patent expired: decarboxylation of ibotenic acid in Amanita

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patent expired: decarboxylation of ibotenic acid in Amanita

Post by amafoo » Sat Feb 08, 2020 4:19 am

There is a patent: Method for producing muscimol and/or reducing ibotenic acid from amanita tissue. Link https://patents.google.com/patent/US20140004084A1/en

I don't know how to validate this, but Google says it got expired today, because fees weren't paid:

2020-02-07 Application status is Expired - Fee Related

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Re: patent expired: decarboxylation of ibotenic acid in Amanita

Post by amanitadreamer » Sun Feb 23, 2020 7:48 pm

amafoo wrote:
Sat Feb 08, 2020 4:19 am
There is a patent: Method for producing muscimol and/or reducing ibotenic acid from amanita tissue. Link https://patents.google.com/patent/US20140004084A1/en

I don't know how to validate this, but Google says it got expired today, because fees weren't paid:

2020-02-07 Application status is Expired - Fee Related
It expired almost 10 years ago. In discussing in my community we think it's because of sourcing amanita. Since you can't grow or cultivate it, supply would be an issue. Everything they did warranted creating a mass produced product but you can't if you only have a few weeks to gather and dry them. Most products made today like this one sell out by March or so and that's it until next year. Buying them is sketchy if you're going to be turning around and selling them. Even if you paid someone elsewhere you'd still lower profits and still run out. So we think they let the fees go and let the patent go. It's important for research purposes though.
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Re: patent expired: decarboxylation of ibotenic acid in Amanita

Post by amafoo » Sun Feb 23, 2020 8:02 pm

> It expired almost 10 years ago

This doesn't seem to be the case according to the US patent office, as it says it was only granted in 2014 and expired in 2020.

But it doesn't matter, since it's expired anyway.

And your reasoning makes total sense. Thank you for sharing.

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Re: patent expired: decarboxylation of ibotenic acid in Amanita

Post by PeaceEva » Tue Feb 25, 2020 7:32 pm

My seller sent me a variation of the patent information for “my research thesis”. It may be of interest here.

I’m unsure if he’d want credit or not, so I’ll omit his details unless he contacts me.
How to increase the potency 3X or more and minimize negative side effects from consuming Amanita muscaria and Amanita pantherina.

…Notes on decarboxylation of ibotenic acid to muscimol for your research thesis...

According to patent# US 2014/0004084 A1- Method for producing muscimol and/or reducing ibotenic acid present in Amanita tissue, only about 30% maximum of the ibotenic acid present in amanita tissue is decarboxylated to muscimol by air drying under the best conditions
This leaves a ratio of 3 parts ibotenic acid/1 part muscimol present in the Amanita tissue. The majority of negative side effects after consuming this mushroom are from ibotenic acid, a neurotoxin, present in the mushroom tissue according to the patent. So, the full potential of the mushroom is not realized and it can give you more negative side affects compared to consuming mushroom tissue that has a very low concentration of ibotenic acid.
More treatment is necessary to drive the decarboxylation reaction to completion and thus to maximize the concentration of muscimol, the target ingredient, and minimize the amount of ibotenic acid and negative side effects. This treatment will increase the potency up to 3X or more compared to dried mushroom tissue with no further treatment.
Here are two options described in the patent:

There isn't a significant difference in the result between the two options. Both methods will drive the reaction to completion. Option #1 is simpler and takes less time. Option 2 yields a pro-biotic substance.

#1 Experimental
A hot water extract from ground mushroom tissue is ph adjusted to less than Ph6 or more than Ph 8 and simmered for 2-3 hours at 190F with the lid on. This is called refluxing. In a laboratory, refluxing is done by attaching a condenser to a round bottom flask and heating. The condenser returns evaporated water back to the reaction. The ph is then neutralized if desired. Decarboxylation of ibotenic acid will not go to completion if the Ph is 7 (neutral). One part vinegar to 10-15 parts water will make it sufficiently acidic. This yields a ratio as high as 1:50 ibotenic acid:muscimol.

#2 Description: Some sugar and vitamin B6 are added to a hot water Amanita extract. Inoculate the extract with a tsp or two of active, unpasteurized yogurt. Yogurt with active cultures contains lactobacillus bacteria. This is incubated at 90-130F for 3 days. These bacteria contain glutamate decarboxylase, an enzyme that will decarboxylate ibotenic acid to muscimol. Vitamin B6 (P-5-P) is a necessary cofactor. This yields a ratio as high as 1:90 ibotenic acid:muscimol. Decarboxylation of ibotenic acid has been driven to completion.

