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Full Version: Theory: MAOI B-carbolines causing food intolerances/hyperactivity
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While leafing through Alexander Shulgin's book TIHKAL (a treatise on psychedelic tryptamines), I came accross a reference, to acid hydrolysis of caseine, producing some fairly fruity bits and pieces, among them, three caught  my eye, namely 1-methyl-1,2,3,4-beta-carboline,1,3-dicarboxylic acid, and harman, harmalan and the last two compounds tetrahydro derivatives.

Harman, and the like, are beta-carbolines, basically, 3-(2-aminoethyl)indoles (tryptamines, such as serotonin, melatonin, acting as neurotransmitters, and some such as n,n-dimethyl-T acting as fairly potent hallucinogens), cyclized with an amino acid, or aldehyde, now, assuming some biological process is capable of performing such a hydrolysis of caseine, which us auties are known sometimes to be intolerant to, then a decarboxylation in vivo, of the above dicarboxylic acid to give 1-Me-1,2,3,4-beta-carboline, is quite probable.

Ok, thats the chemistry out of the way, beta carboline alkaloids occur naturally in many plants, some fungi, and some marine creatures, and quite a few act as monoamine oxidase inhibitors, or MAOIs, inhibiting the enzymes that detoxify dietary amines such as tyramine, and affecting metabolism of such neurotransmitters as serotonin and dopamine, MAOIs are clinically used as antidepressants, although rarely used nowadays, because of some fairly severe side effects, including CNS stimulation, and if food containing tyrosine is eaten, which gets decarboxylated in the body to tyramine, causing a severe hypertensive crisis.

So, anyone got any input to share on this idea? caseine is known to be a culprit in causing hyperactivity and dietary sensitivity, I propose that instead of hydrolysis to form endogenous peptides with opioid-like activity, which being big, bulky protein chains, would be pretty unlikely to cross the lipophillic blood-brain barrier, even if they did "leak" from a compromised intestine, caseine might just instead, or even alongside the opioid peptide theory, be getting metabolised to some of these beta-carboline MAOIs, and from then, going on to cause the hyperactivity.

My apologies in advance for being unable to provide references, I haven't had the ability, or time, since getting out of prison, to get online and dig them up, if they exist, as my sole internet access is through the local library, this is just an idea, based on some chemical references, that although not in any way geared towards autism, are quite feasibly interacting in this way.
Can you explain this again at the level of high-school chemistry? It's rather confusing to me as it is.
I've read PiHKAL -it's one of my favourite books- but I have yet to read TiHKAL.
Many traditions acknowledge the medicinal properties of food, while western medicine has lagged sadly behind.

I doubt that casein would produce a notable opioid-type activity. Casual observation would show that those sensitive or intolerant to casein are often in some discomfort, contrary to the analgesic effects of opioids. The diarrhoea associated with this intolerance also contradicts an opioids tendency to constipate. The hallmarks of typical opioid intoxication (endogenous or otherwise), constricted pupils and drowsiness, are not present. As for this theory, and the following theory of a possible relationship with hyperactivity, I'll look into it further. Having done no previous study on the subject, I can't tell you off the top of my head. I personally have a dietary sensitivity to casein, and I am not hyperactive. That's not to refute your theory completely, just to suggest that the mechanism involved may be more complex.
I don't particularly put much credence in the opioid theory myself, there is no way big, bulky *** peptides like that are going to stand all that much of a chance of penetrating the BBB.

I agree with PIHKAL being one of my favourite books too, damn coppers seized my copy after I got arrested, and I haven't got it back yet Sad

Have you got Shulgins newer book? he has done a dirty great index of isoquinoline chemistry, and where the naturally occuring ones are found, AFAIK, for some sort of appendix to a possible future book on cactus alkaloids.

Quote:
Harman, and the like, are beta-carbolines, basically, 3-(2-aminoethyl)indoles (tryptamines, such as serotonin, melatonin, acting as neurotransmitters, and some such as n,n-dimethyl-T acting as fairly potent hallucinogens), cyclized with an amino acid, or aldehyde, now, assuming some biological process is capable of performing such a hydrolysis of caseine, which us auties are known sometimes to be intolerant to, then a decarboxylation in vivo, of the above dicarboxylic acid to give 1-Me-1,2,3,4-beta-carboline, is quite probable.


Ow.My brain hurts.

just to input, dimethyltryptamine works for me without MAOI inhibs.
not at full strenght but for "normal" ppl it should not even work.
the digestive system breaks it down.
...not for me.
orally i mean.
Really? wow, thats quite something, are you definately confidant in your source of DMT? if you did the extraction yourself from plant material then I would be quite amazed at oral activity without a MAOI, if it was synethetic stuff from one of the RC companies, then they have been known to be iffy at times,  DOI turning up in 2C-I, and even 2C-T-7 and 2C-TFM turning up in samples of other materials, that kind of thing is known to go on, and anything above a methyl group on the tryptamine amine nitrogen makes it too bulky for the MAO-a enzyme to chew it up fast enough to prevent oral activity (that is, with the N,N-dialkyl-T series, AFAIK, NET is without oral activity, but NPT and NiPT are bulky enough to resist attack)

Out of curiosity, what doses are we talking about, of DMT, and to what effect, compitively to an equal effect produced dose-to-dose equivalent while using an MAOI?

You really got my curiosity piqued here, do tell more Big Grin
I'm not sure I believe in "leaky gut".

Lestat Wrote:
Really? wow, thats quite something, are you definately confidant in your source of DMT? if you did the extraction yourself from plant material then I would be quite amazed at oral activity without a MAOI, if it was synethetic stuff from one of the RC companies, then they have been known to be iffy at times,  DOI turning up in 2C-I, and even 2C-T-7 and 2C-TFM turning up in samples of other materials, that kind of thing is known to go on, and anything above a methyl group on the tryptamine amine nitrogen makes it too bulky for the MAO-a enzyme to chew it up fast enough to prevent oral activity (that is, with the N,N-dialkyl-T series, AFAIK, NET is without oral activity, but NPT and NiPT are bulky enough to resist attack)

Out of curiosity, what doses are we talking about, of DMT, and to what effect, compitively to an equal effect produced dose-to-dose equivalent while using an MAOI?

You really got my curiosity piqued here, do tell more Big Grin




i used plant material.
banesteriapsis caapi, i guess there could be other psychoactives in the plant but i doubt it.
and i did not feel alot of effect, i just felt effect, and that should not be possible.
might be a mind game, i do not know.
ive always been very sensitive to chemical compounds.
but i build up tolerance very quickly aswell.
i think i read a report on that about <1% of ppl who use dmt get effect without MAOIs, but i am not sure if its a valid report.



"DMT is generally not active orally unless it is combined with a monoamine oxidase inhibitor (MAOI), such as harmaline. Without an MAOI, the body quickly metabolizes orally-administered DMT, and it therefore has no effect unless the dose exceeds monoamine oxidase's metabolic capacity (very rare)."

i dont think i exceeded that though.
it was many years ago (without MAOIs), i should prolly try it again.

I didn't think as much, DMT being orally active, that is, as chances are, if the body had a lack of MAO enzymes sufficient to allow oral use of DMT, then pressors from the outside, such as tyramine, or OTC sympathomimetics like ephedrine and the like could cause some nastiness of a decidedly unpleasant source.

Banisteriopsis Caapi contains harmine, and tetrahydroharmine, not DMT, both of which are potent MAOIs, so from what you say, it seems like you took a Caapi brew, without any DMT in the mix, never tried that myself, but many native shamans do not add any DMT-containing admixtures in their ayahuasca brews, and Caapi vine is quite definately active on its own.
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