Acacia and Entheogenic tryptamines

A simple start to a complex area.

Entheogenic literally means ‘realising the divine within’, and designates plants or compounds that provoke ‘ecstatic’ experiences or have been used as shamanic or religious inebrients, including artificial cogeners. The term has been proposed by many well known writers and researchers in the field of psychoactive compounds and states of consciousness, in place of such terms as ‘psychedelic’ and ‘hallucinogen’.

Information here is regarding mostly members of section Juliflorae, from SE Australia that can or have been used as a source of tryptamine alkaloids, or specifically methylated tryptamines such as N,N-dimethyltryptamine (DMT). As well as one Australian species from the Plurinerves that is reported to contain b-carboline alkaloids. One of these species is rare and indigenous to only one mountaintop in Vic, three are reasonably common, the last being a relatively uncommon species.
Other species in sub-genus Phyllodineae, acacia simplex ( formerly a. simplicifolia) has been found to contain 0.81% DMT in the bark, it is however not naturally found in Australia but in New Caledonia and other islands in the SW Pacific. Another species, acacia confusa has been reported to contain also high amounts of methylated tryptamine alkaloids in the root bark. This is also an extra Australian species, from Taiwan and the Phillipines, that is used in Traditional Chinese Medicine.
I have tried to compile all the information I have on the alkaloids of each species and supplemented it with information from my own and associates research.

Especially in the case of rarer plants it is recommended that wild plants are not used as a source of alkaloids, as this may cause a problem for the survival of the species. Taking plant material from national parks is illegal, and these places are the only refuge many plants and animals have from us, leave them be. Roadsides, wastelands and other disturbed areas are quite often colonised by acacias.
Generally acacias are easily grown from seed and can grow extremely quickly, planting more acacias will benefit a planet already suffering from too much pollution and land degradation.
Also there are plants from other families that can also be utilised as a source of alkaloids, including possibly phalaris tuberosa and phragmites australis, from the poacea or grass family and also common and easily obtainable.

N,N-dimethyltryptamine (DMT) is a reasonably widely occurring alkaloid, present in other members of the mimosacea, ie mimosa hostilis, andenanthera peregrina, species from the leguminosae and other genera including the poacea, myristicaceae and rubiacea. It is a potent entheogen, and has been used, through plants, by people for hundreds of years in places like central and south America. Plants there were and are still used as sources of entheogenic snuffs and drinks for at least 1500 years. With the people there having an intimate relationship with these plants and their component compounds/ spirits.
DMT is also a natural component of human (mammalian) neurochemistry, a research team in the USA finding it in brain tissue and cerebrospinal fluid, and may even be a neurotransmitter, along with it’s analog 5-methoxy-DMT, which is also present in human (mammalian) brain and cerebrospinal fluid. There is in fact an enzyme known as indole-N-methyl transferase (INMT), present in many different parts of the body ( and in other species of animals and even plants), that with other enzymes and processes converts tryptamine, N-methyltryptamine (NMT) and possibly tryptophan to DMT and 5-methoxy-DMT in the body. The activity of this enzyme is affected by some drugs, environmental factors such as stress may increase or effect the activity as well, DMT is closely related to the neurotransmitter serotonin, 5-hydroxy-tryptamine, and psilocin, 4-hydroxy DMT, one of the active alkaloids of some ‘magic mushrooms’, as well as melatonin, 5-methoxy-N-acetyl -tryptamine, a hormone produced by the pineal gland at night and used as a drug to treat insomnia.

Recent work has also found it to be one of the active compounds in a seaweed extract ‘kelpak’, along with other related compounds, such as indole acetic acid (IAA), it was found to promote root growth in seedlings.
DMT freebase or alkaloid can be smoked to produce a very intense though short lived ‘trip’, lasting up to 20 to 30 minutes. Your body rapidly breaks down the DMT, most of (more than 95%) it being metabolised by the end of the experience. It is very potent, active above 10-15 mg, above 60 mg the experience may be overwhelming, 20-35 mg depending on body weight is about a ‘smoking’ dose. 5-methoxy DMT is even more potent, with a dose of about 10 mg being the equivalent of 30 mg DMT. Though the effects are supposedly different, shorter and not so visual, more intense, sounds like it can be very uncomfortable, though some people seem to get something out of it.
Caution should be taken, set and setting are very important, if you are stressed out tired or unsure the effects can be overwhelming. Not recommended if you have high blood pressure or heart problems. Any effects from large smoked doses (more than 60 to 70 mg) is unknown, may repress breathing.
DMT is not orally active normally, though can be made so by combination with MAO (mono-amine oxidase) inhibitors, such as the b-carboline alkaloids, another class of related alkaloids that have been used for this purpose in the orally active entheogenic ‘ayahuasca’ brews of the Amazon. b-carboline alkaloids are even more widely occurring than tryptamine alkaloids it seems. Banisteropsis Caapi, a rainforest vine, is the traditional source of the b-carboline alkaloids, with two other unrelated species also reported to contain the same alkaloids,Peganum Harmala and Passiflora Incarnata.
Mono-amine oxidase, an enzyme, is the body’s main means of metabolising mono-amine compounds such as serotonin, dopamine, epinephrine (adrenaline) etc, as well as breaking down other amine compounds from food and drugs such as tyramine, amphetamines, tryptamines etc.
When MAO is inhibited your body’s defences are down and some compounds that are normally harmless or mild may have a very strong action. Drugs and compounds that may be potentiated include barbiturates, alcohol, amphetamines, ephedrine, analgesics, tyramine ( a fermentation product in many foods) etc. In this state DMT also becomes orally active as it is not broken down after ingestion, or at least the process is delayed.

Many b-carboline alkaloids have been found to be potent short term inhibitors of MAO, lasting about six hours. Some are reported to be entheogenic alone, but doses required tend to be quite high ( > 4 mg /kg) and produce more unpleasant physical symptoms. They have in the past been used as anti-depressant drugs alone, and although they seem not to be used for this anymore many modern synthetic anti-depressant drugs are also MAO inhibitors, generally their action is greatly extended, over days or even weeks. DMT is reportedly orally active with some of these drugs also, care should be taken by people on these drugs as they will most probably potentiate any effects that DMT or many other compounds would have. An MAO inhibition effect has not been demonstrated for all b-carboline alkaloids in the body, DMT is itself a weakly MAO inhibiting compound but is not effective alone orally.
For a review of the pharmacology of b-carbolines and tryptamines, Ayahuasca Analogues by Jonathon Ott is an excellent one.

Care should be taken when ingesting MAO inhibiting compounds, there can be adverse reactions to compounds that would otherwise be harmless or of little consequence, they may even be fatal. Don’t consume alcohol, fermented foods such as cheeses, yeast products inc bread, yoghurt etc, amphetamine based drugs, some dried fruits such as figs, raisins, some types of legumes such as broad beans etc before, during or after taking MAO inhibitors.
It is generally a good idea to fast before taking any entheogenic to lessen nausea or discomfort, and try to refrain from ingesting any of the above until the experience is totally over. Set and setting are again important, be somewhere comfortable and relaxed, with people you trust. Most plant derived extracts can contain more than one alkaloid, even other compounds that are not alkaloidal in nature, and is generally a mix of similar types of alkaloids. It depends on how well produced it is also.

In the Australian acacias only DMT or DMT in combination with N-methyl tryptamine(NMT) has been found, but this is only from two or three tests on two species, further study may find other related alkaloids. Acacia simplex also contains N-formyl-N-methyltryptamine with DMT and NMT and 2-methyl-1,2,3,4,tetrahydro-b-carboline in it’s phyllodes, but is not found in Australia.. NMT is not particularly psychoactive, but under conditions of MAO inhibition may be converted into DMT and other related compounds by enzymes such as INMT when ingested.
With keeping or under certain conditions DMT and other tryptamine alkaloids may react or change, eg DMT may change to 5-hydroxy-DMT (Bufotenine), an alkaloid also found with DMT in some plants, but generally not recognised as being ‘hallucinogenic’, it does however have a strong and possibly dangerous effect on the heart. I have no information on the effects of N-formyl-N-methyltryptamine. 5-methoxy-DMT occurs quite commonly with DMT in many of the plants from central and south America and elsewhere. Both 5-methoxy-DMT and DMT under certain conditions, possibly including in the body during metabolism, may convert into b-carboline alkaloids such as 1,2,3,4-tetrahydro-b-carboline and it’s 2-methyl analog, which interestingly is found along with DMT in a. simplex.
Acacia complanata has been reported to contain the b-carboline alkaloids N-methyl-tetrahydroharman and tetrahydroharman, and a.. baileyana has been reported to contain the alkaloids tryptamine and/ or tetrahydroharman at different times of the year in the foliage.
It seems that the metabolic pathways for these two types of alkaloids have some relationship as they are found together in plants from not only the mimosaceae, but also the poacea (phalaris spp), myristicaceae (virola spp) and other sections of the leguminosae (desmodium spp).
The b-carboline alkaloid, 6-methoxy-tetrahydroharman is reported to occur naturally as a hormone in the pineal gland and to be ‘hallucinogenic’ above 1.5 mg/ kg ( this may infact be 5-methoxy-N-acetyltryptamine, or melatonin, a hormone produced at night by the pineal gland, whereas serotonin, 5-hydroxytryptamine, is produced during the day. Melatonin has recieved much attention recently as a nootropic type drug, and to treat insomnia. It is obviously very closely related to the entheogenic tryptamines.).

For further references and information see the links provided