Re: Aspirin

[hanson]

"Dirk Bruere at NeoPax" <dirk....@gmail.com> wrote in
message news:6eceu2F...@mid.individual.net...
>
>> Dirk Bruere at NeoPax wrote:
>>> Why is acetyl salicylic acid such an all round wonder drug?
>>> Is it the acetyl, or the salicylate?
>>
> Mark Thorson wrote:
>> Salicylates are found in willow bark, the original
>> folk medicine for headache and inflammatory pain
>> relief. The breakthrough made at Bayer was forming
>> the acetic ester, which is much less irritating
>> to the stomach.
>
Dirk Bruere at NeoPax wrote:
> Yes, I know that.
> However, compounds such as methyl salicylate can readily
> pass through the skin without much of a problem. So is methyl
> salicylate as effective in preventing (say) heart attacks as aspirin?
>
hanson wrote:
There are still, after more than a century, hot debates going on
as to why Aspirin works the way it does, including its anti-platelet
aggregative activities, to "thin" blood and prevent stroke & heart
attack, & many other promised wonders that are attributed to it.
Some attribute it to Aspirin's equipotent inhibition of enzymes called
COX1 &2. (cyclooxygenase.) . --- Google for ---[ COX inhibitor ]---
and see whether/if you can find a story/theory that appeals to you.
>
Now, take a look at the chem. structure of the 2:
Aspirin: o- CH3COO-Ph-COOH
MethSali: o- HO-Ph-COO-CH3
The former is an aromatic ACID, the latter one an arom. alcohol.
Aspirin is an Aliphatic ester, the latter one an Aromatic ester,
& their mol weight is 180.16 vs 152.15, a 15% difference in size.
>
The physical structure of these 2 molecules is architecturally quite
different, which is important because one of the 2 forms (aspirin)
fits like a key into the receptors of COX enzyme... the other one
does not. --- This also accounts for the toxicity of the 2 molecules:
Aspirin has an LD50 of: 1500 mg/kg
MethSali has an LD50 range of : 4 - 880 mg/kg ... this latter one
being 2 to 400 times as toxic as is Aspirin. ... actually IIRC, some
sporty broad died last year, in 2007, from having smeared too
much MethSali on her ass to prevent muscle aches
>
MeSals official sanction & use is that of a "COUNTER-IRRITANT"
and very different from Aspirin's, the "ANTI-INFLAMMATORY".
Aspirin is not used in food because it has an bad bitter taste.
And not surprisingly, in food, only 0.04% MeSali is allowed.
>
The biological evolutionary raison d'etre for Salicylic acid (Aspirin)
is to regulate/increase plant temperature during blooming,--- but
the Ester, the Methyl Salicylate, is thought to be the plant's chemical
anti-herbivore defense.
>
Dirk Bruere at NeoPax wrote:
> And sticking to the acetyl theme, why does acetylating morphine
> make it so much more effective? Is the increased effectiveness
> related to the effectiveness of aspirin?
>
hanson worte:
One of the many ways of looking at the "Acetylating" influence is
that narcotics & pain killers do acts on nerve cells. The processes
of nerve numbing involves the choline transport/exchange which is
facilitated by the presence of CH3CO-/CH3COO- the Acetyl radials
/Acetate ions. So, one can expect that if the painkilling molecule
brings along is own "grease", the "Acetyl" supply, you'll be getting
better "action"... the more, the better.... ahahahaha....
>
Take care and don't do dangerous things by reaching into nooks
and crannies that are too "remote"... ahahaha.... ahahahanson