Friday, March 31, 2017

N-Methylphenethylamine (NMPEA), positional isomer of amphetamine, found in nature and also endogenous? A plant containing it may also contain DMT and Methamphetamine (and be growing in your back yard).

Wikipedia for NMPEA:
"PEA and NMPEA are both alkaloids that are found in a number of different plant species as well.[5] Some Acacia species, such as A. rigidula, contain remarkably high levels of NMPEA (~2300–5300 ppm).[6] NMPEA is also present at low concentrations (< 10 ppm) in a wide range of foodstuffs.[7]"
That was one of the primary parts that caught my eye. What is the effects of this substance? It may not be too active orally...

NMPEA is a pressor, with 1/350 x the potency of epinephrine.[17]
As with PEA, NMPEA is metabolized relatively rapidly by monoamine oxidases during first pass metabolism;[3][18] both compounds are preferentially metabolized by MAO-B.[3][18]
If it is vaporized or injected, what are the effects like? Euphoria? Stimulation? Obviously there are things that could be combined with it, orally, to inhibit the process that breaks it down...
N-Metyl-Phenylethylamine's half-life is very short. .It is metabolized by MAO-A, MAO-B, aldehyde dehydrogenase and dopamine-beta-hydroxylase. If you like to get long effect take an MAO inhibitor (MAOI) like Phenalzine
When the initial phenylethylamine brain concentration is low, brain levels can be increased 1000-fold when taking an MAO inhibitor (MAOI) and by 3times when the initial concentration is high.
Phenethylamine, similar to amphetamine in its action, releases norepinephrine and dopamine.

What else may be combined with it to make it stronger, make the effects more pronounced, or to maybe even alter it slightly into something more viable for recreational purposes?
It is listed in some places as aiding fat burning, meaning it may be available in some dietary supplements, which would not be surprising.
Then, here is the real gem I found researching this so far (and a commentary by Shulgin!)

In 1997[1] and 1998,[2] researchers at Texas A&M University reported finding amphetamine and methamphetamine in the foliage of two Acacia species native to Texas, A. berlandieri and A. rigidula. Previously, both of these compounds had been thought to be human inventions.[3] Like methylphenidate (Ritalin), amphetamines also prevent the monoamine transporters for dopamine and norepinephrine from recycling them (called reuptake inhibition), which leads to increased amounts of dopamine and norepinephrine in synaptic clefts.

Now remember, A. Rigidula is the plant mentioned way up above this that contains NMPEA. What else does it contain?

Amines and Alkaloids:
phenethylamine N,N-dimethylphenethylamine N,N-dimethyl-"-methylphenethylamine p-hydroxyamphetamine tyramine 3-5-dimethoxytyramine 3,4-dimethoxy-5-hydroxy-$-phenethylamine hordenine N,N-dimethyldopamine tryptamine N,N-dimethyltryptamine N-methylmescaline nicotine anhalamine peyophorine nortryptyline 3-"-cumyl-1,3,4-oxadiazolidine-2,5-dione p-hydroxypipecolamide 4-methyl-2-pyridinamine
N-methylphenethylamine amphetamine methamphetamine p-methoxyamphetamine N-methyltyramine candicine dopamine N-methyldopamine 3-methoxytyramine N-methyltryptamine mescaline trichocereine nornicotine anahalidine mimosine (methyl ester) musk ambrette pipecolamide 1,4-benzezediamine
octylphenol \ aristolone (Z)-9-octadecenoic acid (Z,Z,Z)-9,12,15-octadecatrienoic acid 3b-acetoxy-17-methyl-5a-18-abeoandrost-13-ene
nonylphenol 3b-cholest-5-en-3-ol (Z,Z)-9,12,-octadecanoic acid

