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Wikipedia

2,4-Dinitrophenol

January 01, 1970

2,4-Dinitrophenol (2,4-DNP or simply DNP) is an organic compound with the formula HOC6H3(NO2)2. It has been used in explosives manufacturing and as a pesticide and herbicide.

2,4-Dinitrophenol
Chemical structure (top) and sample of pure compound (top)
Clinical data
Routes of
administration		Oral
Drug classUncoupling agents
Legal status
Legal status
  • Banned for human consumption in many countries
Pharmacokinetic data
MetabolismNitro reduction
Elimination half-lifeUnknown
Identifiers
CAS Number
  • 51-28-5
PubChem CID
  • 1493
DrugBank
  • DB04528 Y
ChemSpider
  • 1448 Y
UNII
  • Q13SKS21MN
KEGG
  • C02496 Y
ChEBI
  • CHEBI:42017 Y
ChEMBL
  • ChEMBL273386 Y
CompTox Dashboard (EPA)
  • DTXSID0020523
ECHA InfoCard100.000.080
Chemical and physical data
FormulaC6H4N2O5
Molar mass184.107 g·mol−1
3D model (JSmol)
  • Interactive image
  • O=[N+]([O-])c1cc(ccc1O)[N+]([O-])=O
  • InChI=1S/C6H4N2O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H Y
  • Key:UFBJCMHMOXMLKC-UHFFFAOYSA-N Y

In humans, DNP causes dose-dependent mitochondrial uncoupling, causing the rapid loss of ATP as heat and leading to uncontrolled hyperthermia—up to 44 °C (111 °F)—and death in case of overdose. Researchers noticed its effect on raising the basal metabolic rate in accidental exposure and developed it as one of the first weight loss drugs in the early twentieth century. DNP was banned from human use by the end of the 1930s due to its risk of death and toxic side effects. DNP continues to be used after its ban and experienced a resurgence in popularity after it became available on the Internet.

Chemical properties edit

 
Synthesis of DNP (right) from phenol and nitric acid via 2-Nitrophenol and 4-Nitrophenol

DNP has the chemical formula HOC6H3(NO2)2. As a solid, it is a yellow, crystalline and has a sweet, musty odor.[1][2] It sublimates, is volatile with steam, and is soluble in most organic solvents as well as aqueous alkaline solutions.[2] DNP is a member of the dinitrophenols chemical family.[1]

DNP can be produced by hydrolysis of 2,4-dinitrochlorobenzene.[1][3] Other routes of DNP synthesis include nitration of monochlorobenzene, nitration of benzene with nitrogen dioxide and mercurous nitrate, oxidation of 1,3-dinitrobenzene,[4] and nitration of phenol with nitric acid.[5]

A dust explosion is possible with DNP in powder or granular form in the presence of air. DNP may explosively decompose when submitted to shock, friction or concussion, and may explode upon heating.[6] DNP forms explosive salts with strong bases as well as ammonia, and emits toxic fumes of nitrogen dioxide when heated to decomposition.[7] DNP's explosive strength is 81% that of TNT, based on the Trauzl lead block test.[8]

Uses edit

Industrial edit

Historically, DNP has been used as an antiseptic and as a non-selective bioaccumulating pesticide.[9]

DNP was particularly useful as a herbicide alongside other closely related dinitrophenol herbicides like 2,4-dinitro-o-cresol (DNOC), dinoseb and dinoterb.[10] Since 1998 DNP has been withdrawn from agricultural use.[11] Currently, there are no actively registered pesticides containing DNP in the United States or Europe.[12][13] Dinoseb is used industrially as a polymerisation inhibitor during styrene production. In 2023, the Home Office said it could not determine any legitimate industrial uses for DNP in the United Kingdom.[14]

It is a chemical intermediate in the production of sulfur dyes,[3] wood preservatives[9] and picric acid.[15] A precursor to 2,4,6-trinitrotoluene (TNT), DNP has also been used to make photographic developers and explosives.[16][17] DNP is classified as an explosive in the United Kingdom[18] and the United States.[19]

In humans edit

 
Histogram of DNP doses reported on online forums and the subreddit /r/DNP[20]

DNP raises energy expenditure by 30 to 40 percent and causes a weight loss of 0.7–0.9 kilograms (1.5–2.0 lb) per week.[21] Although DNP is no longer in clinical use as a weight loss drug due to its dangerous side effects, its mechanism of action remains under investigation as a potential approach for treating obesity and non-alcoholic fatty liver disease.[1][22][23] Researches developed a prodrug, HU6, which is metabolized to DNP in the liver to provide more stable blood concentrations. HU6 completed a phase II trial in which it produced significant reductions in liver fat and body weight in overweight people with elevated liver fat, without serious adverse effects.[24]

