Chemical Structures Of Hallucinogens

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Chemical determination of the molecular structure of the hallucinogenic principles in sacred plants has led to remarkable results.

Almost all plant hallucinogens contain the element nitrogen and therefore belong to the large class of chemical compounds known as alkaloids.

divinorum are the most significant examples that do not contain nitrogen. The main active principle of Cannabis is tetrahydrocannabinol (THC), while the main active principle of Salvia divinorum is salvinorin.

The principal plant hallucinogens are closely

Hallucingens

Tetrahydrocannabinol (THC)

related in their chemical structure to hormones present in the brain—that is, to physiological agents that play a role in the biochemistry of mental functions

The active principle in the Peyote cactus is the alkaloid mescaline, a compound closely related to the brain-hormone norepinephrine (noradrenaline). Norepinephrine belongs to the group of physiological agents known as neurotransmitters because they function in the chemical transmission of impulses between neurons (nerve

Tetrahydrocannabinol (THC)

The term alkaloid is used by chemists for the nitrogenous metabolic products of plants that have alkaline properties and are therefore "alka"-like" (alkaloid). Among the more important plants with psychoactive properties, only Hemp and Salvia

The molecular models of hallucinogens on pages 186-87 show the chemical elements of which these substances consist and the manner in which the atoms of these elements are related to one another in the molecules. The black balls mean carbon atoms, the white hydrogen the red oxygen, the green nitrogen, and the yellow ball in the psilocybine molecule indicates a phosphoric atom. There Is, in fact, no space between atoms connected with each other; they touch. Moreover, atoms of various elements are of different sizes. Only the especially small size of the hydrogen atoms has been indicated in these models.

The molecular models of hallucinogens on pages 186-87 show the chemical elements of which these substances consist and the manner in which the atoms of these elements are related to one another in the molecules. The black balls mean carbon atoms, the white hydrogen the red oxygen, the green nitrogen, and the yellow ball in the psilocybine molecule indicates a phosphoric atom. There Is, in fact, no space between atoms connected with each other; they touch. Moreover, atoms of various elements are of different sizes. Only the especially small size of the hydrogen atoms has been indicated in these models.

It Is hardly possible to imagine the real dimension of atoms and molecules: 0.1 mg (a tenth of a thousandth of a gram of a hallucinogen,

It Is hardly possible to imagine the real dimension of atoms and molecules: 0.1 mg (a tenth of a thousandth of a gram of a hallucinogen,

Mescaline Chemical Structure

cells). Mescaline and norepinephrine have the same basic chemical structure. Both are derivatives of a substance known to chemists as phenylethylamine. Another derivative of pheny lethylamine is the essential amino acid phenyla-

Hecent studies show differences in the internal structure of wood between Cannabis saliva (far left) and C. indica. As shown in these microscopic cross-sections, one of the most significant differences is the usually single conducive vessels in the former species as contrasted with the consistently grouped vessels In the latter.

THC, found only in Cannabis, is concentrated in the resin and is abser.i from the woody tissuo, which for this reason is specifically exempted from control In American Cannabis legislation.

lanine, which is widely distributed in the human organism.

The models of mescaline and noradrenaline molecules on page 186 clearly show the close relationship in chemical structure of these two agents.

Psi'ocybine and psilocine, the active principles of Teonanacatl, the hallucinogenic Mexican mushrooms, are derived from the same basic compound as the brain hormone serotonine: tryptamine. Tryptamine also is the basic compound of an essential amino acid, which is tryptophane. The re lationship can be clearly seen in the molecular models shown on page 186.

There is another Mexican sacred plant. Ololiu qui (Morning Glory), the hallucinogenic principles of which are derivatives of tryptamine. In this case, tryptamine is incorporated in a complex ring structure that has been called ergolin. The molecular models on page 187 show the structural relationship between lysergic acid amide and lysergic acid hydroxyethylamide (the two principal active constituents of Ololiuqui), the neu rotransmitter serotonine, and psilocybine and psilocine

That the important plant hallucinogens and the brain hormones serotonine and noradrenaline have the same basic structure cannot be due to mere chance. This astounding relationship may explain the psychotropic potency of these hallucinogens. Havins; the same basic structure, these

hallucinogens may act at the same sites m the nervous system as the above-mentioned brain hor mones, like similar keys fitting the same lock. As a result, the psychophysiaiogical functions asso ciated with those brain sites are altered, suppressed, stimulated, or otherwise modified.

The ability of hallucinogens to produce changes in brain function is due not only to their having a particular chemical composition, but also to the peculiar spatial arrangement of the atoms in their molecules. This can be seen very clearly in the case of the most powerful hallucinogen known today, lysergic acid diethylamide. LSD may be regarded as a chemically modified form of an active princi pie in Ololiuqui. The only difference between the semi-synthetic drug lysergic acid diethylamide and the natural Ololiuqui hallucinogen lysergic acid amide is that two hydrogen atoms of the

Psilocybine

(hallucinogenic principle of Teonanácatl)

Noradrenaline (a brain hormone)

Peyotl (Lophophora willimasii)

(hallucinogenic principle of Teonanàcatl)

Peyotl (Lophophora willimasii)

amide have been replaced in the diethylamide by two ethyl groups. With LSD, a dose of 0.05 milligram will produce a deep hallucinogenic intoxication of some hours' duration. With iso-LSD. which differs from LSD only in the spatial arrangement of the atoms, ten times that dose has no effect whatsoever.

The molecular models of LSD and iso LSD on page 187 show that, while the atoms are linked to each other in the same way, their spatial arrangement is different.

Molecules differing only in spatial arrangement are known as stereoisomers. Stereoisomers can exist only with molecules that are asymmetrical in structure, and one of the theoretically possible spatial arrangements is in general more active.

Psilocybine

(hallucinogenic principle of Teonanácatl)

Next to chemical composition, spatial coniigura tion plays the most crucial role in determining not only hallucinogenic but also general pharmacological activity

(hallucinogenic principle of Teonanàcatl)

Noradrenaline (a brain hormone)

Mescaline

(vision-causing hallucinogenic principle of Peyote)

Mescaline

(vision-causing hallucinogenic principle of Peyote)

Dr. Albert Hofmann, born 1906, discoverer of LSD and the hallucinogenic principles of Teona-näcatl and of Ololiuqui is shown here with the molecular model of LSD in his pharmaceutic-chemical research laboratory, Sandoz, Basel, Switzerland, 1943.

Page 186: The comparison between Mescaline and Noradrenaline and between Psilocybine and Psiloclne with Serotonine shows the relationship in the chemical structure between the hallucinogens and brain hormones

The close chemical relationship between the active principles of Ololiuqui and LSD, the most potent hallucinogen known today, is evioent when comparing the molecular models of Lysergic Acid Amide and Lysergic Acid Hydroxyethy-lamide with Lysergic Acid Diethylamide

Serotonine (a brain hormor.e)

Lysergic acid amide (hallucinogenic principle of Ololiuqui)

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