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licue
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Registered: 07/21/06
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Re: Psilocybin as an evolutionary bi-product? [Re: Zen Peddler]
#6324781 - 12/01/06 03:40 PM (17 years, 5 months ago) |
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Quote:
bluemeanie said: you could argue bothways with this one. Mushroom poisons in mushrooms like amanitas, etc, are not fast acting - so are not designed to be deterent - whether an animal/dumb human realises the connection between their kidney and liver failure and the mushrooms they ate two days beforehand doesnt really matter as they will die and will not live on to eat further mushrooms.
I'm not sure how you arrive at the conclusion that killing your predator is not a deterrent?
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VampireSlayer
killing ghosts,zombies andvampires forlife


Registered: 08/26/06
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Re: Psilocybin as an evolutionary bi-product? [Re: licue]
#6340993 - 12/06/06 03:19 PM (17 years, 5 months ago) |
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magic mushrooms came from aliens
-------------------- I Don't come to fight flesh and blood but spiritual wickedness in high and low places
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shroomydan
exshroomerite


Registered: 07/04/04
Posts: 4,126
Loc: In the woods
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Re: Psilocybin as an evolutionary bi-product? [Re: Blek]
#6341401 - 12/06/06 05:12 PM (17 years, 5 months ago) |
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Quote:
Blek said:
Is it by coincidence that magic mushrooms, which arguably spread environmental awareness only grow in places where there is environmental devastation? I think not. Mother Earth's way of sending a message perhaps? The same laws that govern the Universe govern our planet, Earth as well.

These potent Psilocybes that shroomydan originally identified as Psilocybe caerulipes but are now thought by Guzman to be a new species have taken a liking to Japanese Knotweed (Polygonum cuspidatum), an invasive Asian species that was introduced to North America as an ornamental but escaped cultivation and is now crowding out native species of plants and animals along the edges of many of our streams and rivers. It seems with the ecological threat comes a metaphysical warning.
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VampireSlayer
killing ghosts,zombies andvampires forlife


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Re: Psilocybin as an evolutionary bi-product? [Re: shroomydan]
#6341442 - 12/06/06 05:21 PM (17 years, 5 months ago) |
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wait so psilocybes from asia are invading america at an alarming rate? hell yea bring them on!
-------------------- I Don't come to fight flesh and blood but spiritual wickedness in high and low places
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shroomydan
exshroomerite


Registered: 07/04/04
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Re: Psilocybin as an evolutionary bi-product? [Re: VampireSlayer]
#6341538 - 12/06/06 05:37 PM (17 years, 5 months ago) |
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I don't know where Bluefoot came from, but the plant he likes to grow under came from asia, and the mushroom seems to have tagged along for the ride.
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Chemiker
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Re: Psilocybin as an evolutionary bi-product? [Re: shroomydan]
#6346817 - 12/08/06 01:46 AM (17 years, 5 months ago) |
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Most plants and fungi make small molecules.
It's hard to avoid teliological explanations, but small molecules do serve as a a deterrent against the plant being eaten because any organism ingesting them has to detoxify them. Thus, organisms that produce a wide variety of small molecules would be selected for.
I am not aware of many genetic analyses having been done on cubies or any psiloc(yb)in bearing mushrooms. I only have one article detailing the identification of different strains through a genetic analysis.
I also have not seen any detailed studies on the genes involved in psiloc(yb)in production, metabolism, etc. Without an understanding of the biochemical processes involved in psiloc(yb)in regulation, then it is hard to say what role the substance plays in the organism.
Ergot, on the other hand, has been studied to death and the biosynthetic pathway and genes and such involved in ergot alkaloid production are well characterized.
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fastfred
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Re: Psilocybin as an evolutionary bi-product? [Re: Chemiker]
#6347867 - 12/08/06 12:04 PM (17 years, 5 months ago) |
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Psilocybin isn't really a "small molecule". It would be interesting to study the pathway and figure out what other uses the involved enzymes might have.
TDC is present in quite a few organisms and isn't specific to fungi. 4-hydroxylase seems fairly nonspecific and might have some other use in the fungi. N-methylase also seems like it would be useful for other reactions, but adding carbon to nitrogen seems somewhat energy wasteful and would seem to be counterproductive in relation to consuming nitrogen.