DNP is used by bodybuilders, fitness enthusiasts, and people with an eating disorder to lose weight. The user profile is similar to that of anabolic steroids; many perceive it to be effective and with manageable risks.[25] Despite health warnings from regulators, DNP is readily available online[25] sometimes under other names such as Dinosan, Dnoc, Solfo Black, Nitrophen, Aldifen, and Chemox.[17][25] DNP is often sold in tablets containing 100 to 200 mg[1] and may be sold alongside other substances such as anabolic steroids and thyroxine.[17] It may also be found as a contaminant in other bodybuilding supplements not advertised as containing DNP.[25] Online message boards provide information on dosage and regimens for DNP use, and describe the risks of taking the compound and provide advice on how to mitigate hyperthermia.[17][25][26] According to a study published in 2023, the most commonly reported doses were between 150 and 300 mg/day.[20] Between 2010 and 2020, reports of overdoses were higher in Australasia, Europe and North America than in Asia, Africa, and South or Central America.[27]

It is also used as a suicide method.[17]

Biochemistry edit

Mechanism of action edit

Main article: Uncoupler
 
Nitro reduction of DNP

In living cells, DNP acts as a protonophore, an agent that can shuttle protons (hydrogen cations) across biological membranes. It dissipates the proton gradient across the mitochondrial membrane, 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.[17] 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.[citation needed]

DNP raises the basal metabolic rate (BMR) and lowers T4 (thyroid hormone) levels by increasing T4 metabolism and reducing thyroid hormone secretion. Because it binds to thyroxine-binding globulin, overall thyroid function may not be affected. DNP cannot substitute for thyroid hormone in myxedema.[28]

Pharmacokinetics edit

Information about pharmacokinetics and pharmacodynamics of DNP in humans is limited.[23] DNP is metabolized via nitro reduction. Its major metabolites are 2-amino-4-nitrophenol [de] and 4-amino-2-nitrophenol.[16] In overdoses, symptom onset can be as soon as 3 hours and the average time to death was 14 hours.[16][17]

As a pollutant edit

Although many militaries are replacing traditional 2,4,6-trinitrotoluene (TNT)-based explosives for insensitive munitions, DNP is a degradation byproduct of the IMX-101 insensitive munition used by the United States Army.[29]

While the Meisenheimer charge transfer reaction is effective at detecting TNT, it is not effective at detecting many other explosives including DNP. Researchers are studying colorimetric detection and other methods for DNP to find if water or solids such as soils are contaminated with DNP.[30][31][32][33] UiO-66-NH2 can be used to bind to and remove DNP from solution.[34]

Adverse effects edit

DNP has a low therapeutic index, meaning that the dosage required for a desired effect is not much smaller than that which produces toxicity.[17] Individual tolerance to DNP's harmful short- and long-term effects varies greatly.[1] The most common adverse effect reported is a rash, which could be maculopapular, urticarial, angioedema, or an exfoliative dermatitis.[17] Cataracts can form, causing a permanent loss of vision in days to months of usage, and permanent deafness has also been reported.[17][35] Other adverse effects reported include peripheral neuritis, agranulocytosis, and neutropaenia.[17] Negative effects on the central nervous system, cardiovascular system, and bone marrow can occur.[1] In animal studies, DNP acted as a teratogen, mutagen, and carcinogen and caused developmental and reproductive harm.[17] An unusually yellow coloring of the skin, mucous membranes, sclera, urine, stomach contents, and internal organs is an indication of DNP exposure, but does not occur in every case.[36] Contact with skin or inhalation can cause DNP poisoning. Symptoms are typically mild with dermal exposure, but inhalation can lead to systemic effects, the same way as oral exposure.[17]

Overdose edit

Overdose is extremely dangerous;[17] cases reported to poison control centers had a 11.9 percent fatality rate between 2010 and 2020.[27] Although the largest number of overdose deaths occurred in the 1910s and 1920s when the chemical was in more widespread industrial use,[1] the substance's use as a dieting aid has caused a number of fatalities in the twenty-first century:[17] at least 50 overdose deaths were reported worldwide between 2010 and 2020.[27] Although the lowest published fatal ingested dose is 4.3 mg/kg,[17][16] a typical overdose death occurs at a higher level of exposure, around 20-50 mg/kg.[1]

The first symptoms to appear are nausea, vomiting, abdominal pain, and perhaps diarrhea.[16] The typical overdose syndrome seen with DNP and other phenols is a combination of hyperthermia, tachycardia, diaphoresis, and tachypnoea.[16][17] Because of the heat produced during uncoupling, DNP overdose will overpower the body's attempt to maintain thermal homeostasis and cause an uncontrolled, fatal rise in body temperature up to as high as 44 °C (111 °F). The disruption of metabolism also leads to the accumulation of potassium and phosphate, potentially contributing to toxicity. DNP can cause T wave and ST segment abnormalities; heart muscle, kidney, and liver damage have been found on autopsy.[16][17] According to an analysis of United Kingdom and United States overdose cases, tachycardia, hyperpyrexia, acidosis, and agitation or confusion are independent predictors of overdose death.[37]

