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Chemistry and Psychopharmacology

harmine
2D image of a harmine molecule
dmt
2D image of a dimethyltryptamine molecule
Ayahuasca is as complex as both chemistry and psychopharmacology can get. There's a uniquely vast array of botanical sources, and an infinite amount of preparation methods, usually involving psychoactive compounds that we're only beginning to comprehend scientifically, such as DMT and 5-MeO-DMT. The plant sources, the chemical processes and psychopharmacological actions described below are the ones that are generally considered to be the most remarkable ones.

Banisteriopsis caapi

The primary active compounds in B. caapi are the alkaloids harmine, harmaline and tetrahydroharmine. They all belong to the β-carbolines group, which implies they are MAO-inhibitors. Harmine was first called 'telepathine'. Later scientists discovered they had already come across the same compound in P. harmala seeds, so 'telepathine' has become obsolete.

In the recipes of the Amazonian Indians, the liana itself is typically the main ingredient. Tests of different samples have found 20 to 40 mg, 144 to 158 mg, and even 401mg of β-carbolines per dose. Other alkaloids found in B. caapi are harmine-N-oxide, harmic acid methylester, harmalinic acid, harmic amide, acethylnorharmine and ketotetrahydronorharmine.

Harmine and other MAO-inhibitors prevent the breakdown of monoamine neurotransmitters by inhibiting the action of monoamine oxidase enzymes. Apart from creating a path for otherwise orally inactive tryptamines, this renders certain substances harmful, most notably tyramine and tryptophan. These compounds are present in many kinds of food, like cheese and ripe fruit.

Psychotria viridis and Diplopterys cabrerana

The primary active compound in P. viridis and D. cabrerana leaves is the indole ethylamine alkaloid n,n-dimethyltryptamine. Tests of different samples of Amazonian brews have found 25 to 36 mg of N,N-DMT per dose. It has a similar structure to serotonine and thus has affinity for several serotonergic 5-HT2 receptors. DMT is, like LSD, a partial-agonist on the receptor subtype 5-HT2A. When humans take DMT by itself orally, it is converted into inactive aldehydes by the endogenous enzyme monoamine oxidase.

The β-carbolines in the vine temporarily inhibit the production of this enzyme, allowing the DMT to reach the sensitive parts while still active. Inside the nervous system these are located near most of the serotoninergic terminal rich areas, including the neocortex (mainly the prefrontal, parietal, and somatosensory cortex) and the olfactory tubercle. Outside the nervous system 5-HT2A receptors are present in platelets (cell fragments, circulating in the blood, that are involved with clotting) and some muscles.

When inhaled through a vaporizer or bong, DMT gives pronounced effects without the intervention of an MAOI. The same goes for parenteral administration (injecting). Inhalation causes effects that last up to 30 minutes. Nasal insufflation, which is an important tradition of the Yanomamo tribe (see Wikipedia's Yopo page) of DMT causes an experience that lasts up to 60 minutes. Oral administration of DMT after a corresponding amount of MAOIs causes an experience of at least 3 hours. Intra-muscular and intravenous administration is effective without an MAOI.

Unlike P. viridis, D. cabrerana doesn't only contain DMT (between 0.17 and 1.75% of the leaves), but also N-methyltryptamine, 5-MeO-DMT, bufotenine and N-methyltetrahydro-β-carboline. The stems contain roughly the same set, excluding bufotenine. 5-MeO-DMT (5-methoxy-dimethyltryptamine) is, like DMT, a psychedelic agent.

DMT

The status quo of DMT in prevailing science, despite the compound's visionary properties, is that DMT is a by-product of metabolism. In the light of an ayahuasca experience, this conclusion obviously calls for more scientific research. Since DMT is every bit as illegal as LSD and heroin, however, it is a tough process for interested parties to actually get to research DMT.

Dr. Rick Strassman, a professor at the University of New Mexico medical school, has managed to survive the bureaucratic jungle of the FDA, DEA and other authorities. In 1991 he commenced the first official psychedelic research program in the U.S. since 1970. In 2001, Strassman published his findings in 'DMT: The Spirit Molecule'.

DMT is being produced in the body all the time, and it is probably involved in the process of dreaming. DMT is also one of the few substances which can cross the blood-brain barrier. Hardly anything is known about how the extreme psychedelic activity of DMT really works.

