Alfatoxins

[kidamnesiac]

Bumbing through the literature on fungal metabolites, I came across this cute molecule, Alfatoxin:

That substitution on the ring is beautiful.
Apparently there was some scare in the EU about contamination of foods with alfatoxin and worries about it's carcinogenic potential. Otherwise, in a cursory glance, I didn't see anything related to psychoactivity. Obviously, it's not aminated. But it's got electron density in a lot of the right places.
Thoughts, comments, possibilities for amination/derivitization?

 

[kidamnesiac]

Actually, I'm not sure that picture accurately depicts the proper substitution pattern on the phenyl ring. All of the other alfatoxins I have seen have the methoxy group at what us PEA-types would call the 6 position, which is still very interesting.

 

[vecktor]

Afla not alfa
leave well alone it is a very potent hapatotoxin and a potent carcinogen. its too big to get into the cns thankfully. one aflatoxin I forget which was weaponised by Iraq in the mid 80's
almost all substituted variations retain the activity. it is just one of the many extremely dangerous metabolites produced by Aspergillis fumigatus. some varieties of aspergilis produce ergine and clavine alkaloids too.
I believe the hepatotoxicity comes from the two linked furans, and this is a general rule, avoid benzofurans with substitutions in the furan, the liver can open the furan ring and it does serious damage

 

[Crimethink]

Aspergillus FLAvus is from whence its namesake is had. In case you didn't have occasion to run accross it here's Aflatoxin B1-8,9-epoxide C17H12O7 MW 328.28 CAS 42583-46-0 Which is the active metabolite of Aflatoxin B1, the first picture posted.

 

[kidamnesiac]

Whoops, should really pay more attention to detail...
The first structure is actually wrong as far as I can tell, I've yet to see another aflatoxin with the methoxy in the "5" position

 

[vecktor]

Whoops, should really pay more attention to detail...
The first structure is actually wrong as far as I can tell, I've yet to see another aflatoxin with the methoxy in the "5" position

I am not certain but I think there are scores of different aflatoxins, the b one is the common one. so possibly the structure is one of the other members of the group.