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2-methyl-1,2,3,4-tetrahydro-beta-carboline Options
 
ms_manic_minxx
#1 Posted : 7/18/2010 6:31:59 AM

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2-methyl-1,2,3,4-tetrahydro-beta-carboline

What is this?? What does it do?? It is in jungle spice??

I did some random poking around the internet, and some sites are alluding to vague potentials of neurotoxicity? Then other random sites allude to it being something completely positive, like harmalas? I haven't found anything to satisfy my curiosity (including a totally credible and coherent source Razz ).

Thoughts? Anyone?

Thank you! Smile
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SnozzleBerry
#2 Posted : 7/18/2010 3:23:30 PM

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Using my university account, I've begun to look at some of the available papers related to this compound. The vast majority of them refer to it as "neurotoxic" or as a "neurotoxin" and there seem to be a good number of studies looking at the relationship between endogenous 2-methyl-1,2,3,4-tetrahydro-beta-carboline in the urine and alcohol consumption (they determined there was no causation) in both rats and humans. I haven't found anything commenting specifically on how it relates to other harmalas. Do you want me to attach any papers or can you think of other keywords or directions I should be using/looking in?
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Ginkgo
#3 Posted : 7/18/2010 3:43:37 PM

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Interesting subject! 2-methyl-1,2,3,4-tetrahydro-ß-carboline is often shortened to MTHC. It is a common substance in trace amounts in many plants with entheogenic tryptamines, including Mimosa hostilis and Phalaris spp.

These studies you are referring to SnozzleBerry, could you post them? I have not found one single study about MTHC's effects in man.
 
SnozzleBerry
#4 Posted : 7/18/2010 4:05:16 PM

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Here are some of the articles that came up, I dunno how relevant they are for our interest in MTHC, but perhaps they're a good jump off. I still can't seem to find anything talking about MTHC in relation to other beta carbolines, any suggestions?
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endlessness
#5 Posted : 7/18/2010 4:18:09 PM

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A few things to consider...

2-methyl-1,2,3,4-tetrahydro-beta-carboline has been detected as a minor component in jungle spice according to Burnt's tests .

Now, the funny thing is, when reading about this substance, I found that in TIHKAL, in one of the proposed synthesis, Shulgin describes that "There was thus obtained 0.40 g of dimethyltryptamine (DMT) with a mp 67-68 °C. The distillate contained about 3% of 2-Methyl-1,2,3,4-tetrahydro-b-carboline (parent peak mass 186, major peak mass 186) as an impurity which was lost upon recrystallization.". So there is the same substance in the same amount (around 3%) present.

So I was wondering if either mimosa's biosynthetic pathway of 2-MTHBC is similar to the synthetic pathway Shulgin took, or if maybe its an artifact that was generated in Burnt's tests due to the chemicals used.

In this discussion in bluelight, seems one guy has also detected 2-MTHBC in mimosa (though most of the links/papers are dead in that thread now), but it seems the OP had used DCM for the extraction and in a comment someone says that "If you used dichloromethane, it could be possible that the beta-carboline is an artifact produced by the extraction process. Dichloromethane in contact with aqueous alkali will cause a substitution recation to take place, the final product being formaldehyde. From what I remember, formaldehyde and acetaldehyde very easily react with tryptamines to form beta-carboline structures via Picter-Spengler reaction (the 2,3-double bond being the active methylene bond)." .

Though burnt's tests did not use DCM...

Another interesting paper I was asking Snozz if he could help me find the full version of a study that shows that 2-methyl-1,2,3,4-tetrahydro-beta-carboline is also present in phalaris arundinacia (and interesting enough, the paper seems to state that there is an inverse relationship between the presence of gramine and of tryptamines/beta carbolines, but this is the subject of another thread I guess Very happy )

2-methyl-1,2,3,4-tetrahydro-beta-carboline is a normal metabolite of DMT in rats, I dont know if its also a metabolite of in human beings. It appears to be an endogenously produced substance in rats too, regardless of dmt ingestion .. ?

