Harmala alkaloid

Harmala alkaloids are a class of chemicals that include compounds with psychoactive effects.

Chemistry

Harmala alkaloids are based upon the molecule beta-carbolines, beta-Carboline itself is made up of an indole ring attached to a pyridine ring.

Pharmacology

Harmala alkaloids all function as reversible inhibitors of monoamine oxidase A (RIMAs). This is a class of drugs which selectively and reversibly inhibits the enzyme known as monoamine oxidase A (MAO-A) and is therefore combined with ayahuasca brews, to prevent the breakdown of DMT in the digestive system by inhibiting the enzyme monoamine oxidase. Due to their reversibility and selectivity, RIMAs are safer than the older monoamine oxidase inhibitors (MAOIs) and do not require that people follow a tyramine free diet.

Examples

Common Harmala alkaloids include:

Harmine

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

Harmaline

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

Tetrahydroharmine

Tetrahydroharmine does not inhibit monoamine oxidase A; instead it weakly inhibits serotonin reuptake. At dosages of 200mg it has been reported to cause dream like euphoria, pleasurable tingling sensations and a head space similar to that of LSD.

Toxicity and Harm Potential

Drug Interactions

While safer than general MAOIs, RIMAs still have highly dangerous and sometimes fatal interactions with many common drugs; in particular, they can cause serotonin syndrome or hypertensive crisis when combined with almost any antidepressant or stimulant, common migraine medications, certain herbs, or even most cold medicines (including decongestants, antihistamines, and cough syrup).

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.

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 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 are contain harmala alkaloids and is freely available and legal to purchase online through the use of google. Powdered Syrian rue seeds act as a reversible inhibitor of MAO-A (RIMA) at dosages of 2 - 5g.

Syrian rue seeds contain several different harmala alkaloids at slightly varying percentages, only some of which are are monoamine oxidase A inhibitors MAOI. 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%

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

• Beta-Carbolines
• Psychedelics
• Tryptamines
• Phenethylamines
• Lysergamides