Sodium Carbonate wash is washing out DMT

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Hi,

I've discussed part of this already on the Soxhlet Extraction thread but as this is related less to the use of soxhlet than to a standard extraction I wanted to raise it seperately here.

I extracted ~60g of MHRB (known quality) in a soxhlet using Isopropyl Alcohol (99.5%). This IPA had distilled water added to it & was basified with lye (though initially 1st heptane pull was added before lye). I did a number of heptane pulls
I did pulls with Heptane (3), Toluene (1) and Xylene (2). Yields from the latter 2 solvents appear to be low.

Unlike the other solvents I did a Sodium Carbonate (anhydrous) pulls on the combined Heptane, as I'd done previously on another (failed) extraction, on both occassions I noticed the following:
Once Sodium Carbonate wash was done subsequent washes with distilled water to remove any residual Sodium Carbonate were carried out. After agitation with the Heptane the water washes became cloudy, but in the sep funnel the cloudiness seperated out upwards. That is the cloudiness (presumably residual Sodium Carbonate) inside the waterlayer drifted upwards slowly forming a thicker whitish layer between the Heptane and the now clear water. Now apart from these 2 times using IPA as the initial extraction liquid I've never experienced an emulsion/whitish layer forming with Sodium Carbonate washes of Heptane. This leads me to speculate that it is occurring because of the fact that IPA was used initially - I can't think of any other explanation. I'm thinking that its possible something from the IPA was pulled by the Heptane in the soxhlet and is affecting the Sodium Carbonate wash. Does this sound plausible?

I've now freeze precipitated the Heptane & also evaporated some of it. The total yield is about 17mg of oily waxy yellow spice. The Xylene & Toluene pulls look to be similarly low yield, not having produced their characteristic splotchy evap pattern yet.
I am working on the assumption that the Sodium Carbonate wash is affecting yields from the Heptane (I'm satisfied alkaloids were pulled into IPA only other possibilities for low yield are ineffective mixing of solvent & IPA in FB flask which I'm testing now or that DMT was destroyed by heat of soxhlet which I discount).
I have seperately collected the water used in SC/water washes and have evaporated this. It evaporates down to ~900mg of dirty powder which has a faint DMT smell, though 50mg of this - which was hardest to scrape off the evap plate - has a stronger DMT smell and is visually darker and waxy. It seems clear that I've lost some yield to the wash and I intend to attempt to recover this later. I'm planning to dissolve it all in heptane, remove heptane leaving undissolved sodium carbonate & then seperately evap off heptane. Will this work?

Before I do that can anyone shed any light on what has happened and how? I think it must be related to the use of IPA as I've previously experienced no problems with sodium carbonate washes and have been using the same SC, bark, heptane as previously.

 

[downwardsfromzero]

Hi,

I've discussed part of this already on the Soxhlet Extraction thread but as this is related less to the use of soxhlet than to a standard extraction I wanted to raise it seperately here.

I extracted ~60g of MHRB (known quality) in a soxhlet using Isopropyl Alcohol (99.5%). This IPA had distilled water added to it & was basified with lye (though initially 1st heptane pull was added before lye). I did a number of heptane pulls
I did pulls with Heptane (3), Toluene (1) and Xylene (2). Yields from the latter 2 solvents appear to be low.

So far, so good (but see the end of this post)...

Unlike the other solvents I did a Sodium Carbonate (anhydrous) pulls on the combined Heptane,

What do you mean, 'sodium carbonate (anhydrous)' pulls? This is not immediately clear. Sorry.

as I'd done previously on another (failed) extraction, on both occassions I noticed the following:
Once Sodium Carbonate wash was done subsequent washes with distilled water to remove any residual Sodium Carbonate were carried out. After agitation with the Heptane the water washes became cloudy, but in the sep funnel the cloudiness seperated out upwards. That is the cloudiness (presumably residual Sodium Carbonate) inside the waterlayer drifted upwards slowly forming a thicker whitish layer between the Heptane and the now clear water.

SWIM obtained a similar white emulsion, albeit under different circumstances (rebasifying an ascorbic acid cleanup and pulling into heptane/hexane blend). SWIM had a feeling SWIM's emulsion was undissolved DMT as there were crystals forming in the aqueous layer too. This has nothing to do with your problem, though.

Perhaps your emulsion is from DMT pulled into the sodium carbonate by the IPA. Not sure why it refuses to pull into the hydrocarbon though - presumably from lipophilicity in the aqueous layer via the IPA, which has gone into the heptane and then come back out into the sodium carbonate wash.

