Sciencemadness Discussion Board

tryptamines in RCG

chemrox - 29-6-2012 at 07:46

I got a call for papers from a wetland science org I belong to. I have planned to study Phalaris arundinacea to see whether reports of it's containing psychoactive tryptamines are true. If it does, is it subspecies dependent? Location dependent? Time of year? The last will have to wait until I've gathered more data but I was planning on doing a month long study using ultra simple techniques. I understand a good solvent for N,N-dimethyl tryptamine is ethyl acetate. However diethyl ether is cheaper and easier to work with so I plan to use it as the extraction solvent. My 1.5 liter extractor is missing the bottom screen so I will have to fabricate. I have a reference sample of 5-meo dmt so I will have a spot for comparison. Obviously I don't have dmt but I am looking for any published rf values I can use. Any feedback on solvents (or anything else) would be appreciated. Also I don't have a lot of refs yet. A good application for scifinder...anyway; if you know some please pass along. If the alleged dmt content turns out to be more than a bio-suburban legend I will present the finding as a possible solution to the growing populations of RCG.

Diablo - 29-6-2012 at 12:56

Phalaris arduinacea aontains in varying amounts N,N-Dimethyltryptamine 5-meo-Dmt, 5-oh-dmt, gramine and some others. Alkaloid content can be increased by stressing the plants and seem to be concentrated in the leaves. Xanthydrol can be used to determine the dominant alkaloid present as it will change color in their presence although I am having trouble finding the color chart again.
Usually either N,N-DMT or 5-meo-dmt is the dominant alkaloid present in most phalaris species.
Also gramine has been found to have an ld50 of around 50 mg/kg in mice, which if tre for humans would likely not be a concern considering that 70 mg of alkaloid is a high dose.
Some subspecies of Phalaris arundinacea have higer concentrations of alkaloids, I have also read that shaded plant produce a higher concentration of alkaloids.
When running an acid base extraction on phalaris a defatting step is highly recommended.

[Edited on 29-6-2012 by Diablo]

bbartlog - 29-6-2012 at 13:37

You can get ethyl acetate pretty cheap at Lowe's (as MEK substitute), and it's 100% ethyl acetate according to : http://www.wmbarr.com/ProductFiles/1636%20KS%20MEK%20Substit... . Was about US $6 per liter as I recall.
As for references, did you follow up the links from Wikipedia? Couple of steps shows you:
Smith, T.A. 1977. Review: Tryptamine and Related Compounds in Plants. Phytochemistry 16 171-175.
...as the source for the claim of dmt content.

refs

chemrox - 29-6-2012 at 15:03

Yes-I should have mentioned having those refs. They're pretty old.. same ones Shulgin cited and I'm a little skeptical. A lot of sketchy stuff happens in academic biochemistry when publication deadlines come due. Anyway (self slap on hand) there are regional variations and time of year variations in phytochemistry. Maybe all the rich silt in the Willamette Valley makes them too 'happy' to make much dmt or maybe they make all kinds. Thanks for the information on et-acetate. I still lean toward ether just because it flashes off so quickly. It's not like I'm expecting grams of dmt per run.

Adas - 9-7-2012 at 11:20

I think that the presence of the toxic gramine is not worth the DMT extraction.

Diablo - 9-7-2012 at 13:41

Gramine might not be toxic in recreational dmt doses.

White Yeti - 10-7-2012 at 19:44

Perhaps the gramine can be selectively degraded by using a carefully engineered bacterium?

Adas - 11-7-2012 at 01:54

Quote: Originally posted by White Yeti  
Perhaps the gramine can be selectively degraded by using a carefully engineered bacterium?


Or just engineer the plant to produce no gramine and more DMT :D

White Yeti - 11-7-2012 at 07:10

Quote: Originally posted by Adas  

Or just engineer the plant to produce no gramine and more DMT :D


That's definately a possibility. Let us know when you've succeeded:D;)

Does anyone know of a biochemical pathway used to degrade gramine specifically? Monoamine oxidase is not an option, as it would degrade DMT as well.

Adas - 11-7-2012 at 09:41

I think no one does :) I don't think there was any research on this. But we can probably lower the gramine : DMT ratio by evaporation - Wikipedia says (I don't know whether it is legit or not), that MP of gramine is around 120°C and that of DMT is around 40°C. If this is true, their boiling points also differ greatly, so we can just evaporate DMT and catch its vapors, while gramine remains in the container.

[Edited on 11-7-2012 by Adas]

Diablo - 11-7-2012 at 13:26

There's always chromatography.

bbartlog - 13-7-2012 at 05:31

I'd be skeptical that gramine has a higher bp than DMT. It's a similar but slightly smaller molecule. Quite possible that wikipedia has the melting point wrong as well.

Adas - 13-7-2012 at 08:55

Quote: Originally posted by bbartlog  
I'd be skeptical that gramine has a higher bp than DMT. It's a similar but slightly smaller molecule. Quite possible that wikipedia has the melting point wrong as well.


But I have seen another sources, stating te same...

Diablo - 31-8-2012 at 18:21

According to some research done on another forum, gramine is practically insoluble in cold limonene and naptha.