#2a Experimental :
To a hot water extract of 60 gr of ground, dry mushroom caps, add 10-20 mg of vitamin B6 (P-5-P) and 3.5 tsp sugar, 1-3 tbsp of yogurt that contains active cultures. Vitamin B-6 is a co-factor and is part of the reaction, so don't omit this ingredient. Mix well and put in freezer until frozen completely. Then place in an incubator and incubate at 90-130F for 3 days. After the first 12 hours, inoculate again with a tbsp of active culture yogurt and continue incubating for 2.5 days. Keep refrigerated until use.
It is claimed in the patent that these procedures yield a substance that can be marketed as a supplement.

Making a hot water extract (tea) from ground mushroom tissue is also important since consuming uncooked mushroom tissue can cause adverse physical effects (nausea) since uncooked mushrooms are more difficult to digest than plant matter. This is true for all species. Some mushroom species are toxic unless cooked first. Cooking also helps release more nutritional potential from any species of edible mushroom and kills non-endospore forming opportunist pathogens.

For perspective, a similar decarboxylation process occurs in Cannabis. Fresh cannabis is not psychoactive unless it is cooked, dried, or smoked. Drying or smoking cannabis decarboxylates the THC to an active form. THC happens to be an easier compound to decarboxylate than ibotenic acid. Another note about cannabis is that when it is consumed orally, THC is metabolized by the liver before it travels to your brain. The metabolic product of THC metabolized in the liver is about 5X stronger then smoked THC which goes straight to the brain before being metabolized by the liver.

Decarboxylation of tryptophan yields tryptamine. Both substances fluoresce under a black light. Your hands may look clean after washing off all the tryptophan powder until you turn on the black light. Any part of your body your hands touched will also fluoresce. Ground Syrian Rue seed and the extract from these seeds will also fluoresce under a black light.

Feb 2019
This is for information purposes only and not meant to imply consumption of Amanita mushrooms.

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Re: patent expired: decarboxylation of ibotenic acid in Amanita

Post by amanitadreamer » Thu Feb 27, 2020 1:52 pm

PeaceEva wrote:
Tue Feb 25, 2020 7:32 pm
My seller sent me a variation of the patent information for “my research thesis”. It may be of interest here.

I’m unsure if he’d want credit or not, so I’ll omit his details unless he contacts me.
How to increase the potency 3X or more and minimize negative side effects from consuming Amanita muscaria and Amanita pantherina.

…Notes on decarboxylation of ibotenic acid to muscimol for your research thesis...

According to patent# US 2014/0004084 A1- Method for producing muscimol and/or reducing ibotenic acid present in Amanita tissue, only about 30% maximum of the ibotenic acid present in amanita tissue is decarboxylated to muscimol by air drying under the best conditions
This leaves a ratio of 3 parts ibotenic acid/1 part muscimol present in the Amanita tissue. The majority of negative side effects after consuming this mushroom are from ibotenic acid, a neurotoxin, present in the mushroom tissue according to the patent. So, the full potential of the mushroom is not realized and it can give you more negative side affects compared to consuming mushroom tissue that has a very low concentration of ibotenic acid.
More treatment is necessary to drive the decarboxylation reaction to completion and thus to maximize the concentration of muscimol, the target ingredient, and minimize the amount of ibotenic acid and negative side effects. This treatment will increase the potency up to 3X or more compared to dried mushroom tissue with no further treatment.
Here are two options described in the patent:

There isn't a significant difference in the result between the two options. Both methods will drive the reaction to completion. Option #1 is simpler and takes less time. Option 2 yields a pro-biotic substance.

#1 Experimental
A hot water extract from ground mushroom tissue is ph adjusted to less than Ph6 or more than Ph 8 and simmered for 2-3 hours at 190F with the lid on. This is called refluxing. In a laboratory, refluxing is done by attaching a condenser to a round bottom flask and heating. The condenser returns evaporated water back to the reaction. The ph is then neutralized if desired. Decarboxylation of ibotenic acid will not go to completion if the Ph is 7 (neutral). One part vinegar to 10-15 parts water will make it sufficiently acidic. This yields a ratio as high as 1:50 ibotenic acid:muscimol.

#2 Description: Some sugar and vitamin B6 are added to a hot water Amanita extract. Inoculate the extract with a tsp or two of active, unpasteurized yogurt. Yogurt with active cultures contains lactobacillus bacteria. This is incubated at 90-130F for 3 days. These bacteria contain glutamate decarboxylase, an enzyme that will decarboxylate ibotenic acid to muscimol. Vitamin B6 (P-5-P) is a necessary cofactor. This yields a ratio as high as 1:90 ibotenic acid:muscimol. Decarboxylation of ibotenic acid has been driven to completion.