Now apart from these 2 times using IPA as the initial extraction liquid I've never experienced an emulsion/whitish layer forming with Sodium Carbonate washes of Heptane. This leads me to speculate that it is occurring because of the fact that IPA was used initially - I can't think of any other explanation. I'm thinking that its possible something from the IPA was pulled by the Heptane in the soxhlet and is affecting the Sodium Carbonate wash. Does this sound plausible?

Would soxhletting have pulled out some weird fats or waxes that don't show up any other way? This seems unlikely, doesn't it?

I've now freeze precipitated the Heptane & also evaporated some of it. The total yield is about 17mg of oily waxy yellow spice. The Xylene & Toluene pulls look to be similarly low yield, not having produced their characteristic splotchy evap pattern yet.
I am working on the assumption that the Sodium Carbonate wash is affecting yields from the Heptane (I'm satisfied alkaloids were pulled into IPA only other possibilities for low yield are ineffective mixing of solvent & IPA in FB flask which I'm testing now or that DMT was destroyed by heat of soxhlet which I discount).

What was the temperature in your thimble? Doesn't IPA boil at about 82degC and DMT at about 80degC? Could it have vaporised and, er, sneaked off somewhere? But it wasn't present as freebase in the soxhlet apparatus. So probably not.

I have seperately collected the water used in SC/water washes and have evaporated this. It evaporates down to ~900mg of dirty powder which has a faint DMT smell, though 50mg of this - which was hardest to scrape off the evap plate - has a stronger DMT smell and is visually darker and waxy. It seems clear that I've lost some yield to the wash and I intend to attempt to recover this later. I'm planning to dissolve it all in heptane, remove heptane leaving undissolved sodium carbonate & then seperately evap off heptane. Will this work?

Before I do that can anyone shed any light on what has happened and how? I think it must be related to the use of IPA as I've previously experienced no problems with sodium carbonate washes and have been using the same SC, bark, heptane as previously.

It will surely work, to extract the dried sodium carbonate wash with heptane. And I think you've essentially answered your own question!8) But I would add, after soxhletting, maybe evaporate your IPA then add the sodium carbonate and extract with heptane. Then the IPA won't be able to screw things up. I don't understand why you were wanting to extract from aqueous IPA into heptane when it's so easy to evaporate IPA before adding any water.

 

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Hi downwardsfromzero, thanks for the reply.

What do you mean, 'sodium carbonate (anhydrous)' pulls? This is not immediately clear. Sorry.

I meant Sodium Carbonate wash rather than pull, agitating the heptane with a mix of water & anhydrous sodium carbonate to remove any lye from the heptane & then washing with water to pull out any retained sodium carbonate from the heptane.

Perhaps your emulsion is from DMT pulled into the sodium carbonate by the IPA. Not sure why it refuses to pull into the hydrocarbon though - presumably from lipophilicity in the aqueous layer via the IPA, which has gone into the heptane and then come back out into the sodium carbonate wash.

Its possible, I'll know more once I've re-pulled out any DMT from the evaporated wash water, though I can't do that till next week.

Would soxhletting have pulled out some weird fats or waxes that don't show up any other way? This seems unlikely, doesn't it?

I considered this, I think the pull from a soxhlet does produce a more oily product simply because its more efficient in extracting whatever is there, I don't think the problem is down to too much oil/fat though.

What was the temperature in your thimble? Doesn't IPA boil at about 82degC and DMT at about 80degC? Could it have vaporised and, er, sneaked off somewhere? But it wasn't present as freebase in the soxhlet apparatus. So probably not.

I don't know the temp, my hotplate is strictly analogue so no helpful digital temp display. I did set it at just aboe the minimum required to boil the IPA. I don't think that the DMT could have been destroyed or vapourised as in brewing Ayahuasca the mix is boiled for quite a while & its effective enough. Also others with more experience of a soxhlet assured me extracting with IPA would be fine.

But I would add, after soxhletting, maybe evaporate your IPA then add the sodium carbonate and extract with heptane. Then the IPA won't be able to screw things up. I don't understand why you were wanting to extract from aqueous IPA into heptane when it's so easy to evaporate IPA before adding any water.

Do you mean evap right down to dry, or close to dry as it'd get?
I don't think that'd work as for a sodium carbonate wash to do any good it needs to be 2 liquids - if IPA is evaped off it won't work & if I just add sodium carbonate to IPA it would just mix permanently rather tha forming 2 seperate layers like it does with heptane.
I wanted to extract from heptane as I wanted pure (as possible) DMT rather than just dried IPA containing alkaloids/fats/oils, etc. Do you mean evap IPA & then extract with heptane? presumably I'd need to basify 1st before evaping down?

Thanks