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Ayahuasca: alkaloids, plants & analogs
assembled by Keeper of the Trout
Section 1 :
The Hasenfratz Method of Harmine and Harmaline Isolation
With additional comments by Keeper of the Trout

Photo by Trout

The green seeds of Peganum harmala, if available, will give a higher yield than the ripe seeds. Roots of Peganum harmala may also be used and, while somewhat lower in total alkaloid, will have a much cleaner alkaloid profile.

Banisteriopsis caapi may be used as well but gives a substantially lower return and thus requires a far larger amount of dried plant material. For example, an extraction of 95 grams (dry weight) of cultivated B. caapi leaf yielded a total of 0.6 grams (600 milligrams) of alkaloid. (i.e. 0.63% total alkaloid. This is nearly 4.5 kilograms of leaf per ounce of total alkaloid recovered as the hydrochloride salts. Recovery would be higher if stem bark or roots were used but it would still fall short of Peganum harmala's yield.)

In the case of B. caapi the principle alkaloid present will be harmine, with lesser amounts of tetrahydroharmine; if harmaline is present at all it will usually be as a minor component (but the odd exception has been reported). It also lacks peganine etc. found in P. harmala as well as the fixed oils so it will start out as a greenish white to white precipitate and will not need as many recrystallizations to purify.

A few other plants are potential sources of harmine or harmaline such as Tribulus terrestris, and Passiflora incarnata. These have tetrahydroharmine [1], harmine or harmaline in even lower amounts and require far larger quantities of plant material to be processed. [Hundreds of grams of dried leaf and stem per dose in the case of Passiflora incarnata or an even larger quantity of fruit with Passiflora edulis [2] These also have other alkaloids present in greater quantities than the harmine and require more complex purification.

Tribulus is used medicinally due to the presence of some of these other compounds.

Passiflora is also used medicinally due to the presence of some of these other compounds. Its most abundant beta-carboline alkaloid should always be expected to be harman, never harmine.

The following approach came from Marion's article in Manske & Holmes (eds.) The Alkaloids Volume Two (1952), from page 393 and Hasenfratz (1927) Annales de Chimie 10 (7) 151-226 [pages 154-155]). [Marion cited Hasenfratz.]

The seeds of Peganum harmala are crushed or ground [3] and covered with 3 times their weight of 3% acetic acid [4]. A thick dough is formed which is pressed [5] after 2 or 3 days. Then, twice the weight of seeds worth of acetic acid is added and after maceration they are pressed again. The two liquids are combined and sodium chloride (100 grams per liter of liquid; i.e. 1 gram per 10 ml) is added. This is then refrigerated until cold and the bulk of the liquid is siphoned off leaving the crystalline residue layer on the bottom. The crystalline residue is filtered with suction (i.e. with a Buchner Funnel) and then redissolved in hot water. The subsequent addition of sodium chloride and chilling will cause the hydrochlorides (harmine and harmaline) to precipitate as a "crystalline mush". Recrystallization is to be repeated (i.e. redissolving in hot water, adding salt and then chilling to precipitate the crystals) until the hydrochlorides acquire a yellow color (they start out reddish). Usually 3 to 5 times are sufficient. Occasionally two such recrystallizations are enough. At this point the material can be dried by gentle heat [6]. The paper and material will dry rapidly and the yellowish or greenish material thus obtained will fall off easily and should then be packed in a tightly sealed lightproof container and kept refrigerated.

A crucial point is the removal of fine particulates from the first step (acetic acid extracts). Careful and thorough filtration or use of a centrifuge is recommended. Otherwise these particles will remain with the product. Another potential source of (a trivial) adulterant is trying to work the powder loose from the dried paper. If a person merely removes what falls off easily as chunks this is not a issue [7].

Excess salt is not desirable. Measure all liquids and weigh the salt carefully. (Any excess salt will become a part of the product [8].

Salt is the most likely, and single largest, potential adulterant when using this process. Careful measurement of salt can help minimize it.)

Vacuum filtration with a Buchner funnel and Whatman filters will make this easy. Otherwise, the tendency of all of the above solutions to clog filter paper will cause it to be tedious and time consuming [9].

The above separation takes advantage of the fact that when sodium chloride is added to a solution of harmine and harmaline acetate it transforms them into their hydrochloride salts.

The hydrochloride salts of harmine and harmaline are insoluble in cold sodium chloride solutions and thus precipitate during the chilling.

Further purification is possible by separating the alkaloids (see below) or the mixed alkaloids can readily and simply be sublimated to further purify them (Sublimation will not separate them but will highly purify them.)

Similarly, simply dissolving the hydrochlorides into warm water, neutralizing them with ammonia, and recovering the precipitated free base by filtering, will purify the product and remove any excess salt.

