|
Some of these posts are very old and might contain outdated information. You may wish to search for newer posts instead.
|
Ped
Interested In Your Brain



Registered: 08/30/99
Posts: 5,494
Loc: Canada
Last seen: 7 years, 2 months
|
Re: Guess The Fungi/Mushroom Chemical ! [Re: Blind fool]
#21035379 - 12/28/14 12:51 PM (9 years, 1 month ago) |
|
|
>> Arsphenamine-pentamer?
That's the one!
--------------------
Dark Triangles - New Psychedelic Techno Single - Listen on Soundcloud Gyroscope full album available SoundCloud or MySpace
|
The Lightning
Mycology Enthusiast


Registered: 09/06/11
Posts: 3,889
|
Re: Guess The Fungi/Mushroom Chemical ! [Re: Ped]
#21035562 - 12/28/14 01:50 PM (9 years, 1 month ago) |
|
|
Ok. Here's a new one.
Try to get the chemical, the mushroom species, and lay down a statement that explains something about either the covalent bond(s) or the molecular structure. Teach!

Here it is again in 3-D:
|
RuralAnomaly
Sporadic



Registered: 10/05/13
Posts: 2,153
Loc: Spitzenkörper Ohio
|
Re: Guess The Fungi/Mushroom Chemical ! [Re: Ped]
#21035583 - 12/28/14 01:55 PM (9 years, 1 month ago) |
|
|
i don't know what that one is......... 
but it looks like a KEY to open SOMETHING lol
i realized i shoulda done the asking belatedly... less werk. but i have a good question ready once we're finished with this one. i'm still opting out for the moment. just checked in to see what was up.
|
RuralAnomaly
Sporadic



Registered: 10/05/13
Posts: 2,153
Loc: Spitzenkörper Ohio
|
Re: Guess The Fungi/Mushroom Chemical ! [Re: RuralAnomaly]
#21046511 - 12/30/14 10:28 PM (9 years, 1 month ago) |
|
|
ok, i have a few minutes. i am really not close enough to this stuff anymore to be doing any real teaching about it but i'm totally on board with the spirit of the idea, so maybe it can be a guided discussion in which some other people might feel more comfortable participating, because quite honestly i haven't really thought about this stuff much for decades. literally decades. that said, here goes. anyone please feel free to jump in to correct me at any time, in fact i hope you do so i don't feel like i'm talking to myself.
ok so our target molecule is Psilocybin http://en.wikipedia.org/wiki/Psilocybin
looking at it and just thinking out loud from what i remember, the greater the number of double bonds, the more 'stiff' the structure is at those points, and if the bonds are distributed pi bonds it gives the overall thing more rigidity and fewer degrees of freedom. benzene is like a poker chip whereas cyclohexane is more like a soggy potato-chip.
covalent bonds share electrons as opposed to ionic bonds that more or less give up a proton when in solution and disassociate as ions in soluton (like salt becoming Na+ and Cl-.) So, if two different elements have a bond it is likely that the electron may spend more time hovering around one nucleus than another and this is what is known as a dipole, where one bit of something has more of a charge than the other bits. we see this when oxygen is attached to carbon, it gets a 'negative' bias around the oxygen, implying that the oxygen holds the electrons more tightly in its 'share'. Nitrogen contributes a bit of electron charge to a carbon bond so it has a positive bias.
the way the atoms are arranged in space in a molecule depends on a variety of factors - size of the atom is important for example, the number of electrons shared is another. bond angles are maximized to reduce repulsion between like charges on adjacent atoms and maximize vibrational freedom.
so, looking at our molecule from that perspective i would say that the cyclical fused rings rife with extra electrons zipping around and reducing bond lengths, are decreasing vibration and stretching and bending around and generally creating a more rigid structure that is not doing a lot of flipping about in shape.
it also has a big fat phosphate stuck on its electron rich hind end, which also donates some charge i imagine to the resonance structure in the rings, but also due to its rather large relative size (oxygens and phosphoruses have lots of big ass shells) and affinity for juice that its impact is also to draw some of that charge to itself and keep itself nicely negative.
this is in contrast to the other bit, which is a wiggly bit of carbon backbone with a nitrogen stuck on the end spinning like a top in a gale because it has no such restrictions on its greasy little self and is free to bend and do lewd hip gestures at Schrodinger's cat or whoever else happens to be watching.
this might be handy for sticking itself into whatever receptor site perhaps lined with nitrogen atoms that likes big ass kardashian-type phosphates rubbing up to it and has another 'socket' just waiting for something oily and vibrating to wave a positive charge over it to cause some effect or other.
most of the other hallucinogens are based on this model with various wobbly bits giving you different effects. same with amphetamines i believe as a side note. negatively charged poker chips with some warm wiggly grease on. mda and mdma are lovely little hybrids of the two ideas with results you might expect.
ok, this tutorial degenerated a bit cuz it was getting a little dry for my tastes, but is this what kind of approach you were looking for TL?
|
The Lightning
Mycology Enthusiast


