Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H4N2O5 |
Molecular Weight | 184.1064 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=C(C=C1[N+]([O-])=O)[N+]([O-])=O
InChI
InChIKey=UFBJCMHMOXMLKC-UHFFFAOYSA-N
InChI=1S/C6H4N2O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H
Molecular Formula | C6H4N2O5 |
Molecular Weight | 184.1064 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
2,4-dinitrophenol (DNP) is a FDA-banned weight-loss agent and EPA-regulated environmental toxicant, traditionally used in research labs as an uncoupler of OXPHOS. Although not licensed for human consumption, DNP and DNP crystal form are used by
bodybuilders and extreme dieters for their fat burning
properties through inhibiting efficient energy (ATP) production
in cells. Through uncoupling mitochondrial oxidative
phosphorylation by facilitating proton transport
across the mitochondrial membrane, DNP leads to rapid
consumption of energy without generating ATP and
consequently, to increased fat metabolism.
However, the weight-loss effect comes with serious, and
in some cases potentially fatal, adverse side effects,
namely hyperthermia (the leading cause of fatality with
acute DNP toxicity) and cardiac arrest, but also diaphoresis,
tachycardia, tachypnea, skin toxicity, Fourier’s gangrene
and cataracts with low dose chronic exposure. The proposed mechanism of DNP induced toxicity suggests the activation of ATP-sensitive K+ channels.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0006754 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26466580 |
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Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Characterization of long-lasting histaminergic inhibition in a beating pacemaker neuron of Onchidium. | 1985 Apr 15 |
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In vitro culture and embryo metabolism of cattle and sheep embryos - a decade of achievement. | 2000 Jul 2 |
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Converging catabolism of 2,4,6-trinitrophenol (picric acid) and 2,4-dinitrophenol by Nocardioides simplex FJ2-1A. | 2001 |
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Comparative study of toxicity of 4-nitrophenol and 2,4-dinitrophenol in newborn and young rats. | 2001 Dec |
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The 143 and 300 K polymorphs of hexamethylenetetraminium 2,4-dinitrophenolate monohydrate. | 2001 Dec |
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Spectroscopic study of nitroaromatic-smectite sorption mechanisms. | 2001 Dec 15 |
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Inhibitors of mitochondrial ATP production at the time of compaction improve development of in vitro produced porcine embryos. | 2001 Jan |
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Mitochondrial uncoupling as a target for drug development for the treatment of obesity. | 2001 Nov |
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Thyroxine reversibly inhibits the uncoupling action of protonophores on energy production in rat thymus lymphocytes. | 2002 Apr |
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Effects of K(ATP) channel openers, P-1075, pinacidil, and diazoxide, on energetics and contractile function in isolated rat hearts. | 2002 Apr |
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Effects of dinoseb on the life cycle of Daphnia magna: modeling survival time and a proposal for an alternative to the no-observed-effect concentration. | 2002 Apr |
|
Efflux of organic acids in Penicillium simplicissimum is an energy-spilling process, adjusting the catabolic carbon flow to the nutrient supply and the activity of catabolic pathways. | 2002 Apr |
|
Long-chain fatty acids increase basal metabolism and depolarize mitochondria in cardiac muscle cells. | 2002 Apr |
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Correlation between GABA release from rat islet beta-cells and their metabolic state. | 2002 Apr |
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Inhibition of transthyretin amyloid fibril formation by 2,4-dinitrophenol through tetramer stabilization. | 2002 Apr 1 |
|
Metal complexes of tetrapodal ligands: synthesis, spectroscopic and thermal studies, and X-ray crystal structure studies of Na(I), Ca(II), Sr(II), and Ba(II) complexes of tetrapodal ligands N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine and N,N,N',N'-tetrakis(2-hydroxyethyl)ethylenediamine. | 2002 Apr 22 |
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Cyclic AMP has distinct effects from Ca(2+) in evoking priming and fusion/exocytosis in parotid amylase secretion. | 2002 Aug |
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The internal pH of synaptic-like microvesicles in rat pinealocytes in culture. | 2002 Aug |
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Hydrogen peroxide photolysis, fenton reagent and photo-fenton for the degradation of nitrophenols: a comparative study. | 2002 Feb |
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Detoxication mechanism of exogenous monatomic phenols in pea seedlings. | 2002 Feb |
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Thyroid status is a key regulator of both flux and efficiency of oxidative phosphorylation in rat hepatocytes. | 2002 Feb |
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Effect of the new matrix metalloproteinase inhibitor RO-28-2653 on mitochondrial function. | 2002 Feb 15 |
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A cuboctahedral supramolecular capsule by 4:4 self-assembly of Tris(Zn(II)-cyclen) and trianionic trithiocyanurate in aqueous solution at neutral pH (cyclen=1,4,7,10-tetraazacyclododecane). | 2002 Feb 15 |
|
Accumulation of ciprofloxacin and lomefloxacinin fluoroquinolone-resistant strains of Escherichia coli. | 2002 Jan |
