![[dr. bob]](/dr-bob-sm.gif)
Dr. Bob is Robert Hsiung, MD,
bob@dr-bob.orgShown: posts 1 to 9 of 9. This is the beginning of the thread.
Posted by linkadge on June 2, 2004, at 19:22:46
Does anyone know the difference between the two ??
Linkadge
Posted by skeptic on June 6, 2004, at 21:19:04
In reply to diference between phenylaline and phenylethylamine, posted by linkadge on June 2, 2004, at 19:22:46
I'm not familiar with phenylalanine, but I have read that phenylethylamine (also referred to as PEA) likely plays a significant role in the attachment process (more specifically, the 'high' produced by falling in love) and I believe that its production is also increased during exercise, linking it to at least some of the antidepressant effect of exercise.
> Does anyone know the difference between the two ??
>
>
> Linkadge
Posted by Teknohead on June 8, 2004, at 9:29:42
In reply to diference between phenylaline and phenylethylamine, posted by linkadge on June 2, 2004, at 19:22:46
> Does anyone know the difference between the two ??
>
>
> Linkadge
If by phenylaline you mean L-phenylalanine, then it is an essential amino acid. It is a precursor for L-tyrosin, another amino, which in turn is a precursor for adrenalin, noradrenalin and dopamine. I think it's also a precursor for phenylethylamine but I don't know by which process.Although Skeptic seems correct in the connection of phenylethylamine and the 'love' feeling (chocolate is full of it), and this is a generaly accepted fact, there is one source I've found which disagrees. In Alexandra Shulgin's book PIHKAL (PHENETHYLAMINES I HAVE KNOWN AND LOVED), he concludes that it has no noticable effect in man, even via i.v. administration. Have a read, it's an imazing book. You'll probably have to order a copy though.
Posted by Larry Hoover on June 12, 2004, at 11:45:51
In reply to diference between phenylaline and phenylethylamine, posted by linkadge on June 2, 2004, at 19:22:46
> Does anyone know the difference between the two ??
>
>
> LinkadgeYes.
Oh, you want to know what the difference is, too?
PEA is decarboxylated phenylalanine. The carboxyl group (COOH) is what confers the acid aspect of the latter being an amino acid. Enzymes called decarboxylases remove the carboxyl group.
So, phenylalanine minus carboxyl is PEA.
Lar
Posted by chemist on June 19, 2004, at 3:19:59
In reply to Re: diference between phenylaline and phenylethylamine » linkadge, posted by Larry Hoover on June 12, 2004, at 11:45:51
> > Does anyone know the difference between the two ??
> >
> >
> > Linkadge
>
> Yes.
>
> Oh, you want to know what the difference is, too?
>
> PEA is decarboxylated phenylalanine. The carboxyl group (COOH) is what confers the acid aspect of the latter being an amino acid. Enzymes called decarboxylases remove the carboxyl group.
>
> So, phenylalanine minus carboxyl is PEA.
>
> Lar
>
>
hello there, chemist here....actually, phenethylamine does not contain a carboxylate group: what you are looking at at is a phenyl group to which there is an ethyl linkage to a primary amine. phenylalanine, which is what i presume the poster was referring to, exists as the zwitterionic form and does include a carboxylate (in addition to a protonated amine). of course, if you do decarboxolate phenylalanine, you get phenethylamine, but as the salt at circuneutral pH. and you still carry a formal charge, so not the free base.
all the best, chemist
Posted by Larry Hoover on June 19, 2004, at 7:43:49
In reply to Re: diference between phenylaline and phenylethylamine » Larry Hoover, posted by chemist on June 19, 2004, at 3:19:59
> > > Does anyone know the difference between the two ??
> > >
> > >
> > > Linkadge
> >
> > Yes.
> >
> > Oh, you want to know what the difference is, too?
> >
> > PEA is decarboxylated phenylalanine. The carboxyl group (COOH) is what confers the acid aspect of the latter being an amino acid. Enzymes called decarboxylases remove the carboxyl group.
> >
> > So, phenylalanine minus carboxyl is PEA.
> >
> > Lar
> >
> >
> hello there, chemist here....actually, phenethylamine does not contain a carboxylate group: what you are looking at at is a phenyl group to which there is an ethyl linkage to a primary amine. phenylalanine, which is what i presume the poster was referring to, exists as the zwitterionic form and does include a carboxylate (in addition to a protonated amine). of course, if you do decarboxolate phenylalanine, you get phenethylamine, but as the salt at circuneutral pH. and you still carry a formal charge, so not the free base.
