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Harmala alkaloid

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The Harmala alkaloid "Harmine", also known as Telepathine and Banisterine, is a naturally occurring beta-carboline alkaloid that is structurally related to harmaline. Harmine and harmaline are reversible monoamine oxidase inhibitors. They can stimulate CNS by inhibiting the metabolism of serotonin and other monoamines.

Some harmala alkaloids, particularly harmine and harmaline, are found in the seeds of the Middle Eastern plant Harmal (Peganum harmala, from which the name derives), commonly known as Syrian Rue. They occur in the seeds 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 vine Banisteriopsis caapi 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] Banisteriopsis caapi is the key plant ingredient in the sacramental beverage Ayahuasca. Leaves from "Psychotria viridis", a source of DMT, are often added to Ayahuasca to achieve visionary states of consciousness. Many other psychoactive plants are often added to Ayahuasca. The harmala alkaloids serve the purpose of potentiating these compounds in the brew by preventing their breakdown in the digestive tract. Nevertheless, the harmala alkaloids are psychoactive on their own if the dosage is sufficient.

Harmala alkaloids are also found in many other plants, such as tobacco and passion flower.

TelepathineEdit

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).

UsesEdit

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.

It is important to note that unlike synthetic reversible MAOIs such as moclobemide, harmine is still capable of interacting adversely with monoamines found in everyday foods such as cheese and yeast extracts. Individuals should not attempt to self-medicate themselves for depression using harmine. One specific example is tyramine, an amine present in a variety of foods, but with higher concentrations in hard cheeses and aged/canned meats (tyramine is formed from the gradual breakdown of some proteins). Normally, it is oxidized quickly in the body and is harmless. However, when the MAO enzymes are inhibited, tyramine concentrations can rapidly increase and become toxic. Tyramine mimics dopamine and norepinephrine structure and toxicity includes hypertensive crisis and possibly heart failure.


ReferencesEdit

  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.

Chemical FormsEdit

  • Harmine: C13H12N2O
7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole
  • Harmaline: C13H14N2O
4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido[3,4-b]indole
  • Tetrahydroharmine: C13H16N2O4P
7-Methoxy-1,2,3,4-Tetrahydro-Harmine
  • Harman: C12H10N2
1-methyl-9H-b-carboline
  • 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

See alsoEdit



Antidepressants (ATC N06A) edit
Monoamine oxidase inhibitors (MAOI) Harmaline, Iproclozide, Iproniazid, Isocarboxazid, Nialamide, Phenelzine, Selegiline, Toloxatone, Tranylcypromine
Reversible inhibitor of monoamine oxidase A (RIMA) Brofaromine, Moclobemide
Dopamine reuptake inhibitor (DARI) Amineptine, Phenmetrazine, Vanoxerine, Modafinil
Norepinephrine-dopamine reuptake inhibitors Bupropion
Norepinephrine reuptake inhibitor (NRI) or (NARI) Atomoxetine, Maprotiline, Reboxetine, Viloxazine
Serotonin-norepinephrine reuptake inhibitor (SNRI) Duloxetine, Milnacipran, Venlafaxine
Selective serotonin reuptake inhibitor (SSRI) Alaproclate, Etoperidone, Citalopram, Escitalopram, Fluoxetine, Fluvoxamine, Paroxetine, Sertraline, Zimelidine
Selective serotonin reuptake enhancer (SSRE) Tianeptine
Tricyclic antidepressants (TCA) Amitriptyline, Amoxapine, Butriptyline, Clomipramine, Desipramine, Dibenzepin, Dothiepin, Doxepin, Imipramine, Iprindole, Lofepramine, Melitracen, Nortriptyline, Opipramol, Protriptyline, Trimipramine
Tetracyclic antidepressants Maprotiline, Mianserin, Nefazodone, Trazodone
Noradrenergic and specific serotonergic antidepressant (NaSSA) Mirtazapine


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