As for all the discussion of neurotoxicity, we have to check what dosages are being talked about because so many normal things are neurotoxic in ridiculously high doses, and also the animal models arent always transferible to human beings.

 
SnozzleBerry
#6 Posted : 7/18/2010 4:20:34 PM

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endlessness wrote:
Another interesting paper I was asking Snozz if he could help me find the full version of a study that shows that MTHC is also present in phalaris arundinacia (and interesting enough, the paper seems to state that there is an inverse relationship between the presence of gramine and of tryptamines/beta carbolines, but this is the subject of another thread I guess Very happy

Ask and ye shall receive Wink ...I figured I'd put it in this thread for now (why not compile any and all relevant articles to the compound here) and we can move it to a phalaris thread later, should anything warrant that.
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endlessness
#7 Posted : 7/18/2010 5:02:48 PM

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Thanks snozz!

Seems 2-methyl-1,2,3,4-tetrahydro-beta-carboline (Evening Glory said MTHC but from what I see its more often called as 2-MTHBC, because MTHC/MTBC/MTHBC is the 1-methyl THBC) is present in Psychotria viridis and consequently ayahuasca too, as stated in this paper:

"Direct analysis of psychoactive tryptamine and harmala alkaloids in the Amazonian botanical medicine ayahuasca by liquid chromatography–electrospray ionization-tandem mass spectrometry"

Journal of Chromatography A
Volume 1216, Issue 51, 18 December 2009, Pages 8960-8968

(im attaching it to this post)


So considering its naturally present in ayahuasca (and possibly a metabolite of dmt in human beings too?), and regular ayahuasca use has been studied without showing any neurotoxicity, then at least in the dosages that psychonauts, entheogenic church members and indigenous people seem to be exposed to, its apparently safe.
 
ms_manic_minxx
#8 Posted : 7/19/2010 3:28:59 AM

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Amazing! Thank you!

Nexus makes me love science. Smile

Edit: Question! Does anyone suppose smoking said compound is different than orally ingesting it? Or, would it be the same or similar to smoking because of MAOI presence? Or...? O.o
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Ginkgo
#9 Posted : 7/19/2010 7:26:04 PM

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The pharmacology of said compound isn't known good enough to answer properly, or rather it isn't known at all. Generally, inhalation of most substances is much more effective than orally consuming it. This is especially apparent with the harmala alkaloids - assuming 2-MTHBC acts as one, it would be many times as potent by inhalation compared to eating it.

But you know, there's no reason to be concerned about the 2-MTHBC present in various extracts, no matter if intended for smoking or oral use. The substance is always seen in trace amounts too low to be of any real concern, and as endlessness said, it is indeed present in Ayahuasca. Regular users of mother Ayahuasca is of very good health on all accounts.

Oh, and by the way, thanks a lot for correcting me on the abbreviation, endlessness! You are absolutely correct that 2-MTHBC is the proper name, although I have seen it described as MTHC.

 
Ginkgo
#10 Posted : 8/19/2010 2:38:05 AM

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Sorry for the late answer! There's two normal ways to draw ß-carbolines - the way I did it in the previous drawing, and 180° turned around. Here's a picture of harmine with all the position counts in the drawing .
Ginkgo attached the following image(s):
harmine counts.jpg (9kb) downloaded 762 time(s).
 
1992
#11 Posted : 8/19/2010 3:44:11 AM

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In response to the neurotoxicity comments, harmaline is neurotoxic too.
 
endlessness
#12 Posted : 8/19/2010 4:07:41 AM

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ahmmmm... source?
 
Ginkgo
#13 Posted : 8/19/2010 4:26:52 AM

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That is most likely misinformation. Indeed harmaline and ibogaine have been shown to cause degeneration of cerebellar Purkinje cells in high doses (O'Hearn, 1993), but later studies have proven that this neurotoxicity is dose-dependent. See the attached paper, where the case of ibogaine neurotoxicity is proven to be false at dosages relevant for this discussion. Absolutely everything points to the fact that this also is the case with harmaline, as the high-dose neurotoxicity with ibogaine occurs the same way as with harmaline.
 
