1840s – Harmaline and Harmine Are Isolated from the Seeds of Peganum harmala (Syrian rue)
The same active alkaloids that exist in the ayahuasca vine, B. caapi vine, were first isolated from a different plant almost two centuries ago. Growing wild across Eurasia and North Africa, the seeds of Peganum harmala (Syrian rue) contain an almost identical molecular profile to what is in the ayahuasca vine.
There has been an awareness of Syrian rue since ancient times, with the Greek-Roman physician Galen, for example, mentioning the plant in the second century AD. The seeds of Syrian rue have a long history of both ritual and medicinal use, used mainly as incense (still to this day in the Near East and North Africa).
This desert plant also holds a special place in Persian cultural traditions, as it is viewed as a sacred plant. Like the B. caapi vine, it is also known for its psychoactive properties. The Persian philosopher Avicenna was aware that Syrian rue had such properties.
It was some time, however, before scientists discovered the compounds that accounted for the effects of Syrian rue. In 1841, German chemist H. Göbel isolated harmaline from the seeds of Syrian rue. Six years later, in 1847 J. Fritsch isolated harmine from Syrian rue. These are two of the main compounds also found in the B. caapi vine.
Harmaline, harmine, tetrahydroharmine and harmalol belong to a group of substances with similar chemical structure collectively known as harmala alkaloids, which are in a class of compounds known as β-carbolines. Harmala alkaloids are present in Syrian rue in concentrations of about 3%, although the range is 2-7% and possibly even higher than that. In the B. caapi vine, the concentrations for harmala alkaloids range between 0.31-8.43% for harmine, 0.03-0.83% for harmaline, and 0.05-2.94% tetrahydroharmine.
Harmala alkaloids are responsible for the hypnogogic effects (shadowy, dreamlike visions) produced by the ayahuasca vine, as well as by Syrian rue. However, on their own, even at very high doses, harmala alkaloids are not known to produce very hallucinogenic effects, not like that seen with ayahuasca. On their own and at high doses, Syrian rue and B. caapi can lead to some psychoactive effects, such as a ‘buzz’ or feeling of intoxication, or slight psychedelic effects, such as minor visual changes.
Interestingly, the unextracted active ingredient of the ayahuasca vine was first called “telepathine”, based on the belief that this was the chemical responsible for the experiences of telepathic communication that supposedly occur under the influence of ayahuasca. This name stuck when the active ingredient was later isolated. However, it was soon realised that telepathine was the same as harmine, which was discovered in Syrian rue and named as such before the chemical was isolated from the ayahuasca vine.
Harmala alkaloids inhibit MAOIs, making DMT orally active and thus be able to enter the blood stream through the stomach. They also potentiate the effects of many other substances. MAOI stands for monoamine oxidase inhibitor; this chemical stops monoamine oxidase (MAO), an enzyme in the body, from breaking down DMT when it is orally ingested.
Since Syrian rue can also allow DMT to become orally active, it can be combined with DMT-containing plants – such as Psychotria viridis (chacruna) or Mimosa hostilis – to create an ayahuasca-like brew. There is now a variety of ayahuasca “analogue” brew consumed around the world that mimic the effects of the classic Amazonian brew but using different botanical sources. Since the MAOIs in Syrian rue can strengthen the effects of other compounds, some people will combine Syrian rue with psychedelics, especially the tryptamine psychedelics. This might involve drinking Syrian rue tea, for example, before consuming magic mushrooms or smoking DMT. Syrian rue, along with other herbs and plants, is sometimes mixed with freebase DMT, creating ‘changa’ (also known as ‘smokable ayahuasca’).
In higher doses, harmala alkaloids can induce vomiting or diarrhoea. This is known as the ‘purging’ that takes place during an ayahuasca session. As a purgative, harmala alkaloids can have medical benefits, helping the body to flush out worms or parasites. But for many people, there is a spiritual cleansing that takes place with the purge as well, with the ayahuasca vine helping to expel negative feelings.
In the early twentieth century the German pharmacologist Louis Lewin conducted various experiments on harmala ayahuasca extracts. This was paralleled by early research into the possible therapeutic effects of ayahuasca vine extracts on Parkinson’s Disease. Today, it is recognized that the alkaloids in the ayahuasca vine appear to have unique therapeutic properties which include anti-anxiety effects and anti-depressant effects.
Callaway, J. C.; Brito, Glacus S.; Neves, Edison S. (2005). “Phytochemical analyses of Banisteriopsis caapi and Psychotria viridis“. Journal of Psychoactive Drugs. 37 (2): 145–150.
McKenna, Dennis. 2014. “Ayahuasca: An ethnopharmacological history.” In The Ayahuasca Experience: A Sourcebook on the Sacred Vine of Spirits. Ed. Ralph Metzner. Inner Traditions.