Ayahuasca (Harmalas,
N,N-Dimethyltryptamine

ayahuasca chemistry

 

1. Overview
2. Chemistry
3. History
4. Ingestion
4.1 Preparation
4.2 Dosage
4.3 Pharmahuasca
4.4 Techniques
- 4.5 Retreats
5. Effects
6. Botany
7. Legality


1. Overview

‘Ayahuasca’ is the Quechua name for a psychotropic brew based around the psychoactive properties of the Banisteriopsis caapi vine. This brew and its cognates have been ceremonially prepared for thousands of years by the indigenous peoples of Northwestern South America in healing, divining, teaching, and shamanistic rituals. In the concoction, B. caapi vineonce macerated and boiled, is often mixed with other psychoactive compounds such as tobacco, coca, or an element of Justicia pectoralis. Most commonly, however, ayahuasca brews include plant material containing N,N-Dimethyltryptamine (also known as ‘DMT’), a potent psychoactive tryptamine with a rich history of shamanic use. When DMT is ingested by smoking, insufflation, or injection (intravenous/intramuscular), the effects are both short-lived (peaking within 20 minutes and lasting up to 1 hour) and extremely intense, producing inscrutable and ineffable experiences that are, some complain, difficult to integrate and reap personal rewards from.

DMT is not orally active in humans without the co-ingestion of a monoamine inhibitor (‘MAOI’), e.g. the harmala alkaloids found in Banisteriopsis Caapi and Syrian Rue. MAOIs temporarily inhibit MAO-A, preventing the destruction of monoamines. In the presence of an MAOI, orally administered doses of DMT generate longer lasting, less ineffable, and more personal trips (with an onset of roughly 30 minutes, a peak around 2 hours, and a cessation of psychoactivity within 6 hours). This is the mechanism behind ayahuasca brews.

Note: Oral ingestion of MAOIs requires caution and a familiarity with the range of dietary requirements and adversely interacting substances (e.g., stimulants and SSRIs). For further guidance, see MAOIs.

Warning: Ayahuasca is not a ‘recreational’ drug. It is a serious, sacred, plant teacher, and there is nothing entertaining about the experiences, which can be overwhelmingly intense. The rigorous self-examination that comes from ingesting ayahuasca is the antithesis of escapism. Only those with stable mental conditions would consider approaching the substance. Ingesting ayahuasca is also often a gruelling physical process, with vomiting and diarrhoea being natural side effects. Though many have found a rejuvenated spirituality, connection to life, positive outlook, source of creative insights, inspiration, and personal guidance, ayahuasca is not for everyone.


2. Chemistry

N,N-Dimethyltryptamine is an agonist of the serotonin receptors 5-HT2A, 5-HT2c and 5-HT1a. As with classical hallucinogens such as psilocybin, LSD, and mescaline, much of DMT’s psychedelic effects can be attributed to a functionally selective activation of the 5-HT2A serotonin receptor. However, DMT has stronger efficacy at the human serotonin 2C receptor than at the 2A receptor, so the former may also play a role in explaining its psychoactive character.

Though DMT is in many ways best handled and stored as a fumarate, psychonauts generally prefer DMT in freebase form, since whilst it is less stable than DMT fumarate, it has a lower boiling point and so is easier to smoke/vaporize. In solution, DMT degrades quickly and should be protected from air, light, and heat (in a freezer) when stored. Freebase DMT (C12H16N2) has the appearance of white/translucent crystals. Its melting point hovers between 44°C and 68°C. It has a molecular weight of approximately 188.26884 g/mol.


