phenibut chemistry and metabolism

[atara]

Looking at the structure of phenibut, it occurred to me that it should be rather prone to decarboxylation, by analogy with beta-keto carboxylic acids (at least, the way I heard it, an electron-withdrawing substituent on the beta position promotes decarboxylation). Phenyls are less electron-withdrawing than ketones, but it doesn't seem like too much of a stretch to me.

Where this gets interesting is that the decarboxylation leaves you with beta-methylphenethylamine, and there's been a decent amount of speculation as to whether that actually presents any activity. Is it possible that bMPEA is an active metabolite (in particular, could it be responsible for the dopaminergic effects)?

 

[Eliphaz]

Is it possible that bMPEA is an active metabolite (in particular, could it be responsible for the dopaminergic effects)?

Well done. That would explain why I get a paradoxical reaction verging on panic, whenever ingesting a small amount of phenibut at a time when the adrenals are far out of homeostasis.

 

[Phener]

would also explain why **from personal experience** transfering from baclofen to phenibut is not possible. Phenibut seems so much more heavy on the body. Due to the dose difference bMPEA would be manufactured in far higher quantities than baclofen, it would also not have a bit fat clorine sinking it's ship in to different receptors.

 

[MurphyClox]

1. If you like to know if the decarboxylation is possible chemically, well, then the answer would lead us to the immediate shutdown if this thread, as such a transformation falls clearly into the area of synthesis.

2. If you like to know if the decarboxylation is possible biochemically (read: by metabolism), then this can't be answered easily, as phenibut's metabolism was not published (...if it's known at all; this was quite surprising). Some comparison could be drawn from baclofen's metabolism, which is excreted 85% unchanged, and 15% deaminated. I don't see any immediate reason why this shouldn't apply to phenibut, too. So, the carboxyl-function stays untouched...


Peace! - Murphy

 

[seep]

The answer is no.

From Uniprot:

Decarboxylase

Enzyme that belongs to the lyase family and which catalyzes the spliting of CO(2) from the carboxylic group of amino acids, beta-keto acids and alpha-keto acids.

Notice the trend?

 

[negrogesic]

Who the fuck knows when their "adrenals are far out of homeostasis. " Do I smell Judaism?

Who is interested in such a round about way to obtain such dumb compound? Potent, stimulants that are highly are made by the 3 toothed 7th grade drop out in the mid-west. Evidently the Nazi cold-cook method (using RP, I, catalyst metal like Li and Ammonia, Liquefied )

 

[Limpet_Chicken]

Not to take this to synth discussion, but the red phosphorus (or hypophosphorus/phosphorus acid) and I2 (or HI) synthesis is a totally seperate reaction than the birch reduction.

It is the latter that is referred to as the nazi method.

 

[Eliphaz]

Who the fuck knows when their "adrenals are far out of homeostasis. " Do I smell Judaism?

Judaism, LMFAO thanks, I'll be sure to use that term myself! As for using it here, whether that is prematurely frank conclusion arising from a handle and a simple anecdote, or stimulant driven arrogant hypocrisy, no need to give a fuck.

A fact is I get idiosyncratic reaction from phenibut for the past two years, which would support the existence of active bMPEA as I tend to become overstimulated from a lot of stuff. On the idiosyncracy side, I also get panic & extreme hypertension off piracetam and tianeptine for instance. If I happen to know whether my adrenals are fine or not may / may not be worth mentioning depending on the reader, debating that is outside the scope of this discussion and thus irrelevant.

 

[seep]

Judaism, LMFAO thanks, I'll be sure to use that term myself! As for using it here, whether that is prematurely frank conclusion arising from a handle and a simple anecdote, or stimulant driven arrogant hypocrisy, no need to give a fuck.

It was a reference to non-classical adrenal hyperplasia.

 

[Eliphaz]

It was a reference to non-classical adrenal hyperplasia.

Didn't quite catch it, sorry for that one.

Anyhow - speaking of anecdotes, the only part for which I have qualifications regarding this, there was something wicked with phenibut metabolism even when my adrenals were relatively healthy. Minimum 4 hours for onset on empty stomach and full 24 hours or more duration, might imply intermediary active metabolite that takes long to process given impaired metabolic rate for a reason or another.