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QUEST FOR YUREMAMINE

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Dr_Sister

Dr_Sister

Synaptic cleft explorer
Senior Member
Senior member Chemical engineer
Your sister has been reading up on Yuremamine (there isn’t a lot to read!) And has decided that it is time to take this quest to the field. So how best to isolate this shy bird? Cannot use an acid, cannot use a base, cannot use heat.

The only feasible method gleaned thus far is a cold alcohol extraction of MHRB, which is also going to pick up all kinds of other things.

Sister has no column or any experience using one so here is what she proposes
1. cold methanolioc extraction (methanol chosen for low BP)
2. Strip off alcohol under low vacuum (should be able to do this at RT)
3. Dissolve residue in ethyl acetate (hoping this is polar eneough to dissolve the salts if enough is used)
4. Filter any insolubles
5. Wash with 10% sodium bicarbonate
6. Wash with 10% sodium hydroxide (hoping that the fleeting contact with NaOH will not cause the yuramine to decompose, but simply drive it into the organic layer)
7. Wash with brine
8. Treat ethyl acetate with CO2 to precipitate any NMT (or other primary or secondary amines that may be present)
9. Treat ethyl acetate with FASA to precipitate nn-DMT and Yuramine as fumarates (hoping fumaric acid will be mild enough not to cause decomposition of yuramine, adding it it small portions so there is never an excess)
10. Filter
11. Attempt slow fractional crystallization to separate the two amines (open to suggestions about what solvent to use, but would prefer not to use Naptha as heat will be required)
12. Recrystallize as necessary – use hot Naptha on dmt fraction (open to sugestions about solvent for yuremamine fumarate though.)

This is only a proposal to initiate some discussion, feel free to add steps, remove steps or suggest alternative steps or solvents.
 
This is awesome Sister!

I wish I had something to contribute to this but hopefully some of our more chem savvy members will be able to help.

I'm definitely down for some experimentation once we get a concrete theory going.

Thanks for getting this started!
 
Perhaps sister would be more successful in finding reading material if she searched for "Yuremamine"? Just a thought...not sure if you were actually dealing with something called "yuramine" instead.
 
Yes, forgive the typo. The searchs turned up
Isolation and Characterization of Yuremamine, a New Phytoindole.pdf
and
the Yuremamine entry on wiki

Which is, as Sister mentioned, scant reading and neither of which gives a chemist much to go on, lacking NMR or LC-MS. The gist being avoid basic conditions and that mildly acidic conditions might be tolerated.
 
I'm not sure if it would be of any help/use/interest to you, but I also turned up a paper entitled Expedient synthesis of pyrrolo[1,2-a]indoles: preparation of the core of yuremamine. It's attached :d
 

Attachments

  • Expedient+synthesis+of+pyrrolo%5B1%2C2-a%5Dindoles+-+preparation+of+the+core+of+yuremamine.pdf
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I would probably try to run a chromatography column on the methanolic extraction. Might take several runs. First to remove the garbage, then a different solvent system to selectively isolate the yuremamine. Obviously TLC would be critical here as well. No acid and no base involved though ;).
 
Snozzleberry - Thanks for the paper! I'll see if there are any clues within.

Mydriasis – Sister had hoped to avoid running a column, but it may be the way to go in the end. Any thoughts on what solvents might work best here? Sister recalls seeing someone mention using DCM with 5% MeOH and a few drop of ammonia when running a column to purify dmt freebase. But because the anticipated alkaloids will be in salt form here, Sister thinks a more polar eluent might work better after the garbage has been flushed with something non polar.
 
Well Ethyl acetate(maybe even methyl) and short chain alcohols are what I would start playing with, because of it being a salt. Maybe even water?. I've yet to run my first column(will by next week though!). So I'm far from an expert hopefully someone else can chime in here. This Yuremamine has quite an interesting structure, I'm very curious about the end results of this.

Though I see no way around this except for short path distillation. If we were shulgin this is where we might pull out a Kugelrohr hehe.
 
Mydriasis said:
Though I see no way around this except for short path distillation. If we were shulgin this is where we might pull out a Kugelrohr hehe.
Click to expand...

The limited info available seems to suggest that yuremamine wouldn't withstand that kind of heat. In the characterization paper they kept the temps below 35°C. Otherwise I think distillation would be the way to go.
 
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