Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H3N3O7 |
| Molecular Weight | 229.1039 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=C(C=C(C=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O
InChI
InChIKey=OXNIZHLAWKMVMX-UHFFFAOYSA-N
InChI=1S/C6H3N3O7/c10-6-4(8(13)14)1-3(7(11)12)2-5(6)9(15)16/h1-2,10H
| Molecular Formula | C6H3N3O7 |
| Molecular Weight | 229.1039 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Picric acid is used as a high explosive, an oxidant in rocket fuels, in matches and leather processing, as a laboratory reagent for serum creatinine analysis in humans and experimental animals. There is not much information related to pharmacological and biological application of picric acid. But is known, that during the 1920s-30s, it was used either alone or in combination with butyl aminobenzoate as an antiseptic dressing for burn wounds. About 4% of patients treated with picric acid developed sensitization local dermatitis and at least one case of serious central nervous system dysfunction occurred following topical picric acid application. Picric acid does not sensitize directly, but only after conversion to a more reactive compound. Picric acid was positive in the Ames salmonella assay for mutagenicity when metabolic activation was present. It has also been reported to be non-mutagenic in the Ames test. Those contradictory results did not allow to draw a conclusion on picric acid mutagenicity. A review by a committee of the Health Council of the Netherlands in 2002, did not find published data on long-term toxicity, carcinogenicity, or reproductive toxicity.
Approval Year
Doses
| Dose | Population | Adverse events |
|---|---|---|
10 % 1 times / day multiple, topical Dose: 10 %, 1 times / day Route: topical Route: multiple Dose: 10 %, 1 times / day Sources: |
unhealthy, 28 years |
Disc. AE: Edema face, Eyelid oedema... AEs leading to discontinuation/dose reduction: Edema face Sources: Eyelid oedema Nausea |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Edema face | Disc. AE | 10 % 1 times / day multiple, topical Dose: 10 %, 1 times / day Route: topical Route: multiple Dose: 10 %, 1 times / day Sources: |
unhealthy, 28 years |
| Eyelid oedema | Disc. AE | 10 % 1 times / day multiple, topical Dose: 10 %, 1 times / day Route: topical Route: multiple Dose: 10 %, 1 times / day Sources: |
unhealthy, 28 years |
| Nausea | Disc. AE | 10 % 1 times / day multiple, topical Dose: 10 %, 1 times / day Route: topical Route: multiple Dose: 10 %, 1 times / day Sources: |
unhealthy, 28 years |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Catalytic degradation of explosives with goethite and hydrogen peroxide. | 2008-03-01 |
|
| Synthesis and infrared and fluorescent spectra of rare earth complexes with a new amide ligand. | 2007-11 |
|
| Amitriptylinium picrate: conformational disorder. | 2007-09 |
|
| Hexaaquazinc(II) dipicrate trihydrate. | 2007-09 |
|
| An aerobic sequencing batch reactor for 2,4,6-trinitrophenol (picric acid) biodegradation. | 2007-08-15 |
|
| Hydration effect on the ion-pair extraction of lithium picrate by hydrophobic benzo-15-crown-5 ether into various less-polar diluents. | 2007-08 |
|
| Cytotoxicity of purified cassava linamarin to a selected cancer cell lines. | 2007-07 |
|
| Synthesis and spectroscopic properties of rare earth picrate complexes with a new biphenylamide. | 2007-07 |
|
| Synthesis, characterization and catalytic application of silver nanoshell coated functionalized polystyrene beads. | 2007-06 |
|
| Comparison of estimated glomerular filtration rate with routine creatinine clearance using a kinetic alkaline picrate assay from Olympus Diagnostica. | 2007-06 |
|
| Perfluoroalkylated 4,13-diaza-18-crown-6 ethers: synthesis, phase-transfer catalysis, and recycling studies. | 2007-05-11 |
|
| Expressing the Modification of Diet in Renal Disease Study equation for estimating glomerular filtration rate with standardized serum creatinine values. | 2007-04 |
|
| Vibrational spectroscopic studies of an organic non-linear optical crystal 8-hydroxyquinolinium picrate. | 2007-04 |
|
| A phase I and pharmacokinetic study of indisulam in combination with carboplatin. | 2007-02-26 |
|
| Anion partitioning and ion-pairing behavior of anions in the extraction of cesium salts by 4,5' '-Bis(tert-octylbenzo)dibenzo-24-crown-8 in 1,2-dichloroethane. | 2007-01-08 |
|
| Urinary eosinophil protein X in children with atopic asthma. | 2007 |
|
| Hydrogen-bond interactions of nicotine and acetylcholine salts: a combined crystallographic, spectroscopic, thermodynamic and theoretical study. | 2007 |
|
| Measurement of serum creatinine--current status and future goals. | 2006-11 |
|
| Vibrational spectral analysis of DL-valine DL-valinium and DL-methionine DL-methioninium picrates. | 2006-11 |
|
| Silver(I) complexation of linked 2,2'-dipyridylamine derivatives. Synthetic, solvent extraction, membrane transport and X-ray structural studies. | 2006-10-28 |
|
| Spectral investigations of amino acid picrates. | 2006-10 |
|
| L-prolinium picrate and 2-methylpyridinium picrate. | 2006-09 |
|
| No association between the aluminium content of trabecular bone and bone density, mass or size of the proximal femur in elderly men and women. | 2006-08-23 |
|
| Pyridoxinium picrate. | 2006-07 |
|
| Antimicrobial and toxicological evaluation of the leaves of Baissea axillaries Hua used in the management of HIV/AIDS patients. | 2006-06-21 |
|
| Mechanism of a four-phase liquid membrane oscillator containing hexadecyltrimethylammonium bromide. | 2006-06-08 |
|
| Thermal hazard of iron picrate. | 2006-05-20 |
|
| Simple hydrogen-bonded chains in 2,2'-bipyridinium thiocyanate, hydrogen-bonded chains of rings in 2,2'-bipyridinium picrate and hydrogen-bonded sheets in 2,2'-bipyridinium hydrogensulfate. | 2006-04 |
|
| On the mechanism of nitrobenzene liquid membrane oscillators containing hexadecyltrimethylammonium bromide. | 2006-03-20 |
|
| Asymptomatic bacteriuria in sickle cell disease: a cross-sectional study. | 2006-03-15 |
