2,4-dinitrophenol appears as solid yellow crystals. Explosive when dry or with less than 15% water. The primary hazard is from blast of an instantaneous explosion and not flying projectiles and fragments. slightly soluble in water and soluble in ether and solutions of sodium or potassium hydroxide.
2,4-DNP and two of its metabolites, 2-amino-4-nitrophenol and 4-amino-2-nitrophenol, were monitored in plasma of mice at 0.5, 1, 2, 4, 6, 9, 12, 24, 48, and 96 hours following a single gavage dose of 22.5 mg/kg using a highly specific capillary GC/MS technique. /It was/ concluded that the amount of 2-amino-4-nitrophenol formed was 7.9 times the amount of 4-amino-2-nitrophenol, and that 50% of 2,4-DNP elimination involved direct conversion to these two compounds. Plasma concentrations of these two metabolites reached their highest levels within the first half hour after dosing, indicating rapid metabolism. The results demonstrate that 2-amino-4- nitrophenol is the major circulating metabolite of 2,4-DNP and that 4-amino-2-nitrophenol is also a significant circulating metabolite.
/An/ investigation of the in vitro metabolism of 2,4-DNP by rat liver homogenates found that, under optimal pH and cofactor levels, 81% of the 2,4-DNP was metabolized. 2-Amino-4-nitrophenol accounted for 75%, 4-amino-2-nitrophenol for 23%, and 2,4-diaminophenol for approx 1% of the total amine metabolites produced. Even under suboptimal conditions, 2-amino-4-nitrophenol was the predominant metabolite.
The distribution of enzyme activity was analyzed in subcellular fractions: nucleic, mitochondrial, microsomal, and cytosol. The maximum activity was found in the cytosol, which is the site of other nitroreductases, although nitroreductases can also be located in microsomes. The properties of nitroreductases have been extensively studied for the reduction of p-nitrobenzoic acid. Two separate enzyme systems are involved, one located in the cytosol, and the other in the microsomes. Both forms require the presence of reduced nicotinamide adenine dinucleotides (NADH or NADPH). The cytosolic reducing activity for 2,4-DNP required NADPH, since the activity in both the whole homogenate and in the cytosol was enhanced by adding glucose-6-phosphatase and NADP. The fact that the washed microsomal fraction contained no appreciable activity with 2,4-DNP could be due to the absence of soluble NADPH-generating enzymes, such as a glucose-6-phosphate dehydrogenase. Oxygen partially inhibited the formation of the aminonitrophenols. This inhibition is consistent with a reoxidation of cofactors FADH2 or NADPH in the presence of oxygen. Reduction of (14)C-2,4-DNP to 2-amino-4-nitrophenol and 4-amino-2-nitrophenol by rat liver homogenates was not affected by the addition of p-nitrobenzoic acid, suggesting that different nitroreductases are involved. However, p-nitrophenol, o-nitrophenol, and 2,4-dinitro-6-sec-butylphenol inhibited the reduction of 2,4-DNP. The reduction was competitively inhibited by o-nitrophenol and noncompetitively inhibited by p-nitrophenol and 2,4-dinitro-6-sec-butylphenol. These results indicate separate metabolic pathways for 2,4-DNP and p-nitrobenzoic acid. The competitive inhibition by o-nitrophenol, however, suggests that 2,4-DNP and o-nitrophenol compete for the same active site on the nitroreductase, while the noncompetitive inhibition by the other two nitro compounds suggests binding at different sites on the enzyme. Limited information indicates that 2,4-DNP may also be conjugated to glucuronic acid or sulfate in the liver and then be excreted in the urine.
In urine of /sc/ treated rabbits, dinitrophenol glucuronide, 2-aminonitrophenol & its ether sulfate were found. In vitro, but not in vivo, studies indicated presence of 4-aminonitrophenol. Latter was unstable ... .
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)
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)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
致癌物分类
对人类不具有致癌性（未被国际癌症研究机构IARC列名）。
No indication of carcinogenicity to humans (not listed by IARC).
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)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
暴露途径
这种物质可以通过皮肤接触和摄入被身体吸收。
The substance can be absorbed into the body through the skin and by ingestion.
来源:ILO-WHO International Chemical Safety Cards (ICSCs)
2,4-DNP appears to be readily absorbed from the respiratory and gastrointestinal tracts. Some evidence suggests significant absorption through the skin as well. 2,4-DNP is relatively lipophilic with a pKa of 4.09 and therefore is likely to be rapidly absorbed by passive diffusion of the un-ionized form from acidic compartments like the stomach. Another factor favoring the rapid absorption of 2,4-DNP is its small molecular weight (184.1). Molecules with a molecular weight below 600 daltons can permeate cell membranes through aqueous channels regardless of their ionization state.
