I’ve read that to clean up harmaline hydrochloride, the recommended procedure is to dissolve it in hot water with activated charcoal and mix it hot for a few minutes and then filter. This should remove the impurities.

How effective is this activated charcoal at removing the impurities?

What kinds of impurities are removed by the activated charcoal, and what isn’t?

Wouldn’t it also absorb some of the harmaline too?

Would this also work with DMT?

activated carbon is choice, extremely good at removing impurities. it's particularly good at binding tannins and particulates, excellent decolorizer. another way is to dissolve in hot water, add a small layer of the activated carbon on a filter, and pour it through. think of it as really efficient column chromatography (pore sizes are ~ 1 nm), eventually the harmaline should elute through

it would work for dmt as well

swim just got some USP grade powder from a health food store, has a surface area of 900 sq.m./g.

Ok, benzyme, so let’s say one did the following:

1) Extract impure DMT as HCl in water
2) Pour through activated carbon to remove impurities
3) Discard activated carbon after washing with more HCl water to get out all the DMT HCl
4) Freebase the DMT HCl in the water with ammonia
5) Pour water through activated carbon to remove the DMT
6) Pour alcohol through the activated carbon to extract the DMT from the carbon

Would that work?

This question has come up because of an experiment SWIM is doing with Yopo. He’s extracted Yopo many times and ends up with a dry crystalline material that is easy to vaporize, but once in a while the extract is sticky and difficult to clean up.

Attempting to crystallize bufotenine in ethyl acetate is REALLY DIFFICULT. Especially if DCM is used to extract it instead of chloroform. SWIM uses DCM most of the time.

He wants to get rid of the sticky material that is extracting along with the bufotenine. It seems to be causing nausea and making the smoke harsh.

So his question for this problem is: would it be possible to clean up the extract using activated carbon (i.e., activated charcoal)?

If so, what would be the best procedure?

Should he dissolve the sticky impure bufotenine in acid, then filter through activated carbon, then discard the carbon, then freebase with ammonia, and filter through more activated carbon to trap the bufotenine and then extract it from the carbon with IPA or acetone?

Or am I totally on the wrong track with that approach?

yes.

alcohols are ideal, since many alkaloids are readily soluble in them, and activated carbon does not absorb alcohol well at all

he should do a regular a/b, evap, redissolve in hot alcohol, then run through a.c.

The extract in question was triple A/B extracted and still sticky. The particular batch of seeds is to blame because the extraction tech used is the same one SWIM's used dozens of times without getting sticky results. Normally just 1 A/B extraction works fine, but with this batch even 3 A/B extractions on it evaporate to a sticky mess!

SWIM has about 15 grams of sticky bufotenine from this extraction. It’s a lot. Judging by the potency, its about 85% pure with some sticky crap in it causing nausea. He already removed the stuff that causes head tension.

So you’re saying take the final freebase extract from the A/B extraction, dissolve in hot alcohol, and then run through activated carbon. How much should be used. Would he use 15 grams of activated carbon? Should the alkaloids be highly diluted in the alcohol?

Would much bofotenine get lost in the carbon?

15g is a bit much. remember, a.c. has a VERY large surface area.
swim would use 5g tops

as for the bufotenine, keep running alcohol through. shouldn't lose too much to the activated carbon.
this stuff works on binding via Van Der Wahls interactions, electronegative/electropositive compounds are more likely to get trapped

What’s more effective?

A) Dissolve alkaloid salts in hot acidic water, filter through activated carbon

Or

B) Dissolve freebase alkaloids in hot alcohol, filter through activated carbon

*edit* swim would go with the freebase in alcohol, then (post-filtration)convert it to a salt if necessary

http://www.cerlabs.com/experiments/1087540703X.pdf
general exp. of recrystallization of acetanilide

see page 3, discusses decolorization, and mentions how an excess of a.c. will lower yield

One thing SWIM wants to mention is that there should be no sticky N-Oxides present. He did a thorough N-Oxide reduction on the extract after purifying it by 3 A/B extractions.

He doesn't know what the sticky stuff is. But it definitely makes the smoke harsher and causes nausea.

