alanine

bio · Working Bee

Showing my ignorance here, but after a little research I am unable to determine the difference between Beta alanine and DL alanine. Yes I know DL is the mixed isomer etc.

Was able to find that a kilo of the 98% B is $34 and 98% DL is $58.

Maybe we should start an Akobori thread! What do you think Organikum?

Guest · Fri Feb 18, 2005 8:28 am

Good idea, I am just so very busy these days.
Hope that I will have more time for research at hand in about two weeks again.

/ORG

PS: The MERCK tell me that beta-alanine has the amino-group on the end of the chain, whilst alanine has it in the middle.:

beta alanine: NH2CH2CH2COOH

alanine: CH3CH(NH2)COOH

icecool · Insistent Chemist

SWIM has got 250g of analine standing around, but doesn't know what to do with it he has got is a couple of years now he misread and thought he took aniline with him but it was a bottle of alanine...

IndoleAmine · Dreamreader Deluxe

ANALine?

(but I'm curious too..)

i_a

Lep.CON · Mon Mar 28, 2005 6:51 am

the discussion is actually going on over at wetdreams right now you can make ppa using the synth posted there and then continue with an hi reduction to amphetamine or use bandil's shake and bake recipe for ice
https://www.wetdreams.ws/forum/topic.asp?TOPIC_ID=1716&whichpage=4

Bumblebee · Mon Mar 28, 2005 8:03 am

I had some experience with the Akabori/Momotani condensation of l-alanine with benzaldehyde.
the reaction isn´t that ease it seems to bee...
l-alanine is found widely for medical use. Old men take a teaspoon of it when they have something like "prostata glands" (sorry don´t know the right spelling for this... has something to do with mens midlife problems you know??)
benzaldehyde is no Problem too....
the alanine should be ground to a fine powder and it should be added slowly bit by bit.... but is always problematic to dissolve the whole alanine...
The magnetstirrer is sticked with a white polymer-like reaction product wich forms in the reaction container.
i refluxed for at least 10 hours... CO2 production didn´t stop...
The deep red tarry reaction product was solved in toluene and extracted with dil.HCL 3 times.
The HCL extract was evaporated to third of its former level, and made strongly alkaline with NaOH.
the freebase that floats on top was extracted with toluene or chloroform and gassed or titrated with HCL to get the salt.
The yield was poor anyway, and i decided that it isn´t worth the effort.
if you got better results let me know.
i decided to try the P2nP way of dreamin´
BB

Guest · Mon Mar 28, 2005 9:30 am

ORG,

If you have any problems activating your username, just pm us,
And we'll sort it out,

syn

IndoleAmine · Dreamreader Deluxe

Bumblebee: can you be so kind and give us a few more experimental details? Like time, temp., amounts of reagents used, solvent etc.?

Also, where did you get the procedure from? Did you follow some example, or did you just try the rxn all by yourself?

i_a

Bumblebee · Tue Mar 29, 2005 12:50 am

The originally Procedure was taken from Chem. Abs. Volume 47, column3347.
They did the Akabori with N-methyl-d,l-alanine to yield a mixture of d,l-Pseudoephedrine and d,l-ephedrine.
I substituted food grade l-alanine for the N-methyl-d,l-alanine, to yield PPA.
100g Benzaldehyde was placed in an flask and heated on an oil bath to 140-160°C. as the Benzaldehyde reached the temerature i started adding 40g l-alanine. the magnet stirrer was set to "high" to achive a heavy stirring.
after one hour the addition of l-alanine was complete, an i began refluxing for 4 hours.
while adding the benzaldehyde became first yellow then orange and later deep red to brown in colour.
the mixture was cooled and mixed with 300ml of toluene, and filtered.
something like unreacted alanine (a white clumpy mass) was filtered off.
the PPA was extracted by shaking this solution with 300ml of 10% HCl.
the dil. hydrochloric acid was boiled down to a volume of 50 -100 ml and cooled to room temperature. A little bit of activated carbon was added to decolorize the solution.
the solution was made alkaline with lye (don´t know anymore how much i used) until it was strongly alkaline to litmus paper.
the PPA Freebase was extrcted three times with toluene and finally bubbled with dry HCl-gas to get PPA Hydrochloride.
i got never more then 5-8 grams PPA-HCl out of it.
I think i did something wrong while Extraction. after shaking with HCl there were 2 layers the toluene layer above and the aqueous layer at the bottom, but there was always a brown mess at the bottom that seemed to have the same or higher density than water, so it sank to ground.
let me know what your experiences are if you try to do this reaction.
BB

IndoleAmine · Dreamreader Deluxe

"Chem. Abs. Volume 47, column3347" - do you have that paper by coincidence?
(I just requested it in the "wanted articles" thread BTW)

i_a

Astrum · Tue Mar 29, 2005 9:20 am

You don't want to use B alanine for sure if you're doing the akabori-momotani reaction. You need an alpha amino acid for it to work.

Bumblebee - I think adding more l-alanine would improve yields. Did you use any solvents or simply heated benzaldehyde and added l-alanine?

I'll run a few experiments when I get the time.

Bumblebee · Tue Mar 29, 2005 7:31 pm

-Astrum: I tried Adding more l-alanine, but the mix got too sticky to stir anymore since more crap precipitated out (and more l-alanine didnt dissolve). I tried to increase the amount of l-alanine to 60 g without increasing the yield much. I think i gave up a bit to early because the use of a solvent would be a great idea.
l-alanine doesn´t dissolve in unpolar solvents but the solvent can act to keep the reaction temperature down and it will help to keep the reaction liquide. Smile

what abut dissolving the l-alanine in an adequate solvent before dripping it into the benzaldehyde that is thinned with solvent too?
toluene can hold the reaction temperature at 110°C. when there is CO2 evolving @ 110°C you can add more alanine and let the reaction go on until no more or less benzaldehyde smell is noticed.

I havn´t the paper anymore. Found it via internet one or two years ago. but it has got lost, so as the many many wonderful hivedreams too... Crying or Very sad

PPA is wonderful when you get a cold. it lets disappear the pains of the joints, and you get a clear head. It works.
I reduced it with HI/RP method that product works much better Wink

DrugPhreak · Working Bee

Do you think that Bumblebee would of got a better yield if they doubled the amount of toluene and HCl also?

isaw_elves · Fri Jun 03, 2005 6:21 am

The discussion is actually going on over at wetdreams right now you can make ppa using the synth posted there and then continue with an hi reduction to amphetamine or use bandil's shake and bake recipe for ice.

SWIc has been trying to get an answer on this on a variety of boards. The result of this akabori/decarbox is PPA, which is norpseudoephedrine if his memory doesn't fail him. Isn't there a difference between norephedrine and norpseudoephedrine?

Norpseudoephedrine can bee taken to the many forms of amphetamine but isn't norephedrine necessary to get "ice" (4-MAR)

Theoretically, is SWIy sure that the end product from this rxn, can bee taken to ice with KOCN? Can somebee/dreamer settle this?

Piece

hahas · Fri Jun 03, 2005 7:45 am

the result of the Akabori as CA abstracted is not PPA (which is not norpseudoephedrine), it is a mixture of crap which may include it. in none of the abstracts were yields given, but the impression left on me was that it was not a major product, and there were several other products listed. i found, then lost, a JCS citation where no PPA was isolated at all, just bis-crap. maybe its a matter of finding the right conditions. the abstracts did indicate that N-methylalanine did go in the desired direction and so-so yields could apparently be easily isolated.