cyanomethylene amines

[EN21]

I just thought about a dicyanomethylene tryptamine. It looks a little bit like a cousin of DALT with some exceptions:
A nitrogen at the end of the chain.
A triple bond instead of a double bond.
A straight chain instead of an angulated.
And last but not least a nitrogen atom that is not basic any more.

Can this compound be active?
What would you speculate about its toxicity and possible metabolites?
Has anybody ever seen a cyanomethylene group in any pharm?

 

[johanneschimpo]

isn't that called a nitrile?

 

[EN21]

Nomenclature is not really clear. IUPAC would call it multiplicative nomenclature, but right, you could also call it a diacetonitrilo-tryptamine.

 

[hussness]

I was wondering whether enteral administration of such a compound would alter the nitrile group functionality or not. Would there be a possibility of double-protonation by HCl to form an amine?

 

[Ylide]

I highly doubt that those nitriles are going to hydrolyze under biological conditions, unless they are the substrate of or acted upon by some enzyme. Nitriles tend to be relatively stable, and in any case converting them to amines would require a strong reducing environment. Your body would more likely be apt to convert them to amides and then to carboxylic acids through acidic or basic catalyzed hydrolysis. But I doubt that's going to happen relatively quickly without the help of some metabolic protein.

 

[fastandbulbous]

^ Still, because of the different charge separation going on with the nitrile groups compared with alkyl/alkenyl groups, it is in no way certain that they'd even be active. If I remember correctly, the nitrogen of the side chain forms hydrogen bonds with an acidic amino acid group (aspartate, glutamate etc) where the competition from the lone pairs of the nitrile might completely fuck up the binding of the whole compound to the 5HT2a receptor - it doesn't take much to bugger up the binding of that part of the molecule, as evidenced by the lack of activity of a whole load of different groupd attached to the sidechain nitrogen

 

[EN21]

it doesn't take much to bugger up the binding of that part of the molecule, as evidenced by the lack of activity of a whole load of different groupd attached to the sidechain nitrogen

f&b: Do you have some references for those inactive tryptamines with the diferent sidechains?
I always thought that only the size of the chain is crucial.
Bulkier chains than dipropyl- , diisopropyl- or diallyl are largely inactive, but most of the somewhat smaller residues i hypothesized to be active.
BTW: I am convinced that the dicyclopropyl-tryptamine is active, too.