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T3D0087 - 2,4-Dinitrophenol
| Record Information | |
|---|---|
| Version | 1.0 |
| Creation Date | 2009-03-06 18:58:03 UTC |
| Update Date | 2013-04-25 08:32:47 UTC |
| Accession Number | T3D0087 |
| Identification | |
| Common Name | 2,4-Dinitrophenol |
| Description | 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. (R326, R328) |
| Compound Type |
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| Chemical Structure |
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| Synonyms |
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| Chemical Formula | C6H4N2O5 |
| Average Molecular Weight | 184.1064 |
| Monoisotopic Molecular Weight | 184.012021248 |
| Chemical IUPAC Name | 2,4-dinitrophenol |
| CAS Registry Number | 51-28-5 |
| SMILES | OC1=CC=C(C=C1[N+]([O-])=O)[N+]([O-])=O |
| InChI Identifier | InChI=1S/C6H4N2O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H |
| InChI Key | InChIKey=UFBJCMHMOXMLKC-UHFFFAOYSA-N |
| Chemical Taxonomy | |
| Kingdom | Organic Compounds |
| Super Class | Benzenoids |
| Class | Benzene and Substituted Derivatives |
| Sub Class | Phenols and Derivatives |
| Direct Parent | Nitrophenols and Derivatives |
| Alternative Parents |
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| Molecular Framework | Aromatic Homomonocyclic Compounds |
| Substituents |
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| External Descriptors |
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| External Links | |
| DrugBank ID | Not Available |
| PubChem Compound ID | 1493  |
| KEGG ID | C02496 |
| UniProt ID | Not Available |
| OMIM ID | Not Available |
| ChEBI ID | 918 |
| BioCyc ID | CPD-8179 |
| CTD ID | D019297 |
| Stitch ID | 2,4-Dinitrophenol |
| PDB ID | Not Available |
| ACToR ID | 532 |
| Wikipedia Link | http://en.wikipedia.org/wiki/2,4-Dinitrophenol |
| Physical Properties | |
| Appearance | Yellow, crystalline solid. |
| Melting Point | 115.5 C |
| Solubility | 2.79 mg/mL at 20 °C [SCHWARZENBACH,RP et al.(1988)] |
| Predicted LogP | 1.549648873 |
| Toxicity Profile | |
| Route of Exposure | Oral (R329); inhalation (R329) ; dermal (R329) |
| Mechanism of Action | 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. (R286, R348, R349) |
| Metabolism | 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. (R326, R330) |
| Toxicity Values | LD50: 14-43 mg/kg (Oral, Human) (R330) |
| Lethal Dose | Not Available |
| Carcinogenicity (IARC Classification) | Not Available |
| Uses/Sources | 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. (R326, R328) |
| Minimum Risk Level | Acute Oral: 0.01 mg/kg/day (R326) |
| Health Effects | 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.(R326) |
| Symptoms | Dermal contact may results in redness, roughness, yellow staining of the skin. Nausea, vomiting, palpitations, collapse, sweating occur after inhalation or ingestion. (R329) |
| Treatment | 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. (R352) |
| References | |
| General References |
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Targets
1. Transthyretin
Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain.
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. (R348,R349)UniProt ID: P02766
Gene: TTR
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report
References:
- R348 — Morais-de-Sa E, Neto-Silva RM, Pereira PJ, Saraiva MJ, Damas AM: The binding of 2,4-dinitrophenol to wild-type and amyloidogenic transthyretin. Acta Crystallogr D Biol Crystallogr. 2006 May;62(Pt 5):512-9. Epub 2006 Apr 19.
[16627944 ]
- R349 — Xie Y, Zhang D, Ben-Amotz D: Protein-ligand binding detected using ultrafiltration Raman difference spectroscopy. Anal Biochem. 2008 Feb 1;373(1):154-60. Epub 2007 Nov 4.
[18023404 ]