88 T3D0087 2,4-Dinitrophenol 2,4-Dinitrophenol, also called DNP is a yellow solid with no known smell. It dissolves slightly in water. DNP present in water and soil as a pollutant does not easily evaporate to air. It uncouples oxidative phosphorylation by carrying protons across the mitochondrial membrane, leading to a rapid consumption of energy without generation of ATP. 2,4-DNP was used in the 1930s as a weightreduction drug, but this was discontinued in 1938 because of the many reports of adverse effects in people who used it. (L168, L169) 51-28-5 1493 C6H4N2O5 184.012020 Yellow, crystalline solid. 115.5°C 2.79 mg/mL at 20 °C [SCHWARZENBACH,RP et al.(1988)] Oral (L170); inhalation (L170) ; dermal (L170) Acute 2,4-dinitrophenol poisoning (from ingestion) involves uncoupling of oxidative phosphorylation, which presumably reduces body's reservoirs of high-energy phosphate. This stimulates oxidative metabolism and, in turn, the heat production of the body. Oxygen consumption, body temperature, respiration and heart rate are all increased. 2,4-Dinitrophenol has been suggested to bind serum proteins such as transthyretin. In fact it was proposed as a therapeutic agent for the prevention/inhibition of amyloid diseases through stabilization of the native fold of transthyretin. (T21, A126, A127) 2,4-DNP can readily enter the body through inhalation and ingestion. It can probably be absorbed through the skin also. Animal studies show that after 2,4-DNP enters the body, the blood can carry it to organs and tissues such as the liver, the kidneys, and the eyes. DNP does not build up in organs and tissues, but it is metabolized via reduction of the nitro groups or broken down to other chemicals. The parent compound and metabolites such as 2-amino-4-nitrophenol, 4-amino-2-nitrophenol and diaminophenol are excreted in the urine. 2,4-DNP is also excreted by mammals, partially unchanged, partially conjugated with glucuronic acid and probably as 2,4-diamenolphenol. (L168, T30) LD50: 14-43 mg/kg (Oral, Human) (T30) No indication of carcinogenicity to humans (not listed by IARC). 2,4-Dinitrophenol has been used to make dyes, other organic chemicals, and wood preservatives. It has also been used to make photographic developer, explosives, and pesticides. 2,4-Dinitrophenol exposure may occur from breathing contaminated air, drinking contaminated water, eating contaminated food, or by contact with contaminated soil. (L168, L169) Acute Oral: 0.01 mg/kg/day (L168) 2,4-DNP can cause cataracts following ingestion of a small dose for short or long periods. This condition could lead to blindness in both eyes. Breathing in, swallowing, or having skin contact with large amounts of DNP can lead to death.(L168) Dermal contact may results in redness, roughness, yellow staining of the skin. Nausea, vomiting, palpitations, collapse, sweating occur after inhalation or ingestion. (L170) There is no specific antidote for 2,4-DNP poisoning. Symptomatic treatment includes replacing oxygen and fluids, controlling temperature by administering sponge baths and ice packs, and using a fan to promote air flow and evaporation. In fully conscious patients, administer cold, sugar-containing liquids by mouth as tolerated. In cases of skin contact, bathe and shampoo contaminated skin and hair promptly. (L179) 2009-03-06T18:58:03Z 2026-03-31T19:11:23Z http://en.wikipedia.org/wiki/2,4-Dinitrophenol C02496 918 CPD-8179 D019297 2,4-Dinitrophenol DB04528 532 true OC1=CC=C(C=C1[N+]([O-])=O)[N+]([O-])=O C6H4N2O5 InChI=1S/C6H4N2O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H UFBJCMHMOXMLKC-UHFFFAOYSA-N 184.1064 184.012021248 Exogenous Solid <p>Otto Arndt, Theodor Papenfuhs, &#8220;Process for the preparation of 6-chloro-2,4-dinitrophenol.&#8221; U.S. Patent US4540832, issued September, 1984.</p> CHEM000081 DTXSID0020523 NS00010496 2,4-dinitrophenol