Harmala alkaloid

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Harmala alkaloids are a group of naturally occurring alkaloids found primarily within the seeds of peganum harmala (syrian rue) which exhibit psychoactive effects.

Chemistry

Harmala alkaloids are substituted derivatives of the molecule beta-carboline. The structure ofbeta-carboline is comprised of an indole skeleton fused to a pyridine ring. Harmine, harmaline, and tetrahydroharmine share structural substitutions and they all contain a methoxy group at R7 and a methyl group at R1. They differ in the saturation of their six-member nitrogenous ring. Harmine contains an unsaturated pyridine ring while harmaline contains a dihydrogenated pyridine ring. Tetrahydroharmine is saturated with four additional hydrogen bonds than harmine.

Pharmacology

Harmala alkaloids are classed as MAOIs. This means that they inhibit the activity of monoamine oxidase metabolic enzymes of which two varieties exist: MOA-A and MOA-B. The alkaloids bind reversibly to the active site of the enzyme, inhibiting its endogenous function of destroying amine functions of neurotransmitters and externally administered centrally active drugs. This has the effect of potentiating and prolonging the central and peripheral activity of both neurotransmitters and a variety of drugs.

Harmala alkaloids are selective for MOA-A at reasonable doses and bind to the enzyme temporarily, so they are classed as a reversible inhibitor of monoamine-A (RIMA). At higher doses, they also begin to affect the MOA-B enzyme. Because of the reversible selectivity for MAO-A, harmala alkaloids are considered to be less dangerous in combination with food which contains tyramine and other substances with monoamine moieties which are reliant on monoamine oxidase for decomposition.

However, it is important to understand that this does not imply that harmala alkaloids will not cause neurotoxicity. Harmala alkaloids temporarily disable the brain's primary mechanism for breaking down neurotransmitters and drugs which can have negative consequences as material builds up in the synapses, leading to a huge range of downstream central and peripheral effects including sedation, stimulation, anxiety, cognitive dysphoria, euphoria, headaches, eye strain, and muscle convulsions.

Since DMT is broken down by monoamine oxidase A, inhibition of this enzyme allows for the oral activation of DMT and prolongs the experience for the duration of the harmala alkaloid effects. In combination, harmala alkaloids and DMT are known as ayahuasca.

Harmala alkaloids, along with other beta-carbolines, also function as GABA-A receptor (benzodiazepine site) inverse agonists, likely contributing to their anxiogenic and convulsant effects.[1]

Examples

Common harmala alkaloids include:

Harmine

Harmine.svg

Harmine is a reversible inhibitor of MAO-A (RIMA) at doses of 200mg.

Harmaline

Harmaline.svg

Harmaline is a reversible inhibitor of MAO-A (RIMA) at doses of 100mg.

Tetrahydroharmine

Tetrahydroharmine.svg

Tetrahydroharmine does not inhibit monoamine oxidase A. Instead, it weakly inhibits reuptake of serotonin . At doses of 200mg, it has been reported to cause dream-like euphoria, pleasurable tingling sensations and an extensive array of psychedelic effects.

Subjective effects

The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors.


Physical effects
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Auditory effects
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Toxicity and harm potential

Drug interactions

While safer than general MAOIs, RIMAs still have highly dangerous and sometimes fatal interactions with many common drugs.[2] In particular, they can cause serotonin syndrome or hypertensive crisis when combined with almost any antidepressant, stimulant, common migraine medication, certain herbs, most cold medicine (including decongestants, antihistamines, and cough syrup), nicotine, caffeine, etc. Sedatives are likely easier tolerated, but potentiation should be expected.

Lethal dosage

When intravenously injected into mice, the LD50 of harmine is 38mg/kg. There is no data for the other harmala alkaloids in humans or animals.

It is strongly recommended that one use harm reduction practices when using this drug.

Tolerance and addiction potential

There is no tolerance built up with harmala alkaloid use. There are no real reports of addiction to harmala alkaloids.

Natural sources

Banisteriopsis caapi

Banisteriopsis caapi

Banisteriopsis caapi (also known as ayahuasca, caapi or yajé) is a South American jungle vine of the family Malpighiaceae. It contains harmine, harmaline, and tetrahydroharmine in the following proportions:

  • Harmine: 0.31-8.43%
  • Harmaline: 0.03-0.83%
  • Tetrahydroharmine: 0.05-2.94%

Peganum harmala (syrian rue)

Syrian rue seeds

Peganum harmala, commonly called esfand (native name), syrian rue, is a plant native to the eastern Iranian region west to India. It has also spread invasively throughout Arizona, California, Montana, Nevada, Oregon, Texas and Washington. The plant itself produces seeds which contain harmala alkaloids and is easily accessible and legal to purchase online through the use of google. Powdered syrian rue seeds act as a reversible inhibitor of MAO-A (RIMA) at doses of 2 - 5g.

Syrian rue seeds contain several different harmala alkaloids at slightly varying percentages. Only some are monoamine oxidase A inhibitors. In one study, total harmala alkaloids were at least 5.9% of dried weight.

  • Harmane: 0.16%
  • Harmine: 0.44% (The coatings of the seeds are said to contain large amounts of harmine.)
  • Harmaline: 0.25%
  • Harmalol: 0.6%
  • Tetrahydroharmine: 0.1%
  • Vasicine (peganine): 0.25%<
  • Vasicinone: 0.0007%

Extraction

Though ground seeds can be consumed raw, this is an unreliable method of accessing the contained harmala alkaloids. The stomach can only soak the seed material in gastric juice for a limited period before it is moved further along the digestive system for absorption of molecules in solution. Because of this, whole seeds are ineffective; ground or pulverized seeds work in some circumstances, but to reliably and predictably achieve psychoactivity, it is most efficient to first extract the alkaloids from the seeds of peganum harmala into a solution by brewing it for at least 30 minutes.

The brewing environment can be enhanced by acidifying the water, using stronger solvents, and increasing the temperature. Using more water will also increase the concentration gradient, allowing more alkaloids to dissolve.

Legal issues

Harmala alkaloids and their natural sources are legal in most parts of the world.

  • Australia: Harmala alkaloids are Schedule IX drugs.
  • Canada: Harmala alkaloids are Schedule III drugs.
  • France: Possession and sale of harmala alkaloids is illegal.

See also

External links

References

  1. From the behavioral pharmacology of beta-carbolines to seizures, anxiety, and memory. | https://www.ncbi.nlm.nih.gov/pubmed/17334612
  2. Reversible inhibitor of monoamine oxidase A - Wikipedia, https://en.wikipedia.org/wiki/Reversible_inhibitor_of_monoamine_oxidase_A (accessed November 22, 2016).