3. History

‘Ayahuasca’ is the Quechua name for a psychotropic brew, based around the psychoactive properties of the Banisteriopsis caapi vine, used by the indigenous peoples of Northwestern South America. This brew and its cognates have been ceremonially prepared for thousands of years in healing, divining, teaching, and shamanistic rituals. It is believed to have been used extensively throughout Northwestern South America (in particular from Panama, Colombia, Ecuador, Peru, and Bolivia, to the Rio Negro in Brazil). The origins of the brew, and, in particular, the source of knowledge as to the synergistic properties of MAOIs and orally ingested DMT, are unknown, though some interesting speculations have been made. Artifacts of pottery that may well have been used for ceremonial preparation and ingestion of ayahuasca have been found to date back as far as 2000 BC. Surprisingly, though, ayahuasca appears to have been unknown outside of these South American communities until as recently as the 17th/18th Century. Shortly after its first reference in a publication (by Jesuit priests, well into the 18th Century ), botanist Richard Spruce, in 1852, observed the use of ayahuasca among the Tukanoan tribes. Though he partook of the brew himself and experienced little more than nausea, he recorded the character of the experiences that fellow travelers had enjoyed:

Northwestern South America

Northwestern South America

“Alternations of cold and heat, fear and boldness. The sight is disturbed, and visions pass rapidly before the eyes, wherein everything gorgeous and magnificent they have heard or read of seems combined; and presently the scene changes to things uncouth and horrible… A Brazilian friend […] saw all the marvels he had read of in the Arabian Nights pass rapidly before his eyes in a panorama; but the final sensations and sights were horrible, as they always are” (Spruce, 1908).

Ayahuasca experiences set in after around half an hour after consumption, peak after two hours, and generally last under six hours. Physiologically, ayahuasca increases both heart rate and diastolic blood pressure. Vomiting and diarrhoea are very common. In some cases, individuals experience considerable psychological stress during the experience. Extreme caution should be taken by those who are at risk of heart disease, and it would be wise to avoid the substance if one is, in one way or another, psychologically unstable.

Whilst many of these indigenous groups (of which there are over 70) have employed different terms for the brew – from ‘Yagé’ in Southern Colombia to ‘Hoasca’ in Brazil – the omnipresent ingredient is the vine of Banisteriopsis caapi. B. caapi is rich in β-carboline alkaloids, such as harmine and d-THH, as well as harmaline, harmol, and harmalol (McKenna et al., 1984), and so acts as an MAOI.

In the concoction, B. caapi vine, once macerated and boiled, is mixed with other psychoactive compounds such as tobacco, coca, or an element of Justicia pectoralis. Most commonly, however, ayahuasca brews included a DMT-containing plant. Although MAOIs do have psychoactive properties of their own, it is generally agreed that they are neither of sufficient strength nor psychedelic character to be capable of producing experiences of the quality and intensity that ayahuasca has often been attributed with. Harmine (a principal β-carboline alkaloid in MAOIs such as B. Caapi and Syrian Rue), like harmaline, is a mild sedative in low doses (1.5mg/kg), and causes only unpleasant, vegatative states and numbness in doses  reaching 200mg (Ott, 1999). Above 200mg, visual imagery may occur with one’s eyes closed. At 300-500mg, nausea and general malaise are particularly prominent (Shulgin and Shulgin, 1997). The experiments of Sai-Halasz (1963), where subjects were administered 100mg of iproniazid daily for four days prior, seems to suggest that chronic/persistent MAOI administration actually leads to a reduction in the potency of subjective effects of DMT.

The primary mechanism behind many ayahuasca brews, then, is thought to be the combination of a DMT-containing plant and an MAOI-containing plant. Crucially, MAOIs are needed in order for DMT to become orally active. Though the vine of B. Caapi is thought to have been used exclusively as the MAOI throughout the region, the plants used to play the DMT role varied between communities. In much of Brazil and Peru, the DMT component was frequently Psychotria viridis, whereas Diplopterys cabrerana was more commonly used in Colombia. (The Christian ayahuasca church União do Vegetal prepare hoasca exclusively from B. caapi vine and Psychotria viridis.)

The preparation techniques also vary somewhat between these communities. Whilst in the Colombian Amazon a cold-water extract is often employed, in Pucallpa (Peru), the admixture is simmered for up to 15 hours before being concentrated (generating a much more potent substance).