Such potent psychoactives probably have their own evolutionary reasons simply due to the fact that they are potent, and so they certainly cause evolutionary effects and affect selection. Terrence McKenna theorizes that man has been using mushrooms as long as 150,000 years, possibly much longer. That is plenty of time to have greatly affected mushroom evolution. The fact is that mushrooms enjoy their current status because of the attractant properties of psilocybin, and it may have been helping them for as long as 150,000 years. There's no reason to think that this hasn't been the case for the majority of time that psilocybin has been on this earth.
-FF
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creamcorn
mad scientist


Registered: 03/13/06
Posts: 2,962
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Re: Psilocybin as an evolutionary bi-product? [Re: fastfred]
#6348023 - 12/08/06 01:10 PM (17 years, 5 months ago) |
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Quote:
fastfred said: TDC is present in quite a few organisms and isn't specific to fungi. 4-hydroxylase seems fairly nonspecific and might have some other use in the fungi.
This would be the enzyme that reverts psilocybin back to psilosin, correct? My apologies if its a dumb question, chemistry terms boggle my mind... i know -ase=enzyme then my eyes glaze over 
If that's not it... I know there is one... any information on the process by which that happens? (ff i'm looking at you, i can manage to understand what you've got to say most of the time ) I can look at your avatar and grasp how you come to those conclusions there and follow the process, just trying to picture the reaction in the case of psilocybin being reverted back into psilosin in the fruitbody, the by-products, how its split up, etc
I'm a bit out of my element to even be discussing this so again my apologies if it sounds silly or elementary... but my theory is this:
psilocybin is just a "carrier" of phosphorus... its attached to compounds closely related to simple amino acids found in the substrates it grows on and in the process we end up with something that just so happens to be psychoactive in humans. DNA production requires phosphorus, does it not? pyschoactive mushrooms have the ability to produce psilocybin, and have then also contain enzymes to strip that phosphorus off as part of the process by which its reverted back to psilosin again (which is the reaction i'm wondering about, does it really leave a free phosphorus?) psilocybin is also easily soluble in water. so its my thinking that the psilocybin is produced, "dissolved" in water that's pumped up into the fruitbody, esentially allowing it to travel from the mycelial network base up to the cap of the mushroom. up there, the phosphorus is stripped off, and then used in DNA production... spores are little DNA packets after all, and they're produced up top there. as for the psychoactive aspect then, i believe its just coincidence that its so similar to our own neurotransmitters - if there's a "greater purpose" that led to that coincidence, perhaps in the spiritual realm or what have you, is up to your interpretation i suppose...
it just for the most part fits with things we anecdotally observe about mushrooms... consider the following:
-psilocybin production doesn't seem to really ramp up to appreciable levels until fruits are developing. we know there's little to be found in mycelium prior to fruiting. that makes me believe its not "needed" by the organism until mushrooms are growing. if it were some sort of evolutionary protection/defense mechanism i'd think it would be formed from the get-go. by the time its fruiting its likely overcome most "predators" and some fruitbodies are bound to make it far enough to drop spores (reproduce), doesn't seem to me they need a whole lot of protection given their brief lifespan... and anyway, wouldn't a poison be a more effective deterrent than a hallucinogen? 
-many believe potency is best just prior to spore production (hence the tradition of harvesting as the viel tears)... a question here is, is there any data that takes into account specifically and separately BOTH psilocybin and psilosin, studying concentrations before and after spore production? by my theory and intuition i'd wager high psilocybin/low psilosin prior to spore production, and the reverse - low psilocybin/high psilosin after spore production. bioassay of fresh fruits is of little value here because assuming not much oxidation has occurred the perceptible difference would be negligible, since both are active... though along the same lines it could be said that over-mature mushrooms then lose a greater deal of potency when dried/stored since the psilosin is vulnerable to oxidation
so questions that this leaves me with,
if this is really how it works, then why the difference with non-active mushrooms? where might they get their phosphorus from for spore formation? are there any other non-psychoactive compounds/reactions that would parallel this "shipping" of phosphorus to the spore production site?