#2a Experimental :
To a hot water extract of 60 gr of ground, dry mushroom caps, add 10-20 mg of vitamin B6 (P-5-P) and 3.5 tsp sugar, 1-3 tbsp of yogurt that contains active cultures. Vitamin B-6 is a co-factor and is part of the reaction, so don't omit this ingredient. Mix well and put in freezer until frozen completely. Then place in an incubator and incubate at 90-130F for 3 days. After the first 12 hours, inoculate again with a tbsp of active culture yogurt and continue incubating for 2.5 days. Keep refrigerated until use.
It is claimed in the patent that these procedures yield a substance that can be marketed as a supplement.

Making a hot water extract (tea) from ground mushroom tissue is also important since consuming uncooked mushroom tissue can cause adverse physical effects (nausea) since uncooked mushrooms are more difficult to digest than plant matter. This is true for all species. Some mushroom species are toxic unless cooked first. Cooking also helps release more nutritional potential from any species of edible mushroom and kills non-endospore forming opportunist pathogens.

For perspective, a similar decarboxylation process occurs in Cannabis. Fresh cannabis is not psychoactive unless it is cooked, dried, or smoked. Drying or smoking cannabis decarboxylates the THC to an active form. THC happens to be an easier compound to decarboxylate than ibotenic acid. Another note about cannabis is that when it is consumed orally, THC is metabolized by the liver before it travels to your brain. The metabolic product of THC metabolized in the liver is about 5X stronger then smoked THC which goes straight to the brain before being metabolized by the liver.

Decarboxylation of tryptophan yields tryptamine. Both substances fluoresce under a black light. Your hands may look clean after washing off all the tryptophan powder until you turn on the black light. Any part of your body your hands touched will also fluoresce. Ground Syrian Rue seed and the extract from these seeds will also fluoresce under a black light.

Feb 2019
This is for information purposes only and not meant to imply consumption of Amanita mushrooms.
I need to make a video about that patent. People are not reading it correctly.
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Re: patent expired: decarboxylation of ibotenic acid in Amanita

Post by Sid_Hatrack » Thu Feb 27, 2020 7:00 pm

This is interesting information that I would like to hear more about it and hopefully with specifics regarding procedure.

Not to nitpick, but a few statements are unclear to me. The statement “since uncooked mushrooms are more difficult to digest than plant matter” seems contradictory. What plant matter is being talked about here? If it is the mushroom, then would not uncooked mushrooms be considered plant matter? So how could it be more difficult to digest if it is the same thing?

Also, I would appreciate some clarification as to proportions of ibotenic acid to Muscimol. Percentage is expressed as a fraction of 100, so a ratio of 3 parts to 1 part is 300% not 30%. 30% would be expressed as a ratio of 3 to 10 not 3 to 1. Am I missing something here?

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Re: patent expired: decarboxylation of ibotenic acid in Amanita

Post by Donn » Fri Feb 28, 2020 2:08 am

Sid_Hatrack wrote:
Thu Feb 27, 2020 7:00 pm
The statement “since uncooked mushrooms are more difficult to digest than plant matter” seems contradictory. What plant matter is being talked about here? If it is the mushroom, then would not uncooked mushrooms be considered plant matter? So how could it be more difficult to digest if it is the same thing?
That may be about chitin, which is largely what mushrooms are made of. It's somewhat like cellulose - cellulose with an acetyl amine group (which is why fungal decomposition temporarily raids the soil of nitrogen.) It's tougher than cellulose (but not as tough as chitinous arthropod exoskeleton, which have some extra stuff larded in.)

Contrary to popular belief, we do have enzymes to break up chitin. I am pretty sure that you can digest raw mushrooms. Like plant material, of course it goes faster it's cooked, but it isn't as black and white as the internet quack story that's been going around.
Also, I would appreciate some clarification as to proportions of ibotenic acid to Muscimol. Percentage is expressed as a fraction of 100, so a ratio of 3 parts to 1 part is 300% not 30%. 30% would be expressed as a ratio of 3 to 10 not 3 to 1. Am I missing something here?
Not sure exactly what you're looking at, but if it's this -
only about 30% maximum of the ibotenic acid present in amanita tissue is decarboxylated to muscimol by air drying under the best conditions
This leaves a ratio of 3 parts ibotenic acid/1 part muscimol present in the Amanita tissue.
There is indeed a mathematical problem with that, though I wouldn't put it the way you did. The problem is that if you can convert 30%, then you have at least a ratio of 70/30 if it was all ibotenic acid to start with; if there's any muscimol in the raw material, then the ratio is even lower, so there's no way to end up with 3:1.

