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The Large and Nifty Not-quite-advanced Drug Chemistry, Pharmacology and More Thread

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Sulfuric Acid Question

Why exactly is sulfuric acid most often used for acid catalysis?
 
But the pKa of HCl is -7 and the pKa of H2SO4 is -3, so are you saying that sulfuric acid is cheaper?
 
aparenz said:
Why exactly is sulfuric acid most often used for acid catalysis?
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Because it will protonate an alcohol group but it won't react with tertiary alcohols to form alkyl halides through an SN1 reaction.
 
Anyone have any information about 4-phenyl-2-pyrrolidone? By what I can tell it should be a prodrug to phenibut, possibly more potent?

I found a cas number and MSDS for it, but not much else...

http://www.chemcas.com/msds/cas/msds120/1198-97-6.asp

this says it produces analgesia and "changes in motor function" in mammals... I wonder if it would be worhtwhile in any way? Have any human bioassays been made ever?
 
I've been having some trouble understanding what causes conditions in a reaction to be acidic or basic.

For instance in the formation of a nitronium ion, nitric acid and sulfuric acid are reacted to form a nitronium ion by loss of water. So this happens because the nitric acid is protonated forming water which is an effective leaving group. What exactly gives the nitric acid the urge to become more acidic? Is it because sulfuric acid is more acidic and willing to protonate it?

Any help with an explanation on acidic and basic conditions in organic chemistry would be greatly appreciated because I've been having trouble incorporating it into mechanisms as needed.
 
aparenz said:
Is it because sulfuric acid is more acidic and willing to protonate it?
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"Willing" invites metaphoric confusion. Better to consider the resonance forms of bisulfate ion:

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This anion is more stable than the nitrate anion.
 
I know my library has an up to date (2007) March's, and Carey and Sundberg's Advanced from (1990)
thanks for the advice and the link
 
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I'm looking to know more into the mechanism of actions of different drugs, I've seen the Color Atlas of Pharmacology recommended earlier in the thread, is this a good starting point? Any other books to recommend to an amateur?

Reason to ask is : I've been dabbling in RCs for the past few years, and would like to know more about how they work so as to evaluate the dangers of those I'm interested in and better understand the journal articles to make more informed decisions as to what I choose to experiment with (eg to be more aware of the dangers of the drugs in themselves and also possible interactions with other medications I take... read to many horror stories about this).
 
Any recommendations for advanced organic chemistry books? I've taken two semester of organic and my university doesn't offer higher level classes.
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Wileys Intermediate Organic Chemistry, 2nd Edition

It's weird that your university doesn't have more than 2 organic courses, most offer some kind of stereochemistry heavy upper level ochem course too
 
My university only has a few departments that even have a graduate program, and I believe only 2 departments with a doctorate program. Its a good university, but small (15000 including grad students) and up an coming. The chem program isn't very good. I should have thought about this before I went, but oh well...
 
Just got chemoffice08, having fun playing around with it, seems like a great suite so far. Hopefully I'll will advance my mind on chemistry greatly
 
forgive me for the stupid question, but:

isn't cynanide toxic? what would the effects of 2c-cn be in terms of cynanide's ability to inhibit oxygen transport by blood cells (the way it poisons you, i believe)? would this be negated by its being bound in the phenethylamine?

enlighten me, someone who knows more.
 
Cyanide, per definition of the nomenclature, is an ion, i.e. CN-. That is the toxic species that inhibits the respiratory chain and, by the way, which is as toxic agents in the US' gas chambers nowadays (and in German gas chambers during 1933-45, too). :\

The CN in 2C-CN is bound covalently and for this reason should be called "nitrile", not "cyanide" (this naming is often confused).

The difference is that the former one is an independend molecule, able to reach its target (...CYPs of the respiratory chain), while the latter will stick to the ring until it gets metabolized. I have no idea at the moment what the metabolism for 2C-CN in particular is (if it was ever studied), but usual pathways go e.g.
-CN + water to -CONH2 (by nitrile hydratase)
...followed by -CONH2 + water to -COOH + NH3(by amidase)
-CN + water to -COOH & NH3 (by nitrilase)
-CN + water to -CH=N-OH (by aldoxime dehydratases)​
None of these liberates cyanide at any stage.
There may be exceptions, but in general are aromatic nitriles not extraordinarily toxic.

Peace! - Murphy
 
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