how does this jive across the range of psilo* containing species? can we find correlations between the physical mushroom cap sizes and the spore loads they produce with the different psilosin/psilocybin ratios they're thought to contain? if my idea is to be true those that produce the greatest number of spores would be expected to be higher in psilosin and lower in psilocybin... less spores, less dna, therefore less phosphorus is gonna be needed, and therefore not so much of the reverting from psilocybin back to psilosin
-last but not least, why else would the mushroom have the ability to convert from one to the other? there *must* be a purpose to that! i think that stomps on the "defense mechanism" idea a little more. if it was for defense it would only need one or the other, not both? (if both were achieved in the first place due to incomplete reactions i could see maybe - and that may be the source of where some of the related compounds come from, but here's we're talking a deliberate ability to convert one to the other.)
again sorry if i botched up most of that but hopefully i convey the point without too many holes or technical inaccuracies in my theory, but if it makes sense maybe somebody who knows more about it could elaborate and help me develop that theory?
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fastfred
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Re: Psilocybin as an evolutionary bi-product? [Re: creamcorn]
#6348225 - 12/08/06 02:48 PM (17 years, 5 months ago) |
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>chemistry terms boggle my mind... i know -ase=enzyme then my eyes glaze over

Tryptophan is a basic amino acid. TDC (tryptophan decarboxylase) decarboxylates tryptophan to tryptamine. Tryptamine is N-methylated to N-methyltryptamine and then again to N,N-dimethyltryptamine (DMT). DMT is then 4-hydroxylated to psilocin. Psilocin is then phosphorylated to psilocybin.
So it's decarboxylation, N-methylation, N-methylation, 4-hydroxylation, and phosphorylation.
The decarboxylation is the only step that has been nailed down for sure, the others are just the proposed, and most reasonable, mechanism. TDC and phosphorylase are the only characterized enzymes in the process. We say there is also N-methylase and 4-hydroxylase because it's just assumed that there are enzymes catalyzing the reactions.
4-hydroxylase is interesting because it 4-hydroxylates many indole substances. It's somewhat odd to hydroxylate in the 4 position.
To get from psilocin to psilocybin the psilocin is phosphorylated to psilocybin. That's pretty normal, many things (like base pairs) get phosphorylated all the time. It's a phosphorous backbone that connects all the base pairs in DNA and RNA.
DNA and RNA need to get snipped up all the time also, so it's not strange that there are a lot of dephosphorlation reactions going on. Phosphatases are the enzymes that dephosphorylate molecules. When tissue damage happens it's not surprising that phosphatase runs wild and starts dephosphorylating things like psilocybin.
So it seems pretty normal to me that hydroxyl groups get phosphorylated and that phosphate gets dephosphorylated from free molecules, especially ones that aren't incorporated into a larger phosphate backboned molecule like DNA.
So I don't really see much in the theory that psilocin is some sort of phosphate transport mechanism because the same reactions would occur anyways.
Psilocybin is a potent molecule, so once it came into being it was certainly capable of affecting selection by itself and doesn't need any biochemical pathway explanation to justify it's continued existence. I don't think it serves any useful purpose biochemically.
-FF
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creamcorn
mad scientist


Registered: 03/13/06
Posts: 2,962
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Re: Psilocybin as an evolutionary bi-product? [Re: fastfred]
#6348358 - 12/08/06 03:36 PM (17 years, 5 months ago) |
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Quote:
fastfred said: 4-hydroxylase is interesting because it 4-hydroxylates many indole substances. It's somewhat odd to hydroxylate in the 4 position.
so in other words, i have it backwards, 4-hydroxylase "adds" the 4-hydroxyl group, it doesn't take it away? and just to make me understand the terms, the reverse would be 4-dehydroxylase? (not that there's necessarily such a thing, but assuming there is that's how it would be named based on convention?)
this sounds like one of those things that i understand juuust enough to be totally wrong about it... like someone who just learned how to delete files on their computer erasing all their system files to "save space" (haha sorry thats an analogy in a field i actually work in)
Edited by creamcorn (12/08/06 03:43 PM)
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fastfred
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Re: Psilocybin as an evolutionary bi-product? [Re: creamcorn]
#6349899 - 12/09/06 01:18 AM (17 years, 5 months ago) |
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Yep. Enzymes are named to best characterize their activity. Sometimes it can get confusing like phosphorylase and phosphatase. They name it phosphatase because it creates a phosphate, rather than dephosphorylase.
