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OfflineLoveLightPeace
Male


Registered: 08/26/11
Posts: 286
Last seen: 5 years, 1 day
Question about the molecular structure of psilocin and psilocybin
    #18740872 - 08/22/13 04:15 AM (10 years, 6 months ago)

Are both psilocin and psilocybin structurally related to serotonin or just one of the two?


--------------------
I am so small I can barely be seen.
How can this great love be inside me?

Look at your eyes. They are small,
but they see enormous things.

(Rumi)


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OfflineDystopianUtopia
The Psilocybin Experience
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Registered: 07/13/12
Posts: 19
Loc: United Kingdom
Last seen: 8 years, 11 months
Re: Question about the molecular structure of psilocin and psilocybin [Re: LoveLightPeace]
    #18740966 - 08/22/13 05:37 AM (10 years, 6 months ago)

Psilocybin and psilocin are both structurally related to serotonin.

Psilocin is 4-hydroxy-N,N-dimethyl-tryptamine
Psilocybin is 4-phosphoryl-hydroxy-N,N-dimethyltryptamine
Serotonin is 5-hydroxy-N,N-dimethyltryptamine.

The only different between psilocin (which the psilocybin is metabolised into anyway) and serotonin is that the hydroxy group is moved from the 4 to the 5 position on the indole ring, and psilocin has two additional methyl groups are attached to the nitrogen atom.

The only different between psilocin and psilocybin is the addition of the phosphoryl group at the 4 position.

They all share the same basic structure, the tryptamine structure. This is an indole ring with an ethyl group in the 3 position attached to an amine (NH2).

Look up indole and tryptamine on wikipedia to get a better understanding. They're all very similar molecules.

Hope this helps.


--------------------
“Psychedelics are illegal not because a loving government is concerned that you may jump out of a third story window. Psychedelics are illegal because they dissolve opinion structures and culturally laid down models of behaviour and information processing. They open you up to the possibility that everything you know is wrong.” - Terence McKenna


Edited by DystopianUtopia (08/22/13 05:39 AM)


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OfflineAgentchewy
Pantheism.
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Registered: 12/12/12
Posts: 3,960
Loc: vietnam Flag
Last seen: 1 year, 5 months
Re: Question about the molecular structure of psilocin and psilocybin [Re: DystopianUtopia]
    #18740975 - 08/22/13 05:45 AM (10 years, 6 months ago)

Doesn't it blow your mind that a mushroom used for centuries if not millennia for sacrament is actually more closely related to us than any other non animal source,

Not in the sense of being related directly but the sheer fact the chemicals could be synthesized from one another shows how little we really know of the purpose psilocybin has in nature.


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If I knew the way, I would take you home.


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OfflineDystopianUtopia
The Psilocybin Experience
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Registered: 07/13/12
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Loc: United Kingdom
Last seen: 8 years, 11 months
Re: Question about the molecular structure of psilocin and psilocybin [Re: Agentchewy]
    #18741018 - 08/22/13 06:18 AM (10 years, 6 months ago)

Quote:

Agentchewy said:
Doesn't it blow your mind that a mushroom used for centuries if not millennia for sacrament is actually more closely related to us than any other non animal source,





It's fun to think about I guess. There are chemicals more similar to serotonin than those in shrooms, believe it or not. Bufotenin, aka 5-HO-DMT is just serotonin with two methyl groups added. Hence, it's often refereed to as dimethyl-serotonin.

While I'm always open to entertaining the possibly, I don't think it's indicative of anything supernatural or paranormal.
We know the purpose of many other indoles both in animals and plants, and given that plants are often synthesizing indoles, it's quite conceivable that they could synthesize something that is psychoactive in humans or similar to our brain chemistry without them having any purpose which concerns their psychoactivity in animals, given that plants and animals both use similarity structure chemicals for their survival.

It's either that, or their psychoactivity gives them some evolutionary advantage. If all the animals eating X mushroom have terrifying trips, those animals are going to avoid mushrooms. Or, on the other hand, if humans enjoy and worship taking X DMT containing plant with an MAOI, those plants are going to be spread by humans which rapidly speeds up their evolution.

Most of this stuff can be explained with reference to evolution, and Ockham's razor seems to suggest this is the most likely explanation.

But you never know...