Those two numbers may not have been meant to be applied that way, though. "Maximum ... under the best conditions" leaves room to suppose that a reasonably typical outcome might be something else altogether. If you were doing pretty well and got 23% conversion, and started with 100:1, you'd come pretty close to 3:1 result, and that may be the point here.

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Re: patent expired: decarboxylation of ibotenic acid in Amanita

Post by amanitadreamer » Fri Feb 28, 2020 3:40 pm

Sid_Hatrack wrote:
Thu Feb 27, 2020 7:00 pm
This is interesting information that I would like to hear more about it and hopefully with specifics regarding procedure.

Not to nitpick, but a few statements are unclear to me. The statement “since uncooked mushrooms are more difficult to digest than plant matter” seems contradictory. What plant matter is being talked about here? If it is the mushroom, then would not uncooked mushrooms be considered plant matter? So how could it be more difficult to digest if it is the same thing?

Also, I would appreciate some clarification as to proportions of ibotenic acid to Muscimol. Percentage is expressed as a fraction of 100, so a ratio of 3 parts to 1 part is 300% not 30%. 30% would be expressed as a ratio of 3 to 10 not 3 to 1. Am I missing something here?
Since plants and fungi are in completely different kingdoms, they are completely different living things. Plant cell walls are made of cellulose and sugars which are digestible by us. Mushroom cell walls are made of chitin which are not as easily digestible by us. You have to cook them to break them down before eating them. Also different mushrooms will affect us differently and some are more easily digestible than others. Some people do it easier than others and for some it can make them sick. In general, you gotta apply heat, break the cell wall, consume.

3 to 1 is 75% / 25%
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Re: patent expired: decarboxylation of ibotenic acid in Amanita

Post by amanitadreamer » Fri Feb 28, 2020 3:45 pm

Donn wrote:
Fri Feb 28, 2020 2:08 am
Sid_Hatrack wrote:
Thu Feb 27, 2020 7:00 pm
The statement “since uncooked mushrooms are more difficult to digest than plant matter” seems contradictory. What plant matter is being talked about here? If it is the mushroom, then would not uncooked mushrooms be considered plant matter? So how could it be more difficult to digest if it is the same thing?
That may be about chitin, which is largely what mushrooms are made of. It's somewhat like cellulose - cellulose with an acetyl amine group (which is why fungal decomposition temporarily raids the soil of nitrogen.) It's tougher than cellulose (but not as tough as chitinous arthropod exoskeleton, which have some extra stuff larded in.)

Contrary to popular belief, we do have enzymes to break up chitin. I am pretty sure that you can digest raw mushrooms. Like plant material, of course it goes faster it's cooked, but it isn't as black and white as the internet quack story that's been going around.
Also, I would appreciate some clarification as to proportions of ibotenic acid to Muscimol. Percentage is expressed as a fraction of 100, so a ratio of 3 parts to 1 part is 300% not 30%. 30% would be expressed as a ratio of 3 to 10 not 3 to 1. Am I missing something here?
Not sure exactly what you're looking at, but if it's this -
only about 30% maximum of the ibotenic acid present in amanita tissue is decarboxylated to muscimol by air drying under the best conditions
This leaves a ratio of 3 parts ibotenic acid/1 part muscimol present in the Amanita tissue.
There is indeed a mathematical problem with that, though I wouldn't put it the way you did. The problem is that if you can convert 30%, then you have at least a ratio of 70/30 if it was all ibotenic acid to start with; if there's any muscimol in the raw material, then the ratio is even lower, so there's no way to end up with 3:1.

Those two numbers may not have been meant to be applied that way, though. "Maximum ... under the best conditions" leaves room to suppose that a reasonably typical outcome might be something else altogether. If you were doing pretty well and got 23% conversion, and started with 100:1, you'd come pretty close to 3:1 result, and that may be the point here.
Hey don, How's your organic chemistry? I have a quandry.
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Re: patent expired: decarboxylation of ibotenic acid in Amanita

Post by Donn » Fri Feb 28, 2020 7:56 pm

amanitadreamer wrote:
Fri Feb 28, 2020 3:45 pm
Hey don, How's your organic chemistry? I have a quandry.
It was somewhat elementary in the mid '70s, probably hasn't improved with age.

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