Alipt

[kidamnesiac]

I'm always weary of the potential for alkylating my important parts with compounds able to cross the BBB.

 

[dorothyperkins]

What, with the allyl? Never thought of that, is it likely to be epoxidised or something? Seems unlikely to fall off as the cation. Any pharms contain N or O-allyl substituents?

 

[vecktor]

What, with the allyl? Never thought of that, is it likely to be epoxidised or something? Seems unlikely to fall off as the cation. Any pharms contain N or O-allyl substituents?

quite a few, Nalorphine for example. I don't think allyls alkylate though they do rearrange to propenyl and subsequently fall off.

the propargyl (N-propynyl moety triple bond in place of the allyl double bond) is an alkylator as in selegiline which is why selegiline is a very effective MAOI.

v

 

[dorothyperkins]

the propargyl (N-propynyl moety triple bond in place of the allyl double bond) is an alkylator as in selegiline which is why selegiline is a very effective MAOI.

Does it alkylate itself to the active site of the enzyme or something!? Wonder if the N-desmethyl analog would do the same to the dopamine transporter. Though it seems PROPYNYL doesn't irreversibly attach itself to the 5ht2a receptor, not into the active site at least!

 

[kidamnesiac]

perhaps allyls won't alkylate readily, just seems that if the terminal C got close to say, a cysteine S, one could imagine a very simple addition taking place.

i think selegiline attacks PLP in mao-B? lots of suicide inhibitors hit this guy and i know at least one MAO uses PLP