The sociological function of this pan-Amazonian psychotropic beverage is thought to range from its use as a means to contact the supernatural world, to practice divination, to determine the cause of disease or to cure the ill, to decipher enemy plans and strategize means of attack and defense, to facilitate sexual activity, to welcome foreign travellers, and, more generally, at least by the Cashinahua Indians: “to learn of things, persons, and events removed from them by time/space” (Der Marderosian et al., 1970). Its medicinal use should also not be underestimated. The purgative properties of ayahuasca work to expel parasites through vomiting and diarrhoea, and, simultaneously, harmala alkaloids have been shown to act against parasites inside the body. Unlike what is suggested by research on DMT, there is allegedly some natural tolerance to habitual (i.e. weekly) use of ayahuasca. This may develop through upregulation of the serotonergic system.

In recent times, ‘ayahuasca churches’ have adopted the brew as a sacrament in religious (often Christian) contexts. It has also spread to urbanized areas (e.g., Iquitos, Peru), where ayahuasqueros, as experienced shamans, offer healing ceremonies. Its use has in recent years spread throughout much of Europe and North America as interest in exotic psychotropics has increased. ‘Pharmahuasca’ is a variant on the traditional ayahuasca brew that uses pharmaceutical drugs in place of plant materials. Contemporary ayahuasqueros maintain that the B. caapi vine is the essential, defining ingredient of ayahuasca, and is considered to be the ‘spirit’ of the brew – the guardian and guide to the transcendental realms it makes accessible.

Despite a temporary ban from 1985-1987 in Brazil, ayahuasca and its cognates remain widely legal throughout South America, provided it is used in a ritualized context.


4. Ingestion

As discussed, the mechanism behind ayahuasca brews is often the combination of a plant containing N,N-Dimethyltryptamine (DMT) with a plant rich in harmala alkaloids (an MAOI). MAOIs are needed in order for DMT to become orally active. Though ayahuasca has historically been prepared with Justicia pectoralis in place of a DMT-component, DMT incarnations of the brew will be the topic of this section.

Ayahuasca experiences set in half an hour after consumption, peak after two hours, and generally last under six hours. Subjectively, users often report spiritual revelations concerning the nature of the universe as well as deep, personal epiphanies as to how they can be a better person. Physiologically, ayahuasca increases both heart rate and diastolic blood pressure. Vomiting and diarrhoea are common. In some cases, individuals experience considerable psychological stress during the experience. Extreme caution should be taken by those who are at risk of heart disease, and it would be wise to avoid the substance if one is, in one way or another, psychologically unstable.


4.1 Preparation

Ayahuasca experiences are profoundly spiritual, and they can also be tough, emotionally and physically. They require considered preparation.

First, it is good to go into these sorts of entheogenic journeys with a clear and honest purpose in mind – what is it that you want to learn, to clarify, to explore; what do you intend to bring back? Over what do you wish to commune with your deep self? Having some sense of an objective can help give shape to your experience, can prevent you from punishing yourself for being disrespectful should the experience become unexpectedly intense, and can quell fear and anxiety should it arise. The purpose need not be anything grandiose or philosophically engaged; it just needs to be honest and clear. It may just be ‘to explore the psychedelic realms of this plant’. (As a rule of thumb, the deeper you intend to go, the more considered your purpose(s) should be.) If there is psychic turbulence, you could recite your intentions to regain direction and courage.

Peruvian Ayahuasca

Peruvian Ayahuasca

The setting should be tailored to facilitate your experience. Turn off/dim the lights, unplug any distractions (phones, etc.), and cover up clocks and windows. The more you are disconnected from your external environment, the easier it will be to tune into the inner fireworks and symphonies.

At any reasonably high dosage, ayahuasca will stone your CNS, and you will not be very good at, nor very willing, to move about. (Move about slowly, too, since dizziness and purging can result from abrupt motion.) So it’s a good idea to have everything you need at arm’s reach, whilst giving yourself enough space so as to not feel encumbered, and so that you can spread out and roll around freely.

  • Firstly, and crudely, you will need a bucket or two… preferably lined with a plastic bag. (If you venture to the bathroom at any point, take the bucket with you.)
  • A bunch of pillows and blankets should provide a comfortable area for you to lie down. You may also want to angle yourself so that your head is elevated.
  • A glass of water or fruit juice and some tissues nearby may come in handy.
  • Everyone, especially those who are new to this, should have a sitter either present or nearby that they can call on if things get turbulent.

