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hydrolosis of gaba

Vibrata_Lumine - 8-10-2005 at 12:14

Could one possibly turn the NH2 On the gaba molecule into the OH with a simple NaOH Hydrolosis and at the same time make the Sodium salt.

Eclectic - 8-10-2005 at 12:21

No.

hinz - 8-10-2005 at 12:54

If you reflux GABA with NaOH you'll get the sodium salt of gama-Amino butyric acid.

NH2-(CH2)3-COOH+XOH==>NH2-(CH2)3-COOX + H2O
X is an alkali atom

But I think if you reflux with HCl you should get 3-chlor butyric acid and ammonium chloride (excess of HCl).
because the amino group is an H+ aceptor (Lewis base). Then you reflux the 3-chlor butyric acid with an excess of NaOH (don't dissolve your glassware

and you'll get the OH group at the carboyl-end and the chlorine atom will get exchanged by an OH group.
Then you have your GHB alkali salt or I hope so.

[Edited on 8-10-2005 by hinz]

thank you

Vibrata_Lumine - 9-10-2005 at 10:42

do you not mean 4chlor butyric acid as the NH2 is in the 4 position. also does anyone have mp/bp data and hazmat for the chlor compound. Chemfionder ws bare

[Edited on 9-10-2005 by Vibrata_Lumine]

Nicodem - 9-10-2005 at 11:46

Quote:

But I think if you reflux [GABA] with HCl you should get 3-chlor butyric acid and ammonium chloride (excess of HCl).

That's nonsense.

Quote:

BUt can anybody tell me why the Nh2 Wont Hydrolize with a base.

I guess "Nh2" should be NaOH. Anyway, alkylamines do not hydrolyze. There is nothing to be hydrolyzed here. In theory you could make a nucleophylic substitution, but since the -NH2 (or -NH3+) is a many, many magnitudes worse leaving group than -OH (or -OH2+) this is not possible without special tricks. In organic synthesis there is a way to make the -NH2 group a good leaving group by ditosylating it making –N(Ts)2 from it (the "unpoolung" of the amine). This is electrophylic enough for reaction with many nucleophyles including the hydroxyde. But needless to say that applying this to GABA would be stupid. There is another "unpoolung" method applicable to your substrate. It goes by nitrosation and reaction with H2O (use the search engines).

hinz - 9-10-2005 at 13:01

Quote:

In theory you could make a nucleophylic substitution

But isn't the reaction with HCl a nucleophilic substitution where the Cl- ion act as a nucleophil?

If you make ethylamine you take ethyl bromide and add ammonia (@ 180°C and pressure to be exact) and you'll get ethyl amine and ammonium bromide (excess of ammonia) Here ammonia acts as a nucleophil. I assume that you can't take ethyl chloride because the C-Cl enthalpy is too great. (C-Br enthalphie is -285 KJ/mol,C-Cl enthalphy is -339 KJ/mol,C-N (single bound) enthalphy is -305 KJ/mol,C-OH enthalphy is -358 KJ/mol.)

If you would reflux an amine with HCl the N-Cl bond wold be energetic more stable compared with H2N-C (according to the enthalpies above) and the nature tends to let only the less energetic exist.

But I think you're right and the HCl would only form GABA hydrochloride at normal temperatures.

dr. nick - 12-8-2013 at 03:19

i know - this thread is very old and i'm rather OT, but anyways i just wanted to say thanks!

after reading this i guess i have the answer to my question and Gaba can be neutralized by NaOH (or maybe something more "palatable") without degrading or changing it since the best way of using Gaba to me is putting it under my tongue till it dissolves. Now the Gaba HCL i use is pretty harsh to my mucosae, i usually have a "burned mouth" most of the day after

I hope i can fix this with neutralizing and letting the liquid evaporate from the solution, that would be a real win.

thanks!

elementcollector1 - 12-8-2013 at 08:29

Make ABSOLUTELY SURE you use stoichiometry - no matter how bad you think Gaba HCl is, NaOH in your mouth is going to be a whole hell of a lot worse.
Better yet, just use something different?

bfesser - 12-8-2013 at 08:33

Not meaning to take this thread off topic—not that it's a great thread to begin with—but what does "OT" stand for?

Nicodem - 12-8-2013 at 08:48

Quote: Originally posted by bfesser

Not meaning to take this thread off topic—not that it's a great thread to begin with—but what does "OT" stand for?

OT stands for "off topic".

elementcollector1 - 12-8-2013 at 09:37

Quote: Originally posted by bfesser

Not meaning to take this thread off topic—not that it's a great thread to begin with—but what does "OT" stand for?

The irony of this is killing me. XD

Rich_Insane - 12-8-2013 at 12:50

What could be hydrolyzed is the diazonium salt of GABA... (Hint hint)

Finnnicus - 13-8-2013 at 04:44

Diazonium salts of alkanes are way to unstable to be practically used. Although, not sure if you'll get:
X^- R-N≡N⁺ --> R-X + N₂ or it will just hydrolyse, giving your product.

(Sorry just learnt this, so I was enthusiastic to write unneeded equations, and I'm probably wrong.)

PS: bfesser, I actually lol'd!

[Edited on 13-8-2013 by Finnnicus]

dr. nick - 17-8-2013 at 03:59

Hi, thanks for the reply!