There is no antidote to DNP and management strategies are based on expert opinion and case studies.[17] Treatment for overdose is supportive, and often involves aggressive cooling using methods such as ice baths and intravenous fluids.[35][17] Grundlingh et al. recommend administering activated charcoal if the patient presents within an hour of ingestion and using intravenous vasopressors or inotropes to control blood pressure if necessary. Intravenous methylthioninium chloride can treat methaemoglobinaemia. Benzodiazepines can help control seizures and dantrolene has been used in an attempt to control hyperthemia.[17] Cardiopulmonary resuscitation (CPR) has been used on people who died of DNP overdoses but has no known successful outcomes.[17]

History edit

During World War I, munitions workers in France fell ill and some died from DNP exposure.[38] Stanford University academic Maurice L. Tainter learned of DNP's effect in raising the metabolic rate and causing weight loss and pioneered its use as a weight loss drug.[1][38] Although he was aware of DNP's narrow therapeutic index, Tainter tried the drugs on obese patients and published successful results in 1933; average weight loss was 20 pounds (9.1 kg) and most recipients did not report adverse effects. In 1934, Tainter estimated that at least 100,000 people had been treated with DNP in the United States during its first year on the market and there had been three reported fatalities connected to the drug.[38][1] Tainter argued that DNP was highly effective in raising the metabolic rate (up to 50 percent) and avoided the negative circulatory effects of desiccated thyroid, another weight loss drug in use at the time.[38]

 
DNP explainer in the FDA publication "Chamber of Horrors"

Other physicians were less optimistic about the adverse effects of DNP, and in 1935 the American Medical Association's Council on Chemistry and Pharmacy declined to list DNP in the New and Nonofficial Remedies on the grounds that its benefits did not exceed its risks to health.[38] Reports of cataracts forming during DNP usage administered by a physician appeared the same year; in 1936 an ophthalmologist based in San Francisco estimated that 2,500 American women had gone blind from DNP use.[38] Physician opinion turned against the drug, but many people bought direct-to-consumer preparations of DNP—marketed as a cosmetic rather than a drug to evade existing regulations.[38][39]

DNP's risks were highlighted in the "Chamber of Horrors", an exhibit assembled by the Food and Drug Administration to explain the limitations of existing American drug regulations. In 1938, the Food, Drug, and Cosmetic Act increased the FDA's ability to regulate drugs. DNP was deemed so toxic as to be banned for human consumption and in 1940 the FDA reported that there was no evidence of continued sale for this purpose.[39][38] Nevertheless, it continued to be used for weight loss.[35] William F. Loomis and Fritz Albert Lipmann discovered DNP's mechanism of action and reported it in a 1948 publication.[38] Reports of its use increased in the twenty-first century after the drug became available on the Internet.[35]

Legal status edit

DNP is banned for human consumption in many countries.[1] Because it has some legitimate uses, in many jurisdictions, DNP is legal to sell not for human consumption.[25][40][41] In Australia, all dinitrophenols were classified as Schedule 1 dangerous drugs in 1956. In February 2017, DNP was reclassified as Schedule 10, "Substances of such a danger to health as to warrant prohibition of sale, supply and use".[40] From 1 October 2023, DNP will be classified as a regulated poison in the United Kingdom.[42] It is a prohibited substance (class F4) in Brazil.[43] In the United States, DNP is classified as an investigational new drug; it received orphan drug status for Huntington's disease.[44] DNP has been banned by the World Anti-Doping Association since 2015.[45]

Petróczi et al. recommend against campaigns informing people of the risks of DNP because it could increase use of the drug.[25] However, Sousa et al. argue that publicity campaigns in the United Kingdom in the early and mid-2010s reduced DNP usage.[1] In 2015, Interpol and the World Anti-Doping Agency released an orange notice warning of the dangers of DNP.[25]

In 1941, the Eastman Kodak Company, a bulk distributor of DNP, was investigated after some of its product was found in illegal diet pills.[39] Nicholas Bachynsky, a Texas physician, provided the drug to patients under the name "Mitcal". He was convicted of violating drug laws in 1986, but continued to work with DNP and was additionally convicted of fraud in 2008.[35][17] In 2018, a seller in the United Kingdom was convicted of manslaughter for selling DNP for human consumption. The conviction was sent to retrial in 2020 by the English Court of Appeal, where the seller was, once again, convicted of gross negligence manslaughter.[46]

References edit

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Further reading edit

  • Shea, P. J.; Weber, J. B.; Overcash, M. R. (1983). "Biological activities of 2,4-dinitrophenol in plant-soil systems". Residue Reviews: Residues of Pesticides and Other Contaminants in the Total Environment. Springer. pp. 1–41. ISBN 978-1-4612-5479-9.