As you will be aware, if you plan on orally ingesting MAOIs, you need to make dietary preparations. (See MAOI safety.) You should weed out MAOI-offensive food and drinks 24-48 hours before and after taking ayahuasca. It is also, as always, better to take your psychoactives on a fairly empty stomach. So eat light and healthy (e.g., fruit), give yourself 4 hours to digest, and then take your ayahuasca. (Remember: there’s a good chance that whatever you eat beforehand will be coming back up again.) The relationship you have with your body may feature in your ayahuasca experience, so feeling fit and healthy is likely to enhance your experience.

You should also be mentally and emotionally receptive to the ayahuasca. If you have little prior experience with entheogens, this will be difficult to gauge. The primary hurdle is resistance. The more you resist and refuse to accept your synthesis with the plant, the more likely you are to undergo a partly negative, fearful, anxious, or incomplete trip. If you have made the right preparations, you can trust whatever you feel is coming over you, even if it feels foreign and alien.

Any lurking emotions will be dredged up for your scrutiny. This is the main source of truth and revelation in entheogenic experiences, so you should be ready to welcome it – it will be valuable to you. If you think you may have particular repressed or reserved emotions, you should consider whether you really want to confront these in the context of an intense psychedelic experience. The process will certainly be healing, but it will be painful, too.

Other tips:

  • Incantations, recitations, mantras, and prayers can be useful in much the same way as repeating your intentions, stabilizing you.
  • Listen and attend to your breath. Breathing is a peculiarly direct connection that life has to the universe. If you practice meditation, it can be a very powerful tool in guiding and directing your experience.
  • ‘Spirit’ guides can be invoked to anchor and embody advice.


4.2 Dosage

As always, dosage advice must be taken with caution. Because of the number of variables involved in judging the potency of psychedelic substances (e.g., the variance in the source of the plant, the purity of the substance, the temperature at which the substance is smoked, the background brain chemistry of the user, the user’s level of physical tolerance, etc.), it is not possible to give sound advice that covers all circumstances.

Banisteriopsis caapi vine

Banisteriopsis caapi vine

It is recommended that users try preparing a pure B. caapi brew, learning how much vine is required for a psychedelic experience. Start low and raise the dosage as required. (Systematically determining the quality of material relative to the individual’s unique metabolism is much better, and safer, than a psychedelic lottery.) When the experience begins, you will be locked for hours. An ungrounded experience with too much admixture can easily result in fear and panic. One should always begin slowly and cautiously with any admixture, including (especially) DMT.

DMT-containing plant materials commonly used as admixtures:

Psychotria viridis/’Chacruna’ (leaves): 40-160g

The alkaloid content of P. viridis varies over the course of the day, making harvesting somewhat tricky and internet vendors somewhat unreliable. The N,N-DMT content is much lower than most other admixture plants, so a much higher volume must be brewed. Chacruna reportedly has a green energy, with visions typically involving symbols of ancient language and the presence of natural surroundings, or even conversations with plants.

Diplopterys cabrerana/’Chaliponga’: 2-8g

Psychotria viridis leaves

Chaliponga is much more potent than Chacruna. Chaliponga is sometimes noted to be ‘darker’ and more occult in experiences.

Mimosa hostilis (inner rootbark): 1-3g.

Warning: Mimosa hostilis must be brewed separately from B. caapi. The sediment that drops out of Mimosa hostilis, unlike B. caapi and many other admixture plants, is inedible. It can be prepared in just the same way as B. caapi, but it must be in a separate pot. After decanting, a dark sludge will emerge from the rootbark. This sludge is responsible for much of the peculiar nausea relating to M. hostilis. Filter the brew an appropriate material after decanting.

MAOI plant materials commonly used for oral DMT ingestion:

Banisteriopsis caapi (vine): 40-120g
Syrian Rue (seeds): 2-5g


4.3 Pharmahuasca

‘Pharmahuasca’ refers to a variant brew in which one of the two roles (DMT component or MAOI) is played by a pharmaceutical drug or extracted freebase compound, as opposed to a natural plant material.

Note: Pharmahuasca brews vary greatly depending on individual metabolism, etc. It is best to avoid freebase pharmahuasca unless you know very well what you are doing. Novice users would, it is said, be wise to start with no more than 60mg freebase DMT. Go for the plants the first few times.

