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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
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
Record UNII
A49OS0F91S
Record Status Validated (UNII)
Record Version