January 01, 1970
dinitrophenol, simply, organic, compound, with, formula, hoc6h3, been, used, explosives, manufacturing, pesticide, herbicide, chemical, structure, sample, pure, compound, clinical, dataroutes, ofadministrationoraldrug, classuncoupling, agentslegal, statuslegal. 2 4 Dinitrophenol 2 4 DNP or simply DNP is an organic compound with the formula HOC6H3 NO2 2 It has been used in explosives manufacturing and as a pesticide and herbicide 2 4 DinitrophenolChemical structure top and sample of pure compound top Clinical dataRoutes ofadministrationOralDrug classUncoupling agentsLegal statusLegal statusBanned for human consumption in many countriesPharmacokinetic dataMetabolismNitro reductionElimination half lifeUnknownIdentifiersCAS Number51 28 5PubChem CID1493DrugBankDB04528 YChemSpider1448 YUNIIQ13SKS21MNKEGGC02496 YChEBICHEBI 42017 YChEMBLChEMBL273386 YCompTox Dashboard EPA DTXSID0020523ECHA InfoCard100 000 080Chemical and physical dataFormulaC 6H 4N 2O 5Molar mass184 107 g mol 13D model JSmol Interactive imageSMILES O N O c1cc ccc1O N O OInChI InChI 1S C6H4N2O5 c9 6 2 1 4 7 10 11 3 5 6 8 12 13 h1 3 9H YKey UFBJCMHMOXMLKC UHFFFAOYSA N Y In humans DNP causes dose dependent mitochondrial uncoupling causing the rapid loss of ATP as heat and leading to uncontrolled hyperthermia up to 44 C 111 F and death in case of overdose Researchers noticed its effect on raising the basal metabolic rate in accidental exposure and developed it as one of the first weight loss drugs in the early twentieth century DNP was banned from human use by the end of the 1930s due to its risk of death and toxic side effects DNP continues to be used after its ban and experienced a resurgence in popularity after it became available on the Internet Contents 1 Chemical properties 2 Uses 2 1 Industrial 2 2 In humans 3 Biochemistry 3 1 Mechanism of action 3 2 Pharmacokinetics 3 3 As a pollutant 4 Adverse effects 4 1 Overdose 5 History 6 Legal status 7 References 8 Further readingChemical properties edit nbsp Synthesis of DNP right from phenol and nitric acid via 2 Nitrophenol and 4 Nitrophenol DNP has the chemical formula HOC6H3 NO2 2 As a solid it is a yellow crystalline and has a sweet musty odor 1 2 It sublimates is volatile with steam and is soluble in most organic solvents as well as aqueous alkaline solutions 2 DNP is a member of the dinitrophenols chemical family 1 DNP can be produced by hydrolysis of 2 4 dinitrochlorobenzene 1 3 Other routes of DNP synthesis include nitration of monochlorobenzene nitration of benzene with nitrogen dioxide and mercurous nitrate oxidation of 1 3 dinitrobenzene 4 and nitration of phenol with nitric acid 5 A dust explosion is possible with DNP in powder or granular form in the presence of air DNP may explosively decompose when submitted to shock friction or concussion and may explode upon heating 6 DNP forms explosive salts with strong bases as well as ammonia and emits toxic fumes of nitrogen dioxide when heated to decomposition 7 DNP s explosive strength is 81 that of TNT based on the Trauzl lead block test 8 Uses editIndustrial edit Historically DNP has been used as an antiseptic and as a non selective bioaccumulating pesticide 9 DNP was particularly useful as a herbicide alongside other closely related dinitrophenol herbicides like 2 4 dinitro o cresol DNOC dinoseb and dinoterb 10 Since 1998 DNP has been withdrawn from agricultural use 11 Currently there are no actively registered pesticides containing DNP in the United States or Europe 12 13 Dinoseb is used industrially as a polymerisation inhibitor during styrene production In 2023 the Home Office said it could not determine any legitimate industrial uses for DNP in the United Kingdom 14 It is a chemical intermediate in the production of sulfur dyes 3 wood preservatives 9 and picric acid 15 A precursor to 2 4 6 trinitrotoluene TNT DNP has also been used to make photographic developers and explosives 16 17 DNP is classified as an explosive in the United Kingdom 18 and the United States 19 In humans edit nbsp Histogram of DNP doses reported on online forums and the subreddit r DNP 20 DNP raises energy expenditure by 30 to 40 percent and causes a weight loss of 0 7 0 9 kilograms 1 5 2 0 lb per week 21 Although DNP is no longer in clinical use as a weight loss drug due to its dangerous side effects its mechanism of action remains under investigation as a potential approach for treating obesity and non alcoholic fatty liver disease 1 22 23 Researches developed a prodrug HU6 which is metabolized to DNP in the liver to provide more stable blood concentrations HU6 completed a phase II trial in which it produced significant reductions in liver fat and body weight in overweight people with elevated liver fat without serious adverse effects 24 DNP is used by bodybuilders fitness enthusiasts and people with an eating disorder to lose weight The user profile is similar to that of anabolic steroids