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Author: Subject: MAOI(harmine) extraction of tobacco
ni3rtap
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[*] posted on 22-9-2013 at 00:11
MAOI(harmine) extraction of tobacco


Harmine is the most active, relevent MAOI in tobacco(~1nM/k binding). The nomenclature on the harmala alkaloids is very inconsistent so I mean the fully aromatic, tricyclic, one methyl group, with no methoxy group.

My plan is to soak some ground tobacco in 50% isopropanol and see if it extracts something the lights up under UV. I'm really unsure about how to purify it.

Also I'm am unsure if it actually is in tobacco. I've seen articles identify it as the main MAOI in smokers, but not in smokeless tobacco users. This makes me think norharmaline( loses the methoxy and becomes more aromatic) is reacting during combustion to produce it.



I would really appreciate anyone's 2 or even lesser number of cents.



EDIT: All i've seen on the forum is 1 post about analysis of the MAOI extractions on DIY TLC plates.

[Edited on 22-9-2013 by ni3rtap]
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[*] posted on 22-9-2013 at 01:24


If you extract a carrot with 50% IPA I suspect that you will get something that glows under UV light, but it won't be harmine.
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Nicodem
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22-9-2013 at 02:33
sonogashira
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[*] posted on 22-9-2013 at 03:26


What evidence do you have that tobacco contains harmine? I had a quick look and could only find evidence of harman and nor-harman being detected in cigarette smoke, but not harmine. I didn't look very thoroughly though. It seems a poor choice of material to extract harmine from, especially when harmine rich plant sources are well known and availible.
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Mesa
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[*] posted on 23-9-2013 at 04:45


I've read reports on beta carbolines being responsible for the addictive quality of tobacco that were referred to as "harmala type MAOI's." I'd kinda assumed it was referring to harmaline/harmine. songashira's post prompted me to do further searching and I too cannot find any evidence pointing to harmine being present in tobacco, but plenty of harman/norharman.
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bfesser
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23-9-2013 at 05:15
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[*] posted on 23-9-2013 at 05:31


[pruned double-post]
Quote: Originally posted by ni3rtap  
The nomenclature on the harmala alkaloids is very inconsistent so I mean the fully aromatic, tricyclic, one methyl group, with no methoxy group.
My 2&cent;; use <a href="https://en.wikipedia.org/wiki/IUPAC_nomenclature_of_organic_chemistry" target="_blank">IUPAC systematic nomenclature</a> <img src="../scipics/_wiki.png" />&mdash;this is why it exists.<table><tr><td><img src="http://webbook.nist.gov/cgi/cbook.cgi?Struct=C486840" /></td></tr><tr><td align="center"><a href="http://webbook.nist.gov/cgi/cbook.cgi?ID=486-84-0" target="_blank">1-methyl-9H-pyrido[3,4-b]indole</a> <img src="../scipics/_ext.png" /></td></tr></table>



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sonogashira
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[*] posted on 23-9-2013 at 06:18


In which case:
http://www.sciencedirect.com/science/article/pii/S0031942200...

[Edited on 23-9-2013 by sonogashira]

Attachment: sdarticle(12).pdf (467kB)
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arsphenamine
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[*] posted on 23-9-2013 at 06:59


Quote: Originally posted by sonogashira  
In which case:
http://www.sciencedirect.com/science/article/pii/S0031942200...
If you read the abstract more closely, there is:
Quote:
The tobacco itself contained only about 1 per cent of the amount found in smoke.


Searching on "tobacco leaf alkaloids" produces assays dominated by nicotinic structures.

Perhaps you could obtain/grow Syrian Rue, from whose botanical name harmaline derives.
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hive3
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[*] posted on 26-9-2013 at 12:52


The studies show very low levels ie 20 Billionths of a gram in the smoke. Stick with Syrian Rue.
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sonogashira
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[*] posted on 27-9-2013 at 01:54


Harman is a minor alkaloid in Syrian Rue. It would be simpler to synthesise it from tryptophan and acetaldehyde, eg. http://pubs.acs.org/doi/abs/10.1021/ja01181a064?journalCode=... and cited papers.

[Edited on 27-9-2013 by sonogashira]
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[*] posted on 27-9-2013 at 05:45


In comparison to a messy Syrian rue extraction anything is preferable. The harmalas fluoresce under black light and after my last extraction my kitchen had glowing splatter patterns on every wall and the ceiling.

My only point was that at a concentration of .0016g harman per gram of syrian rue, compared to .0000002g per gram tobacco (If the tobacco had the same concentration as the smoke), the extraction would require about 10,000g of tobacco to get the same amount of product as 1g Syrian rue.
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[*] posted on 27-9-2013 at 18:17


If I recall correctly, the Pictet-Spengler (probably misspelled) cyclization reaction is quite straightforward and is an easy way to prepare beta-carbolines from tryptamine or tryptophan.
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