Registered: 09/06/11
Posts: 3,889
|
Re: Guess The Fungi/Mushroom Chemical ! [Re: RuralAnomaly]
#21047910 - 12/31/14 09:29 AM (9 years, 1 month ago) |
|
|
Quote:
ok so our target molecule is Psilocybin http://en.wikipedia.org/wiki/Psilocybin
So close - but nope! I appreciate your elaboration on the molecule Psilocybin. It is helpful.
Quote:
is this what kind of approach you were looking for
I think I should NOT be the judge of another person's methods for teaching chemistry to others. I'm just as much of a student as you.
I do recommend two things to everyone:
1. Consider changing your Shroomery - Account - Display preferences (...) to reflect the following:

This should make this thread a little smoother to view.
2. When you post an answer, I recommend adding cool images and explaining things based on those images. Everyone, including the most intelligent people on the planet, loves images to learn with.
Here's a hint I gave RuralAnomaly via PM relating to the species of mushroom in the Guess: It is Psilocybe y________.
Here's another image of this species of mushroom:
|
RuralAnomaly
Sporadic



Registered: 10/05/13
Posts: 2,153
Loc: Spitzenkörper Ohio
|
Re: Guess The Fungi/Mushroom Chemical ! [Re: The Lightning]
#21051580 - 01/01/15 09:09 AM (9 years, 1 month ago) |
|
|
oops! Psilocin (also known as 4-HO-DMT)
you're right, for some reason i was thinking the phosphate was still on lol.
same holds as far as i know as far as my general description. please refine it TL.
Psilocybe yungensis
http://en.wikipedia.org/wiki/Psilocybe_yungensis
google tells me its the only psilocybe with a y
HAPPY NEW YEAR
may all your projects bear fruit
|
The Lightning
Mycology Enthusiast


Registered: 09/06/11
Posts: 3,889
|
Re: Guess The Fungi/Mushroom Chemical ! [Re: RuralAnomaly]
#21051645 - 01/01/15 10:03 AM (9 years, 1 month ago) |
|
|
Quote:
HAPPY NEW YEAR
may all your projects bear fruit
Thank you, RA! May your year also yield successes and new fruits!
Quote:
Psilocin (also known as 4-HO-DMT)
Yes!
Quote:
Psilocybe yungensis
http://en.wikipedia.org/wiki/Psilocybe_yungensis
Yes, again!

When someone eats an active (psilocybin) mushroom, psilocybin is quickly converted by the body to psilocin.
Chemically, psilocybin and psilocin are indole hallucinogens that block the action of serotonin (the indole amine transmitter of nerve impulses) in brain tissue. For this reason, I would consider the POSSIBILITY of serotonin syndrome (too much serotonin) or serotonin depletion. I would ponder on this when considering the side effects mentioned in the thread that discusses Psilocybe azurescens muscle soreness/absence of coordination, and even seizure.
The difference between Psilocybin and Psilocin, as you discussed, is the the presence or absence of a phosphate group attached to the Psilocybin molecule at the oxygen atom.
Here are the molecules again, sitting at a different angle:
|
The Lightning
Mycology Enthusiast


Registered: 09/06/11
Posts: 3,889
|
Re: Guess The Fungi/Mushroom Chemical ! [Re: The Lightning]
#21051712 - 01/01/15 10:23 AM (9 years, 1 month ago) |
|
|
There is also a Hydrogen atom bonded to a Nitrogen atom on the psilocybin molecule.

I'm sure we could further examine these two molecules and see at least one other difference!
|
The Lightning
Mycology Enthusiast


Registered: 09/06/11
Posts: 3,889
|
Re: Guess The Fungi/Mushroom Chemical ! [Re: The Lightning]
#21061688 - 01/03/15 03:35 PM (9 years, 1 month ago) |
|
|
This mushroom has anticancer, antimicrobial, and Radical Scavenging Capacity (abbreviated RSC).

