Know the enemy: More data on polysorbate 80.

[Prepuce]

Elf: Sorry to have brought on that exasperated sigh, but thanks for spelling it out. SWIP will report back on his findings.

He should have been familiar with the terminology, but with no tests in this class it's easy to allow memory of such data to slide away.

Os: SWIP has been harping on chromatography, he thinks, longer than you have. He has even made a few sad, abortive attempts. The more he learns the more complicated it all sounds, however. Suppose, for example, we found just the right mix of materials to seperate out polysorb. Everyone would start using it until they stick something new in the mix. Then it would all start again.

That's what we do now, but column chromatography looks like a fairly painstaking, complicated process. If it could really be done effectively with something like diatomaceous earth as a substrate, a florescent tube, and an eluent that wasn't any more exotic than what's found at the hardware store it would be great. Any suggestions along those lines will be gratefully accepted.

None of the research he did on polysorb 80 spoke at any length on CC, but SWIPs impression is that it is one of the more difficult substances to deal with. He might be wrong, but for now it didn't look like it was going to be an expedient means.

PP

[auntyjack]

what items do you need for column chromatography....i've got a column!!.....no, a real one....

[Rhodium]

See the chromatography section at my page.

[ADDkid]

The polysorbate is a long fucking carboxylic acid right?  Then if you put the P-fed powder in a sep. funnel (Don't extract with any solvent at all), and put either ether chloroform, toluene, or one time with each, and and add enough water to disolve the p-fed, then make the shit very strongly acid, like pH of 1 and below. Then all the acid(carboxylic acid) should go to the organic layer, well maybe not with chloroform, not sure. Isn't Carboxylic acids neutral in strong acid solutions, and since it contains amines, it is not in strong acid solutions to begin with. I also read that gak is put in the pills in both salt form and organic form to make it more difficult.

[Rhodium]

The polysorbate is a long fucking carboxylic acid right?

No, it is an ester of a C18 fatty acid (oleic acid) and a behemoth-sized alcohol. See

Post 501313

(Osmium: "Here's the chemical formula of Tween80: ...", Stimulants)

(the oleic acid is by mistake drawn as oleyl alcohol instead in that picture though. Imagine a carbonyl next to the oxygen bridge for completeness)

[Osmium]

Let me repeat it, removing that C18 chain by NaOH hydrolysis will not significantly alter the surfactant/gaak properties of the residual big ass molecule. You will still be fucked with that shit being present in your precursor extraction.

[ADDkid]

Even if it is an ester, any ester in water and proton source can be turned into a carboxylic acid right, does this including fatty acids?

[Rhodium]

Yes, but as Osmium says, it's still the alcohol which is the problem.

[ADDkid]

Rhodium have your looked at my Adderall extraction post? I understand the problem now, however I have notice a big drop in gak when I just extracted with water and added a mineral acid, to acheive a pH of 1 or below, then I put my N.P. Sovlent in the sep. funnel, to remove any gak.  I then took that layer and I let it dry on a pyrex dish to see what gak was present.  NO doubt, the acid addition in the first part, push a shit load of gak to the N.P. layer. I belive this to be mostly carboxylic acids. Since I mention the adderall extraction,

P.S. I might have been wrong to assume that the shit left in the foil (adderall) was salt. Is the HCL a less smokeable form then sulfate, because of dipole forces.  I am not quite sure why they use sulfate, is it better for aborbtion?

[embezzler]

since the links are ether then the gaak can be broken own by HI and heat correct? the gaak would seem to work also by depleting the HI for the desired reduction.

i just came across this in a txt book while revising.
as an example:

CH3CH2OCH(CH3)2 + HI ->(heat) ->CH3CH2I + HOCH(CH3)2

perhaps this is not the case for our gaak maybe a better bee can shed some light on this how likely is this mode of action? anyone got more info on the reaction mechanism or conditions (how much heat)?

[Rhodium]

since the links are ether then the gaak can be broken own by HI and heat correct? the gaak would seem to work also by depleting the HI for the desired reduction.

Yes, that is a real possibility. And as the product of that ether cleavage is ethylene glycol, it can in turn deplete even further equivalents of HI, see

Post 499279 (missing)

(Rhodium: "Pop Quiz: Why is ethylene glycol a bad idea?", Stimulants)

[embezzler]

deconstructing this isnt going to be enough is it? chromatography or distillation seem the only options now.

breaking this own could leave us with a bigger problem then we would have with it intact, the high relative mol weight difference(between this and ephedrine) would lead one to assume chromatography would be made easier than with dozens of unknown byproducts.

[elfspice]

I'm inclined to think that one should exploit the fact they're putting such goddamn large molecules to fuck with extraction, and use heat to superheat the ephedrine so that it can be crystallise on a cooling surface. Under vacuum would probably be a good idea, to reduce pyrolysis.

