2,4-Dinitrophenol
描述
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)
类别
"Pesticide", "Industrial/Workplace Toxin", "Pollutant", "Airborne Pollutant", "Food Toxin", "Synthetic Toxin"
同义词
"1'alpha-2,4-Dinitrophenol", "1-Hydroxy-2,4-dinitrobenzene", "2,4 Dinitrophenol", "2,4-DNP", "Aldifen", "Alpha-dinitrophenol", "Alpha.-dinitrophenol", "Dinitra", "Dinitrophenol", "Dinofan", "DNF", "DNP", "Fenoxyl", "Fenoxyl carbon N", "Maroxol-50", "NIN", "Nitro kleenup", "Osmoplastic-R", "Osmotox-plus", "Solfo black", "Tertrosulfur black PB", "Tertrosulfur PBR", "Tertrosulphur black PB", "Tertrosulphur PBR"
IUPAC 名称
2,4-dinitrophenol
简化分子线性输入规范
OC1=CC=C(C=C1[N+]([O-])=O)[N+]([O-])=O
InChI 标识符
InChI=1S/C6H4N2O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H
键
InChIKey=UFBJCMHMOXMLKC-UHFFFAOYSA-N
另外分类
"1-hydroxy-2-unsubstituted benzenoids", "Hydrocarbon derivatives", "Nitroaromatic compounds", "Nitrobenzenes", "Organic oxides", "Organic oxoazanium compounds", "Organonitrogen compounds", "Organooxygen compounds", "Organopnictogen compounds", "Propargyl-type 1,3-dipolar organic compounds"
取代基
"1-hydroxy-2-unsubstituted benzenoid", "Allyl-type 1,3-dipolar organic compound", "Aromatic homomonocyclic compound", "C-nitro compound", "Dinitrophenol", "Hydrocarbon derivative", "Monocyclic benzene moiety", "Nitroaromatic compound", "Nitrobenzene", "Organic 1,3-dipolar compound", "Organic nitro compound", "Organic nitrogen compound", "Organic oxide", "Organic oxoazanium", "Organic oxygen compound", "Organonitrogen compound", "Organooxygen compound", "Organopnictogen compound", "Propargyl-type 1,3-dipolar organic compound"
分子框架
Aromatic homomonocyclic compounds
地位
Detected and Not Quantified
蜂窝位置
"Cytoplasm", "Extracellular"
外貌
Yellow, crystalline solid.
熔点/沸点/溶解度
115.5°C//2.79 mg/mL at 20 °C [SCHWARZENBACH,RP et al.(1988)]
暴露途径
Oral (L170); inhalation (L170) ; dermal (L170)
毒性机制
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)
代谢
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)
毒性值
LD50: 14-43 mg/kg (Oral, Human) (T30)
致癌性
No indication of carcinogenicity to humans (not listed by IARC).
用途/来源
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)
最低风险等级
Acute Oral: 0.01 mg/kg/day (L168)
健康影响
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)
症状
Dermal contact may results in redness, roughness, yellow staining of the skin. Nausea, vomiting, palpitations, collapse, sweating occur after inhalation or ingestion. (L170)
治疗
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)
维基百科链接
http://en.wikipedia.org/wiki/2,4-Dinitrophenol
创建于
2009-03-06 18:58:03 UTC
更新于
2014-12-24 20:21:04 UTC