Hints: The mushroom goes by at least two other names. You might end up reading Chinese to find this species. The chemical starts with a 2, (or its abbreviated version is four letters and starts with a D).
Final hint: "Stable free-radical molecules."
|
The Lightning
Mycology Enthusiast


Registered: 09/06/11
Posts: 3,889
|
Re: Guess The Fungi/Mushroom Chemical ! [Re: The Lightning]
#21100243 - 01/11/15 07:29 AM (9 years, 1 month ago) |
|
|
Hint: It's in the genus Tricholoma. Go big.
|
raceme
Neither D nor L


Registered: 11/26/12
Posts: 663
Last seen: 5 years, 10 months
|
Re: Guess The Fungi/Mushroom Chemical ! [Re: The Lightning]
#21103315 - 01/11/15 06:27 PM (9 years, 1 month ago) |
|
|
OK, since no one's biting…
The mushroom is Tricholoma giganteum (AKA Macrocybe gigantea, not sure which is the accepted name), an edible species from India. According to this paper [PDF], it is an up-an-coming cultivated edible, and can achieve some fantastic biological efficiency when grown on straw.
The chemical is DPPH, AKA 2,2-diphenyl-1-picrylhydrazyl. DPPH is a very effective antioxidant, which is probably responsible for its potential anti-cancer properties [PDF].
The dot you see next to one of the nitrogen atoms in the chemical structure is a lone electron. Electrons tend to want to be in pairs (a normal covalent bond being a shared pair of them), and lone electron is usually quite reactive since it would be much happier in a pair. Atoms or molecules that have a lone electron are referred to as "radicals". The oxygen we breathe, O2, is actually a di-radical, each atom having one unpaired electron, and this is one of the main reasons behind its reactivity. Radical oxidation, where the lone electron on oxygen reacts with some substance, is the cause behind oils turning rancid, can contribute to cancer by reacting with DNA, and is thought to play a large role in the aging process.
DPPH's lone electron is actually quite stable. The highly conjugated nature (read: lotsa double-bonds) of the surrounding molecules "smears out" the lone electron and, through quantum-mechanical mumbo-jumbo, makes each atom in the conjugated system bear a "portion" of the lone electron, making them all a tiny bit less stable, but much more stable overall than if the electron were localized on a single atom.
Lighting, if you're taking the structures from Wikipedia, you should either capture them through a screenshot, or paste them onto a white background. The .SVG files have a transparent background, making them a bitch to read against the dark Shroomery background.
|
The Lightning
Mycology Enthusiast


Registered: 09/06/11
Posts: 3,889
|
Re: Guess The Fungi/Mushroom Chemical ! [Re: raceme]
#21103445 - 01/11/15 06:58 PM (9 years, 1 month ago) |
|
|
You got it, man! Excellent response as well.
Quote:
if you're taking the structures from Wikipedia, you should either capture them through a screenshot, or paste them onto a white background. The .SVG files have a transparent background, making them a bitch to read against the dark Shroomery background.
I agree. I'll make that happen.
And....You're up!
|
raceme
Neither D nor L


Registered: 11/26/12
Posts: 663
Last seen: 5 years, 10 months
|
Re: Guess The Fungi/Mushroom Chemical ! [Re: The Lightning]
#21103624 - 01/11/15 07:37 PM (9 years, 1 month ago) |
|
|
Here's the chemical:

And here's a fungus that's in the same genus as the fungi that produce the chemical:

Hint: This chemical is sometimes given to patients who have just had an organ transplant.
|
The Lightning
Mycology Enthusiast


Registered: 09/06/11
Posts: 3,889
|
Re: Guess The Fungi/Mushroom Chemical ! [Re: raceme]
#21105607 - 01/12/15 02:10 AM (9 years, 1 month ago) |
|
|
Mycophenolic acid found in Penicillium carneum.

