U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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
n = 1
Health Status: unhealthy
Age Group: 28 years
Sex: F
Population Size: 1
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
n = 1
Health Status: unhealthy
Age Group: 28 years
Sex: F
Population Size: 1
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
n = 1
Health Status: unhealthy
Age Group: 28 years
Sex: F
Population Size: 1
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
n = 1
Health Status: unhealthy
Age Group: 28 years
Sex: F
Population Size: 1
Sources:
PubMed

PubMed

TitleDatePubMed
Electrophoretically mediated microanalysis with small molecules: the Jaffé method for creatinine carried out in a capillary tube.
2001 Aug
Development of marine toxicity data for ordnance compounds.
2001 Oct
Anion effects on the recognition of ion pairs by calix[4]arene-based heteroditopic receptors.
2002 Aug 23
Cimetidine improves prediction of the glomerular filtration rate by the Cockcroft-Gault formula in renal transplant recipients.
2002 Mar 15
Some errors from the crystallographic literature, some amplifications and a questionable result.
2002 Oct
Hexaaquairon(II) dipicrate dihydrate.
2003 Aug
On benzo[b][1,4]diazepinium-olates, -thiolates and -carboxylates as anti-Hückel mesomeric betaines.
2003 Dec 7
Degradation of picric acid and 2,6-DNT in marine sediments and waters: the role of microbial activity and ultra-violet exposure.
2004 Aug
Simple synthesis of a weak nucleophilic base (4-ethyl-2,6-diisopropyl-3,5-dimethylpyridine) evidencing a double Janus group effect.
2004 Jan 23
Atomic resolution structures and solution behavior of enzyme-substrate complexes of Enterobacter cloacae PB2 pentaerythritol tetranitrate reductase. Multiple conformational states and implications for the mechanism of nitroaromatic explosive degradation.
2004 Jul 16
A simplified method for HPLC determination of creatinine in mouse serum.
2004 Jun
Binding of acetylcholine and tetramethylammonium to flexible cyclophane receptors: improving on binding ability by optimizing host's geometry.
2004 May 28
Transport properties and electroanalytical response characteristics of drotaverine ion-selective sensors.
2005 Aug
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
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 Aug 23
Pyridoxinium picrate.
2006 Jul
Antimicrobial and toxicological evaluation of the leaves of Baissea axillaries Hua used in the management of HIV/AIDS patients.
2006 Jun 21
Mechanism of a four-phase liquid membrane oscillator containing hexadecyltrimethylammonium bromide.
2006 Jun 8
Thermal hazard of iron picrate.
2006 May 20
Vibrational spectral analysis of DL-valine DL-valinium and DL-methionine DL-methioninium picrates.
2006 Nov
L-prolinium picrate and 2-methylpyridinium picrate.
2006 Sep
Vibrational spectroscopic studies of an organic non-linear optical crystal 8-hydroxyquinolinium picrate.
2007 Apr
Comparison of estimated glomerular filtration rate with routine creatinine clearance using a kinetic alkaline picrate assay from Olympus Diagnostica.
2007 Jun
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.
Name Type Language
PICRIC ACID
HSDB   MI   WHO-DD  
Systematic Name English
NSC-36947
Code English
PICRICUM ACIDUM
HPUS  
Common Name 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 Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
Code System Code Type Description
FDA UNII
A49OS0F91S
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY
EVMPD
SUB14869MIG
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY
ChEMBL
CHEMBL108541
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY
PUBCHEM
6954
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY
CHEBI
46149
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY
WIKIPEDIA
PICRIC ACID
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY
NSC
36947
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY
MERCK INDEX
m8792
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY Merck Index
SMS_ID
100000079446
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY
MESH
C005858
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY
CAS
88-89-1
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY
RXCUI
1443000
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY
CHEBI
86297
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY
DRUG BANK
DB03651
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY
RXCUI
1320642
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY RxNorm
HSDB
2040
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY
DRUG CENTRAL
4626
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-865-9
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID4025909
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY
NCI_THESAURUS
C80865
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY
DAILYMED
A49OS0F91S
Created by admin on Fri Dec 15 16:42:00 GMT 2023 , Edited by admin on Fri Dec 15 16:42:00 GMT 2023
PRIMARY