Monday, August 31, 2015

Sodium formaldehyde sulfoxylate is a picky antidote

Sodium formaldehyde sulfoxylate, a small sulfur-containing molecule with a propensity to give away its electrons (i.e. a strong reducing agent), has many names and many uses. One of its aliases, rongalite, comes from “rongeage", a French word meaning discharge. It refers to the industrial use of the molecule as a bleaching agent to remove colour from textiles (e.g. to create a white design on a dyed background) and other materials (e.g. to clear up discoloured sugar juice squeezed from plants). Due to its bleaching ability, sodium formaldehyde sulfoxylate is also found in commercial products for removing or correcting hair dye colour.

The patterned fabric at the bottom was created using rongalite (Source)

In the early 20th century, sodium formaldehyde sulfoxylate was identified as an antidote for acute mercury poisoning (e.g. a one time ingestion of a bunch of corrosive mercuric chloride). An intense treatment regimen from 1942 called for (1) immediately swallowing a bunch of it, (2) injecting it into a vein, (3) irrigating the colon with it twice daily, (4) swallowing and injecting a bunch more of it twice a day for two days, and (5) rising the mouth out with it. Even with this effort, the antidote was eventually determined to only be effective if administered immediately (i.e. within minutes) after mercury exposure, which isn't at all practical in most poisoning cases. Presumably it worked by adding electrons to mercury cations in the stomach and intestines, reducing them to the less harmful elemental form of the metal.

In the 1930s, sodium formaldehyde sulfoxylate was demonstrated to be capable of curing mice intentionally infected with disease-causing bacteria. It's unstable in water or aqueous solutions (like, say, body fluids), decomposing to produce formaldehyde and a bunch of sulfur compounds (sodium sulfite, sodium sulfide, sulfur dioxide, and hydrogen sulfide). Formaldehyde is really good at killing things, so at first glance it appears to be responsible for the curative effect. However, sodium formaldehyde sulfoxylate only ended up working against one of the thirty two types of bacteria tested, so there was probably something else going on.

Sodium formaldehyde sulfoxylate has also seen use as a photographic developer and as a relatively environmentally friendly reagent for adding sulfur+oxygen groups to various organic molecules and doing other useful chemical synthesis stuff.


References

Draelos ZD. 2004. Hair care: An illustrated dermatologic handbook. CRC Press.

Kotha S, Khedkar P. 2012. Rongalite: A useful green reagent in organic synthesis. Chemical Reviews 112(3):1650-1680.

Rosenthal SM. 1937. Studies in chemotherapy: II. Chemotherapy of experimental pneumococcus infections. Public Health Reports 52(2):48-53. [First page]

Swensson A, Ulfvarson U. 1967. Experiments with different antidotes in acute poisoning by different mercury compounds. Effects on survival and on distribution and excretion of mercury. Internationales Archiv für Gewerbepathologie und Gewerbehygiene 24(1):12-50.

Wolpaw R, Alpers N. 1942. The treatment of acute mercury poisoning with sodium formaldehyde sulfoxylate with a review of twenty cases. The Journal of Laboratory and Clinical Medicine 27(11):1387-1395.

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