  
Leprachaun (Leprachaun)
| | Posted on Wednesday, July 30, 2003 - 12:38 am: | 
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From the IRANIAN JOURNAL OF PHARMACOLOGY & THERAPEUTICS:
Harmine (banisterine). C13H12ON2 - It is present in P. harmala and in some species of Banisteia, viz., B. caapi, Spruce., B. lutea and B. metallicolor. The alkaloid is optically inactive and forms colorless rhombic prisms from methanol. It is slightly soluble in water, alcohol or ether. Solutions of its salts show a deep blue fluorescence. Pharmacologically, harmine resembles harmaline in its actions but is less toxic. The hydrochloride has been found to be highly active against Mycobacterium tuberculosis [7].
Harmaline (harmidine). C13H15ON2 - First isolated by Göbel [5] from the seeds and roots of P. harmala, this is the major alkaloid of this plant. It crystallizes in colorless or pale yellow prisms and is optically inactive. This compound is slightly soluble in water, alcohol and ether, quite soluble in hot alcohol and dilute acids. Its hydrochloride dihydrate, which crystallizes as yellow needles, is moderately soluble in water and alcohol. Harmaline is almost twice as toxic as harmine and in moderate doses causes tremors and clonic convulsions but with no increase in spinal reflex excitability [6]. Lethal doses bring about convulsions, which are soon followed by motor paralysis due to the marked depressive action upon the central nervous system. Respiration is paralyzed and a decrease in body temperature occurs. The perfused heart is arrested in diastolic phase and the contractions of smooth muscle are diminished with the exception of the uterus, which may be made to contract more powerfully. Over a wide range of doses there is a reduction in blood pressure due to a pronounced weakening of the heart muscle.
I presume they are talking about the freebase alkaloids here. In the raw plant material, the alkaloids may be in some other salt form. The solubility info is vague. It isn't expressed in g/litre etc. Even though they are "slightly" soluble, there is only a tiny amount of alkaloids in the plant material. So maybe a small amount of herbs in a large amount of hot water would allow the tiny amount of alkaloids to dissolve fully. I think I am now more confused than I was before.
I have some books in the mail which should fill in the picture more fully. I will post the info here when I get it. |
Leprachaun (Leprachaun)
| | Posted on Wednesday, July 30, 2003 - 11:45 pm: |
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Got "Ayahuasca Analogs" by Jonathan Ott today. Plenty of general info about ayahuasca but very little practical brewing info, to my surprise.
Here are some things he says:
There is evidence that prolonged heating (10-15hrs) degrades some of the alkaloids. Harmaline seems to be largely or completely destroyed by the heating process, but harmine and tetrahydroharmine (d-leptaflorine) may be degradation products. Harmine is a more stable compound than harmaline.
In his brewing experiments, he only used syrian rue and extracted it with a 30% solution of lime juice. He used just enough solution to cover the powdered seeds, brought to the boil and strained through a fine wire mesh coffee filter. Then did a second quick extraction and that was it, total time 15-20 mins. He doesn't recommend prolonged heating. I presume this is only an issue when using syrian rue which contains mostly harmaline. He then quickly moves onto pharmahuasca. He seems to be more interested in dosage levels than brewing methods.
He says the lime juice was to enhance alkaloid solubility. But this presumes the alkaloids were already in their freebase forms and were free to bond with citric acid, which I doubt they are. In acid/base extractions, a strong alkali is added to the aqueous solution of plant material first in order to liberate the alkaloids into freebases, then they are extracted into an organic solvent. Only THEN is the acidified water added to form water-soluble salts which are crystalized out.
From the Encyclopedia Brittanica:
Preparation from natural sources
The alkaloids
As mentioned above, the first pure pharmaceuticals isolated from natural sources were the alkaloids. Although the methods adopted for their extraction from plants vary in detail, all are based on three general characteristics of these compounds. First, most alkaloids are only slightly soluble in water but readily soluble in certain organic solvents such as benzene, chloroform, ether, and light petroleum. Second, alkaloids combine with acids to form salts that are usually freely soluble in water but only slightly so in organic solvents. Third, alkaloids are liberated from their salts by alkalies.
