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The Mysterious Bufotenine

Migrated topic.
Well I'm excited anyway. I'd be quite happy with just managing to purify bufotenine, as efforts so far have been fruitless but from the descriptions written above on this red bufotenine I've gotten very curious indeed.

Was there any differences noted in the temperature at which it vapourises, or is it the same as bufotenine in that respect?
 
It is certainly not 5-Acetoxy-DMT there is not even a small chance. It could be calcium bufotenine. It would be stable in water. There is no reason it would not be, it should be water soluble and stable at normal pH ranges. Similar compounds are stable. In acidic water is where the calcium will be lost. It may also be forming dehydrobufotenine. The native americans would treat there Bufotenine containing snuffs with calcium hydroxide. The snuffs were believed to then contain calcium bufotenine.

SWIM will have to talk to a friend about getting the melting point data as it must exist for dehydrobufoteine it is well versed in the literature.
 
While more work is required SWIMs friend ran a TLC on the red solid comparing it to B. (2:1:0.1) Chloroform:MeOH: + 2 drops Nh4OH
The Rf was slightly lower than B implying the compound has a greater affinity for the silica than for the mobil phase relative to B .
This would be suggestive of a calcium B or ketone degradation product forming. Although SWIm does not know as maybe since DehydroB is charged do to the tertiary nitrogen? It could be all. Melting points will have to be taken.



Interestingly there is another strange compound that was formed:
10mg Pure B freebase was dissolved in hot water 5mL (some did not dissolve and water was decanted) (The B had been at RT for several days and may have been the N-oxide but not sure someone will have to check this out although B is supposedly very stable but salt SWM doesn't know about as freebase? )
After sitting 1 hour the water turned transparent blackish and upon evaporation of the water via a hair drier a blackish solid residue precipitated out
and was collected. Strangely the Rf showed almost identical to the reddish compound. It may be that heat is forming this compound if they are in fact the same.

Activity Unknown. SWIMs friend said he has yet to try either of the strange colored products.
 
The XlogP3 of bufotenine is 1.2, it's 2.3 for dehydrobufotenine, so dehydrobufotenine should be less water soluble.

Has anyone here ever made dehydrobufotenine from bufotenine or knows of a published tech for doing this? Shulgin believes bufotenine forms dehydrobufotenine in alkali solutions.
 
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