SODIUM PICRAMATE

Basic Info:

  • Chemical Synonym(s): Sodium 4,6-dinitro-2-aminophenate,dry or wetted with less than 20% water,by mass;Sodium 4,6-Dinitro-2-aminophenolate;SODIUM PICRAMATE;Sodium picramate,wetted with not less than20% water,by mass;SODIUM 2-AMINO-4,6-DINITROPHENOXIDE;2-AMINO-4,6-DINITRO-PHENOL SODIUM SALT (SODIUM PICRAMATE);Sodium Picramate (>88.0% anhydrous basis);2-Amino-4,6-dinitro-phenol, Natrium-Salz
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  • CAS Number: 831-52-7
  • Chemical Formula:

    C6H4N3NaO5

  • MSDS: Download

Characteristics: 

Appearance & Physical State
Dark red prescake
Boiling Point
386.3ºC at 760 mmHg
Flash Point
187.5ºC
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Introduction:

Sodium picramate is a salt of picric acid and sodium hydroxide. It can be used in the treatment of burns. However, it has been mainly replaced by silver sulfadiazine.

It is prepared by the reaction of picric acid with sodium carbonate, forming sodium carbonate monohydrate and 2,4,6-trinitrophenol. The last is distilled off and treated with caustic soda to afford the picrate salt, crystallising in needles. It is soluble in water, slightly soluble in alcohol and practically insoluble in ether.

It is used as an adjunct for chemotherapy as a chelating agent to bind heavy metals such as lead and mercury, but the risk of side effects has limited its use. It also has been used as a dye for children's clothing and carpeting but was banned in the US by CPSC due to its high toxicity.

Applications:

Sodium picramate has been found to have the ability to crosslink DNA, which inhibits the proliferation of cells, especially in cancerous conditions.  It is thus used heavily in chemotherapy drugs because it targets rapidly dividing cells.

It is used as an adjunct for chemotherapy as a chelating agent to bind heavy metals such as lead and mercury, but the risk of side effects has limited its use. It also has been used as a dye for children's clothing and carpeting but was banned in the US by CPSC due to its high toxicity.

It is also used in biological stains to stain tissue for diagnosis. For example, sodium picramate-H3+ is one of the most widely used reagents for staining cells and tissues in electron microscopy. It was shown that this compound reacts with free amino groups, which makes it useful in staining.

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