Application of these general principles can be seen in the following generalized outline of extraction methods. The crude drug, ground to a suitable state of subdivision, is mixed with water, a water-soluble alkali such as lime, and some organic solvent that does not mix with water. The mixture separates into two layers: one contains water, lime, and impurities and is discarded; the other contains the alkaloid dissolved in the organic solvent. Fresh water and dilute acid are now added to the mixture. Again there are two layers, but the acid has caused the alkaloids to pass from the organic layer into the aqueous layer. The aqueous layer is now separated, and the alkaloidal salt or salts may be crystallized out by cooling or concentrating the solution. The process described above is used to obtain quinine sulfate from cinchona bark.
Here are the main questions I want answers to:
1. What salt form (if any) are the alkaloids in, in the raw plant material?
2. What are their precise levels of solubility at various temperatures?
3. What are their melting and boiling points, and how sensitive are they to heat?
I hope the other books on the way will have more relevant info. They better!!! |
Redmonk (Redmonk)
| | Posted on Thursday, July 31, 2003 - 12:09 am: |
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Thorough reporting as usual ! Thanks for the info. |
Hippie3 (Admin)
| | Posted on Thursday, July 31, 2003 - 02:45 am: |
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the last two should be in the merck index,
once you know the names of the compounds. |
Leprachaun (Leprachaun)
| | Posted on Thursday, July 31, 2003 - 02:06 pm: |
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Thanks for the support, Redmonk.
The problem with the Merck index is that it would only give info on the freebases. Also, another vital piece of info is the temp at which the alkaloids DECOMPOSE. With many compounds, this can be well below the boiling point, or even melting point.
The Sigma Aldrich chemical website says freebase (?)harmine has a melting point of 262-264*C. It says the solubility of the hydrochloride salt (?) is 50mg/ml.
It also says that freebase harmaline melts at 232-234*C. It gives a melting point of 69-70*C for 5meo dmt and a storage temp of 2-8*C. It had nothing on DMT.
Shulgin says that DMT is insoluble in ether! He gives a melting point from his own experiments of 47-68*C, apparently for the freebase. He says the hydrochloride salt melts at 165-167*C. He says DMT base can be dissolved in dilute hcl (making a soluble hydrochloride salt) and the solution then neutralised with an alkali to bring the ph up to 6. He says the chemical literature gives melting points of 44-68*C, and says the Merck values of mp 44.6-46.8 and bp 60-80*C are clearly wrong and too low.
The interesting thing about the acid/base extraction method mentioned above is that it would remove all the water-soluble tannin. Presumably, just adding a strong alkali to the aqueous solution of plant material would remove all the tannin too by bonding with the tannic acids and making sure all the alkaloids are insoluble freebases. Then the liquid could be decanted or put through a vacuum filter. All the alkaloids would be in the filtrate. The only problem would be lots of sediment. Coarse filtration before fine filtration would remove a lot of it.
I think the extraction method that DeKorne describes in his book is a disaster. It doesn't conform to the extraction methods in my chemistry books. |
Leprachaun (Leprachaun)
| | Posted on Friday, August 08, 2003 - 01:05 am: |
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I got Ott's "Pharmacotheon" and Entheogen Review's "Ayahuasca Analogues and Plant-Based Tryptamines".
Pharmacotheon has very dense text and is a heavy read. The ayahuasca section doesn't seem to contain anything more than was in Ott's other book. There is a section near the end giving chemical data on loads of alkaloids. It confirms that harmine and harmaline are only slightly soluble in water, and implies that dmt is totally insoluble due to not mentioning anything about water solubility. Interestingly, it mentions dmt fumarate with a melting point of 152*C. Fumaric acid is present in plants and is involved in the synthesis of biocompounds. Maybe this is the natural salt form of dmt. It doesn't say if the solubility of it is different from the freebase.