If it turns out that 4-hydroxylase only works on indoles they'll probably call it indole 4-hydroxylase. And N-methylase might be two different enzymes, one for each step. They would probably call them N-methylase and N,N-dimethylase.
> 4-hydroxylase "adds" the 4-hydroxyl group, it doesn't take it away?
Yep. I'll redo my diagram when I have some extra time. There are a couple errors in it... I think the baeocystin is in the wrong place and I want to try to fit everything in a little nicer and add norbaeocystin. I've also been back and forth on the structure of psilcybeen, but I'm pretty sure it's right.
The psilocin/psilocybin ratio issue is an interesting one. Most of the literature is a little wacked out and can't be effectively compared because everyone used different extraction methods and a lot of them falsely increase the psilocin content because they either selectively extract (acid-base extractions) or they let phosphatase convert too much psilocybin to psilocin during the extraction.
-FF
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Acinaxuz
In SomnisVeritas.

Registered: 06/20/06
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Re: Psilocybin as an evolutionary bi-product? [Re: fastfred]
#6370349 - 12/14/06 01:03 PM (17 years, 5 months ago) |
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I haven't read the entire post, haven't really had the time.
I did a post a few months back about tryptamines, and the purpose of psilocin/psilocybin. According to research, more evidence points to the purpose being like that of our own serotonin --regulating cycles-- as opposed to a defense system. Though, I will say that in regulating cycles in mushrooms, the end result is the dropping of the spores, it's the last punch in the cycle, and is no longer needed post spreading it's seed.
Just my take
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Chemiker
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Re: Psilocybin as an evolutionary bi-product? [Re: fastfred]
#6370484 - 12/14/06 01:38 PM (17 years, 5 months ago) |
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Quote:
fastfred said: Psilocybin isn't really a "small molecule".
It certainly is a small molecule. Of all the molecules that living organisms make, molecules that are the size of monomeric units of biomacromolecules like proteins are definitely small. No matter how you slice it, on any scale, psilocybin is a small molecule. Even a small polypeptide is many times larger than psilocybin.
Quote:
It would be interesting to study the pathway and figure out what other uses the involved enzymes might have.
Yes. If the enzymes involved only produce psilocybin, then cells are expending a lot of energy just to produce psilocybin. If, on the other hand, the enzymes involved catalyze a large number of reactions, then psilocybin suddenly wouldn't seem to be such an important part of the mushroom .
Quote:
but adding carbon to nitrogen seems somewhat energy wasteful and would seem to be counterproductive in relation to consuming nitrogen.
Such potent psychoactives probably have their own evolutionary reasons simply due to the fact that they are potent, and so they certainly cause evolutionary effects and affect selection. Terrence McKenna theorizes that man has been using mushrooms as long as 150,000 years, possibly much longer. That is plenty of time to have greatly affected mushroom evolution. The fact is that mushrooms e
Some have suggested that the role of psilocybin is merely to carry away excess nitrogen, though I think this explanation is not considered likely.
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fastfred
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Re: Psilocybin as an evolutionary bi-product? [Re: Chemiker]
#6377583 - 12/16/06 06:47 PM (17 years, 5 months ago) |
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Quote:
Chemiker said: It certainly is a small molecule. Of all the molecules that living organisms make, molecules that are the size of monomeric units of biomacromolecules like proteins are definitely small. No matter how you slice it, on any scale, psilocybin is a small molecule. Even a small polypeptide is many times larger than psilocybin.
I disagree. That would be like saying that lake Superior is small because the ocean is many times it's size.
You can't compare any normal monomeric molecule to a massive polymeric biomolecule like polypeptides or nucleic acids. If you did that you'd have to then say that some DNA and polypeptides are "small" and that other's are large compared to other macromolecules. With that reasoning anything with a MW of 10,000 or less would have to be considered "small" and you'd have to say that psilocybin isn't just small it's minuscule.
I'm not saying that psilocybin is a particularly large molecule, but I wouldn't call it small. Comparing it with other biomolecules that play important roles you can't call it large. But you have to compare it to other molecules in the same process. It's obviously the largest molecule in the psilocybin pathway, and since that's usually what we're talking about you could say it was somewhat large since it's bigger than the other molecules we usually talk about. We're usually talking about solvents, nutrients, precursors, and other additives. In that context it is a larger molecule.