many perceive it to be effective and with manageable risks 25 Despite health warnings from regulators DNP is readily available online 25 sometimes under other names such as Dinosan Dnoc Solfo Black Nitrophen Aldifen and Chemox 17 25 DNP is often sold in tablets containing 100 to 200 mg 1 and may be sold alongside other substances such as anabolic steroids and thyroxine 17 It may also be found as a contaminant in other bodybuilding supplements not advertised as containing DNP 25 Online message boards provide information on dosage and regimens for DNP use and describe the risks of taking the compound and provide advice on how to mitigate hyperthermia 17 25 26 According to a study published in 2023 the most commonly reported doses were between 150 and 300 mg day 20 Between 2010 and 2020 reports of overdoses were higher in Australasia Europe and North America than in Asia Africa and South or Central America 27 It is also used as a suicide method 17 Biochemistry editMechanism of action edit Main article Uncoupler nbsp Nitro reduction of DNP In living cells DNP acts as a protonophore an agent that can shuttle protons hydrogen cations across biological membranes It dissipates the proton gradient across the mitochondrial membrane 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 17 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 citation needed DNP raises the basal metabolic rate BMR and lowers T4 thyroid hormone levels by increasing T4 metabolism and reducing thyroid hormone secretion Because it binds to thyroxine binding globulin overall thyroid function may not be affected DNP cannot substitute for thyroid hormone in myxedema 28 Pharmacokinetics edit Information about pharmacokinetics and pharmacodynamics of DNP in humans is limited 23 DNP is metabolized via nitro reduction Its major metabolites are 2 amino 4 nitrophenol de and 4 amino 2 nitrophenol 16 In overdoses symptom onset can be as soon as 3 hours and the average time to death was 14 hours 16 17 As a pollutant edit Although many militaries are replacing traditional 2 4 6 trinitrotoluene TNT based explosives for insensitive munitions DNP is a degradation byproduct of the IMX 101 insensitive munition used by the United States Army 29 While the Meisenheimer charge transfer reaction is effective at detecting TNT it is not effective at detecting many other explosives including DNP Researchers are studying colorimetric detection and other methods for DNP to find if water or solids such as soils are contaminated with DNP 30 31 32 33 UiO 66 NH2 can be used to bind to and remove DNP from solution 34 Adverse effects editDNP has a low therapeutic index meaning that the dosage required for a desired effect is not much smaller than that which produces toxicity 17 Individual tolerance to DNP s harmful short and long term effects varies greatly 1 The most common adverse effect reported is a rash which could be maculopapular urticarial angioedema or an exfoliative dermatitis 17 Cataracts can form causing a permanent loss of vision in days to months of usage and permanent deafness has also been reported 17 35 Other adverse effects reported include peripheral neuritis agranulocytosis and neutropaenia 17 Negative effects on the central nervous system cardiovascular system and bone marrow can occur 1 In animal studies DNP acted as a teratogen mutagen and carcinogen and caused developmental and reproductive harm 17 An unusually yellow coloring of the skin mucous membranes sclera urine stomach contents and internal organs is an indication of DNP exposure but does not occur in every case 36 Contact with skin or inhalation can cause DNP poisoning Symptoms are typically mild with dermal exposure but inhalation can lead to systemic effects the same way as oral exposure 17 Overdose edit Overdose is extremely dangerous 17 cases reported to poison control centers had a 11 9 percent fatality rate between 2010 and 2020 27 Although the largest number of overdose deaths occurred in the 1910s and 1920s when the chemical was in more widespread industrial use 1 the substance s use as a dieting aid has caused a number of fatalities in the twenty first century 17 at least 50 overdose deaths were reported worldwide between 2010 and 2020 27 Although the lowest published fatal ingested dose is 4 3 mg kg 17 16 a typical overdose death occurs at a higher level of exposure around 20 50 mg kg 1 The first symptoms to appear are nausea vomiting abdominal pain and perhaps diarrhea 16 The typical overdose syndrome seen with DNP and other phenols is a combination of hyperthermia tachycardia diaphoresis and tachypnoea 16 17 Because of the heat produced during uncoupling DNP overdose will overpower the body s attempt to maintain thermal homeostasis and cause an uncontrolled fatal rise in body temperature up to as high as 44 C 111 F The disruption of metabolism also leads to the accumulation of potassium and phosphate potentially