Methyl Valerate / Methyl pentanoate

[Reminisant B]

Noticed an anti-smoking product which contains the following

Methyl Valerate: 100 mgs - A mild sedative which relieves the irritability, excitability and anxiety related to nicotine withdrawal

Quinine: 15mgs - alleviates the craving associated with nicotine withdrawal

Camphor: 10mgs - helps to clear brochial passages, improve breathing and soothe the gastric system.

Oil Of Eucalyptus: 10 mgs - works as an expectorant to loosen up debris laden mucus and provide a productive cough to get rid of it. It also has a soothing effect on the gastric system.


Anyone know any info on this chemical, looks almost like a ghb type molecule?

 

[bigmac74]

Anyone know any info on this chemical, looks almost like a ghb type molecule?

"Validol" contains it in tablets of 60mg, though Sodium GHB requires doses of >1500mg, perhaps polarity is involved on the dosage? (Though non-ionized GHB looks fairly non-polar to me).

 

[Refluxer]

Non polar? You don't think the acid group and alcohol group introduces polarity?

 

[fasteddie]

Sorry to be an irritating smart ass, but...

gamma-hydroxy butryate is, properly speaking, an ion. All ions are polar as hell, relative to anything uncharged. As soon as the pH goes down enough to pop the proton back on the carboxylic acid end of it...bloop! It cyclizes to GBL. Most of it, anyway. It's an equilibrium.

I think there's some data on Erowid about valeric acid derivatives. They're, if memory serves, pretty inactive relative to the corresponding butyric acid compounds.

By the way, wouldn't it be pretty easy to determine the concentration of both GHB and GBL via acid base titration? GHB...titrate with 0.1 N HCl to a methyl orange endpoint, GBL...add known excess NaOH, titrate with 0.1 N HCl to a phenolpthalein endpoint.

 

[bigmac74]

Non polar? You don't think the acid group and alcohol group introduces polarity?

I always think polarity is kind of subjective...

Yes, the alcohol and carboxyl groups are polar, but because they are at opposite ends, don't they cancel each other out? Though you could argue if the GHB molecule was in a 'U' or 'V' shape (whilst undergoing free rotation), the non-polar alkyl chain against the alcohol AND carboxyl groups would mean a dipole is formed. (see pic).

Though, because GHB is hygroscopic, I guess I'm wrong (polarity annoys me, especially when concerning with cell walls etc.).

Sorry to be an irritating smart ass, but...

gamma-hydroxy butryate is, properly speaking, an ion. All ions are polar as hell, relative to anything uncharged. As soon as the pH goes down enough to pop the proton back on the carboxylic acid end of it...bloop! It cyclizes to GBL. Most of it, anyway. It's an equilibrium.

Yea, you're probably right, I wasn't considering stomach acid/body pH etc. at the time.
Irritating smart asses are welcome here IMO. :D

 

[hussness]

I think the situation is more complicated than that. Primary alcohols and carboxyl groups do not have equal polarity, in a scalar sense. Alcohols are far more polar than carboxyl groups. This is generally argued to be due to the resonance stabilization of the conjugate base of the carboxylic acid. As far as I know, the only physiological circumstance where an aliphatic carboxylic acid would be unionized would be in the stomach.
A second consideration, which you have alluded to, is the partial (or complete) cancellation of electrostatic polarity due to the polarity vector sums of certain conformations. However, the set of conformations is (I think) theoretically infinite. The set of energetically favorable conformations is still probably very large, but my guess is a large contributer would be one in which the hydroxyl hydrogen forms an H-bond with the carbonyl oxygen.
Valeric acid, which is probably produced in vivo by this molecule, is thought by some to be one of the pharmacologically active components of valerian. I'm fairly skeptical about this though...
You probably wouldn't want to consume large amounts of this chemical due to methanol being a product of ester hydrolysis.
A final thought that I had is that smaller molecules, like GHB, have significantly more kinetic energy than larger molecules, and this is thought to aid in passive diffusion.