This Is MS Multiple Sclerosis Community: Knowledge & Support

Hey Dig, long time. What is your latest take on BG12? Is this really fumeric acid? All my Neuros seem to think its the Holy Grail but if we can just do it ourselves why would anyone sign on for a high dollar Med? Rituxan coming up hard and fast!
Lars

Hi Lars,
BG-12 and fumaric acid are two different, but related, molecules. BG-12 is dimethyl fumarate. It has the following structure...

It reacts with thiol groups, -SH, such as those found in glutathione and cysteine residues oxidizing them. Cells sense this oxidative stress and activate the transcription of cell protective genes for antioxidant enzymes.

In contrast, fumaric acid is a dicarboxylic acid where the -CH₃ groups are replaced with H.

It doesn't have the same chemical reactivity with thiols and won't activate the cell protectant genes that dimethyl fumarate activates.

One thing to know is that there are many molecules in nature that have similar functional groups as dimethyl fumarate which gives them similar reactivity with thiols. Here's a free review paper which discusses them.

Nrf2 as a master redox switch in turning on the cellular signaling involved in the induction of cytoprotective genes by some chemopreventive phytochemicals.
Planta Med. 2008 Oct;74(13):1526-39. Epub 2008 Oct 20.

NHE

NHE,
Wow, impressive! I guess my only question as a layman now is..........are they close enough for fumeric acid to be of benefit? I know this is a loaded question but what the hell.
Thanks,
L

They are probably trying to keep it a little bit of a secret/confusion, but on the Australian patent application for BG12, they say its "One of dimethyl fumarate or monomethyl fumarate"
http://www.ipaustralia.com.au/applicant/biogen-idec-ma-inc/patents/AU2010242064/

monomethyl fumarate

(I have no idea what difference the above structural change makes, I just posted it to look intelligent...)

Cure,
I think it worked. Told my girlfriend you were a genius! Seriously, that is an interesting twist in this little mystery. I think I'm on my way to the store to try some! Probably should have posted this on the BG12 page. It's been a while. Forgot my manners.
Lars

Hey Lars You stated "I think I'm on my way to the store to try some!" Let us know where you find it and how it worked out.

I think it's unlikely that you will find monomethyl fumarate at a supplement store. A search at vitacost.com and iherb.com only yielded supplements containing fumarate. This is not the ester form of the molecule, but the conjugate base of fumaric acid. Salts of carboxylic acids, such as fumarate, are given a similar nomenclature as the esters, i.e., both names will end with the -ate. This similarity in the name can be confusing.

NHE

I know there are/were people getting "Fumeric acid" compounded from their chemist, anyone know what these people were getting?

http://www.sigmaaldrich.com/catalog/pro ... &region=US

This is an interesting site. They sell everything for research purposes. Not sure the average Joe could buy it. They list the chemical structure differently for Diamethyl, Monoethyl and Fumeric acid. More confused than ever!
All three are available for purchase!
Lars