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chromatographic properties of n oxides? Options
 
burnt
#1 Posted : 3/9/2010 10:55:09 PM

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Alright chemistry folks. We gotta butt our heads on this one. Why? Because n oxides are annoying. So how do we analyze them? GC sucks for this. HPLC and TLC are best bets. Any literature methods ideas thoughts comments etc?

SWIM really wants to know if bufotenin n oxide really exists in seeds. It could explain a lot of discrepancy people have in effects. I am pretty convinced by data reported here by others that dmt n oxide is likely to exist although SWIM SWIM's self has never seen any real evidence for its presence.

I think it would do the community good to get to the bottom of this.
 

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Phlux-
#2 Posted : 3/9/2010 11:04:19 PM

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i very much agree that there is loads of n-oxide in the seed - perhaps its slightly germinating them that converts the n-oxides and dmt to bufo.
iv noticed that one can precip a black mucky fumarate that acts simmilar to bufo fumarate - but if one disolves it in acetone + hcl (a very dark solution) - then does the zink n-oxide reduction step - the solution clears as when doing the harmine/harmaline reduction.

some dude is getting ammonium chloride very soon so he can post pix of all the results.
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69ron
#3 Posted : 3/10/2010 1:36:17 AM

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I've read that bufotenine N-oxide can be up to 50% of the alkaloid content of cebil. I don't recall the source of that data though.
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burnt
#4 Posted : 3/10/2010 8:39:45 AM

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How can one generate a reference n oxide? What kind of reactions would force a normal freebase into n oxide besides just letting it sit around for a long time?
 
burnt
#5 Posted : 3/20/2010 2:16:26 PM

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no one has any literature on presence of n oxides in these plants?
 
endlessness
#6 Posted : 3/20/2010 2:59:46 PM

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Ill see if I can find anything about it burnt.. but what about making n-oxide by mixing dmt with hydrogen peroxide, and then making a reference yourself?
 
burnt
#7 Posted : 3/20/2010 3:03:57 PM

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SWIM wonders if it would be quantitative conversion though? If its not there might be the same problems as a mixture would.

Wasn't there discussion in the past about deliberately making dmt n oxide this way? If so any idea where that thread is? Is it on the wiki?

Anyway SWIM thinks making a reference is the best way to check if any chromatographic method whether it be TLC, HPLC or whatever is trust worthy. But SWIM needs to make sure its a different substance then..
 
endlessness
#8 Posted : 9/26/2011 11:03:28 AM

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Reviving this old thread.

If anybody can get access to this paper, please post here:

Metabolism of the hallucinogen N,N-dimethyltryptamine in rat brain homogenates
Steven A. Barker†, John A. Monti, Samuel T. Christian

Biochemical Pharmacology
Volume 29, Issue 7, 1 April 1980, Pages 1049-1057

EDIT: Here


Also this thread is relevant:

Column chromatography

Can anybody share which eluent mixture would be ideal for TLC separation of 5-meo, dmt, nmt and their n-oxides ? Ron had said ethyl acetate would not really separate dmt, 5meo and n-oxide and that one would need something less polar. Maybe some mixture would be ideal? Which?
 
nen888
#9 Posted : 9/26/2011 11:27:59 AM
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endlessness wrote
Quote:
Can anybody share which eluent mixture would be ideal for TLC separation of 5-meo, dmt, nmt and their n-oxides ?

..gee, there's not a lot to google:
http://www.ncbi.nlm.nih.gov/pubmed/17292904
..have to probably look for 1950s papers..a chemist friend suggested dichloromethane/aqueous methanol for paper chromatoghraphy , which worked for nmt/dmt/betacarbolines..
charts of RF value data may give some clues for solvent systems..would also like to know more about this...
 
endlessness
#10 Posted : 9/26/2011 11:35:56 AM

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Thanks! Im attaching the paper you linked above. Unfortunately out of the mentioned alkaloids it only has 5-MeO-DMT.
 
endlessness
#11 Posted : 9/28/2011 11:12:37 PM

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Quote:
If anybody can get access to this paper, please post here:

Metabolism of the hallucinogen N,N-dimethyltryptamine in rat brain homogenates
Steven A. Barker†, John A. Monti, Samuel T. Christian

Biochemical Pharmacology
Volume 29, Issue 7, 1 April 1980, Pages 1049-1057



Snozz posted it, its the first attached paper here, and it has Retention factor for TLC of DMT, DMT N-Oxide, NMT, IAA, 2-MTHBC in the following solvent systems:

Code:

                                                    DMT-NO DMT  NMT   IAA  2-MTHBC
Methanol, NH40H (1 M), 5:1                          0.74  0.52  0.32  0.92  0.26
Isopropanol, ethylacetate. NH40H  80:20:4           0.09  0.37  0.19  0.14  0.17
Chloroform, methanol. NH40H    6O:10:1              0.42  0.73  0.52
n-Butanol, acetic acid (glacial), water, 8:1:1      0.61  0.50  0.70


So they can be separated using any of these eluent mixtures
 
Dozuki
#12 Posted : 11/1/2011 3:52:08 AM

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I've run about 6 different eluent systems with silica gel TLC. The best separations were usually obtained with IPA:NH4OH:H2O. This differentiated 5-Meo and N,N while some of the others did not (IE these 2 had the same rf values). It also separates the n-oxide, but I'm unsure about your other listed compounds.

Some of the other systems I've run are either listed in the above table or closely related. They were all gleaned from the older articles on Phalaris which were mostly done using TLC or paper chromatography.


That should get you a good start on finding the right system to use.

-D.
 
nen888
#13 Posted : 11/1/2011 3:56:06 AM
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..hey great to have another experimenter on board, Dozuki..Smile
i'm curious..did you use re-agents or UV to ID compounds?
..thanks for that info., the separate N-oxide factor is especially helpful in the light of some current nexus questions...
 
Dozuki
#14 Posted : 11/1/2011 4:02:29 AM

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I used both UV and reagents for visualization. I've used Elrich's, Xanthadrol, and Vanillin. Xanthadrol was the main one I used as it also provided some colorimetric separation of the compounds as opposed to just rf values.

-D.
 
nen888
#15 Posted : 11/1/2011 4:05:35 AM
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..thank you again Dozuki, great info...
if i may ask one more question, does this mean that you did find the n-oxide in a plant or extract? if so, this isn't that trivial..Smile
 
Dozuki
#16 Posted : 11/1/2011 5:09:58 AM

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According to my notes, I did not find it in the plant material. I oxidized a Virola theodora bark extraction with a 30% H2O2 solution and ran this against a MHRB sample that was showing a trace component that I thought was the N-oxide of DMT. This showed different rf values for the trace (.61) and the oxidized sample (.68 ) and a uniform rf for DMT (.75). Unfortunately, my notes on this particular entry are a little unclear on the eluent system used and the notes are over 5 years old. But it looks like like these plates were run with IPA:NH4OH:H2O @ 63:8:8.
 
 
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