2,4-DNP appears to be metabolized to less toxic metabolites (primarily aminonitrophenols) that are excreted in the urine. The mechanism of excretion may be passive diffusion, in part, although there is some evidence from one in vitro study of active secretion of 2,4-DNP by the renal organic acid transport process.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
它很容易通过皮肤、呼吸道和消化道被吸收。
It is readily absorbed from skin and through respiratory tract and GI tract.
Studies of blood aqueous barrier & differences of penetrability of 2,4-dinitrophenol into eye from blood in different species ... have shown that dinitrophenol gets into aqueous humor more readily & reaches higher concn in ducks that develop cataracts than ... rabbits that do not. Also, in immature rabbits, in which cataracts can be produced, dinitrophenol entered aqueous humor more readily than in mature rabbits which did not develop cataracts.
[EN] COMPOUNDS FOR USE AS PROTON CHANNELS AND METHODS THEREOF<br/>[FR] COMPOSÉS DESTINÉS À ÊTRE UTILISÉS EN TANT QUE CANAUX DE PROTONS ET PROCÉDÉS ASSOCIÉS
申请人：AGENCY SCIENCE TECH & RES
公开号：WO2020159441A1
公开（公告）日：2020-08-06
The present disclosure relates generally to compounds or a salt, solvate, stereoisomer and prodrug thereof for forming synthetic membrane channels. The present disclosure also relates to methods of synthesizing the compounds, methods of forming the synthetic membrane channels and methods of use thereof. In particular, the synthetic membrane channels are synthetic proton channels in a lipid membrane.
Kinetic Study of the Phenolysis of <i>O</i>-Methyl and <i>O</i>-Phenyl <i>O</i>-2,4-Dinitrophenyl Thiocarbonates and <i>O</i>-Ethyl 2,4-Dinitrophenyl Dithiocarbonate
作者：Enrique A. Castro、David Arellano、Paulina Pavez、José G. Santos
DOI：10.1021/jo034538+
日期：2003.8.1
(PDNPTOC), and O-ethyl2,4-dinitrophenyldithiocarbonate (EDNPDTC) are studied kinetically in water, at 25.0 degrees C and an ionic strength of 0.2 M (KCl). All reactions show pseudo-first-order kinetics under an excess of phenol over the substrate, and are first order in phenoxide anion. The reactions of EDNPDTC show a linear Bronsted-type plot of slope beta = 0.67, suggesting a concerted mechanism. On the
A Kinetic Study on Nucleophilic Displacement Reactions of Aryl Benzenesulfonates with Potassium Ethoxide: Role of K<sup>+</sup> Ion and Reaction Mechanism Deduced from Analyses of LFERs and Activation Parameters
more reactive than the dissociated EtO–, indicating that K+ ion catalyzes the reaction. The catalytic effect exerted by K+ ion (e.g., the kEtOK/kEtO– ratio) decreases linearly as the substituent X in the benzenesulfonyl moiety changes from an electron-donating group (EDG) to an electron-withdrawing group (EWG), but it is independent of the electronic nature of the substituent Y in the leaving group
Pseudofirst一级速率常数（ķ实测值）已经被分光光度法测量为2,4-二硝基苯基X取代的苯磺酸盐的亲核取代反应4A - ˚F和Y取代的苯基苯磺酸5A - ķ在无水乙醇中与EtOK。的解剖ķ实测值成ķ环氧乙烷-和ķ EtOK（即，二阶速率常数，用于与离解的环氧乙烷的反应中-和离子配对分别EtOK，）示出了离子配对EtOK比离解的环氧乙烷反应性更强–，表示K+离子催化反应。随着苯磺酰基部分中的取代基X从给电子基团（EDG）变为吸电子基团（EWG），K +离子产生的催化作用（例如，k EtOK / k EtO –比）线性降低，但是它与离去基团中取代基Y的电子性质无关。通过线性自由能关系对动力学数据进行分析，得出了通过协调机制进行反应的结论（例如，Brønsted型，Hammett和Yukawa-Tsuno图）。钾+离子通过通过环状过渡态（TS）增加反应中心的亲电子性而不是通过增加离去基团的
Catalysis and inhibition of ester hydrolysis in the presence of resorcinarene hosts functionalized with dimethylamino groups
作者：Giorgio Cevasco、Sergio Thea、Daniele Vigo、Andrew Williams、Flora Zaman
DOI：10.1002/poc.1101
日期：2006.10
Complexation and catalysis of two calixresorcinarene (RES) derivatives with nucleophilic N,N-dimethylamino functions attached to their upper rims in the hydrolysis of carboxylate and sulfonate esters of 4-nitrophenol and 2,4-dinitrophenol have been investigated. Rate constants obey the complexation equation:
