Psilocybin

Chemistry Zumdahl, 7 ed. Houghton Mifflin Company Boston New York

Here is a picture of the artist under the influence of this biologically active substance.

Psilocybin

In Minecraft, this substance together with cellulose can be obtained from any of the two kinds of fungi (red_mushroom and brown_mushroom).

Psilocybin (4-phosphoryloxy-N, N-dimethyltryptamine) is a phosphorylated derivative of psilocin, an alkaloid from the family of tryptamines, a psychedelic.

Once in the Mushroom Biome

One Little Girl traveled for a long time on Minecraft in search of the Forest Temple. She landed in the Mushroom Biome and discovered an unusual house with living walls. She was not afraid and went inside and there in the chest was an unusual helmet.

When you wear this helmet and say in a voice that you want to see more that something alive. The helmet owner falls asleep and metamorphosis occurs in a dream. This living one begins to grow rapidly (perhaps the girl quickly decreases) to such a size that the smallest parts of each chain of molecules are visible, and even the individual trajectories of atoms and electrons.

The construction of a live helmet

On this helmet there are a lot of antennas and antennae that interact with parts of huge molecules and with the help of voice commands control them.

So there are antennae capable of catching the smell, sorting the aromatic elements. To do this, these antennas take the form of various molecules and copy the shape of the magnetic field. In the case of similarity (resonance of the magnetic field), a stronger magnetic field is influenced by the protons of atoms near the rings of aromatic molecules such as benzene and shifts the field direction of the molecule itself to the compass arrows.

The NMR signal of protons in the plane of an aromatic ring are shifted substantially further down-field than those on non-aromatic sp2 carbons. This is an important way of detecting aromaticity. By the same mechanism, the signals of protons located near the ring axis are shifted upfield.

Aromas of natural flowers

Therefore, using a simple voice command, you can change the smell. For example, if the city smells only of gasoline and exhausts, you can change one word to the smell of the flower field.

Or even talk to flowers and the next year bitter flowers will become fragrant and you can use them for tasty and healthy drinks. If you place a ring magnet in a cup holder for tea, then the drinks from the flowers will become even more useful.

Other antennas look like tangles of very long mechanical arms. Which can stretch towards the molecule, wrap around the necessary atoms and carefully change them in places. These antennas are called Proteins or Enzymes. They also obey the voice commands of the helmet’s owner. In order for the helmet to work well, he needs a power source. To do this, make a ring from a fragment of Aquamarine (Prismarin) and charge it from the battery Blaze Rod (the core of the Efreet).

Gold Electrons

Also on this helmet, colored lanterns were strengthened, they could illuminate separate parts of molecules and highlight previously not visible details. So if you shine with the silver light of the Indole ring, you can notice a gold strip in the form of an eight that at first skips around a large Benzene ring then skirts around the next small Pyro ring. This is the trajectory of a separate special electron, which carries more energy than the rest.

But the intersection of the figure eight is practically invisible, because the electron at this moment dissolves in a vacuum and the time for it freezes. More precisely, he himself becomes a quantum of time for a few jumps.

Travel of Alex

Right in the helmet, the girl came out of an unusual live house and just around saw the Mushroom Cow. On the back of the cow grew mushrooms and the cow itself was red in a white pea. Just like Amanita.

The girl looked closely at the mushroom that grew on the head of a cow. The fungus began to grow until the fibers of Cellulose became visible and bunch of amazing multidimensional tori that looked like glomeruli of wool.

Psilocybin

On each such torus was an elongated pyramid from one atom of Phosphorus and 4 oxygen atoms, which strictly pointed in one direction.

But then Alex shook her head and her Magnetic Antenna swung the same way. All the pyramids in the rhythm of the movement of the girl’s head made a curtsey. They turned in the direction of changing the magnetic field.

Signal

“The helmet can touch these pyramids?” – a long folded to the point of the manipulator with neat fingers at the end was wrapped and its tip like a proboscis wound around the pyramid and without touching fingers swung Phosphorus. And then immediately in all directions stretched the path from the pyramids which moved in the same direction.

The glomeruli were pairs of benzene and pyrolytic rings bound together. Then protons (hydrogen atoms) appeared on the pyramids of Phosphorus.

Benzene

“Flashlight show me this ball,” said the girl. And I saw a small red comet (electron), which was moving at high speed around the sphere and every time jumped from the outer side of the sphere to the inner one. The trajectory of the movement was unusual, it was noticeable that there were 4 suns in the center of rotation, each of which flowed in 3 colors. They were arranged in the form of a tetraider.

“I want to look at the protons in the nucleus” – the color of the flashlight changed to a charming flashing one and there were noticeable 4 colored apples each of which described the figure eight in its three-dimensional space. There were 4 such spaces (by the number of apples) and they overlapped. Their common intersection girl and saw as multi-colored apples. Rather, they were elongated spheres with a depression from one end and an ellipsoidal shape from the other end.