--------------------
“Psychedelics are illegal not because a loving government is concerned that you may jump out of a third story window. Psychedelics are illegal because they dissolve opinion structures and culturally laid down models of behaviour and information processing. They open you up to the possibility that everything you know is wrong.” - Terence McKenna


Edited by DystopianUtopia (08/22/13 06:20 AM)


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OfflineKingKnowledge
Around
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Registered: 03/30/13
Posts: 2,876
Loc: East Coast
Last seen: 4 years, 7 months
Re: Question about the molecular structure of psilocin and psilocybin [Re: DystopianUtopia]
    #18741316 - 08/22/13 09:13 AM (10 years, 6 months ago)

It's very interesting to think that all we are is chemicals. We can ingest food/things that contain similar chemicals to those found in our brain; similar enough to fit the lock and key!

Everything that we know about our reality is just because we were born with this set of chemicals that react and do things in our brains every second. If we were born in a different set of circumstances, we would think completely different about our world. Science is only created to explain the unknown based on what we can observe, so if we observed different things with different neurotransmitters, our entire understanding of life/science would change!!


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OfflineLoveLightPeace
Male


Registered: 08/26/11
Posts: 286
Last seen: 5 years, 1 day
Re: Question about the molecular structure of psilocin and psilocybin [Re: KingKnowledge]
    #18744788 - 08/22/13 10:37 PM (10 years, 6 months ago)

Thnx alot Dystopianutopia!:smile:


--------------------
I am so small I can barely be seen.
How can this great love be inside me?

Look at your eyes. They are small,
but they see enormous things.

(Rumi)


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OfflineCatchThirtythr33
Pineal Gland Optics

Registered: 05/03/13
Posts: 214
Loc: Canada Flag
Last seen: 5 years, 2 months
Re: Question about the molecular structure of psilocin and psilocybin [Re: DystopianUtopia]
    #18744814 - 08/22/13 10:42 PM (10 years, 6 months ago)

Quote:

DystopianUtopia said:
Psilocin is 4-hydroxy-N,N-dimethyl-tryptamine
Psilocybin is 4-phosphoryl-hydroxy-N,N-dimethyltryptamine
Serotonin is 5-hydroxy-N,N-dimethyltryptamine.





Not to pry, and correct me if I'm wrong but isn't serotonin 5-hydroxytryptamine (5-HT)?


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Offlineressa69
Stranger
Registered: 07/15/13
Posts: 143
Last seen: 10 years, 2 months
Re: Question about the molecular structure of psilocin and psilocybin [Re: DystopianUtopia]
    #18747056 - 08/23/13 12:16 PM (10 years, 5 months ago)

Quote:

DystopianUtopia said:
Quote:

Agentchewy said:
Doesn't it blow your mind that a mushroom used for centuries if not millennia for sacrament is actually more closely related to us than any other non animal source,





It's fun to think about I guess. There are chemicals more similar to serotonin than those in shrooms, believe it or not. Bufotenin, aka 5-HO-DMT is just serotonin with two methyl groups added. Hence, it's often refereed to as dimethyl-serotonin.

While I'm always open to entertaining the possibly, I don't think it's indicative of anything supernatural or paranormal.
We know the purpose of many other indoles both in animals and plants, and given that plants are often synthesizing indoles, it's quite conceivable that they could synthesize something that is psychoactive in humans or similar to our brain chemistry without them having any purpose which concerns their psychoactivity in animals, given that plants and animals both use similarity structure chemicals for their survival.

It's either that, or their psychoactivity gives them some evolutionary advantage. If all the animals eating X mushroom have terrifying trips, those animals are going to avoid mushrooms. Or, on the other hand, if humans enjoy and worship taking X DMT containing plant with an MAOI, those plants are going to be spread by humans which rapidly speeds up their evolution.

Most of this stuff can be explained with reference to evolution, and Ockham's razor seems to suggest this is the most likely explanation.

But you never know...




You are on the right track. Even insects use the same neurotransmitters as humans do. So it is possible that the compound arose as a deterrent for any number of species.

I can personally attest that when my cat is taking them frequently, he cannot stand the smell, Taste, and even the thought of them makes his innards spin. Impossible to say exactly what selective pressures drove the evolution of these mushrooms, but we can at least agree that it was not by divine will, as illustrated above.


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