> all the best, chemistMethinks you mighta misread what I said. Or did you just want to work the word zwitterionic into a sentence? ;-)
I try to stay away from concepts like zwitterions 'cause I'm not sure they increase comprehension. Just a style thing.
Lar
Posted by chemist on June 19, 2004, at 14:41:18
In reply to Re: diference between phenylaline and phenylethylamine » chemist, posted by Larry Hoover on June 19, 2004, at 7:43:49
> > > > Does anyone know the difference between the two ??
> > > >
> > > >
> > > > Linkadge
> > >
> > > Yes.
> > >
> > > Oh, you want to know what the difference is, too?
> > >
> > > PEA is decarboxylated phenylalanine. The carboxyl group (COOH) is what confers the acid aspect of the latter being an amino acid. Enzymes called decarboxylases remove the carboxyl group.
> > >
> > > So, phenylalanine minus carboxyl is PEA.
> > >
> > > Lar
> > >
> > >
> > hello there, chemist here....actually, phenethylamine does not contain a carboxylate group: what you are looking at at is a phenyl group to which there is an ethyl linkage to a primary amine. phenylalanine, which is what i presume the poster was referring to, exists as the zwitterionic form and does include a carboxylate (in addition to a protonated amine). of course, if you do decarboxolate phenylalanine, you get phenethylamine, but as the salt at circuneutral pH. and you still carry a formal charge, so not the free base.
> > all the best, chemist
>
> Methinks you mighta misread what I said. Or did you just want to work the word zwitterionic into a sentence? ;-)
>
> I try to stay away from concepts like zwitterions 'cause I'm not sure they increase comprehension. Just a style thing.
>
> Lar
>
no, just wondering where that extra proton you need to saturate the alpha carbon would come from :)......all the best, chemist
Posted by Larry Hoover on June 21, 2004, at 10:23:59
In reply to Re: diference between phenylaline and phenylethylamine » Larry Hoover, posted by chemist on June 19, 2004, at 14:41:18
> no, just wondering where that extra proton you need to saturate the alpha carbon would come from :)......all the best, chemist
I studied enzyme kinetics, but it didn't much touch on stoichiometry....do carboxylases require protonation of the carboxyl(ate) moiety? Or are we simply exhibiting differing styles or expression?
I tend to simplify for comprehension, then add detail/conditions later, as needed.
Lar
Posted by chemist on June 21, 2004, at 11:15:55
In reply to Re: diference between phenylaline and phenylethylamine » chemist, posted by Larry Hoover on June 21, 2004, at 10:23:59
> > no, just wondering where that extra proton you need to saturate the alpha carbon would come from :)......all the best, chemist
>
> I studied enzyme kinetics, but it didn't much touch on stoichiometry....do carboxylases require protonation of the carboxyl(ate) moiety? Or are we simply exhibiting differing styles or expression?
>
> I tend to simplify for comprehension, then add detail/conditions later, as needed.
>
> Lar
>
i think our styles are just different, that's all...plus i was giving you a hard time about where the proton comes from, but if you decarboxylate at the alpha carbon, you do need to find a proton somewhere to saturate the carbon...but it depends on conditions, as the pKa of the proton in the COOH is about 2.2, and the pKa of the amino is 9.4 (i'm stealing from voet and voet). so, if the goal is to make a homomeric peptide, then all you're looking at are elimination reactions, and you never have to deal with actually removing the COO- from the alpha carbon. but if you want to get phenethylamine, you have to dump the COOH and replace with a proton (or, more reasonably, you have a cation salt of phenylalanine) and you can do this 2 ways: heat it up, and the COOH proton jumps to the alpa carbon and CO_{2} is lost; or, get involved with acetyl coenzyme A, thiamine, and pyruvate dehydrogenase.....more at ya later, chemist
This is the end of the thread.
Psycho-Babble Alternative | Extras | FAQ
Dr. Bob is Robert Hsiung, MD,
bob@dr-bob.org
Script revised: February 4, 2008
URL: http://www.dr-bob.org/cgi-bin/pb/mget.pl
Copyright 2006-17 Robert Hsiung.
Owned and operated by Dr. Bob LLC and not the University of Chicago.