“Show me the roots of the fungus” – asked the girl at the helmet. The helmet rustled the antennas by reconfiguring the focus. At first everything declined. Then it slid up, and then it increased again.

And Alex’s amazing picture of Mushroom – a fine mesh of mushroom roots was no different from the long molecules of the cortex of the Cow’s brain. It turned out that in places they came very close to each other. And in the gap just were those very little balls with pyramids.

“Show me Tryptophan (The name was added by the helmet when he noticed what Alex points out).” The helmet turned on the ultraviolet flashlight and immediately showed the Black-Violet dots in the Glomeruli. Some were brighter than others. This luminous Indol core consisted of cycles of the Benzene ring and the Pyro ring.

Cefamandole

But some points looked less bright (like distant Stars). These were molecules with tails of both nitrogenous bases of the nucleic acids (In these Indole nuclei there was a lot of dissemination of nitrogen in place of the Atoms of Carbon).

Benzol and Pyrrole

The same gaps were on the Neurons themselves in the cerebral cortex, but on the glomeruli instead of the pyramid was the protrusion of Hydroxide (OH), which did not rotate under the influence of the magnetic field, but the proton H was often replaced and the space was periodically vacant.

Sometimes the glomeruli detached and flew to the other side of the gap. And some directly on the fly with the help of 2 methyl groups converted Serotonin (and it was he in the gaps between the neurons) into Melatonin. And then the cow began to doze off.

But in 15 minutes again everything was restored and the Cow looked quite happy.

“It will be necessary in detail then to consider a multidimensional torus – it has something mysterious” – the girl thought.

Only then did the girl notice that the cow does not moose. How does she talk to other cows?

And then the girl remembered about the Phosphor pyramids, which seemed like antennae reacted absolutely to all changes in the magnetic field. And it is understandable, the girl thought (or maybe this helmet said inaudibly mentally) – they communicate with thought forms. It is worth thinking about something to one cow and then another cow with similar thoughts begins to see the image taken from the first cow.

The most surprising is that some surrounding objects and even cows from other planets could also communicate in this way. It was worth it – to find such a helmet, the girl concluded. Now if that is not clear – you can ask the Sun, Wind or Water or Wolf …

Chemical structure

By chemical structure and effect on consciousness, Psilocybin is similar to dimethyltryptamine, which is produced endogenously (in the human body) by the pineal gland.

Psilocybin and psilocin have a structure similar to serotonin (5-hydroxytryptamine), a neurotransmitter, a biologically active substance that transfers momentum through the synaptic space between neurons.

Psilocin is formed in the intestine during dephosphorylation of psilocybin. The mechanism of action of psilocybin is not completely clear. The most likely is an indirect effect on serotonin 5-HT2A receptors, to a lesser extent on 5-HT1A, 5-HT1D, and 5-HT2C. However, the replacement of serotonin with psilocybin can not explain all the effects.

At high dosages, there is a marked effect on noradrenaline receptors.

N,N-Dimethyltryptamine

N,N-Dimethyltryptamine (DMT)

DMT is a derivative of tryptamine, a molecule of which includes two additional methyl groups at the position of the nitrogen atom of the amine group.

A typical way of obtaining DMT is the synthesis of Speeter-Anthony, where the reagents are indole, oxalic chloride, dimethylamine and lithium aluminum hydride. Typically, DMT is used in the form of a base, although DMT salts, for example, fumaric acid salt, are more stable. DMT salts are soluble in water, and its base is not. DMT in solution rapidly decomposes under the influence of oxygen, light and heat, so it should be stored in a closed container, in the dark, in the refrigerator. The pure substance can crystallize as small white crystals in the form of needles.

Triptamine is a monoamine alkaloid, indole derivative, chemical name: 2- (1H-indol-3-yl) ethanamine. Tryptamine is found in plants and animal organisms. Chemically similar to the amino acid tryptophan. The derivatives of tryptamine play an important role in the vital activity of living organisms.

Most tryptamine derivatives exhibit psychoactive properties. One of the known derivatives of tryptamine is serotonin, the most important neurotransmitter and hormone.

Tryptamine

Triptamine is a monoamine alkaloid (pages 1010-1012 of a chemical textbook), indole derivative, chemical name: 2- (1H-indol-3-yl) ethanamine. Tryptamine is found in plants and animal organisms. Chemically similar to the amino acid tryptophan. The derivatives of tryptamine play an important role in the vital activity of living organisms.

Most tryptamine derivatives exhibit psychoactive properties. One of the known derivatives of tryptamine is serotonin, the most important neurotransmitter and hormone.

Serotonin

Serotonin, 5-hydroxytryptamine, 5-HT – one of the main neurotransmitters. According to the chemical structure, serotonin refers to biogenic amines, a class of tryptamines (pages 1015-1016 of a chemical textbook). Serotonin is often called a “hormone of good mood” and a “hormone of happiness.”