Yes, i'll take care about the pH, just want to make it neutral, i wasn't sure if any degradation was to be taking place upon the Gaba. Maybe instead of NaOH i can use simple baking soda for that.

Why not something else: why not, give me a hint for something

Meanwhile: Gaba is legal, probably not too harmful and cheap and, sublingually used it works for me. Of course i'd rather have GHB, or something, but none of the needed substances are available to me ...

ps.: of course it's nothing especially enjoyable, just burns my tongue, calms me down and makes me sleep when i can't otherwise. kava for example is more enjoyable, but it takes time to prepare, generally is a real mess and isn't especially nice to my digestion

[Edited on 17-8-2013 by dr. nick]

Protium1 - 17-8-2013 at 04:41

If you desire to transform an NH2 group into an OH group, use the Sandemeyer reaction, for which you need NaNO2 (Sodium Nitrite). This is the Hint that was given above, but not fully explained. If you need further help, please research Sandemeyer reaction, diazonium salts, and always exercise caution.
Even a small effort in searching will give you the answer you seek.

dr. nick - 17-8-2013 at 12:19

hi there - no, sorry, i'm not trying to turn Gaba to Ghb - Sodium Nitrite isn't available to me. Just about to make Gaba.hcl less acidic for else it burns holes in my tongue

bfesser - 17-8-2013 at 15:20

dr. nick, we don't talk about drug use on this forum. If you want to discuss the chemistry and theoretical aspects, that's fine, but if you want to discuss getting high or other effects, please do so elsewhere.

dr. nick - 18-8-2013 at 03:01

FUUUUCK!!!

PLEASE: Read what i wrote!!

I'M NOT INTERESTED IN ILLICIT DRUG PRODUCTION HEEERE!!

Uff, ok, i hope that went through! Please, reacting in a deadlocked way to trigger words isn't good at all!

All i wanted to know was if GABA would degrade or react to something unwanted if treated with bases, and i did not even ask, i just wanted to say thanks for this thread where my question was already answered!

blogfast25 - 18-8-2013 at 04:13

Quote: Originally posted by bfesser

dr. nick, we don't talk about drug use on this forum.

Jaysus man, where did he 'talk about drug use'????

Huh? WHERE?

unionised - 18-8-2013 at 04:46

Quote: Originally posted by blogfast25

Quote: Originally posted by bfesser

dr. nick, we don't talk about drug use on this forum.

Jaysus man, where did he 'talk about drug use'????

Huh? WHERE?

Well, what sort of "use" did you think he meant here
"Meanwhile: Gaba is legal, probably not too harmful and cheap and, sublingually used it works for me."

blogfast25 - 18-8-2013 at 05:32

@unionised:

Did he discuss it or did he not? Next you'll be invoking the 'but he was looking at me funny, your Honour!' defence.

bfesser - 18-8-2013 at 05:54

Quote: Originally posted by dr. nick

Guys, settle down. It was just a reminder. <a href="http://en.wikipedia.org/wiki/Gamma-Hydroxybutyric_acid" target="_blank">4-Hydroxybutanoic acid (GHB)</a> <img src="../scipics/_wiki.png" />

[Edited on 18.8.13 by bfesser]

dr. nick - 29-8-2013 at 00:01

sorry for causing such a riot - my first post here was rather point- and useless.
i just get angry when once in a lifetime i really try not to do something i like to do and it's completely ignored that i try and am treated like i did what i didn't - i mean talking about drugs

Sorry for that.

Been reading a lot the last time and came across some studies about some very interesting health benefits of Butyrates (Sodium-, Mg- and Ca, especially) and was wondering if they might have any psychoactive action, too, but couldn't find anything.

Then there are some studies around about Gaba-Esters that sound promising, sorry i can't come up with any links or references at the time, i never thought i would want to.

One last question, please don't get it wrong: I have a friend - she's an apothecary or pharmacist and always is very upset when someone comes in here pharmacy and asks for Butyric acid, because she says it was absolutely clear what they want to do with it.
I always wonder if she's really right there, but i'm not someone who should argue with a pro, so i thought i just ask here: Is it really possible to get GHB or GBL from Butyric acid?
I always believed it wasn't ...

[Edited on 29-8-2013 by dr. nick]

Nicodem - 29-8-2013 at 09:09

Quote: Originally posted by dr. nick

I always wonder if she's really right there, but i'm not someone who should argue with a pro, so i thought i just ask here: Is it really possible to get GHB or GBL from Butyric acid?

No, not in any reasonable way.
I think your friend should be more competent for being a pharmacist. Where I live, the pharmacy students have nearly as much organic chemistry lessons and practice as chemistry students do. I find it difficult to believe that there are pharmacists around so clueless about organic synthesis.

dr. nick - 29-8-2013 at 10:01

she told me about their practices in synthesis at the university - can't have been very extensive, she said most of the syntheses they worked on didn't come out with the wanted result anyway...

But then again - i don't have the feeling she likes her job very much, looks like it's just a job to her, after all. I'd give an arm for having that possibility (was too dumb when i was younger), but well ... In the end working at a pharmacy she's just a sales woman, so maybe it came with the years. Probably people working in industry and science are another story.

[Edited on 29-8-2013 by dr. nick]