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Encyclopedia > Harmala alkaloid
Peganum harmala, commonly known as Syrian Rue
Peganum harmala, commonly known as Syrian Rue

The MAOI (MonAmine Oxidase Inhibitor) alkaloids found in seeds of Peganum harmala (also known as Harmal or Syrian Rue)- harmine, harmaline, and tetrahydroharmine- are collectively known as harmala alkaloids. The harmala alkaloids are of great interest for their complicated relation to phyto-indole entheogens used in Amazonian shamanism. The harmala alkaloid harmine- once known as Telepathine' and Banisterine- is a naturally occurring beta-carboline alkaloid that is structurally related to harmaline. The Shulgins suggest harmaline is a breakdown product of harmine [1]. Harmine and harmaline are reversible MAOIs. They can stimulate the central nervous system by inhibiting the metabolism of monoamines compounds- such as serotonin. Wikipedia does not have an article with this exact name. ... Wikipedia does not have an article with this exact name. ... Monoamine oxidase inhibitors (MAOIs) are a class of antidepressant drugs prescribed for the treatment of depression. ... Chemical structure of ephedrine, a phenethylamine alkaloid An alkaloid is, strictly speaking, a naturally occurring amine produced by a plant,[1] but amines produced by animals and fungi are also called alkaloids. ... A ripe red jalapeño cut open to show the seeds For other uses, see Seed (disambiguation). ... Binomial name Peganum harmala Syrian Rue (Peganum harmala) is a plant of the family Nitrariaceae. ... Binomial name L. Harmal seed capsules Harmal (Peganum harmala) is a plant of the family Nitrariaceae, native from the eastern Mediterranean region east to India. ... Species Pagnum harmala Syrian Rue (Pagnum harmala) is a member of the Zygophyllaceae family. ... Harmala, also known at various times as Telepathine and Banisterine, is a blanket term for a group of naturally occurring beta-carbolines including harmine, harmaline, and others. ... Harmala, also known at various times as Telepathine and Banisterine, is a blanket term for a group of naturally occurring beta-carbolines including harmine, harmaline, and others. ... The Harmala alkaloid Harmine, also known as Telepathine and Banisterine, is a naturally occurring beta-carboline alkaloid that is structurally related to harmaline. ... β-Carboline (9H-pyrid-[3,4-b]-indole) is an organic amine that is the prototype of a class of compounds known as β-Carbolines. ... Chemical structure of ephedrine, a phenethylamine alkaloid An alkaloid is, strictly speaking, a naturally occurring amine produced by a plant,[1] but amines produced by animals and fungi are also called alkaloids. ... Harmala, also known at various times as Telepathine and Banisterine, is a blanket term for a group of naturally occurring beta-carbolines including harmine, harmaline, and others. ... Monoamine oxidase inhibitors (MAOIs) are a class of antidepressant drugs prescribed for the treatment of depression. ... A diagram showing the CNS: 1. ...


The harmala alkaloids occur in harmal in concentrations of roughly 3%, though tests have documented anywhere from 2-7%, as natural sources tend to vary widely in chemical makeup. Harmala alkaloids are also found in the Banisteriopsis caapi vine, the key plant ingredient in the sacramental beverage Ayahuasca, in concentrations that range between 0.31-8.43% for harmine, 0.03-0.83% for harmaline and 0.05-2.94% for tetrahydroharmine [THH].[1] Many other psychoactive plants are often added to Ayahuasca to achieve visionary consciousness, including leaves from "Psychotria viridis", a source of DMT, The harmala alkaloids serve to potentiate these brewed compounds by preventing their breakdown in the digestive tract. The harmala alkaloids are also psychoactive on their own if the dosage is sufficient, perhaps due to endogenous sources of DMT in the human brain. Binomial name L. Harmal seed capsules Harmal (Peganum harmala) is a plant of the family Nitrariaceae, native from the eastern Mediterranean region east to India. ... Binomial name (Spruce ex Griseb. ... Ayahuasca (Quechua, pronounced ) is any of various psychoactive infusions prepared from the Banisteriopsis spp. ... Binomial name Psychotria viridis Psychotria viridis is a shrub from the coffee family, Rubiaceae. ... Dimethyltryptamine (DMT), also known as N,N-dimethyltryptamine, is a psychedelic tryptamine. ...