Indole

Indole (benzopyrrole, 2,3-benzpyrrole) heterocyclic condensed aromatic compound (pages 1008-1010 of a chemical textbook). Colorless crystals with a smell like the smell of cabbage. The indole nucleus is included in many biochemical natural compounds. As an individual substance is contained in coal tar and some essential oils, for example, in jasmine oil.

Aroma is a special property of some chemical compounds, due to which the conjugated ring of unsaturated bonds exhibits anomalously high stability (pages 1008-1010 of a chemical textbook).

How to synthesize indole?

Method of molecular orbitals of Hückel

In the 1930s, Hückel’s first applied methods of quantum mechanics to explain the unusual properties of aromatic compounds. At that time there were no computers capable of finding solutions to the Schrödinger equation for complex systems. In connection with this, an important task was to develop simplified methods for solving similar problems.

In MOX, the π-electron system of the molecule is considered independently of the σ-framework, which substantially simplifies the whole problem.

The presence of an annular magnetic current (observation requires complex apparatus), this current provides a shift in the chemical shifts of protons associated with the aromatic ring in a weak field (7-8 ppm for the benzene ring), and protons located above / below the plane of the aromatic system – in a strong field (NMR spectrum).

Almost always the Hückel Rule is observed: only the system containing (in the ring) 4n + 2 electrons (where n = 0, 1, 2, …) can be aromatic. A system containing 4n electrons is anti-aromatic (in simplified terms, this means excess energy in the molecule, inequality of bond lengths, low stability – propensity to join reactions). At the same time, in the case of peri-articulation (there is an atom (s) that simultaneously belongs to 3 cycles, that is, there are no hydrogen atoms or substituents near it), the total number of pi-electrons does not correspond to Hückel’s rule (phenalene, pyrene, coronene). It is also predicted that if molecules can be synthesized in the form of a Möbius band (a ring of a sufficiently large size, so that twisting in each pair of atomic orbitals was small), then for such molecules the system of 4n electrons will be aromatic, and of 4n + 2 electrons – antiaromatic.

Synthesis

Psilocibin – a compound based on the chemical structure of the amino acid tryptophan, in the biosynthesis of psilocybin comes from tryptamine and is akin to serotonin.

The starting material for the synthesis is 4-benzyloxyindole, from which 4-hydroxy-N, N-dimethyltryptamine (psilocin) is obtained by oxalyl chloride. The latter is esterified with dibenzylchlorophosphate and, after debenzylation, psilocybin is obtained.

Tryptophan

Tryptophan (β- (β-indolyl) -α-aminopropionic acid, abridged: Tri, Trp, Trp, W) is an aromatic alpha-amino acid. There are two optically isomeric forms, L and D, and in the form of a racemate (DL).

L-tryptophan is a proteinogenic amino acid and is part of the proteins of all known living organisms.

Tryptophan has the strongest fluorescence among all 20 proteinogenic amino acids. Tryptophan absorbs electromagnetic radiation with a wavelength of 280 nm (maximum) and solvatochromatically emits in the range of 300-350 nm. The molecular environment of tryptophan affects its fluorescence. This effect is important for the study of proteins. The interaction of the indole nucleus with nitrogenous bases of nucleic acids leads to a decrease in the intensity of fluorescence, which makes it possible to establish the role of this amino acid in protein-nucleic interactions.

Tryptophan in nature is synthesized via anthranilate.

Anthranilic acid

Anthranilic acid (Latin Acidum anthranilicum) is an aromatic amino acid. The derivatives of anthranilic acid are used in the manufacture of dyes and synthetic fragrances.

Anthranilic acid (o-aminobenzoic acid) NH2C6H4COOH, mol. m. 137.14; colorless crystals; melting point 145 ° C; sublime. Solubility (g per 100 g of solvent): in water 0.35 (14 ° C), 90% ethanol 10.7 (9.6 ° C), benzene 1.8 (12 ° C), ether – 16 (6.8 ° C); it is readily soluble in hot chloroform, ethanol, pyridine.

In the process of biosynthesis of anthranilate, intermediate compounds are shikimat, chorizmate (shikimat path).

Shikimate pathway

Shikimat path is a metabolic pathway, the intermediate metabolite of which is shikimic acid (shikimate). The shikimat path is noted as a specialized pathway for the biosynthesis of benzoic aromatic compounds (very often, in this capacity, along with the shikimat way, the polyketide (acetal-malonate) mechanism for constructing benzene nuclei is also noted; the closure (zip-assembly) of aromatic systems by intramolecular crotonic condensation). Shikimate way in nature such known compounds as phenylalanine, tyrosine, tryptophan, benzoate, salicylate are synthesized.

Video «Shikimate Pathway»

The American musical group from Bellingham, Portals Align, playing the genre of groove metal, instrumental music, progressive rock, experimental music, the gentleman, recorded a musical composition called “Shikimate Pathway” in November 2011, a corresponding video clip was posted on YouTube.

Answers

Fischer_indole_synthesis

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