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Ishmael Fleishman

Fermenting San Pedro Cactus

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In the interest of sharing.

 

I was watching ESPD55 - Colin Domnauer - Expanding evidence of Anadenanthera in the pre-Columbian Andes as part of  Ethnopharmacologic Search for Psychoactive Drugs - ESPD55.

 

In the Q and A - Laurel Sugden and Josep Orlovac Del Rio mention that San Pedro cactus juice can be fermented and that it has a positive effect on its actions.

 

The possibility of fermentation raised a question that fermentation of San Pedro might produce beta-carbolines.

 

The production of beta-carbolines might increase the function of MAOI in the San Pedro brew.

 

There is also a possibility that Anadenanthera was in history fermented with San Pedro based on iconography found on drinking vessels. The same way that Anadenanthera was fermented as part of chicha.

 

This seems to be an interesting avenue for exploration.

 

The fermentation could be undertaken pre-cooking or post cooking of the cactus juice.

 

Similar to a raw ale pre-cook ferments would result in the presence of lactobacillus bacteria and some saccharomyces being the primary drivers of fermentation resulting in a sour ferment with a lower PH.

 

Post-cook ferments would reduce the diversity of micro-organism from the raw plant and would rather be inoculated by air born yeasts.

 

A quick search show that their is a long history of fermenting a variety of cactus juices to make drinks. These are often fruit however the cactus flesh is also fermented.

 

The flesh would have limited sugars or carbs and that restrict ethanol production. However certain bacteria and yeast can breakdown cellulose into sugar raising the possibility of more ethanol production.

 

However the introduction of a secondary source of sugar as an adjunct in the fermentation is conceivable.

 

However the production of ethanol is secondary with the formation of enzymatic by-products would be of greater interest.

 

This is definitely an area for possible exploration.

 

 

 

 

 

 

 

Edited by Ishmael Fleishman

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This is an interesting concept. In theory, you could get a tetrahydroisoquinoline form from pyruvate/followed by decarboxylation = equiv. acetaldehyde and mescaline like such.

 

This would bring it's pharmacology potentially more in line with the Lophs. The pharmacology of these THIQ's isn't well studied but they seem to be relatively potent serotonin agonists (nM) for a diverse range of serotonin receptors aside from more classical 5-HT2ARs eg pellotine
 

 In Vitro and In Vivo Evaluation of Pellotine: A Hypnotic Lophophora Alkaloid | ACS Pharmacology & Translational Science

1,2,3,4-Tetrahydroisoquinoline, 6,7,8-trimethoxy-1-methyl-.png

 

https://pubchem.ncbi.nlm.nih.gov/compound/613648

Edited by Alchemica

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@Alchemica Most of the chemistry is way over my head.

 

How to one practically derive a tetrahydroisoquinoline is the question.

 

Acetaldehyde is a defect in beer tastes like green apple - caused by

  • The beer is not fully fermented;
  • Yeast strains are unhealthy and have poor performance;
  • Excessive oxidation reaction occurs, allowing ethanol to be oxidized to acetaldehyde. This usually happens during the bottling process;

 

I think adding a small amount of fruit juice or malt extract syrup as source of sugar to San Pedro brew allowing it to partially ferment then aerating the partial fermented San Pedro brew might possible be one way of allowing ethanol to be oxidised to acetaldehyde?

 

Or would addiing a shot of Vodka then aerating skipping the fermentation of the alcohol step work?

 

Would that get us to tetrahydroisoquinoline? Sorry for the stupid questions.

 

Wiki says that tetrahydroisoquinoline is neurotoxic and so is Acetaldehyde that why it is limited in commercial beer. That is concerning to me.

 

 

 

Edited by Ishmael Fleishman

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You'd want the products that are intermediates to ethanol formation (pyruvate/acetaldehyde) to condense with the phenethylamine and under acidic conditions, undergo a Pictet-Spengler reaction to form THIQs (below). It wouldn't be a high conversion rate as conditions wouldn't be optimal but you'd likely get some conversion, which given the potency of the compounds, may be enough

 

1-Me-THIQ has actually found some putative therapeutic actions, "1-Methyl-1,2,3,4-tetrahydroisoquinoline (1MeTIQ) is an endogenous antidepressant and parkinsonism-preventing substance that demonstrates neuroprotective activity." 

 

Fermentation | Biology OER

image.thumb.png.b1fafb88beaa928520ac9b4ae1b05128.png
 

I've tried to cover some fermentations of plants here The Science of Fermented Fruits, Veggies and Plant Medicines - Pharmacology, Chemistry & Medicine - The Corroboree (shaman-australis.com)

Yeasts are known for reducing some alkene (C=C) and carbonyl (C=O) compounds, which is more applicable to things like mesembrine-type alkaloids in Sceletium

image.thumb.png.8e8132cf17ce2cb70023ca9dca4d8217.png

 

image.thumb.png.b1fafb88beaa928520ac9b4ae1b05128.png

image.thumb.png.8e8132cf17ce2cb70023ca9dca4d8217.png

Edited by Alchemica

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@Alchemica  thank you. for "ethanol formation (pyruvate/acetaldehyde) to condense with the phenethylamine and under acidic conditions, undergoing a Pictet-Spengler reaction to form THIQs"

 

This means that Anean cultures would have fermented Chicha with San Pedro to allow for this reaction to occur.

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Maybe. Cacti are not known for betacarbolines (even though traces were claimed to have been observed in one recent paper, said paper did not engage in an isolation or structural proof).

It is more common for cyclization of phenethylamines in cacti to lead to isoquinoliones. Some of which are known MAOIs.

 

Peyote was fermented also, in ancient Mexico, but the result was described as a vinagre rather than being ethanolic.

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