By almost all accounts harmaline is a stronger MAO inhibitor than harmine and when measuring dosages this should be taken into account.

Notes #
  1. Tetrahydroharmine is said in the literature to be one third the activity of harmaline but this is based on one single bioassay in one individual. It is not known whether it is able to orally activate DMT and apparently no one has looked into the matter beyond evaluating its relative MAOI properties. MAOI capabilities alone apparently do not guarantee effectiveness at oral activation of DMT. While many MAOIs (including many more dangerous prescription MAOIs) can serve as oral activators; there are also good MAOIs that apparently do not. The evidence provided by some ayahusaca brew compositions suggests THH to be an effective oral activator for DMT despite its poor MAOI stature but apparently formal studies are lacking. See comment elsewhere. In one case, the results were undesirable: prior administration of Iproniazid was found to produce such dramatic increases in the action of DMT that the researchers withheld this information from publication out of fear that some moron on the street might try it.
  2. Harman is by far the most common of the Passiflora β-carbolines and the simple β-carbolines in general. It has been present in every species that has a published analysis. Whether more species of Passiflora exist that contain meaningful levels of harmine and/or harmaline has not yet been determined. Pharmacological activity for harman (also norharman) in animals includes "motor depression with catatonic components". Ho 1977. This lends support to the traditional use of Passiflora spp. for their sedative properties. Tetrahydroharman and harmol also produce sedative effects in animals. Harman and norharman are thought by some to play a role in the consciousness altering properties of tobacco smoke; the latter, of the two, also in its carcinogenicity. One species of passionflower, P. rubra, bears the intriguing common names of ‘Dutchman's Laudanum'' and ‘Pomme de liana zombie'. It is apparently lacking chemical evaluation. This species has been offered in recent years by both American and Australian seed suppliers. See Eleusis for an overview of the genus.
  3. If they are finely ground the fine particulates will tend to come through filter paper and may be difficult to separate from the final product. A centrifuge would be very useful for this. Repeated careful filtrations with fresh filters will remove most or all of the plant material. This can be done manually but requires a delicate touch so as not to burst the filter when squeezing it down or to force through a portion of the fine particulates. Repeat until no visible material is left on the filter paper before proceeding to the salting out phase. All of the alkaloid is at this point dissolved in the acetic acid solution as their acetate salts. Cloth filters are preferable to paper if available. A Buchner funnel and vacuum filtration can make this far simpler.
  4. Glacial acetic acid is available through most photo developing supply stores. It will burn one severely if care is not used. (Burns do not always show up immediately!) Vinegar is easier to handle. 100 ml. of 5% vinegar and 66.7 ml. of water equals 3% acetic acid. Special pickling vinegar, that is 9% acetic acid, is available, through restaurant suppliers and larger grocery stores. One part of this to 2 parts of water also forms 3% acetic acid. Truthfully, in this case, the difference between 3 and 5% does not matter.
  5. This is easily accomplished by squeezing the mash into a ball in a clean piece of cotton bedsheet, fine material or white T-shirt if a press or hydraulic juicer is not available.
  6. Several easy methods: Preheat an oven to a maximum of 325° F, turn it off and place a glass pie pan, cookie sheet or tray, with the filter paper on it, into the oven while leaving the door wide open. If it is not totally dry; remove it from the oven, reheat the oven, turn it off and repeat. Another way is to bring a pot of water to a boil , turn off the heat and cover it with a Pyrex plate on top of which is a plate with the filter paper. Similarly, draping the filter across the top of a Pyrex bowl heated with a well regulated and monitored temperature of 105 to 120° F will work well. Such a well regulated heat source can be obtained by using a crockpot with adjustable heat rather than preset temperatures.
  7. If rolling the paper back and forth or otherwise manipulate it to release the residue paper fibers can be introduced into the product. A better way is to only recover what is easy and save the paper with residue. After several dozen are accumulated they can be combined, rinsed with hot water and the harmine recovered by precipitating once again with salt and cold. If they are to be stored for future recombining and recovery the papers should first be dried and tightly sealed unless the recovery is to occur within the next hours or day.
  8. If this occurs and a person did not want to remove it by recrystallization or partitioning between ether and cold water, dosages must be adjusted upward to compensate for the salt diluted product. Lacking analytical equipment, trial and error can be used to determine effective dosages.
  9. It can still be done using round coffee filters but great care must be taken to prevent breakage of the paper when twisting down the final amount. If the paper bursts it will spew its contents everywhere and much product will be lost. Using many papers, each only once, for the filtering of a small lot of liquid will be more productive than trying to build up more product on an already wet filter.