Harmala alkaloids are also found in many other plants, such as tobacco and passion flower. Shredded tobacco leaf for pipe smoking Tobacco can also be pressed into plugs and sliced into flakes Tobacco is an agricultural product processed from the fresh leaves of plants in genus Nicotiana. ... Species Passiflora amalocarpa Passiflora amethystina Passiflora aurantia Passiflora caerulea Passiflora capsularis Passiflora edulis Passiflora foetida Passiflora helleri Passiflora holosericea Passiflora incarnata Passiflora karwinskii Passiflora mucronata Passiflora murucuja Passiflora tenuifila Passiflora tulae Passiflora vitifolia Passiflora yucatanensis Passion flower refers to vines in the genus Passiflora—flowering plants known for their...

Contents

Telepathine

Telepathine was originally thought to be the active chemical constituent of Banisteriopsis caapi, a key plant ingredient in the preparation of Ayahuasca; a sacremental beverage from the Amazon. This isolated chemical was so named because of the reported effects of Ayahuasca among the indigenous users, including: collective contact with and/or visions of jaguars, snakes, and jeweled birds, and ancestral spirits; the ability to see future events; and as the name suggests, telepathic communication among tribal members. It was assumed to be a newly discovered chemical at the time, however, it was soon realized that Telepathine was already more widely known as Harmine from its previous discovery in Syrian Rue (Peganum harmala). Telepathy, from the Greek τῆλε, tele, remote; and πάθεια, patheia, to be effected by, describes the hypothetical transfer of information on thoughts or feelings between individuals by means other than the five classical senses. ... Binomial name Peganum harmala Syrian Rue (Peganum harmala) is a plant of the family Nitrariaceae. ...


Uses

As mentioned above, some harmala alkaloids can be used as an MAOI (MonoAmine Oxidase Inhibitor) to facilitate the oral ingestion of DMT and other tryptamines; while not generally used as a hallucinogen alone, there are reports of such use.[2] In high doses, it acts a purgative. Harmala alkaloids from Banisteriopsis caapi have been used to treat Parkinson's disease. Additionally, Harmaline is used as a model for Essential Tremor when injected to animals. Rats being treated with Harmaline exhibit severe tremors after 5-7 minutes. Monoamine oxidase inhibitors (MAOIs) are a class of antidepressant drugs prescribed for the treatment of depression. ... Dimethyltryptamine (DMT), also known as N,N-dimethyltryptamine, is a psychedelic tryptamine. ... This article or section does not cite its references or sources. ...


It is important to note that unlike synthetic pharmaceitical MAOIs such as Phenelzine, harmine is reversible and selective meaning it does not have nearly as high a risk for the "cheese syndrome" caused by consuming tyramine-containing foods, which is a risk associated with monoamine oxidase A inhibitors, but not monoamine oxidase B inhibitors.[3] Individuals should not attempt to self-medicate themselves for depression using harmine. Phenelzine (brand name Nardil) is an antidepressant drug that belongs to the monoamine oxidase inhibitor (MAOI) class of drugs. ... Monoamine oxidase inhibitors (MAOIs) are a class of antidepressant drugs prescribed for the treatment of depression. ... Monoamine oxidase inhibitors (MAOIs) are a class of antidepressant drugs prescribed for the treatment of depression. ... Cheese syndrome is the name of a condition that is commonly associated with the usage of monoamine oxidase inhibitors (MAOIs), a class of anti-depressants. ... Tyramine (4-hydroxy-phenethylamine) is a monoamine compound derived from the amino acid tyrosine. ... Monoamine oxidase A is an isozyme of monoamine oxidase. ... Monoamine oxidase Monoamine oxidases (singular abbreviation MAO) (EC 1. ...


