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2-(2-Isopropyl-phenyl)-ethylamine

Reminisant B

Reminisant B

Greenlighter
Joined
Nov 3, 2005
Messages
401
Does anyone have any information on this chemical?

Looks like it should block maoi metabolism but I have no information on it.
 

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I meant it looks like it would get past MAOI and be active.

Unfortunately I have no info on it though so is just a guess.
 
What do you base your thinking on it escaping MAO destruction?
(I'm not arguing - i've no idea what SAR there is for escaping MAO, and would love to know!)
 
an unverified info i got:
as mentioned in pihkal tmpea (2,4,5-trimethoxy-pea) is not orally active at 300mg. but 2,4,6-trimethoxy-pea is said to be active at 150mg.

so the methoxy at the 6 (in conjunction with the 2-methoxy group) may prevent mao from doing its job.
 
It's the 3,4-dimethoxy (or methylenedioxy) that allows MAO to act on it. The lack of adjacent methoxy groups prabably makes the 2,4,6-trimethoxy configuration more hardy & resistant (as does 3,4,5 sunstitution). 2,4,5 doesn't have the steric hinderance needed for it to escape metabolism
 
MattPsy said:
What do you base your thinking on it escaping MAO destruction?
(I'm not arguing - i've no idea what SAR there is for escaping MAO, and would love to know!)
Click to expand...

Unfortunately just by me looking at the compound, I definately dont know enough to back this up in anyway, I have no data either. 8(

I was just trying to think if one could make an alkyl chaing stick out from the 6 position and block maoi degredation in a similar way to how the alpha-methyl in amphetamine blocks the compound from being degraded. ?? Kind of like having a long chain that would reach out and block it.
 
It won't stop metabolism on the ethylamine chain, which is where it takes place. The alpha-Me group stops it, but a group on the ring won't help the chain.
 
^ Not entirely true as 4-alkylthio groups give some degree of MAO inhibition, well to a clinically significant degree. All the 2C-x compounds that are active orally have some degree of protection considering the parent molecule, phenethylamine, has a very short half life
 
A 2-Methyl makes DMT active for some reason,could be the same effect here!?
 
morninggloryseed said:
It won't stop metabolism on the ethylamine chain, which is where it takes place. The alpha-Me group stops it, but a group on the ring won't help the chain.
Click to expand...

Sure it will, it the molecule can't fit into the pocket, it won't be able to be metabolized, like F&B pointed out about the 2c family.

to the OP: not to be picky, but methinks you misunderstand the term MAOI. An MAOI is an inhibitor of monoamine oxidase, an enzyme. it's generally a small molecule. the compound you are showing, that you think may inhibit monoamine oxidase, would be an maoi, not an maoi inhibitor. make sense? :)

as to the original question, I wouldn't see why that substitution would be particularly favorable to being an MAOI, although the point about the 6 position in the 2,4, X substitution is well worth considering.
 
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