The other book had a few interesting things. It mentioned a method of simmering plant material in near pure vinegar for 2 X 12hrs, and then evaporating both extracts down to a dry residue. Unfotunatley the dry extract would be loaded with tannin even thought the vinegar would be all gone.
It also mentioned that many alkaloids glow under UV light, and some alkaloids can even be identified by the colour they produce. I heard a few mentions of using a UV light over at aya.com. I might buy one.
There is hardly anything said about caapi and only a few pages on viridis. Trout says that some viridis leaves give an adequate dose of dmt at 10g, most give it at 20-25g, others give it at 50g, and a few batches of viridis leaves are totally inactive. Tell me about it!!!
The most interesting piece was on the potency variation in Phalaris grass. I have no intention of cultivating it but the info would generally apply to all plants. Variables include age of plant, plant part, season, time of day, temperature, moisture and light levels, nutrition and strain. These don't make just little differences like in cannabis. Potency can vary from near inactive to very strong in the same plants harvested at different times under different conditions. Different parts of the plants can have a 5x variation in potency (leaf tips can be 5 times stronger than the roots in the same plant).
I'm thinking that maybe dmt source plants should only be bought in powder form. At least then the herbs would be homogenous, and after one test brew, you could say "X amount of this herb will give me Y buzz". The high potency variation is not only very disappointing in terms of dud brews, but also potentially very dangerous if the herbs turn out to be unusually potent. |
Hippie3 (Admin)
| | Posted on Saturday, August 09, 2003 - 12:13 am: |
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is that book worth adding to my library ?
long wondered about that... |
Leprachaun (Leprachaun)
| | Posted on Saturday, August 09, 2003 - 11:27 pm: |
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The Entheogen Review book? It is more of a compendium of ideas and personal experiences rather than definitive facts, but I would much rather have it than not have it. It has a few plans for building alkaloid vaporisers, and instructions for use. It says that DMT is rapidly destroyed if overheated when vaporising, and that the pure crystals have a "burning, strongly basic taste". |
haha ha (Smilefromaveil)
| | Posted on Tuesday, August 19, 2003 - 08:48 pm: |
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if you want a general book with about 200+ different drugs i'd get the "chemistry of mind altering drugs". it deals a little with the effects of certain drugs but focuses more on the chemical make up. |
Hippie3 (Admin)
| | Posted on Saturday, August 23, 2003 - 02:52 pm: |
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i meant Ott's "Pharmacotheon"... |
Leprachaun (Leprachaun)
| | Posted on Sunday, August 24, 2003 - 12:58 am: |
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Yeah, Pharmacotheon is cool. Very detailed. Contains probably all the general information about every plant entheogen you can think of.
Last week I got a copy of Trout's Notes "Ayahuasca and Ayahuasca Alkaloids". This is THE book that every aya brewer should have. It is absolutely brilliant. Contains too much excellent info for me even to attempt to post it all. It focuses on hard data useful for brewing rather than the more cultural info in other aya books. A gem, brilliantly researched and written. Trout is a genius. |
Hippie3 (Admin)
| | Posted on Sunday, August 24, 2003 - 06:09 pm: |
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a genius eh ?
might have to check that out, too.
thx |
Leprachaun (Leprachaun)
| | Posted on Tuesday, August 26, 2003 - 11:15 am: |
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When I first wrote to Trout about ordering the book, he said he only had 3 copies left. I now have one of them. You better order quick if you really want it. |
Hippie3 (Admin)
| | Posted on Tuesday, August 26, 2003 - 12:13 pm: |
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his site [ http://trout.yage.net/sc/index.html ] sez it's now sold out.
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Leprachaun (Leprachaun)
| | Posted on Wednesday, August 27, 2003 - 12:55 pm: |
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I wrote to him about a month ago and he said he had a few copies left. E-mail him and ask to be sure. The "sold out" message was there when I ordered. |
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