Freebase DMT Oral (with MAOIs): 40-160mg.

Ott (1999) experimented with oral ingestion of freebase DMT with the MAOI harmine (a principal alkaloid in B. Caapi vine). He found that the threshold dose of harmine needed to render DMT orally active was around 1.5mg/kg. At this threshold harmine dose, the threshold dose for oral administration of DMT was established to be 0.38mg/kg.


4.4 Techniques

The internet is flooded with shoddy and ill-informed ayahuasca brew techniques. We provide the following (a combination of online sources from forums, etc.) for research and harm-reduction purposes only – extraction of DMT and preparation of ayahuasca is illegal internationally, except in ritualized contexts in parts of South America. We do not recommend or endorse preparation or human ingestion of ayahuasca in regions where doing so is illegal.

Ayahuasca boiling in the Napo region of Ecuador

Ayahuasca boiling in the Napo region of Ecuador

An example of a contemporary ayahuasca technique:

- Traditionally, P. viridis leaves and B. caapi vine are used in a 1:1 ratio.

1. (Optional) Some would freeze plant materials overnight before cooking to break down cell walls. This would aid the release of the psychoactive contents, increasing the potency of the brew. (There is no need to shred the caapi vine or prepare any other plant materials in this way. Though this would increase surface area, one would be boiling for enough time that this would make little difference.)

2. One would need quite a few pans for this technique, and one might want to boil the DMT-containing plant separately from the B. caapi vine, perhaps even keeping them separate the whole way and ingesting with a slight time interval (e.g., MAOI 30 minutes before tryptamines). Separate cooking would be required if one were using M. hostilis.

3. One would obtain distilled water – tap water contains additives that would make one’s reduction less pure. It is hard to say how much water one would require. The rule: as plant materials are exposed to the surface, one adds water to keep them submerged.

4. Acidify water to approximately ph 3. (One might use lemon/lime juice, though this tastes pretty bad. One tbspn of vinegar per liter of water should suffice.) Though this is not necessary (and would, unfortunately, affect the taste), acidified water is more efficient for brewing, as it pulls more alkaloids. (See picture below – note the lightness of the stronger, acidified brew.)

5. One would then cover the plant materials with the (acidified) water, and bring to a boil, reducing the heat to keep the water just above the threshold of boiling. (When nearing the end of each subsequent wash, one would let the water boil down a little further than the last wash.)

Picture of non-acidified water (left) and acidified water (right) brews.

Picture of non-acidified water brew(left) and acidified water brew (right).

6. After 3 hours of boiling, one would cover a new pot with a cotton t-shirt, and strain all the liquid over the shirt and into the pot.

7. One would submerge the cooked plant materials once again with fresh, acidified, distilled water, and boil for a further three hours. Filter the new liquid into a separate pot as in step 5.

8. Step 6 is repeated once more, brewing plant material for a total of 9 hours.

9. One would then combine all three filtered liquids and reduce. This requires a good deal of care and attention, else the liquid will boil over. One should gradually reduce the heat as the liquid evaporates, until only several ounces are left.

10. Some would store the finished product in sterilized glass jars. It can be kept this way in a fridge for several months, or frozen indefinitely.


4.5 Retreats

Many people have become interested in exploring ayahuasca in ‘retreat’-environments in certain parts of South America, where the brew is legal in ritualized contexts. One must be cautious in finding out about these centers, as there is naturally a possibility that one will be taken advantage of, in one way or another. An excellent independent, third-party review site is ayaadvisor.org. They offer a directory of ayahuasca, iboga, peyote, and san pedro retreats, with ratings and reviews from past visitors. If you are considering a retreat, a good way to prepare is by reading their ‘Education’ section.


5. Effects

Ayahuasca experiences set in half an hour after consumption, peak after two hours, and generally last under six hours. Subjectively, users often report spiritual revelations concerning the nature of the universe as well as deep, personal epiphanies as to how they can be a better person. Physiologically, ayahuasca increases both heart rate and diastolic blood pressure. Vomiting and diarrhoea are common. In some cases, individuals experience considerable psychological stress during the experience. Extreme caution should be taken by those who are at risk of heart disease, and it would be wise to avoid the substance if one is, in one way or another, psychologically unstable.

