the synthesis of ATP from adenosine diphosphate (ADP) and inorganic phosphate (Pi).
2,4-DNP disrupts this process by acting as an uncoupler of oxidative phosphorylation. It freely diffuses across the mitochondrial inner membrane, and once inside the matrix, it accepts protons from the intermembrane space. The movement of protons across the membrane is no longer coupled to ATP synthesis, meaning the electrochemical gradient is dissipated, and the energy from the electron transport chain is wasted as heat instead of being used to produce ATP.
As a result, cells exposed to 2,4-DNP will increase their metabolic rate in an attempt to compensate for the energy loss. This can lead to an elevated basal metabolic rate, increased body temperature, and potential weight loss. However, this uncoupling effect also leads to an inefficient use of energy and can have consequences on the body.
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