contributing to toxicity DNP can cause T wave and ST segment abnormalities heart muscle kidney and liver damage have been found on autopsy 16 17 According to an analysis of United Kingdom and United States overdose cases tachycardia hyperpyrexia acidosis and agitation or confusion are independent predictors of overdose death 37 There is no antidote to DNP and management strategies are based on expert opinion and case studies 17 Treatment for overdose is supportive and often involves aggressive cooling using methods such as ice baths and intravenous fluids 35 17 Grundlingh et al recommend administering activated charcoal if the patient presents within an hour of ingestion and using intravenous vasopressors or inotropes to control blood pressure if necessary Intravenous methylthioninium chloride can treat methaemoglobinaemia Benzodiazepines can help control seizures and dantrolene has been used in an attempt to control hyperthemia 17 Cardiopulmonary resuscitation CPR has been used on people who died of DNP overdoses but has no known successful outcomes 17 History editDuring World War I munitions workers in France fell ill and some died from DNP exposure 38 Stanford University academic Maurice L Tainter learned of DNP s effect in raising the metabolic rate and causing weight loss and pioneered its use as a weight loss drug 1 38 Although he was aware of DNP s narrow therapeutic index Tainter tried the drugs on obese patients and published successful results in 1933 average weight loss was 20 pounds 9 1 kg and most recipients did not report adverse effects In 1934 Tainter estimated that at least 100 000 people had been treated with DNP in the United States during its first year on the market and there had been three reported fatalities connected to the drug 38 1 Tainter argued that DNP was highly effective in raising the metabolic rate up to 50 percent and avoided the negative circulatory effects of desiccated thyroid another weight loss drug in use at the time 38 nbsp DNP explainer in the FDA publication Chamber of Horrors Other physicians were less optimistic about the adverse effects of DNP and in 1935 the American Medical Association s Council on Chemistry and Pharmacy declined to list DNP in the New and Nonofficial Remedies on the grounds that its benefits did not exceed its risks to health 38 Reports of cataracts forming during DNP usage administered by a physician appeared the same year in 1936 an ophthalmologist based in San Francisco estimated that 2 500 American women had gone blind from DNP use 38 Physician opinion turned against the drug but many people bought direct to consumer preparations of DNP marketed as a cosmetic rather than a drug to evade existing regulations 38 39 DNP s risks were highlighted in the Chamber of Horrors an exhibit assembled by the Food and Drug Administration to explain the limitations of existing American drug regulations In 1938 the Food Drug and Cosmetic Act increased the FDA s ability to regulate drugs DNP was deemed so toxic as to be banned for human consumption and in 1940 the FDA reported that there was no evidence of continued sale for this purpose 39 38 Nevertheless it continued to be used for weight loss 35 William F Loomis and Fritz Albert Lipmann discovered DNP s mechanism of action and reported it in a 1948 publication 38 Reports of its use increased in the twenty first century after the drug became available on the Internet 35 Legal status editDNP is banned for human consumption in many countries 1 Because it has some legitimate uses in many jurisdictions DNP is legal to sell not for human consumption 25 40 41 In Australia all dinitrophenols were classified as Schedule 1 dangerous drugs in 1956 In February 2017 DNP was reclassified as Schedule 10 Substances of such a danger to health as to warrant prohibition of sale supply and use 40 From 1 October 2023 DNP will be classified as a regulated poison in the United Kingdom 42 It is a prohibited substance class F4 in Brazil 43 In the United States DNP is classified as an investigational new drug it received orphan drug status for Huntington s disease 44 DNP has been banned by the World Anti Doping Association since 2015 45 Petroczi et al recommend against campaigns informing people of the risks of DNP because it could increase use of the drug 25 However Sousa et al argue that publicity campaigns in the United Kingdom in the early and mid 2010s reduced DNP usage 1 In 2015 Interpol and the World Anti Doping Agency released an orange notice warning of the dangers of DNP 25 In 1941 the Eastman Kodak Company a bulk distributor of DNP was investigated after some of its product was found in illegal diet pills 39 Nicholas Bachynsky a Texas physician provided the drug to patients under the name Mitcal He was convicted of violating drug laws in 1986 but continued to work with DNP and was additionally convicted of fraud in 2008 35 17 In 2018 a seller in the United Kingdom