Callaway (1999) administered doses of ayahuasca with the following average alkaloid content: 35.5mg DMT, 252.3mg harmine, 29.7 harmaline, 158.8 THH. The subjective effects of the experiment were as follows:

“…peak plasma levels of DMT were associated with intricate and colored eyes-closed visual imagery, complex thought processes, and a general state of heightened awareness”. “…overall perceptual, cognitive, and affective processes were significantly modified while maintaining the presence of a clear sensorium”. Nausea, vomiting, and diarrhoea were common, with one subject vomiting only 45 minutes after ingesting the tea. One researcher reported intense fear. Nystagmus and tremor were also observed in some.


6. Botany

Mimosa Hostilis Rootbark

Mimosa Hostilis Rootbark

DMT is present in many plants. The following list is neither exhaustive nor indicative of the amount of DMT content in the plant. The tryptamines may be present with other potentially unwanted alkaloids, so research would be needed before extracting.

Anadenanthera colubrina
Anadenanthera peregrina
Desmodium gangeticum
Diplopterys cabrerana
Justicia pectoralis
Limonia acidissima
Mimosa hostilis
Mimosa ophthalmocentra (Mimosa tenuiflora)
Phalaris acquatica
Phalaris arundinacea
Psychotria viridis

7. Legality

Anyone embarking on a DMT experience and/or extraction should be aware of the possible legal consequences of their actions. Extracted DMT (e.g. in fumarate or freebase form) is considered illegal in all the UN-bound countries. Natural materials containing DMT (e.g., Psychotria viridis) are frequently in a legal grey area, and its control will depend on country’s current specific legislation and priorities.

For further information on Ayahuasca or other entheogens visit our growing Literature page.

Works Cited

Der Marderosian; Kensinger; Chao; Goldstein. (1970). ‘The Use of Hallucinatory Principles of a Psychoactive Beverage of the Cashinahua Tribe (Amazon Basin)’, Drug Dependence, Vol. 5, pp. 7-14.

McKenna; Abbott; Towers. (1984). ‘Monoamine Oxidase Inhibitors in South American Hallucinogenic Plants: Tryptamine and Beta-Carboline Constituents of Ayahuasca’, Journal of Ethnopharmacology, Vol. 10, pp. 195-223.

Ott, Jonathan. (1993). Pharmacotheon: Entheogenic Drugs, their Plant Sources and History, (Washington: Natural Products Co., Kennewick).

Ott, Jonathan. (1999). ‘Pharmahuasca: Human Pharmacology of Oral DMT Plus Harmine’, Journal of Psychoactive Drugs, Vol. 31, pp. 171-77.

Ott, Jonathan. (2001). ‘Pharmapena-Psychonautics: Human Intranasal, Sublingual, and Oral Pharmacology of 5-Methoxy-N,N-Dimethyl-tryptamine’, Journal of Psychoactive Drugs, Vol. 31, pp. 171-77.

Riba, Jordi. (2003). ‘Human Pharmacology of Ayahuasca’. http://www.maps.org/research/ayahuasca/jriba_thesis.pdf

Sai-Halasz, A. (1963). ‘The Effect of MAO Inhibition on the Experimental Psychosis Induced by Dimethyltryptamine’, Psychopharmacologica, Vol. 4, pp. 385-88.

Shulgin, A.; Shulgin, A. (1997). TIHKAL: The Continuation, (Berkeley, CA: Transform Press).

Spruce, Richard. (1908). Notes of a Botanist on the Amazon and Andes, Vol. 2, (London: Macmillan).

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<h4><span style=”text-decoration: underline;”>4.2 Dosage</span></h4>
<p style=”text-align: justify;”>As always, dosage advice must be taken with caution. Because of the number of variables involved in judging the potency of psychedelic substances (e.g., the variance in the source of the plant, the purity of the substance, the temperature at which the substance is smoked, the background brain chemistry of the user, the user’s level of physical tolerance, etc.), it is not possible to give sound advice that covers all circumstances.</p>