When I think of most molecules I've dealt with in chemistry I always consider it a medium sized molecule. Compared to other psychedelics it's not really that small either. It's larger than serotonin, and it's similar in size to many other related biomolecules, psychedelics, etc..
You just jumped an entire scale to think of it as small.
-FF
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Chemiker
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Re: Psilocybin as an evolutionary bi-product? [Re: fastfred]
#6378351 - 12/17/06 12:09 AM (17 years, 5 months ago) |
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I disagree. That would be like saying that lake Superior is small because the ocean is many times it's size.
That's kind of a flawed analogy. Psilocybin MW: 284. That's 142 times larger than the smallest molecule, H2. How many times larger is that lake than the smallest body of water?
It doesn't really matter, but I consider it a small molecule. Molecules can't get much smaller. I mean, sure, it's not hydrogen gas, but it's small. Even as an organic chemist, I consider this a small molecule. In an article I just posted about LSD binding to 5HT2A, the authors call serotonin a small molecule. This just seems to be what it would be called by convention, so that's what I'm going by. Also, I'm an x-ray crystallographer and we commonly refer to two types of crystallography: one of them is "small molecule" crystallography and psiloc(yb)in would definitely fall into that category.
Please don't tell me what my logic is, okay? I consider it a small molecule. If you don't want to, then that's fine. Anyway, it doesn't matter. I think it's small. You don't. Big deal.
[just so we're clear: I call myself both an organic chemist and a crystallographer - most of my background is in organic chemistry and I've worked in organic synthesis. At heart, I consider myself an organic chemist. Currently, I'm an x-ray crystallographer and I don't do small molecules ]
PS - if this starts an argument, I'll delete this, because the judgement is subjective and I don't give a fuck if you call it large or small. That's what I calls it.
I'm curious: what is the difference between an evolutionary product and an evolutionary byproduct supposed to be?
there we go, now my post has purpose.
Edited by Chemiker (12/17/06 12:39 AM)
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RigaCrypto
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Re: Psilocybin as an evolutionary bi-product? [Re: Chemiker]
#6378505 - 12/17/06 02:05 AM (17 years, 5 months ago) |
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Re: the defense mechanism theory, I think it could only be resolved by "proper" scientific studies involving several species the mushroom has or might have had contact with in its evolutionary past. A similar situation exists with Erithroxylum Coca. The vegetal matter is benign to higher animals (including humans) and is actually eaten by some (including monkeys and llamas).
Coca leaves though are very toxic to insects that presumably tried to nibble on them in the plant's evolutionary past. It seems that cocaine inhibits the reuptake of octopamine, a neurotransmitter found in invertebrates, with a much higher efficiency than it does dopamine.
http://www.pubmedcentral.nih.gov/picrender.fcgi?artid=47626&blobtype=pdf
In a similar fashion, psiloc(yb)in might have evolved as a specific defense against certain species which threatened the mushroom. But with research hindered by its illegal status, no wonder that such studies haven't been conducted.
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Chemiker
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Re: Psilocybin as an evolutionary bi-product? [Re: RigaCrypto]
#6383660 - 12/18/06 03:52 PM (17 years, 5 months ago) |
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I've always just figured that it couldn't cost much energy for an organism to allow a metabolic intermediate build up in concentration. If this had helped organisms in the past, since some of those metabolic intermediates would be toxic to predatory organisms, then what would prevent an organism like psilocybe cubensis or the like from doing the same with psilocybin?
After all, evolution is a selective editing process, so if it doesn't harm the organism, there doesn't necessarily need to be a reason, other than that it worked for other organisms and wasn't selected against.
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pokermush
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Been thinking about this a lot [Re: Chemiker]
#6390099 - 12/20/06 12:37 PM (17 years, 4 months ago) |
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I've read the whole thread, but forgive me if I forgot something that was already covered.
Ever since I started learning about psilocybe mushrooms, I've been intrigued by how/why they developed the way they did. Shrooms are odd because they produce (mostly) desired hallucinogenic effects, yet they cause undesired nausea. These seem to be at odds, but they really aren't.
