Talk:4-Aminosalicylic acid

Synthesis

The article writes:"PAS is manufactured by the carboxylation of 3-aminophenol.[6]"

Well PAS is produced in two steps.One is reaction of 3-aminophenol with CO2 and sodium hydroxide, in a process very similar to the production of Salicylic acid:

3-aminophenol + CO2 + NaOH ----->Product 1.This reaction is did under hight temperatures and pressions.

Product 1 + H2SO4 -----> 4-Aminosalicylic acid + Na2SO4(sodium sulfate).sodium sulfate is separeted using organic product such as ethanol or ether.Agre22 (talk) 22:21, 11 January 2010 (UTC)agre22

Model

Isn't the space filling model missing a hydrogen, specifically in the carboxylic acid group? 203.97.134.50 (talk) 22:10, 25 June 2012 (UTC)

The space filling model is for the anionic form, where the carboxylic acid is actually a carboxylate (COO- instead of COOH). This is the predominant form at physiological pH.165.124.215.78 (talk) 18:13, 1 December 2012 (UTC)

Priority

Debates about priority can be complicated, but I feel that some gesture should be made in the direction of the various claims made re PAS & streptomycin. I have been reading "Tuberculosis: the Greatest Story Never Told", Frank Ryan, Swift, 1992. p256: "On 30 and 31 October, 1944, a month before the young woman from Austin was given the first treatment with streptomycin for pulmonary tuberculosis, in Gothenburg, Sweden, Sigrid received her first cautious dose of PAS by mouth ... ". It seems that although human trials of PAS preceded those with streptomycin, the former drug was accepted more cautiously by the medical profession, and therefore the impression has arisen that Streptomycin had priority. It might be justifiable to say that Streptomycin was the first widely used anti tubercular drug, but PAS was apparently the first truly effective drug to be used. g4oep — Preceding unsigned comment added by 77.96.60.31 (talk) 09:16, 31 October 2014 (UTC)

Structure

Is the structural model correct ? I can see only 6 hydrogen atoms. Compare the picture in the article with this:

http://www.shutterstock.com/pic-182779007/stock-photo-para-aminosalicylic-acid-drug-molecule-used-in-treatment-of-tuberculosis-and-inflammatory-bowel.html?src=1wE1kh6d8jlUieMPPtPjgQ-1-57

g4oep — Preceding unsigned comment added by 77.96.60.31 (talk) 09:27, 31 October 2014 (UTC)

It's possible that the model (File:4-Aminosalicylic acid 3d structure vander.png) is intended to be the zwitterionic form with an ammonium (-NH₃⁺) group and a carboxylate anion (-CO₂^-) in which the missing hydrogen atom would be behind the blue nitrogen atom. However, the creator of this image also uploaded an equivalent rotating animation (File:4-Aminosalicylic acid 3d structure.gif) in which there are only two hydrogen atoms on the nitrogen instead of the expected 3. For now, I have simply removed the image - it isn't all that necessary anyway. -- Ed (Edgar181) 10:04, 31 October 2014 (UTC)

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