Chemical Forms

7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole
Harmine
  • Harmaline: C13H14N2O
4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido[3,4-b]indole
Harmaline


Harmaline is a "reversible inhibitor of MAO-A (RIMA)."[4] Harmala, also known at various times as Telepathine and Banisterine, is a blanket term for a group of naturally occurring beta-carbolines including harmine, harmaline, and others. ... Image File history File links Size of this preview: 800 × 445 pixelsFull resolution (807 × 449 pixel, file size: 7 KB, MIME type: image/png) i drew this I, the copyright holder of this work, hereby release it into the public domain. ... Image File history File links Size of this preview: 800 × 445 pixelsFull resolution (807 × 449 pixel, file size: 7 KB, MIME type: image/png) i drew this I, the copyright holder of this work, hereby release it into the public domain. ... Image File history File links Size of this preview: 800 × 418 pixelsFull resolution (807 × 422 pixel, file size: 6 KB, MIME type: image/png) i drew this I, the copyright holder of this work, hereby release it into the public domain. ... Image File history File links Size of this preview: 800 × 418 pixelsFull resolution (807 × 422 pixel, file size: 6 KB, MIME type: image/png) i drew this I, the copyright holder of this work, hereby release it into the public domain. ...

  • Tetrahydroharmine: C13H16N2O
7-Methoxy-1,2,3,4-Tetrahydro-Harmine
Tetrahydroharmine
  • Harman: C12H10N2
1-methyl-9H-b-carboline
Harman
  • Harmine acid: methylester:
Methyl-7-methoxy-b-carboline-1-carboxylate
  • Harmilinic acid:
7-methoxy-3,4-dihydro-b-carboline1-carboxylic acid
  • Harmanamide:
1-carbamoyl-7-methoxy-b-carboline
  • Acethylnorharnine:
1-acethyl-7-methoxy-b-carboline

Image File history File links Size of this preview: 800 × 401 pixelsFull resolution (842 × 422 pixel, file size: 6 KB, MIME type: image/png) i drew this I, the copyright holder of this work, hereby release it into the public domain. ... Image File history File links Size of this preview: 800 × 401 pixelsFull resolution (842 × 422 pixel, file size: 6 KB, MIME type: image/png) i drew this I, the copyright holder of this work, hereby release it into the public domain. ... Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ...

See also

β-Carboline (9H-pyrid-[3,4-b]-indole) is an organic amine that is the prototype of a class of compounds known as β-Carbolines. ... This article does not cite any references or sources. ... Time Machines is Coils landmark drone music album, released under the alias Time Machines. ... A coil is a series of loops. ... Psilocybin (also known as psilocybine) is a psychedelic alkaloid of the tryptamine family, found in psilocybin mushrooms. ... 5-MeO-DMT is a very powerful psychedelic tryptamine. ... DOET, HECATE, or 2,5-dimethoxy-4-ethylamphetamine is an analogue of DOM, and is the three-carbon chain homologue to 2C-E. It produces hallucinogenic, psychedelic, and entheogenic effects. ...

References

  1. ^ Callaway JC, Brito GS & Neves ES (2005). Phytochemical analyses of Banisteriopsis caapi and Psychotria viridis Journal of Psychoactive Drugs 37(2): 145-150.
  2. ^ Shulgin, Alexander. "#13 Harmaline", Erowid Online Texts: TiHKAL #13 HARMALINE, retrieved November 26, 2006.
  3. ^ McKenna, Callaway, & Grb. "Scientific Investigation of Ayahuasca", Scientific Investigation of Ayahuasca, retrieved 2007-06-03.
  4. ^ [http://books.google.com/books?id=2c2K-epbCDQC&pg=PA237&lpg=PA237&dq=harmaline+antidepressant&source=web&ots=IrcpVr4R_H&sig=5FvlysKKEN7Hb4_YjfgoZM8rsTg Edward J. Massaro, Handbook of Neurotoxicology ]

 
 

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