|
| Glass distilling collector applied for HCN recovery from submerged culture broth and fruiting body of Pleurotus eryngii for identification and quantification. | 2006-03-08 |
|
| Sodium dodecyl sulphate as a rapid clearing agent for studying the hard parts of monogeneans and nematodes. | 2006-03 |
|
| Spectroscopic and conductometric studies of molecular complex formation between 2,4,6-trinitrophenol and diaza-18-crown-6, tetraaza-14-crown-4 and cryptand C222 in 1,2-dichloroethane solution. | 2006-02 |
|
| The crystal structures of 3-TAPAP in complexes with the urokinase-type plasminogen activator and picrate. | 2006-01-01 |
|
| Design and synthesis of redox-switched lariat ethers and their application for transport of alkali and alkaline-Earth metal cations across supported liquid membrane. | 2006 |
|
| Vitamin status and cognitive function in a long-term care population. | 2005-12-13 |
|
| Fate and effects of picric acid and 2,6-DNT in marine environments: toxicity of degradation products. | 2005-11 |
|
| Creatinine concentration in plasma from dog, rat, and mouse: a comparison of 3 different methods. | 2005-09 |
|
| Transport properties and electroanalytical response characteristics of drotaverine ion-selective sensors. | 2005-08 |
|
| Dibenzotetraaza crown ethers: a new family of crown ethers based on o-phenylenediamine. | 2005-07-22 |
|
| [Studies on chromatographic properties of 2,4,6-trinitrophenol-modified zirconia-magnesia stationary phase for the separation of fullerenes ]. | 2005-07 |
|
| Prediction of two-sample (99m)Tc-diethylene triamine pentaacetic acid plasma clearance from single-sample method. | 2005-07 |
|
| Bioremediation of polynitrated aromatic compounds: plants and microbes put up a fight. | 2005-06 |
|
| Second-sphere coordination in anion binding: cis-diazidobis(ethylenediamine-kappa(2)N,N')cobalt(III) picrate. | 2005-06 |
|
| Increasing the efficiency of in-capillary electrophoretically mediated microanalysis reactions via rapid polarity switching. | 2005-04-15 |
|
| Surface plasmon resonance immunosensor for highly sensitive detection of 2,4,6-trinitrotoluene. | 2005-03-15 |
|
| Screening of crude extracts of six medicinal plants used in South-West Nigerian unorthodox medicine for anti-methicillin resistant Staphylococcus aureus activity. | 2005-03-11 |
|
| Synthesis, conformation, and complexation of novel 25,26,27,28- tetrahydroxy-5,11:17,23-bis[[2,2'-thioxydi(o-phenylene)dithioxy]- diphenylthio]calix[4]arene. | 2005-01-21 |
|
| Azidocryptands-synthesis, structure, and complexation properties. | 2005-01-21 |
|
| A new type of migrating zone boundary in electrophoresis: 1. General description of boundary behavior based on electromigration dispersion velocity profiles. | 2005-01 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1404487
toxicity tests in rats: The acute toxicity, distribution, and metabolism of picric acid were investigated using Fischer 344 rats. The LD50 for picric acid following oral dosing of male and female rats was established as 290 and 200 mg/kg, respectively. Blood gas analysis indicated severe acidosis during acute intoxication.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3021774
The effect of picric acid on the release of [14C]acetylcholine has been investigated in isolated ileal synaptosomes of guinea-pig. Nicotine, high K-depolarization (50 mM KCl) and electrical field stimulation were employed to characterize the specificity of picric acid. Picric acid induced the release of labelled acetylcholine in a dose-dependent manner and this action was negated by the removal of calcium ions from the bathing medium. Tetrodotoxin (0.1 microM) abolished the actions of picric acid, nicotine or electrical field stimulation (0.1 Hz). It reduced but did not totally suppress the effect of high K-depolarization. Agents capable of affecting the content of cyclic AMP, such as forskolin and alloxan, modified the effects of picric acid or nicotine but did not influence the effects of high K-depolarization or electrical field stimulation.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:34:53 GMT 2025
by
admin
on
Mon Mar 31 18:34:53 GMT 2025
|
| Record UNII |
A49OS0F91S
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C28394
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
A49OS0F91S
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | |||
|
SUB14869MIG
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | |||
|
CHEMBL108541
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | |||
|
6954
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | |||
|
46149
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | |||
|
PICRIC ACID
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | |||
|
36947
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | |||
|
m8792
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | Merck Index | ||
|
100000079446
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | |||
|
C005858
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | |||
|
88-89-1
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | |||
|
1443000
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | |||
|
86297
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | |||
|
DB03651
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | |||
|
1320642
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | RxNorm | ||
|
2040
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | |||
|
4626
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | |||
|
201-865-9
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | |||
|
DTXSID4025909
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | |||
|
C80865
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY | |||
|
A49OS0F91S
Created by
admin on Mon Mar 31 18:34:53 GMT 2025 , Edited by admin on Mon Mar 31 18:34:53 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
SALT/SOLVATE -> PARENT | |||
|
SALT/SOLVATE -> PARENT |
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |