benzyme said:
yeah, I dunno if i'd even consider it a salt (which implies ionic bond between a cation and anion), it's not quite a free base either; though it does have a tertiary amine.
it's most likely a defensive tryptamine metabolite. by definition, a plant alkaloid
what is the physiological pH of the plant alkaloid? some plant alkaloids tend to be slightly basic
Why would it not be a salt? There are plenty of acids in the plant material that could bond with it without adding any acids to the plant material. In such an environment with water flowing through the plant material in nature, how would the plant prevent the DMT from bonding with one of the acids it creates itself? Mimosa is acidic, not alkaline.
I've got to say it's a salt. I don't see any reason it would not be a salt. If the plant was alkaline, then yes, but it's not, it is full of acids and water in nature, so that's the perfect situation for making a salt. Can you explain how that wouldn't make a salt? Is there some special physical force present in the plant that I'm unaware of that would prevent it from becoming a salt? Please explain because that makes no sense to me, considering DMT’s pKa, the presence of acids in the plant, and the presence of water in plant when alive.
An alkaloid by definition can exist in a plant as freebase, a salt, or an N-Oxide. Those are the facts as I have read them to be. What determines the form is acidity, pKa, and exposure to oxygen. In Mimosa, it is exposed to oxygen, so some DMT exists as DMT N-Oxide, also Mimosa is acidic enough, and the pKa of DMT is high enough that DMT will exist as a salt. There is no question about that. Unless there is some special force in the plant shielding the DMT from the pH of the plant and shielding it from contact with water and other acids in the plant, then it must be a salt.
Look here
Alkaloids often occur as salts of plant acids such as malic, meconic, and quinic acids. Some plant alkaloids are combined with sugars, for example, solanine in potato (Solanum tuberosum) and tomatine in tomato (Lycopersicum esculentum). Others occur as amides, for example, piperine from black pepper (Piper nigrum), or as esters, for example, cocaine from coca leaves (Erythroxylum coca). Still other alkaloids occur as quaternary salts or tertiary amine oxides.
Look here
Most alkaloids are well-defined crystalline substances which unite with acids to form salts.
In the plant they may exist in the free state, as salts or as N-oxides.
Also here (from Alkaloids By Manfred Hesse, page 116)
In plants, alkaloids often exist in the form of hydro salts (salts formed with organic acids).
Also here (A Text-book of chemistry By Samuel Philip Sadtler, Henry Trimble, page 738 )
The vegetable alkaloid does not ordinarily exist in the plant in a free state. It is most generally present as a salt, often an acid salt of some organic acid, such as malic or tannic acid.
Also here's the icing on the cake. This is a quote from Albert T. Sneden, Ph.D., Professor Emeritus of Chemistry, College of Humanities and Sciences from a course he teaches on the subject matter of alkaloids!
Many of the earliest isolated pure compounds with biological activity were alkaloids. This was due to the ease of isolation. The nitrogen generally makes the compound basic and the compound exists in the plant as a salt. Thus, alkaloids are often extracted with water or mild acid and then recovered as crystalline material by treatment with base.
Mimosa has LOTS of tannic acid so DMT might exist in Mimosa as DMT tannate.
Those are all verifiable quotes. You can find them on the web using Google.
Most alkaloids are present as salts in plants. Very few plants are alkaline enough to have freebase alkaloids in them.
I can find more references to back this up.
All the facts point towards it being a salt. I have not found any evidence to the contrary.
Only a few DMT techs by some amateur chemists state that DMT is present as freebase in Mimosa, and they never give any such evidence or references to back up their unbelievable claims. The idea goes against all the text books I’ve read on the subject of plant alkaloids. DMT is not any different from the rest of the alkaloids that exist as salts in most plants. Because of the low pH of Mimosa and the high pKa of DMT, DMT must be present as a salt just like the vast majority of plant alkaloids in existence. Only alkaloids with low pKa’s present in plants that are alkaline can exist as freebase in a plant. DMT does not fit that requirement. Mimosa has a low pH and DMT has a high pKa.
Anyway, that's what all the books on plant alkaloids say that I've read. If DMT is somehow an exception, I've not heard a valid explanation of why it could be. If there is evidence somewhere that it is an exception, please post a link or a book or something where I can see it so that I can correct my notes on the subject.
As of yet, I've been challenged on this subject on every forum by someone and no one has once provided any link to any other reference that clearly states that DMT violates the rules of plant alkaloids and can be present in an acidic plant as a freebase compound even though it has a high pKa. Everyone simply posts links to DMT extraction techs. I want to see it from a real scientist, or university or respected author on the subject. I have yet to see such information about how DMT violates the rules of plant alkaloids.