Some kind of pre-extraction would help of course.

I wonder how they could defeat that... they would have to make a binding compound which is hard to chemically and thermally separate. If they make something which defeats molecular distillation i think they probably deserve a nobel prize for achieving it despite the vast amount of problems working against such a compound being found. Ephedrine is a tough molecule, so the binding system would have to be at least as tough.


oh, another vague possiblity - what about using osmosis somehow. I know that this has been explored in the tyvek tea bag method to some extent. And there's always the idea of adsorbing the stuff onto an ion exchange matrix and fractionating the adsorbed materials via progressive elution with increasingly stronger alkaline solution.

[UncleFester]

You overestimate the opposition. After hydrolysis, the goods is separable easily from the gak. Don't build an imaginary mountain for yourself. They are working from off the shelf pre- approved additives.

[elfspice]

well, i think it was me that said hydrolysing the ester will change solubilities, and fester's experiment proves it.

as for overestimating them, there might still be approved food grade additives out there, or a novel combination which creates a little cage to hold the molecules in, and that's all i was meaning by what i said. Those kinds of defenses probably can be violated through using methods involving adsorbing the gak laden nectar (that's the right name for the precursor for honey isn't it?)... so they don't really present any ultimate threat...

as fester points out, they are hamstrung by the FDA approving the compounds that might do it but just happen to be highly toxic, and added to that, when it comes down to it, they cannot do anything that would interfere with absorption through the stomach. Thus methods connected with the kinds of processes that happen in the stomach and small intestines (which does a nice acid/base/enzyme combo attack which renders all gaks null and void) - these must always work, and therefore, there is no way to stop it happening short of taking them off the market.

thinking of the chemistry of absorbing them, isn't the main method that things get through the stomach walls into the bloodstream some kind or kinds of osmosis through special membranes? What about some kind of polymer fabric which has electrical properties which permit polar substances to cross but don't let less polar substances...

hell, has anyone thought of using a phase separating filter (silicone impregnated) which only lets polar compounds through? There's probably a readily available compound which can be soaked into paper that will do the job better than any tyvek tea bag.

[Prepuce]

"I'm inclined to think that one should exploit the fact they're putting such goddamn large molecules to fuck with extraction, and use heat to superheat the ephedrine so that it can be crystallise on a cooling surface."

Elf: SWIP has had success in just extracting with methanol, basing the mixture with a little washing soda (or even in just using the base already resident in 120's), then then carefully heating the bubblegum-like mass in a flask. Into the flask was inserted a test-tube, wrapped the top 1/2 inch or so with a strip of rubber from an inner tube, until it made a nice sealed fit with the neck of the flask. The rubber was then completely covered with teflon tape. After filling the tube with crushed ice, the flask was carefully heated just to the point that a vapor began rising from the mass at the bottom. This was continued, along with replacement of the melted ice and removal with an eye dropper of the water, until no more vapor was produced. It went a little faster when a fan was placed to blow on the outside of the flask, keeping it a bit cooler.

The flask was allowed to cool for several minutes, and then the crystals clinging to the sides of the flask and to the test tube were gently shaken, then scraped, into a beaker.

It's a time conuming and messy process, but yeilds are very clean. The key to the process is to not let the flask get too hot, or the nasty gaak will vaporize along with the pfed fb.

PP

[Prepuce]

"hell, has anyone thought of using a phase separating filter (silicone impregnated) which only lets polar compounds through?"

As SWIP understands it, polysorb has one "end" that's positive and the other "negative" (that's a very crude explanation, but the best SWIP can do without looking it up. It's all in this thread anyway.) Another way he has seen it described is to say that one end of the molecule is attracted to polar solvents and the other to nonpolar. So the net effect is that it grabs hold of the pfed, keeps it mostly basic enough to stay in the fb form, and tends to hold it in suspension in whatever liquid it's combined with. Put it together with two liquids, like H3O and xylene, and you get a nice emulsion that's nearly impossible to deal with.

PP

[elfspice]

i always wondered whether sublimation recrystallisation would work on these things...

here's some info on the use of this shit to encapsulate proteins in emulsions:

http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=10100311&dopt=Abstract

it's good at it.

I would wonder whether it would in fact be possible to defeat sublimation recrystallisation... how many substances that are fda approved (btw, i am appalled to read in chemfinder's entry that polysorbate is a 'toxic food preservative') have the same BP as ephedrine that would also be hard to separate via other methods afterwards... sounds like a good research project for someone who's got some time on their hands

i wonder what is next in the gak war. I know they put phentermine adsorbed onto ion exchange resin beads to make them hard to get off, but i imagine that would just take a long heating to extract.