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1-Benzylpsilocin and psilocin benzoate? Options
 
someblackguy
#1 Posted : 5/12/2021 12:59:52 AM

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1-Benzylpsilocin and psilocin benzoate


Erspamer, V. (1961) Recent research in the field of 5-hydroxytryptamine and related indolealkylamines In Jucker, E. Fortschritte der Arzneimittelforschung/Progress in drug research (Vol. 3). Basel: Birkhäuser.

[p. 266] “The most interesting of these compounds are: N,N-dimethyltryptarnine, N,N-diethyltryptamine, N,N-dipropyltryptamine, N,N-dibutyltryptamine, N,N-dibutyl-5-methoxytryptamine, N,N-dibutyl-5-HT, 5-methoxy-β-methyl-tryptamine and β-hydroxy-bufotenine. Starting from the observation that psilocin and also psilocybin, like bufotenine and N,N-dimethyltryptamine, show definite antagonistic action towards 5-HT, Cerletti et al. [249]† succeeded in preparing psilocin derivatives which manifest anti-5-HT action [antagonism] **considerably greater than that possessed by the parent substance**. 1-Benzylpsilocin and psilocin benzoate, for example, have 10 and 18%, respectively, of the antagonistic potency of LSD.”

†[249] A. CERLETTI, Atti 2° Simp. Centro Cefalee Firenze 1960, pp. 27-59. http://books.google.com/books?id=TJr5BwAAQBAJ

[Note: I came across this outdated text when I was researching nicotine salts. The benzoate salts of nicotine, currently used in certain brand name e-cigarettes, are claimed in a patent, filed in 2013 (link below), to have a significantly increased drug effect. This description of the benzoate salts of substituted tryptamines presented here are an artifact for historical/trivia interest only (as opposed to any valid scientific/pharmacological value). The claims of psilocin derivatives “which manifest anti-5-HT action considerably greater than that possessed by the parent substance” are not necessarily accurate or even applicable to increased potency—nor is there any specific safety information I could find in regards to “psilocin benzoate”.

That said, **it would be interesting to learn more about the underlying claims of increased activity of benzoate salts in general**.

Nicotine levels in plasma after vaping e-liquid, as discussed in the patent, and central 5-HT2A receptor action by psilocin/-cybin from oral ingestion are not just “apples and oranges”—there should be no direct analogy there (i.e. apples and lightbulbs).]



•United States Patent Application Publication – Bowen et al.
– Pub. No.: US2015/0020824A1
– Pub. Date: Jan. 22, 2015
NICOTINE SALT FORMULATIONS FOR AEROSOL DEVICES AND METHODS THEREOF
Applicant: Ploom, Inc., San Francisco, CA (US) [...]
DETAILED DESCRIPTION OF THE INVENTION: [...] Studies on the transfer efficiency of freebase nicotine and nicotine salts are complex and have yielded unpredictable results. [...]
It has also been unexpectedly discovered herein that certain nicotine salt formulations provide greater satisfaction than other nicotine salt formulations, and such effect has been shown in blood plasma levels of example nicotine salt formulations herein[...]
EXAMPLES: Nicotine benzoate salt formulation: 0.15g benzoic acid was added to a beaker followed by adding 0.2g [freebase] nicotine to the same beaker. The mixture was stirred at 55°C for 20 minutes until benzoic acid was completely dissolved and an orange oily mixture was formed.” http://bit.ly/2uK8Niv

Should this information be interpreted in terms of psilocybin mushroom preparation methods? If so, how?
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benzyme
#2 Posted : 5/12/2021 3:27:54 AM

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Extract with methanol first, add benzoic acid; heat in a water bath @ 40C, stir for about 40-50 min. decant/evap the mother liquor, recrystallize with boiling 2:8 acetone:hexane.
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Loveall
#3 Posted : 5/12/2021 10:10:39 AM

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benzyme wrote:
Extract with methanol first, add benzoic acid; heat in a water bath @ 40C, stir for about 40-50 min. decant/evap the mother liquor, recrystallize with boiling 2:8 acetone:hexane.


Do we know if this would result in 1-Benzylpsilocin and/or psilocin benzoate? I assume psilocybin is dephosphorylated and converted also? Is evaporation OK in the atmosphere (any polymerization/oxidation) concerns? Are we expecting the product to be 10x more potent than psilocybin? Have you tested this process Benz?

Thanks for any answers.
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benzyme
#4 Posted : 5/12/2021 6:18:30 PM

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I had not. The temp chosen was a suggestion; two factors are missing... the pKas of the phosphoryl group, and benzoic acid. Also stoichiometric masses (depends on the content of the material). Oxidation shouldn't be much of an issue with a
benzoate salt.
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downwardsfromzero
#5 Posted : 5/12/2021 10:21:38 PM

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Loveall wrote:
Do we know if this would result in 1-Benzylpsilocin and/or psilocin benzoate?
Maybe 1-benzoyl (but not 1-benzyl-)psilocin and psilocin benzoate ester are what you have in mind, but neither of those would result from benzyme's outline method. As stated above, it would result in the benzoate salt. Preparation of the 1-benzyl compound or the benzoate ester (4-benzoyloxy-DMT) would require reagents beyond the scope of typically permitted synthesis discussion here - i.e. dangerous and/or watched materials.
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someblackguy
#6 Posted : 5/13/2021 4:06:49 PM

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I am looking for the original reference (A. Cerletti… 1960) . Here is a link to another (possibly the same?) study by Cerletti in 1960. It mentions the 1-benzyl substituted compound and the benzoic acid ester of psilocin.
Cerletti (1960)
Spellbreaking is the better part of alchemy, extraction, and the art of undoing—but a cocksure kind of lovingkindness, a clockwork clock, works time.

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