He will try dissolving it in hot 99% IPA, and pouring it through activated carbon and see what happens. Hopefully that sticky stuff is not an alkaloid and will be absorbed by the activated carbon.

It's possible that the sticky stuff is another alkaloid present. In that case it won't help and he’ll have to try something else.

15 grams is a lot. That’s roughly 150 strong 10 mg doses. It’s a real pain to use it as is. Because it’s sticky, it’s really hard to measure out the small doses for vaporization. Plus, the nausea felt from the sticky stuff is NOT PLEASANT. He wants it removed completely. He tried crystallizing the bufotenine to remove it, but the sticky stuff is preventing the bufotenine from crystallizing! He hopes to never buy that strain of Yopo again. What a pain. Hopefully a way to remove the sticky stuff can be found.

Yes. I'm worried about that lower yield.

They recommend 60 mg of activated carbon for 1 gram of acetanilide. That's not much at all. Maybe SWIM should follow that? 1 molecule of bufotenine is nearly twice as heavy as acetanilide, so 30 mg maybe is enough for 1 gram of bufotenine. But that should also depend on the amount of impurities too right? With more impurities more activated carbon should be used right?

So for about 15 grams, maybe 500-1000 mg of activated carbon should be used. SWIM has granulated and powdered forms. If using the granulated form, should more be used?

ILPT think active carbon is best to use whilst the goodies are in the organic solvent. Almost Every recrystallization ILPT performed in proper chem lab. for research and manufacturing heterocyclic compounds followed those simple steps

1, Transfer ? mg of your goo to boiling flask

2, Add ? ml of organic solvent (swim should use selective one and as volatile as possible(like DCM,Et2O,CS2, etc. )

3, Provide flask with condenser and slowly bring to boil, let it reflux for few minutes.

4, Add ? grams of active carbon (roughly 1 gram for 100 ml of almost saturated solvent)

5, Reflux for 2 minutes or so.

6, While hot filter out active carbon(use regular filtration, no vacuum).

5, Distil off about three quarters of the solvent(the best is vacuum distillation)

6, Let it cool and crystallize slowly

7, Filter off the crystals on the buchner infundibulum using vacuum

NOTES:

a,in step 2 use a bit more solvent then is your theory because in step 6 some of it will evaporate

b, in step three is optional to remove the flask and gently shake it few times or using stirring rod, just to be sure that more goodies will move from goo to the solvent

c,ILPT would probably decant solvent to the other clean flask before,step 4
leaving undissolved residue(if any presented in solution) behind

d,In step 6, is optional use a litlle bit of clean hot solvent to wash the folded filter paper with charcoal residue after main filtration is done

e, swim can also use freeze precip. but heptane is not as volatile. maybe pentane would be handy (now ILPT talking about dmt, he hasn`t play with bufo or harmala alk. yet )

Swim should definitely try this before start to arsing with time eating chromatography.

?-mean that swim have to find out cos ILPT never played with spicely potent plant extract in lab mentioned above

SWIM will lost some of the precious but most likely end up with non sticky product

GOOD lUCK

What is the volume of IPA used for 15 grams ? Acetanilid is not a heterocyclic compound SWIM should be very careful with a. carbon and not add to much .

isnt it 1500? its 100 10mg doses in 1g..

or am I missing something?

No I’m missing something…I’m missing a zero in there. Its 1500 doses, not 150.

The activated carbon didn’t do the trick. It’s was still sticky after that. It did however eat up a lot of the bufotenine! More than 80% got trapped in the activated carbon.

How does SWIM get his bufotenine back out of the activated carbon? He tried acetone, that got about 10% back out. Any ideas?

damn

flush with hot alcohol. MeOH or EtOH

SWIM will put it in the Soxhlet overnight and extract it back out with some IPA. That will probably work very well.

I think he over did the carbon. He didn’t see good results, so he kept adding more and more and eventually it started looking cleaner. But it was pulling out everything, not just the amber contaminant.

I think the contaminant is an alkaloid, maybe one of the beta-carbolines present in the seeds. But I’m not sure.

understandable

yeah, a.c. isn't really selective, but it does do a good job filtering large particulates and decolorizing, if done right. it's sort of a crude form of prep chromatography. real prep chrom (in the form of flash chrom) would be ideal