Image courtesy of The Artist of The Chapel of Sacred Mirrors, Alex Grey.
Mycophenolic acid (less accurately called mycophenolate) is an immunosuppressant drug used to prevent rejection in organ transplantation. It inhibits an enzyme needed for the growth of T cells and B cells.
|
raceme
Neither D nor L


Registered: 11/26/12
Posts: 663
Last seen: 5 years, 10 months
|
Re: Guess The Fungi/Mushroom Chemical ! [Re: The Lightning]
#21107373 - 01/12/15 12:02 PM (9 years, 1 month ago) |
|
|
Quote:
The Lightning said: Mycophenolic acid found in Penicillium carneum.
Ding ding ding! It's also found in P. stoloniferum and P. echinulatum. Probably other as well.
|
The Lightning
Mycology Enthusiast


Registered: 09/06/11
Posts: 3,889
|
Re: Guess The Fungal / Mushroom Chemical ! [Re: raceme]
#21108192 - 01/12/15 03:01 PM (9 years, 1 month ago) |
|
|

The above chemical is found in the fungal species below. Note: This species and the chemical above are UV (sunlight) sensitive.
Guess the chemical name (there are at least three synonyms), the fungal name, and mention a few features about a particular strain of this species. Hint: Stevens Hall.
Edited by The Lightning (01/12/15 04:10 PM)
|
The Lightning
Mycology Enthusiast


Registered: 09/06/11
Posts: 3,889
|
Re: Guess The Fungal / Mushroom Chemical ! [Re: The Lightning]
#21121151 - 01/14/15 04:08 PM (9 years, 1 month ago) |
|
|
We interrupt this thread for a message from this, our sponsor:
|
The Lightning
Mycology Enthusiast


Registered: 09/06/11
Posts: 3,889
|
Re: Guess The Fungal / Mushroom Chemical ! [Re: The Lightning]
#21146344 - 01/19/15 08:29 PM (9 years, 1 month ago) |
|
|
Hint: The genus Claviceps.
|
ellomello
XP



Registered: 08/11/08
Posts: 2,423
Loc: babilonUSA
|
Re: Guess The Fungal / Mushroom Chemical ! [Re: The Lightning]
#21155310 - 01/21/15 11:02 AM (9 years, 1 month ago) |
|
|
Quote:
The Lightning said:

The above chemical is found in the fungal species below. Note: This species and the chemical above are UV (sunlight) sensitive.
Guess the chemical name (there are at least three synonyms), the fungal name, and mention a few features about a particular strain of this species. Hint: Stevens Hall.
Could it be... ??? (hint: iam not good at reading chemicals yet:) Ergometrine (other names include ergonovine and d-lysergic acid beta-propanolamide)

Medical use
It has a medical use in obstetrics to prevent bleeding after birth.
It can induce spasm of the coronary arteries.[2] It is used to diagnose variant (Prinzmetal's) angina.[3]
Mechanism of action
While it acts at alpha-adrenergic, dopaminergic, and serotonin receptors (the 5-HT2 receptor), it exerts on the uterus (and other smooth muscles) a powerful stimulant effect not clearly associated with a specific receptor type.
http://en.wikipedia.org/wiki/Ergometrine ?
-------------------- PAY NO ATTENTION TO THE MAN BEHIND THE CURTAIN get back to the garden
some came singing, some come to play, some come for keeping the dark away
|
Mr. Bojangles
Breathe In



Registered: 04/08/08
Posts: 1,937
Loc: The Dirty
|
Re: Guess The Fungal / Mushroom Chemical ! [Re: ellomello]
#21156397 - 01/21/15 12:03 PM (9 years, 1 month ago) |
|
|
Quote:
ellomello said: Could it be... ??? (hint: iam not good at reading chemicals yet:) Ergometrine (other names include ergonovine and d-lysergic acid beta-propanolamide)
Nope...but good try. The key is in the amide bond (That's the double bonded oxygen atom attached to the NH at the top of the molecule pictured). In your ergometrine picture you will see that the hydroxyl moiety (that's the -OH) is 2 carbon atoms removed from the nitrogen atom, while in Lightning's post the same moiety is only 1 carbon removed. There is also an extra carbon in this branch, which differentiates ergometrine from the original molecule. Another key is that there is an extra chiral center in Lightning's molecule (for more info on this, see two posts up from yours), which is essentially what those hashed or bolded lines on molecules always indicate. Chiral centers aren't always pictured on molecules in the same way so newbies should take simply counting and comparing the bolded and dashed lines with a grain of salt, rather focusing on understanding how to determine chirality.
I guess I should answer this now . The fungus is Claviceps paspali and the molecule is lysergic acid hydroxyethylamide. Other names include LAH and LSH. From the reference Lightning made to the literature, I would postulate this particular C. paspali strain was found growing on a type of grass called Paspalum distichum. The lysergamide is found predominantly in HBWR and Morning Glory seeds. I believe many of us can deduce the human activity of this compound once ingested
-------------------- "It is dangerous to be right in matters on which the established authorities are wrong." Francois-Marie Arouet
|
|