ni3rtap
Harmless
Posts: 9
Registered: 21-9-2013
Member Is Offline
Mood: No Mood
|
|
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]
|
|
|
unionised
International Hazard
Posts: 5126
Registered: 1-11-2003
Location: UK
Member Is Offline
Mood: No Mood
|
|
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.
|
|
|
Nicodem
|
Thread Moved
22-9-2013 at 02:33 |
sonogashira
National Hazard
Posts: 555
Registered: 10-9-2006
Member Is Offline
Mood: No Mood
|
|
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.
|
|
|
Mesa
Hazard to Others
Posts: 264
Registered: 2-7-2013
Member Is Offline
Mood: No Mood
|
|
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.
|
|
|
bfesser
|
Thread Pruned
23-9-2013 at 05:15 |
bfesser
Resident Wikipedian
Posts: 2114
Registered: 29-1-2008
Member Is Offline
Mood: No Mood
|
|
[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¢; use <a href="https://en.wikipedia.org/wiki/IUPAC_nomenclature_of_organic_chemistry"
target="_blank">IUPAC systematic nomenclature</a> <img src="../scipics/_wiki.png" />—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>
|
|
|
sonogashira
National Hazard
Posts: 555
Registered: 10-9-2006
Member Is Offline
Mood: No Mood
|
|
In which case:
http://www.sciencedirect.com/science/article/pii/S0031942200...
[Edited on 23-9-2013 by sonogashira]
Attachment: sdarticle(12).pdf (467kB)
This file has been downloaded 844 times
|
|
|
arsphenamine
Hazard to Others
Posts: 236
Registered: 12-8-2010
Location: I smell horses, Maryland, USA
Member Is Offline
Mood: No Mood
|
|
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.
|
|
|
hive3
Harmless
Posts: 27
Registered: 3-7-2013
Member Is Offline
Mood: No Mood
|
|
The studies show very low levels ie 20 Billionths of a gram in the smoke. Stick with Syrian Rue.
|
|
|
sonogashira
National Hazard
Posts: 555
Registered: 10-9-2006
Member Is Offline
Mood: No Mood
|
|
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]
|
|
|
hive3
Harmless
Posts: 27
Registered: 3-7-2013
Member Is Offline
Mood: No Mood
|
|
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.
|
|
|
Rich_Insane
Hazard to Others
Posts: 371
Registered: 24-4-2009
Location: Portland, Oregon
Member Is Offline
Mood: alive
|
|
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.
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
