Natural Science Forum / Chemistry / Organic Synthesis / January 2004

Sure!  Tylenol tablet, vinegar, sodium nitrite.

Crush the Tylenol.  Add some to a couple or three milliliters of
vinegar in a small test tube, and dissolve (excipients will not
dissolve).  Add a 100 mg or so of NaNO2, mix, wait.  Do not breathe
the NOx fumes.

The brick red ppt. is the remarkably bioreactive and toxic
N-acetylquinonimine, the first hepatic metabolite of acetaminophen.
It will send cultured cells to Hell.

N-acetylquinonimine is in turn conjugated to reduced glutathione (GSH)
for renal excretion.  What depletes hepatic glutathione and allows
acetaminophen to chew on your liver and kidneys?  A hangover does
nicely as does poor nutritional status like dieting or physical trauma
like over-exercising - just the things to give you a headache or body
pain demanding a facile OTC solution.

Filter, wash, resuspend in saline. Try grabbing the stuff with some
ascorbate, cysteine, etc.  If the red color goes, you've gotten it.
Avoid skin contact.

Nitrite plus stomach acid is nasty stuff.  If you add proline to
vinegar and add nitrite, will you get the yellow carcinogenic
nitrosamine?  Nitrite diazotizes pendant amino acid amines (e.g.,
lysines).  In the presence of pickling brine you get chlorine
subsitution and an alkylating agent.  Is the anomalously high
incidence of upper GI cancer in Japan traceable to heavy consumption
of pickled meat and vegetables in brines containing nitrite?

Drop of nitic acid on skin (then quickly wash off) gives an indelible
yellow stain from nitrated tyrosine and tryptophan residues
("xanthoproteic acid").