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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
Structure of PICRIC ACID

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

HIDE SMILES / InChI

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.

Originator

Curator's Comment: Picric acid was probably first mentioned in the alchemical writings of Johann Rudolf Glauber in 1742

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Doses

Doses

DosePopulationAdverse 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
Health Status: unhealthy
Age Group: 28 years
Sex: F
Sources:
Disc. AE: Edema face, Eyelid oedema...
AEs leading to
discontinuation/dose reduction:
Edema face
Eyelid oedema
Nausea
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Health Status: unhealthy
Age Group: 28 years
Sex: F
Sources:
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
Health Status: unhealthy
Age Group: 28 years
Sex: F
Sources:
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
Health Status: unhealthy
Age Group: 28 years
Sex: F
Sources:
PubMed

PubMed

TitleDatePubMed
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

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
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 Mon Mar 31 18:34:53 GMT 2025
Edited
by admin
on Mon Mar 31 18:34:53 GMT 2025
Record UNII
A49OS0F91S
Record Status Validated (UNII)
Record Version
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Name Type Language
PICRICUM ACIDUM
HPUS  
Preferred Name English
PICRIC ACID
HSDB   MI   WHO-DD  
Systematic Name English
NSC-36947
Code English
Picric acid [WHO-DD]
Common Name English
PICRIC ACID [MI]
Common Name English
TRINITROPHENOL [MART.]
Common Name English
TRINITROPHENOL
MART.  
Systematic Name English
PICRIC ACID [HSDB]
Common Name English
PICRICUM ACIDUM [HPUS]
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
FDA UNII
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
EVMPD
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
ChEMBL
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
PUBCHEM
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
CHEBI
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
WIKIPEDIA
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
NSC
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
MERCK INDEX
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
SMS_ID
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
MESH
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
CAS
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
RXCUI
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
CHEBI
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
DRUG BANK
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
RXCUI
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
HSDB
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
DRUG CENTRAL
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
ECHA (EC/EINECS)
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
EPA CompTox
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
NCI_THESAURUS
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
DAILYMED
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