was convicted of manslaughter for selling DNP for human consumption The conviction was sent to retrial in 2020 by the English Court of Appeal where the seller was once again convicted of gross negligence manslaughter 46 References edit a b c d e f g h i j k l m Sousa Daniela Carmo Helena Roque Bravo Rita Carvalho Felix Bastos Maria de Lourdes Guedes de Pinho Paula Dias da Silva Diana April 2020 Diet aid or aid to die an update on 2 4 dinitrophenol 2 4 DNP use as a weight loss product Archives of Toxicology 94 4 1071 1083 doi 10 1007 s00204 020 02675 9 PMID 32078021 S2CID 211194992 a b Budavari Susan et al eds 1989 The Merck index an encyclopedia of chemicals drugs and biologicals 11th ed Rahway NJ Merck p 1900 ISBN 978 0 911910 28 5 OCLC 21297020 a b Gerald Booth Nitro Compounds Aromatic in Ullmann s Encyclopedia of Industrial Chemistry 2007 Wiley VCH Weinheim doi 10 1002 14356007 a17 411 Shea et al 1983 p 2 Khabarov Yu G Lakhmanov D E Kosyakov D S Ul yanovskii N V 1 October 2012 Synthesis of 2 4 dinitrophenol Russian Journal of Applied Chemistry 85 10 1577 1580 doi 10 1134 S1070427212100163 ISSN 1608 3296 S2CID 98830371 Stellman Jeanne Mager 1998 Encyclopaedia of Occupational Health and Safety Guides indexes directory International Labour Organization ISBN 978 92 2 109817 1 Sax N Irving Bruce Robert D 1989 Dangerous properties of industrial materials Vol 3 7th ed John Wiley amp Sons ISBN 0 442 27368 1 Meyer Rudolf Kohler Josef Homburg Axel 2016 Explosives John Wiley amp Sons ISBN 978 3 527 68961 3 a b 2 4 Dinitrophenol PDF Environmental Protection Agency Retrieved 15 October 2017 Gupta Ramesh C ed 2011 Reproductive and developmental toxicology London Academic Press p 509 ISBN 978 0 12 382032 7 OCLC 717387050 Pohanish Richard P 2011 Sittig s Handbook of Toxic and Hazardous Chemicals and Carcinogens William Andrew ISBN 978 1 4377 7870 0 Toxicological Profile for Dinitrophenols PDF Agency for Toxic Substances and Disease Registry U S Department of Health and Human Services August 2021 Pohanish Richard P 2014 Sittig s Handbook of Pesticides and Agricultural Chemicals William Andrew ISBN 978 1 4557 3157 2 Q Dinitrophenol www parallelparliament co uk Retrieved 7 February 2023 Agrawal Jai Prakash Hodgson Robert 2007 Organic Chemistry of Explosives John Wiley amp Sons ISBN 978 0 470 05935 7 a b c d e f g Bateman Nick Jefferson Robert Thomas Simon Thompson John Vale Allister 2014 Dinitrophenol Oxford Desk Reference Toxicology Oxford University Press pp 258 259 ISBN 978 0 19 102248 7 a b c d e f g h i j k l m n o p q r s t u v w Grundlingh Johann Dargan Paul I El Zanfaly Marwa Wood David M 1 September 2011 2 4 Dinitrophenol DNP A Weight Loss Agent with Significant Acute Toxicity and Risk of Death Journal of Medical Toxicology 7 3 205 212 doi 10 1007 s13181 011 0162 6 ISSN 1937 6995 PMC 3550200 PMID 21739343 Urben Peter 2017 Bretherick s Handbook of Reactive Chemical Hazards Elsevier ISBN 978 0 08 101059 4 Commerce in Explosives 2017 Annual List of Explosive Materials Federal Register 28 December 2017 Retrieved 22 July 2018 a b Abdelati Ali Burns Michele M Chary Michael 2023 Sublethal toxicities of 2 4 dinitrophenol as inferred from online self reports PLOS ONE 18 9 e0290630 Bibcode 2023PLoSO 1890630A doi 10 1371 journal pone 0290630 ISSN 1932 6203 PMC 10499234 PMID 37703241 Christoffersen Berit Ostergaard Sanchez Delgado Guillermo John Linu Mary Ryan Donna H Raun Kirsten Ravussin Eric April 2022 Beyond appetite regulation Targeting energy expenditure fat oxidation and lean mass preservation for sustainable weight loss Obesity 30 4 841 857 doi 10 1002 oby 23374 ISSN 1930 7381 PMC 9310705 PMID 35333444 Ost Mario Keipert Susanne Klaus Susanne March 2017 Targeted mitochondrial uncoupling beyond UCP1 The fine line between death and metabolic health Biochimie 134 77 85 doi 10 1016 j biochi 2016 11 013 PMID 27916644 S2CID 6867183 a b Meyer Lyndsey F Rajadhyaksha Pooja M Shah Dhaval K 1 June 2022 Physiologically based pharmacokinetic model for 2 4 dinitrophenol Journal of Pharmacokinetics and Pharmacodynamics 49 3 325 336 doi 10 1007 s10928 022 09806 y ISSN 1573 8744 PMID 35089483 S2CID 246361178 Harrison Stephen A Loomba Rohit Dubourg Julie Ratziu Vlad Noureddin Mazen July 2023 Clinical Trial Landscape in NASH Clinical Gastroenterology and Hepatology 21 8 2001 2014 doi 10 1016 j cgh 2023 03 041 PMID 37059159 S2CID 258115543 a b c d e f g h Petroczi Andrea Ocampo Jorge A Vela Shah Iltaf Jenkinson Carl New Rachael James Ricky A Taylor Glenn Naughton Declan P 14 October 2015 Russian roulette with unlicensed fat burner drug 2 4 dinitrophenol DNP evidence from a multidisciplinary study of the internet bodybuilding supplements and DNP users Substance Abuse Treatment Prevention and Policy 10 1 39 doi 10 1186 s13011 015 0034 1 ISSN 1747 597X PMC 4607104 PMID 26466580 McVeigh Jim Germain Jennifer Van Hout Marie Claire 2017 2 4 Dinitrophenol the inferno drug a netnographic study of user experiences in the quest for leanness PDF Journal of Substance Use 22 2 131 138 doi 10 3109 14659891 2016 1149238 S2CID 147770507 a b c Gziut Tomasz Thomas Simon H L 23 November 2021 International trends in systemic human exposures to 2 4 dinitrophenol reported to poisons centres Clinical Toxicology 60 5 628 631 doi 10 1080 15563650 2021 2005797 ISSN 1556 3650 PMID 34812657 S2CID 244490656 Weiss Roy E Refetoff Samuel 2016 Chapter 78 Thyroid Function Testing Endocrinology Adult and Pediatric Seventh ed W B Saunders p 1397 ISBN 978 0 323 18907 1 Richard Thomas Weidhaas Jennifer 15 September 2014 Biodegradation of IMX 101 explosive formulation constituents 2 4 Dinitroanisole DNAN 3 nitro 1 2 4 triazol 5 one NTO and nitroguanidine Journal of Hazardous Materials 280 372 379 doi 10 1016 j jhazmat 2014 08 019 ISSN 0304 3894 PMID 25181681 Chen Lili Cheng Zihan Peng Xinyue Qiu Guoqiao Wang Li 2022 Eu Doped MOF based high efficiency fluorescent sensor for detecting 2 4 dinitrophenol and 2 4 6 trinitrophenol simultaneously Analytical Methods 14 1 44 51 doi 10 1039 D1AY01747K PMID 34889337 S2CID 244787652 Feng Hai Tao Zheng Yan Song 3 January 2014 Highly Sensitive and Selective Detection of Nitrophenolic Explosives by Using Nanospheres of a Tetraphenylethylene Macrocycle Displaying Aggregation Induced Emission Chemistry A European Journal 20 1 195 201 doi 10 1002 chem 201302638 PMID 24285612 Adegoke Oluwasesan Daeid Niamh Nic October 2021 Polymeric coated Fe doped ceria gold hybrid nanocomposite as an aptasensor for the catalytic enhanced colorimetric detection of 2 4 dinitrophenol Colloids and Surfaces A Physicochemical and Engineering Aspects 627 127194 doi 10 1016 j colsurfa 2021 127194 S2CID 237672987 Dinesh Bose Aadhav Anantharamakrishnan Devi K S Shalini Krishnan Uma Maheswari 1 June 2022 Electrocatalytic reduction of 2 4 dinitrophenol on carbon black modified glassy carbon electrode and its selective recognition in cold beverages Carbon Letters 32 4 1017 1029 doi 10 1007 s42823 022 00334 w ISSN 2233 4998 S2CID 247942852 Xu Zhuang Wen Yuquan Tian Li Li Guangtao March 2017 Efficient and selective adsorption of nitroaromatic explosives by Zr MOF Inorganic Chemistry Communications 77 11 13 doi 10 1016 j inoche 2017 01 025 a b c d e Yen May Ewald Michele Burns 2012 Toxicity of Weight Loss Agents Journal of Medical Toxicology 8 2 145 152 doi 10 1007 s13181 012 0213 7 ISSN 1937 6995 PMC 3550246 PMID 22351299 Zack F Gummesson A Buttner A 1 October 2022 Morphologische Befunde als Hinweise auf eine 2 4 Dinitrophenol Intoxikation Rechtsmedizin in German 32 5 386 390 doi 10 1007 s00194 021 00552 y ISSN 1434 5196 S2CID 245336193 Potts A J Bowman N J Seger D L Thomas S H L 3 June 2021 Toxicoepidemiology and predictors of death in 2 4 dinitrophenol DNP toxicity Clinical Toxicology 59 6 515 520 doi 10 1080 15563650 2020 1826505 PMID 33021407 S2CID 222159746 a b c d e f g h i Colman Eric 2007 Dinitrophenol and obesity An early twentieth century regulatory dilemma Regulatory Toxicology and Pharmacology 48 2 115 117 doi 10 1016 j yrtph 2007 03 006 PMID 17475379 a b c Swann John P 2010 Reducing with dinitrophenol self medication and the challenge of regulating a dangerous pharmaceutical before the US Food Drug and Cosmetic Act Perspectives on Twentieth century Pharmaceuticals Peter Lang pp 289 292 299 301 ISBN 978 3 03910 920 3 a b Casey Scott 10 December 2019 2 4 Dinitrophenol effective but dangerous fat burner Australian Pharmacist Retrieved 17 September 2023 Hippensteele Alana 7 May 2021 Pharmacy Fact Miracle Weight Loss Drug Successfully Burns Fat Also Cooks Internal Organs Pharmacy Times Retrieved 17 September 2023 Wickware Carolyn 27 January 2023 Government to change law to reclassify so called diet drug as a poison The Pharmaceutical Journal Retrieved 29 January 2023 Anvisa 24 July 2023 RDC Nº 804 Listas de Substancias Entorpecentes Psicotropicas Precursoras e Outras sob Controle Especial Collegiate Board Resolution No 804 Lists of Narcotic Psychotropic Precursor and Other Substances under Special Control in Brazilian Portuguese Diario Oficial da Uniao published 25 July 2023 Archived from the original on 27 August 2023 Retrieved 27 August 2023 Geisler John G 23 March 2019 2 4 Dinitrophenol as Medicine Cells 8 3 280 doi 10 3390 cells8030280 ISSN 2073 4409 PMC 6468406 PMID 30909602 DNP Is it really all that dangerous opss Retrieved 18 September 2023 Eloise Parry Man convicted over diet pill death BBC News 9 March 2020 Further reading editShea P J Weber J B Overcash M R 1983 Biological activities of 2 4 dinitrophenol in plant soil systems Residue Reviews Residues of Pesticides and Other Contaminants in the Total Environment Springer pp 1 41 ISBN 978 1 4612 5479 9 Retrieved from https en wikipedia org w index php title 2 4 Dinitrophenol amp oldid 1219728705, wikipedia, wiki, book, books, library,

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