oxidativeamination
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N-acetyl-phenylethylamine
have read on another forum that it is possible to achieve N-acetylation of PEA by titrating the freeamine to the acetate salt and then distilling this
salt. as it's vapourization point would lie around 200 degrees celcius.
after condensation aparently the acetyl would occupy the nitrogen,
displacing one of the hydrogens.
is there any truth to this reaction?
if so where does this hydrogen go? does it form H20 with an OH from the carboxyl group of the acetate?
[Edited on 13-4-2011 by oxidativeamination]
[Edited on 13-4-2011 by oxidativeamination]
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oxidativeamination
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so the reaction would be= (very basically put i dont have chemdraw)
R-NH2 + CH2CH3COOH=
R-NH2CH2CH3COOH + vapourization/condensation=
R-NH-CH2CH3CO + H2O
is this correct? it seems balanced however i dont know if the mechanism is real.
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ScienceSquirrel
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It is quite common for higher melting point amine salts to eliminate water to form the amide on heating.
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oxidativeamination
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so i'm confused here do you think that this amide would have improved bioavailability/ resistance to mono amine oxidase
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oxidativeamination
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so the substance obtained would be Phenylethylacetamide?
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mr.crow
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Keep trying, mr designer. This will form an amide, which has a very different charge and electron density from an amine. Amides are also very stable
so the acetyl group isn't going anywhere. Yes, N-phenylethylacetamide would be a name for the product
Double, double toil and trouble; Fire burn, and caldron bubble
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oxidativeamination
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so in saying that an amide has a very different electron density and charge from an amine, you are saying that it will become pharmacologically
inactive?
so convertion to the amide will effectively decrease or disable ability to cross the BBB?
one more question how does the amide-acetyl linkages stabilty affect its bioavailability?
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oxidativeamination
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my understanding was that amide groups are common in pharmacueticals....
Lysergic acid diethylamide
N-(4-hydroxyphenyl)acetamide (acetaminophen)
the sulfonamides
ETC.
how do you deduce that ability to cross BBB/bioavailability would be adversely affected??
do not take my post wrong, i do not intend to question your reasoning or knowledge only to understand your position
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ThatchemistKid
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would a bit of molecular modeling and docking studies using the protein and inhibitors in question (assuming a crystal structure exists) answer your
questions more easily?
[Edited on 14-4-2011 by ThatchemistKid]
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oxidativeamination
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well whatever the case i simply intend to synthesize the compound and do some rodent tests. (light rodent tests).
i'm not inhumane and do not intend to become so inclined. if the rodents tests yeild results i will perform allergy tests on myself, followed by
titrated raising of the dose (on different occasions to allow replenishment of neurotransmitters) untill around 150mgs in 10mg increments to determine
if the compound has possible activity. if 150mg even is inactive i will abandon tests.
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Nicodem
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Quote: Originally posted by oxidativeamination  | so in saying that an amide has a very different electron density and charge from an amine, you are saying that it will become pharmacologically
inactive?
so convertion to the amide will effectively decrease or disable ability to cross the BBB?
one more question how does the amide-acetyl linkages stabilty affect its bioavailability? |
Your lack of pharmacology knowledge is only surpassed by the lack of chemical knowledge. This is an honest warning: Please start reading the books and
articles first, or else you are going to hurt yourself.
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oxidativeamination
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| Quote: Originally posted by Nicodem | | Quote: Originally posted by oxidativeamination | so in saying that an amide has a very different electron density and charge from an amine, you are saying that it will become pharmacologically
inactive?
so convertion to the amide will effectively decrease or disable ability to cross the BBB?
one more question how does the amide-acetyl linkages stabilty affect its bioavailability? |
Your lack of pharmacology knowledge is only surpassed by the lack of chemical knowledge. This is an honest warning: Please start reading the books and
articles first, or else you are going to hurt yourself. |
would you care to elaborate on this warning?
i fail to see how linking an acetyl group to the nitrogen makes this compound so much more dangerous than straight PEA.
the material seemed on crystallization to be hygroscopic.
it drew moisture from the air to form a clear sludge.
thus the idea was abandoned.
i am interested to hear how this substance would've been so dangerous though??
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Sedit
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You fail to see it because of your lack of understanding in the area of pharmacokinetics. The amine has specific charge, metabolism, and docking into
the receptors meaning it could possibly be nothing what you would expect it to be. Are you sure the amide of Phenylethylamine does not inhibit any
important enzymes in your body, cause irreversible binding? If not I would highly not suggest undertaking such a project till its understood better.
Also look into Peptide bonding to better understand the question on how the amide forms.
Your amide will undergo hydrolysis to yeild the amine meaning I doubt you will find very much difference in pharmacokinetics between this and normal
PEA. I have heard of various Amino acids being acetylated to increase bioavalibility but I have not been able to test these claims. I have recently
considered testing this with L-DOPA but have not studied it enough to follow thru yet. I would feel better starting with acetylated Phenylalanine
before attempting it with Levo-DOPA.
Would taking the acetate salt of Phenylalanine and slowly heating it to drive of H2O form the amide? I would think so but all references I find
suggest using Acetic Anhydride to perform the reaction.
Knowledge is useless to useless people...
"I see a lot of patterns in our behavior as a nation that parallel a lot of other historical processes. The fall of Rome, the fall of Germany — the
fall of the ruling country, the people who think they can do whatever they want without anybody else's consent. I've seen this story
before."~Maynard James Keenan
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Sedit
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You can see here in these Pubchem results that the compound your looking for is in no way biologically active in the desired fashion.
http://pubchem.ncbi.nlm.nih.gov/assay/assay.cgi?aid=504651 shows that they are inactive as potentiators of the Dopaminic channels.
Here is the results of the active compounds tested in the experiment
Knowledge is useless to useless people...
"I see a lot of patterns in our behavior as a nation that parallel a lot of other historical processes. The fall of Rome, the fall of Germany — the
fall of the ruling country, the people who think they can do whatever they want without anybody else's consent. I've seen this story
before."~Maynard James Keenan
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