1992
#14 Posted : 8/19/2010 5:12:44 AM

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Evening Glory found the original study.

Just because a recreational or whatever dose of harmaline isnt neurotoxic doesnt mean it cant be toxic
 
endlessness
#15 Posted : 8/19/2010 5:16:01 AM

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anything can be toxic at high doses, even water, so its a bit of a random comment to make, saying its 'neurotoxic' if the dosages needed for it being so are far far faaaaaaaaaaar from what anybody will ever consume, dont you think?

not to say its a bad thing that you bring this up, all sides of the story should be looked at, but I think its important to be clear what we are talking about when we use words such as 'toxic'.
 
1992
#16 Posted : 8/19/2010 5:33:05 AM

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Water isn't neurotoxic though... and my original intent by stating that harmaline was neurotoxic was to demonstrate that while MTHC may be unjustly called a neurotoxin in the amount required for monoamine oxidase inhibition.

Nicotine and Erythravine are both commonly used and can be effective neurotoxins too.

Please don't jump on me just because I'm having a little communcation problems tonight hahaha... rereading my original post, "considered" would've been a good word to use.
 
endlessness
#17 Posted : 8/19/2010 5:41:43 AM

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thank you for clarifying, and sorry if I seemed to jump on you, that was definitely not my intention Smile I really just meant that we have to be careful how we word it, because a wrong message might come across, like for example that one might be mislead into thinking a substance is toxic while it isnt so in normal or even high doses.

But you are very right in that you wanted to express the exact opposite of what I understood, not that harmaline can be a problem, but that in the same way, 2mthc's neurotoxicity is probably not significant in the amounts taken (which is sort of what I meant when I posted that paper showing how its also present in ayahuasca and that there is no sign of neurotoxicity with the extensive testing made on regular long time users, therefore it cant really be reasonably called neurotoxic for our purpouses)

sorry for any misunderstanding, and thank you for bringing information up Smile
 
ms_manic_minxx
#18 Posted : 8/19/2010 5:45:41 AM

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Just for the jungle peanut gallery, does anyone care to share (and transliterate into comprehensible perspective Wink ) exactly how much harmaline would be toxic?

And how much... 2-methyl-1,2,3,4-tetrahydro-beta-carboline... might legitimately be toxic? How do these studies translate into human terms, just to illustrate the differences in proportions? (I feel much better knowing this one, too, is found in traditional Ayahuasca!)

Not paranoid... now just curious. Smile
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Ginkgo
#19 Posted : 8/19/2010 8:11:29 PM

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ms_manic_minxx wrote:
Just for the jungle peanut gallery, does anyone care to share (and transliterate into comprehensible perspective Wink ) exactly how much harmaline would be toxic?

And how much... 2-methyl-1,2,3,4-tetrahydro-beta-carboline... might legitimately be toxic? How do these studies translate into human terms, just to illustrate the differences in proportions? (I feel much better knowing this one, too, is found in traditional Ayahuasca!)

Not paranoid... now just curious. Smile

As these studies are done on rats and not on humans, that is a question largely impossible to answer. Last time I checked, very few of us were in fact giant rats. But assuming we are, a dose of 100 mg/kg of ibogaine is neurotoxic while a dose of 40 mg/kg is not. 15 to 20 mg/kg is what normally is used therapeutically.

The numbers for harmaline is not researched, but one may assume that it is similar to ibogaine. That is, a giant rat will have to take >5 times the normal dose for it to be neurotoxic. Humans will likely have to take considerably more.

As earlier stated, you should not be worried by the toxicity of 2-methyl-1,2,3,4-tetrahydro-beta-carboline. It is only found in incredibly small amounts, and has in these amounts been used traditionally for thousands of years.
 
jamie
#20 Posted : 9/6/2011 6:18:26 PM

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bump..I was going to start a new thread but then I found this one Smile

I am planning to at some point in the near future harvest alot of phalaris and try a few different things..one of them being a manske. I know both MTHC and 6-meo-THC are present in the grasses and I want to experiment with them. That would require me to build up to an active dose so if anyone does have information on the toxicity of these substances(im sure they wont), that would be great..
 
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