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A selective PVC membrane for di- or trinitrophenol based on N,N-dibenzyl-3,3',5,5'-tetramethylbenzidine. | 2002 Jan |
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Mechanism-based quantitative structure-activity relationships for the inhibition of substituted phenols on germination rate of Cucumis sativus. | 2002 Jan |
|
Expression of the uncoupling protein 1 from the aP2 gene promoter stimulates mitochondrial biogenesis in unilocular adipocytes in vivo. | 2002 Jan |
|
Barium(II)-2,4-dinitrophenolate-18-crown-6 at 183 K. | 2002 Jan |
|
NO synthesis, unlike respiration, influences intracellular oxygen tension. | 2002 Jan 11 |
|
Hsp70 instability and induction by a pesticide in Folsomia candida. | 2002 Jan-Feb |
|
Entacapone does not induce conformational changes in liver mitochondria or skeletal muscle in vivo. | 2002 Jul |
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Isoflurane-induced facilitation of the cardiac sarcolemmal K(ATP) channel. | 2002 Jul |
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Differential modulation of the cardiac adenosine triphosphate-sensitive potassium channel by isoflurane and halothane. | 2002 Jul |
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ELF magnetic fields increase amino acid uptake into Vicia faba L. roots and alter ion movement across the plasma membrane. | 2002 Jul |
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The origin of calcium overload in rat cardiac myocytes following metabolic inhibition with 2,4-dinitrophenol. | 2002 Jul |
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Bivalent ligands with rigid double-stranded DNA spacers reveal structural constraints on signaling by Fc epsilon RI. | 2002 Jul 15 |
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Spectrophotometric determination of lisinopril in tablets using 1-fluoro-2,4-dinitrobenzene reagent. | 2002 Jul 31 |
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Role of ATP in the sensitivity to heat and the induction of apoptosis in mammalian cells. | 2002 Jul-Aug |
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Stereoselective transport of histidine in rat lung microvascular endothelial cells. | 2002 Jun |
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Kinetic and structural basis of reactivity of pentaerythritol tetranitrate reductase with NADPH, 2-cyclohexenone, nitroesters, and nitroaromatic explosives. | 2002 Jun 14 |
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New approach to immunochemical determinations for triclopyr and 3,5,6-trichloro-2-pyridinol by using a bifunctional hapten, and evaluation of polyclonal antiserum. | 2002 Jun 19 |
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Kinetics and mechanism of the phenolysis of asymmetric diaryl carbonates. | 2002 Jun 28 |
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npd gene functions of Rhodococcus (opacus) erythropolis HL PM-1 in the initial steps of 2,4,6-trinitrophenol degradation. | 2002 Mar |
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Piperazine-1,4-diium--2,4-dinitrophenolate--water (1/2/2). | 2002 Mar |
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ATP depletion is an important factor in DHEA-induced growth inhibition and apoptosis in BV-2 cells. | 2002 Mar 15 |
|
Activation of TiO2 photocatalyst by single-bubble sonoluminescence for water treatment. | 2002 May |
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Dinitrophenol pretreatment of rat ventricular myocytes protects against damage by metabolic inhibition and reperfusion. | 2002 May |
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[Dnitrophenol--a dangerous doping agent]. | 2002 May 30 |
|
Hisactophilin is involved in osmoprotection in Dictyostelium. | 2002 May 7 |
|
Growth and characterization of semi-organic nonlinear optical crystal: sodium 2,4-dinitrophenolate monohydrate. | 2013 Jun |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26466580
The amounts ingested and length
of exposure in 2,4-dinitrophenol (DNP)-related illnesses and deaths range
between (1 to 46 mg/kg/day and 3 to 46 mg/kg/day, respectively).
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20202704
2,4-dinitrophenol (DNP, 50 uM) and isoproterenol (0.1 uM) failed to produce a transient vasodilatory response and caused a significant diastolic pressure increase in Kir6.2(-/-) hearts.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:10:50 UTC 2023
by
admin
on
Fri Dec 15 15:10:50 UTC 2023
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Record UNII |
Q13SKS21MN
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
764820
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EPA PESTICIDE CODE |
37509
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FDA ORPHAN DRUG |
672818
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m4578
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DB04528
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529
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2,4-DINITROPHENOL
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SUB33423
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51-28-5
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100000126132
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DTXSID0020523
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200-087-7
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TARGET->INHIBITOR OF EXPRESSION |
DNP decreases the formation of high-energy phosphate bonds in mitochondria and at the same time stimulates systemic oxygen consumption. This dissociative effect is known as uncoupling of oxidative phosphorylation. Weak uncoupler.
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |