why is harmine toxic and why is harman not toxic?

[red22]

HARMAN

HARMINE

Well, I'm only going by one account, which is obviously not a very reliable way to judge something:

Bioassay of the crystalline extract was confirmed with a pronounced harmala intoxication, though much cleaner feeling than a few grams of syrian rue.

germx99 - 10/17/14 - Russian Olive: MAOi in Our Backyards

I personally tried acid-base extractions of B. caapi as well as Syrian rue (mixed up with water [1] and extracted crudely with salt and vinegar [2]) and I found the effects of both botanicals to be kind off feverish. Harmine is common to both of these plants, however Syrian rue contains a significant amount of harmaline whereas B. caapi does not. Both plants could be described as dirty-feeling.

Harman is found in many plants. The Encyclopedia of Psychoactive Plants* has a table of harman-containing plants. It refers to harman as harmane. Download table here.


edit

There are many harm-type chemicals other than harmine, harmaline (a predominant cehmical found in Peganum harmala), and the stated harman. Shulgin refers to the harm-type chemicals as a "rich and promising virgin field": https://www.erowid.org/library/books_online/tihkal/tihkal44.shtml


*Christian Rätsch, 2005.

 

[sekio]

One account of someone guessing at alkaloid profiles isn't really a data point.

 

[red22]

Just edited the post to include an extensive write-up of Shulgin's on this topic: https://www.erowid.org/library/books_online/tihkal/tihkal44.shtml

 

[Zeds(NCO2CH2CH3)2]

The basis of this thread is tricky but correct- an anecdotal report of someone mentioning the toxicity of alkaloids from b. Caapi vs Syrian rue.

Tetrahydroharmine/harmaline are not toxic but the N-methylated version of tetrahydroharmine which occurs in the plant is because it is readily oxidized to form an analogue of MPP+ proceeding in an MPTP---> MPP+ manner (oxidation of the n-methyl tetrahydrobetacarboline core in an analogous manner)

Check out the study below

Mitochondrial respiratory inhibition by N-methylated b-carboline derivatives structurally resembling n-methyl-4-phenyl-pyridine


You have the right idea, so did the previous guy except you are looking and blaming the wrong molecules when it is but the others located in the plant.

Zedsdead

 

[red22]

Wow, thank you for that rare bit of knowledge!

 

[serotonin2A]

It is easy to see the structural similarities between beta-carbolines and MPTP. I've always been fascinated, and a bit perplexed, by the fact that many beta-carbolines are neurotoxic in model systems, but they don't some to produce any obvious signs of toxicity in humans even though they are routinely ingested and can be ,generated endogenously. MPTP is toxic because of how it is biotransformed (MPTP > MPP+), and the mechanism of beta-carboline neurotoxicity involves a similar conversion to neurotoxic derivatives. Is it possible that the activation step does not occur in humans in vivo?

 

[Zeds(NCO2CH2CH3)2]

Well these compounds are dirty or known as PAINS compounds, they are elusive binders. Most notably many things enter the mitochondria and are oxidized (similar to quinones and NADH /NADPH). So this occurs everywhere in the body, but not as high and dangerous enough of a concentration in the brain most likely, it def happens tho.
Number two i have a strong feeling they are substrates for histone methyl transferase and become rapidly oxidized after methylation. In general the betacarbolines may become oxidized but unless there is a N-methyl component which is oxidized, into the pyridiunium ion- then it may not be as dangerous.. Unsure

 

[red22]

So are you guys confident that harmine from a chemical supplier wouldn't produce what I described as a feverish effect. It's an overly warm, heavyish bodily disassociation feeling and it also makes the body feel kind of metallic. Even in low doses. And this is with an acid-base extraction of the supposedly pure and wonderful B. caapi.

 

[Zeds(NCO2CH2CH3)2]

We aren't confident in anything because a feverish effect is poorly defined and anecdotal reports aren't exactly truly useful. Especially anecdotal reports about chemicals from a third party overseas vendor, it's not safe. We don't know, if you post their analysis and certified materials we can help then but otherwise don't ingest it if you can't classify or confirm it...
Zedsdead