DMT is used more and more these days by psychonauts, also in its smokable form. They use hard to obtain botanical extracts made from Acacia spp. or Mimosa hostilis, which are pure enough for one draw to contain enough DMT to be active through inhalation. If one smokes the unpurified leaf or other DMT carrying plant material, typically many lungfulls are required to achieve even the lightest kinds of effects. This leaves one exhausted before the effects start.

An example DMT extraction is shown below. Please note that DMT extraction, besides being a potentially dangerous chemistry procedure, is illegal in most countries.

Simple Mimosa Hostilis DMT extraction


  1. Before you start, make sure you have all the materials needed:


    - 100 gram of Mimosa Hostilis rootbark powder (MHRB)
    - 250 ml naphtha
    - 150 gram of lye (NaOH, caustic soda)
    - 2 litre mason jar (a glass pickle jar will work also) or wide mouth HDPE jug
    - 2 small glass (mason) jars (~0.5L)
    - Guard
    - Metal spoon
    - Sheet of A4 paper
    - Eye dropper/pipette
    - Freezer

  2. Dissolve 150 grams of lye in 1.5 litre of (tap) water in a large glass jar. It is advised to wear safety goggles and gloves, as lye is a very aggressive substance that can cause burns and blindness. Add the lye in two or three steps, and allow the liquid to cool down in between.
  3. When the water with added lye has cooled down and is clear again, it is time to add the powdered mimosa bark. Add the powder slowly while stirring all the time. After adding the 100 grams of mimosa, leave the brew to stand for about an hour.
  4. Add 100 ml of naphta and put the lid on the jar.
  5. Gently turn the jar end over end for about 5 minutes. It is important not to shake or splash. After 5 minutes, put the jar down for some minutes and repeat the agitating process two more times.
  6. After a short period two separate layers will be distinguishable. Separate the upper layer (naphta) using a pipette or eyedropper. It is important that none of the dark solution is collected.
  7. Again, add 100 to 150 ml naphta to the large jar, and repeat the previous two steps two more times. Separate the upper layer in a new jar
  8. Put the collection jars in the freezer.
  9. After 24 hour the jars can be taken from the freezer. Carefully drain the naphta, making sure any floating crystals remain in the jar. Scoop out the white crystals from the side of the jar using a spoon, and leave them to dry on a folded piece of A4 paper.
  10. After drying, crush any lumps up. The three pulls combined will result in 500-1000 mg pure DMT crystals.
  11. Phalaris arundinacea

    This plant is also called reed canary grass and is one of the few DMT sources that you can find growing outside in the Netherlands. Little research has been done as to how exactly this plant can be used as the botanical DMT source for an ayahuasca analogue. Jim DeKorne, author of "Psychedelic Shamanism", is currently one of the few people who has published information on how P. arundinacea can be processed into an administrable substance. His idea of canary grass extraction is this:
    1. Pulverize the grass clippings
    2. Add water, "enough to make a pourable soup"
    3. Acidify to pH 5 or so
    4. (Optional) Simmer the acidified soup in a slow cooker overnight, not allowing the liquid to evaporate. ("It may take two or three such operations to get all of the alkaloids into solution")
    5. Strain the plant matter through cheesecloth, then through a paper coffee filter
    6. Add 10 to 15% of the mass of the solution in a "defatting solvent" such as methylene chloride, ether, chloroform, or naphtha.
    7. Shake vigorously
    8. The crap will go into the solvent, leaving the good stuff in the water.
    9. Separate the water from the solvent.
    10. Add a base to the aqueous solution in small increments until the pH gets to about 9 or 10. This converts the alkaloids into their free base.
    11. Extract with 10% of the mass of the solution of an organic solvent four times, at one 24-hour and then three weekly intervals. The solvent layer will take on a darker tint, usually yellowish or reddish-brown. It will take almost a month to extract all of the alkaloids, and the solution should be shaken at least twice a day between extractions.
    12. Evaporate the solvent off from the combined extract fractions. You now have the alkaloids.
    In a later publication, "The Entheogen Review", DeKorne has more information on Phalaris extraction:
    "The latest scoop is that you don't even have to use chemical extractions anymore - run several handfuls of grass through a wheatgrass juicer (sold in most health food stores) and you'll wind up with a glass or so of incredibly potent liquid. One teaspoon (with MAO inhibition, of course), is a standard dose with strong grass. Only two teaspoons proved very challenging to one of my correspondents - an OD! The juice can be dried and smoked in a bong - two tokes will usually do it."