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Chemistry of Ayahuasca

The main active biochemical substances in Banisteriopsis Caapi, Banisteriopsis Inebrians and other species of Banisteriopsis are: ß-Carboline alkaloids Harmine, Harmaline, Tetrahydroharmine, Harmol, Harmic acid, MethylesterHarmic Amide, Acetyl Norharmine, Harmine N-oxide, Harmalinic acid and Ketotetra-Hydronorharmine

Banisteriopsis Caapi has a higher level of Tetrahydroharmine than Peganum Harmala (Syrian Rue) and certain species of Passiflora sp. (passionflower), which also contain Harmala alkaloids. This could be the reason for the more complete and longer lasting therapeutic effects genuine Ayahuasca provides compared to "analogue" preparations.


 1. Banisteriopsis caapi

Banisteriopsis Caapi contains Harmine, Harmaline, Tetrahydroharmine, Harmol and 6-Methoxytryptamine. The primary active compounds in Banisteriopsis caapi are the alkaloids Harmine, Harmaline and Tetrahydroharmine. Both Harmine and Harmaline are highly reversible MAO inhibitors, whereas Tetrahydroharmine is a weak Serotonine (5-Hydroxytryptamine) uptake inhibitor. When Harmine was first discovered it was named "Telephatine", but that name was quickly discarded when scientists discovered that the same alkaloid had already been obtained from Peganum harmala. MAO inhibitors, such as Harmine prevent the breakdown of monoamine neurotransmitters by inhibiting the action of MAO enzymes, which would normally degrade DMT and prevent it to pass through the blood-brain barrier.

Harmine

Ayahuasca_HarmineThe crystalline harmala alkaloid Harmine reversibly inhibits monoamine oxidase A (MAO-A) but has no effect on MAO-B. When it was first discovered it was named "Telephatine", but the name was quickly discarded when scientists discovered that the same alkaloid had already been obtained from Peganum harmala. Harmine is an alkaloid of the beta-carboline family and prevents the breakdown of monoamine neurotransmitters by inhibiting the action of MAO enzymes, which would normally degrade DMT and prevent it to pass through the blood-brain barrier.

Harmaline

Ayahuasca_HarmalinHarmaline is the reduced hydrogenated form of harmine and a reversible inhibitor of MAO-A. Harmaline is an alkaloid of the beta-carboline family that acts as a central nervous system stimulant.

 

 

Tetrahydroharmine

TetrahydroharmineTetrahydroharmine is a beta-carboline derivate and a weak serotonin uptake inhibitor, it does not inhibit monoamine oxidase A.

 

 

Harmol

HarmolHarmol is a toxic beta-carboline indoleamine alkaloid (also found in Peganum harmala, Tribulus, Kallstroemia spp., Elaeagnus angustifolia and Passiflora incarnata).

 

 

 

 

6-Methoxytryptamine

6-Methoxytryptamine6-Methoxytryptamine is an indole of the tryptamine family.

 

 

 

2. Psychotria viridis and Psychotria carthaginensis

Dimethyltryptamine, Monomethyltryptamine and 2-methyl-1,2,3,4-tetrahydro-ß-carboline.

Dimethyltryptamine

DMTDimethyltryptamine (abbreviated DMT, also found in Mimosa tenuiflora, Diplopterys cabrerana) is an endogenous chemical exerted by the body during sleep in the REM phase as well as when the body is under extreme stress (near death experience). DMT is structurally similar to Bufotenin, Serotonine and Psilocin and Psilocybin, the active chemicals in many magic mushrooms. It is a powerful hallucinogen more intense than LSD. DMT is orally inactive at reasonable doses and requires a monoamine oxidase inhibitor to pass the digestion system and to cross the blood-brain barrier. DMT was first synthesized in 1931 by Canadian chemist Richard Helmuth Fredrick Manske.

Monomethyltryptamine

Ayahuasca_MethyltryptamineMonomethyltryptamine is a tryptamine alkaloid that has been found in the leaves, bark and shoots of numerous plants; it has also been found in the urine from autistic patients with mental retardation and epilepsy.

 

 

 

 

 

2-methyl-1,2,3,4-tetrahydro-ß-carboline

Ayahuasca_2-methyl-1,2,3,4-tetrahydro-ß-carboline2-methyl-1,2,3,4-tetrahydro-ß-carboline is a common substance in trace amounts in many plants with entheogenic tryptamines, including Mimosa hostilis and Phalaris spp.

 

 

 

 

 

 

3. Diplopterys cabrerana

N-Methyltryptamine, 5-MeO-DMT (5-Methoxy-Dimethyltryptamine), Bufotenine and N-Methyltetrahydro-ß-carboline (Tetrahydroharman).

Diplopterys cabrerana contain the indole ethylamine alkaloid N,N-Dimethyltryptamine, an alkaloid with a similar structure to Serotonine. It binds to the 5-HT2 receptors and partially to the 5-HT2A receptors. DMT itself, when taken orally, does not show any effetcs, because the endogenous enzyme monoamine oxidase converts it into inactive aldehydes. The beta-carbolines in the Banisteriopsis caapi vine temporarily inhibit the production of this monoamine oxidase, which allows the DMT to reach the sensitive parts in the brain, such as the prefrontal, parietal and somatosensory cortex and the olfactory tubercle. Diplopterys cabrerana also contains N-Methyltryptamine, 5-MeO-DMT (5-Methoxy-Dimethyltryptamine), Bufotenine and N-Methyltetrahydro-ß-carboline, alkaloids that are barely found in Psychotria viridis (only traces).

N-Methyltryptamine

Ayahuasca_MethyltryptamineN-Methyltryptamine (abbreviated NMT) is a tryptamine alkaloid that has been found in the leaves, bark and shoots of numerous plants such as Virola, Acacia, Mimosa and Desmanthus and is a natural trace component in human urine. It is also endogenous; it is synthesized in the human body as a metabolic end-product of the amino acid L-tryptophan. NMT appears to be orally inactive and does not produce psychoactive effects, most likely due to the extensive first-pass metabolism.

 

 

5-MeO-DMT

5-MeO-DMT5-MeO-DMT is a member of the tryptamines class and is a crystalline, white substance. Just like N-Methyltryptamine it is synthezised in the human body as a metabolic end-product of the amino acid L-tryptophan. 5-MeO-DMT is a natural substance in some plants; it has been found in the resin of Virola, in the seeds of Mucuna pruriens, Yopo and in the secretions of some toads such as Colorado River Toad, Cane Toad. 5-MeO-DMT is usually smoked but can also be consumed nasally or intravenously.

 

Bufotenine

BufoteninBufotenine (derived from Bufo - Toad) is a hallucinogenic tryptamine alkaloid. Bufotenine is closely related to the human neurotransmitter Serotonine and is structurally similar to Psilocin, 5-MeO-DMT, and DMT. Bufotenine has first been found in the skin secretions of toads, but most notably in the secretions of the Colorado River Toad (Bufo alvarius). It has also been found in Anadenanthera colubrina and Anadenanthera peregrina.

 

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