If you read this properly... then this plant contains methamphetamine, as well as DMT... It also contains 4-Methoxyamphetamine (A schedule I substance, DMT is also Schedule I).
The real kicker though is that Amphetamine and Methamphetamine were thought to be MAN MADE substances, not found in nature. Here is a full commentary by Shulgin in a Question/Answer format:
Question: Are you familiar with Acacia berlandieri and A. rigidula which were noted to contain various a-methyl-b-phenethylamines? Do you have any ideas as to what the botanical origins of these structural carbon skeletons might be? The literature citations are PHYTOCHEM. (1998), 49(5), 1377 and PHYTOCHEM. (1997), 46(2), 249.
Answer: I am familiar with the literature concerning these two West Texas Acacia species, but not with the plants themselves. I had both these PHYTOCHEMISTRY papers in my Acacia file but I must admit that I have some very mixed feelings about them.
What caught my curiosity immediately was the casual indifference shown to what is certainly an extraordinary discovery. Here, amongst some 40 or so alkaloids found in each of these two species, there were five amphetamines that had heretofore been thought to be inventions of man. Two of these are Schedule II drugs, Amphetamine and Methamphetamine. Two are Schedule I drugs, N,N-Dimethylamphetamine and 4-Methoxyamphetamine. And the fifth one is a major human metabolite of Amphetamine, 4-Hydroxyamphetamine. To my knowledge, none of these had ever before been reported as being natural plant alkaloids. This unprecedented discovery elicited only a passing line of comment in the earlier of the two papers.
My first thoughts as to origin were directed towards the well known natural hydroxylated amphetamines such as norephedrine, ephedrine and N-methylephedrine. I know that ephedrine and pseudoephedrine, frequent precursors in the illegal synthesis of methamphetamine, can be reduced to methamphetamine as an artifact of analysis. The sample insertion conditions of the gas chromatograph can effect this conversion. But then, there was no mention of any of these hydroxylated alkaloids as being present in either Acacia.
Might a contaminated round-bottomed flask have been purchased at a garage sale outside an abandoned meth-lab and served as the source of these "man-made" compounds? Unlikely, even in Texas.
Even more dramatic, one of these amphetamines, the 4-Methoxyamphetamine, is the increasingly notorious PMA that is appearing as one of the lethal "Ecstasy" offerings in the rave scene.
Several months ago I tried to contact, individually, the two principal authors, by both e-mail and personal snail-mail, and I have received no response as yet.
There is certainly precedent for a drug which was originally man-made, to be discovered in a plant. N,N-Dimethyltryptamine (DMT) was first synthesized by Manske, in Canada, in the 1930s. It was over twenty years later that it was discovered in a plant from South America. But such an event usually evokes considerable commentary. Here it seems that an exciting story is being ignored. Am I missing something?
-- Dr. Shulgin
Yes, what is he missing? If this is true, this is a rather ground-breaking discovery. Is it well known that methamphetamine and emphetamine, along with DMT and all these other substances are found within this singe plant?
Granted some of the data may be incorrect, but I'd like to first find a source debunking or attempting to debunk this data before I would go that far.
What are the concentrations of these substances in this plant? I know the DMT can't be too high of a concentration, as I've never heard of this plant being used as a source for DMT the way Mimosa Hostilis and a few others are used. If the concentration was high, it was be involved in popular teks...
Wikipedia comments:
A phytochemical study of V. rigidula[6] by workers at the Texas A & M University Agricultural Research and Extension Center at Uvalde, TX, reported the presence of over forty alkaloids, including low amounts (up to ~ 15 ppm) of several amphetamines that had previously been found by the same research group in the related species Senegalia berlandieri,[7] but which otherwise are known only as products of laboratory synthesis. Compounds found in the highest concentrations (ranging from a few hundred to a few thousand ppm) were phenylethylamine, N-methylphenethylamine, tyramine and N-methyltyramine. Other notable compounds reported were N,N-dimethyltryptamine, mescaline, amphetamine, methamphetamine and nicotine, although these were found in low concentrations (e.g. mescaline at 3-28 ppm).
The presence of such an unprecedented chemical range of psychoactive compounds, including ones not previously found in nature, in a single plant species has led to the suggestion that some of these findings may have resulted from cross-contamination or were possibly artifacts of the analytical technique.[8]
Why has this not been further tested, in all of these years?
Where are the A. rigidula teks?

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666IGMA - Magick Trick (2017)