It isn't difficult to see how animals would associate the mushrooms with their hallucinogenic effects. Pets and small children are known to seek psilocybin mushrooms after trying them. The nausea, it seems to me, merely provides the mushroom with an additional propogation opportunity when consumed. Spores may not survive digestion, and if they do, the resulting shit might not be an adequate growing environment. Vomit is a different story. Yes it will be acidic, but will likely provide an ideal nutrient base for the mushroom to grow. The acidity might also serve as a sterilizing agent, giving the mushroom an advantage over competing bacteria/fungi. After the vomit, some spores are likely to remain in the digestive system so they can be deposited elsewhere.
From the perspective of the animal, they eat the mushroom (negative taste), experience nausea (another negative), then experience the hallucinogenic effects of the mushroom (the desired benefit). Observation shows us that the hallucinogenic benefits of the mushroom are enough to bring the animal back to the mushroom again and again. And each time (before the advent of sewers) the mushroom benefits by having its spores deposited in new, nutrient-rich environments.
It seems that amanita muscaria, which also causes nausea but provides hallucinations, employs the same strategy.
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Chemiker
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Re: Been thinking about this a lot [Re: pokermush]
#6390769 - 12/20/06 03:10 PM (17 years, 4 months ago) |
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pokermush said: Shrooms are odd because they produce (mostly) desired hallucinogenic effects, yet they cause undesired nausea. These seem to be at odds, but they really aren't.
It's not odd at all according to the mechanics of evolution. Mushrooms can't intend to produce chemicals for our ingestion, so it's possible for any organism to produce a chemical that we either find very desirable, very undesirable, or somewhere in between.
Pets and small children are known to seek psilocybin mushrooms after trying them.
Reference for you claim about pets and small children? Everything I've read indicates that animals DO NOT self administer hallucinogens, including psilocybin.
The nausea, it seems to me, merely provides the mushroom with an additional propogation opportunity when consumed.
?
Vomit is a different story. Yes it will be acidic, but will likely provide an ideal nutrient base for the mushroom to grow.
Are you at all sure about this?
From the perspective of the animal, they eat the mushroom (negative taste)
Speak for yourself. I love the taste of shrooms. I don't see why you should presume that all animals dislike the taste.
then experience the hallucinogenic effects of the mushroom (the desired benefit).
I don't think it's reasonable to assume that animals would find being under the influence of a hallucinogen beneficial. Humans are the only animals known to self-administer psilocybin bearing mushrooms, so it seems that the cognitive effects are only desired by humans. From an animal's point of view, being intoxicated on a hallucinogen for 4 to 6 hours could be seriously dangerous.
Observation shows us that the hallucinogenic benefits of the mushroom are enough to bring the animal back to the mushroom again and again.
This is the first time I've ever heard of anybody making such an observation. Do you have any credible sources to back that up?
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pokermush
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Re: Been thinking about this a lot [Re: Chemiker]
#6390877 - 12/20/06 03:39 PM (17 years, 4 months ago) |
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I've read so many different things, I don't remember exactly where I read that pets had been observed eating psilocybin mushrooms. I think it was in one of my books, but I'm not sure. If I find it again I'll post here. Basically, it said that pets (dogs) had been observed seeking and eating hallucinogenic mushrooms. Is there any reason to think that an animal consuming shrooms wouldn't enjoy the experience? Even if it might leave the animal more susceptible to danger, if the animal enjoys the experience it will come back for more.
I know that organisms can't intend to evolve anything. But in general, only traits which enhance survival/reproduction persist. That suggests that psilocybin directly contributes to the survival and/or propogation of the mushroom.
I don't know that vomiting would be an effective way of distributing spores to a new location. That is speculation on my part. However, imagining a stomach of partially digested seeds, roots, grasses, leaves, vegetables, or fruits, it's easy to see how those stomach contents could provide an excellent growing environment. I would expect the mushrooms to grow well from the natural vomit and dung of most animals.
Basically, I'm hypothesizing about how the psychedelic properties and the nasea-inducing properties of psilocybe mushrooms would provide a significant evolutionary advantage.
Edit: I had read so often on here that people can't stand the taste that I just assumed they taste bad. You're right about the taste. I ate my first ones a few hours ago and they tasted great! I would eat them just for the taste even if they had no psychoactive properties.
Edited by pokermush (12/21/06 01:06 AM)
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