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Determination of DMT in ayahuasca Options
 
Shaolin
#1 Posted : 2/12/2013 5:40:54 PM

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Determination of N,N-dimethyltryptamine in beverages consumed in religious practices by headspace solid-phase microextraction followed by gas chromatography ion trap mass spectrometry

Alain Gaujac, Nicola Dempster, Sandro Navickiene, Simon D. Brandt and Jailson Bittencourt de Andrade, 2013

http://dx.doi.org/10.1016/j.talanta.2013.01.017

Quote:
A novel analytical approach combining solid-phase microextraction (SPME)/ gas chromatography ion trap mass spectrometry (GC-IT-MS) was developed for the detection and quantification N,N-dimethyltryptamine (DMT), a powerful psychoactive indole alkaloid present in a variety of South American indigenous beverages, such as ayahuasca and vinho da jurema. These particular plant products, often used within a religious context, are increasingly consumed throughout the world following an expansion of religious groups and the availability of plant material over the Internet and high street shops. The method described in the present study included the use of SPME in headspace mode combined GC-IT-MS and included the optimization of the SPME procedure using multivariate techniques. The method was performed with a polydimethylsiloxane/divinylbenzene (PDMS/DVB) fiber in headspace mode (70 min at 60 °C) which resulted in good precision (RSD<8.6%) and accuracy values (71–109%). Detection and quantification limits obtained for DMT were 0.78 and 9.5 mg L−1, respectively and good linearity (1.56–300 mg L−1, r2=0.9975) was also observed. In addition, the proposed method showed good robustness and allowed for the minimization of sample manipulation. Five jurema beverage samples were prepared in the laboratory in order to study the impact of temperature, pH and ethanol on the ability to extract DMT into solution. The developed method was then applied to the analysis of twelve real ayahuasca and vinho da jurema samples, obtained from Brazilian religious groups, which revealed DMT concentration levels between 0.10 and 1.81 g L−1.
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Vodsel
#2 Posted : 2/12/2013 5:55:14 PM

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Awesome share, Shaolin.

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corpus callosum
#3 Posted : 2/12/2013 6:21:31 PM

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Thanks Shaolin for posting this.Good article; they didnt mess about with acidifying the jurema brew for increased DMT in the solution.pH1 !!! Shocked
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ChemisTryptaMan
#4 Posted : 2/13/2013 12:22:59 AM

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Nice article, thanks for posting.
 
nen888
#5 Posted : 2/13/2013 6:41:35 AM
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..very interesting article thank you Shaolin..

haven't read the full article yet..
vinho da jurema is presumably the beverage made with 'A. jurema' or Mimosa in Bahia, Brazil.
 
benzyme
#6 Posted : 2/13/2013 6:52:30 AM

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pH 1 sounds rather excessive, lots of salts
I'd have gone pH 4 at the lowest, nLC-MS with a waters nano-acuity 100 uM i.d. C-18 column, 0.1% FA in H20 in res A, 0.1% FA in ACN in res B, 0 - 20% B for 20 mins, 100% B @ 30 - 40 mins, and 20% B at 45-50 mins. 30 uL/min flowrate, 5 kV electrospray.
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3rdI
#7 Posted : 2/13/2013 9:39:27 AM

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benzyme wrote:
pH 1 sounds rather excessive, lots of salts
I'd have gone pH 4 at the lowest, nLC-MS with a waters nano-acuity 100 uM i.d. C-18 column, 0.1% FA in H20 in res A, 0.1% FA in ACN in res B, 0 - 20% B for 20 mins, 100% B @ 30 - 40 mins, and 20% B at 45-50 mins. 30 uL/min flowrate, 5 kV electrospray.


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cyb
#8 Posted : 2/13/2013 10:31:51 AM

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3rdI wrote:
Surprised


hehe...benz you've been running your text books through Pure Data haven't you? Laughing

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Infundibulum
#9 Posted : 2/13/2013 10:34:07 AM

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Layman summary:

The authors analysed both ayahuasca and vinho da jurema, and quantified dmt in it using admittedly fancy equipment. They also fiddled with extraction parameters and show that 50/50 water:ethanol extracts very high amount of dmt at just room temperature, which is only marginally worse than using hydrochloric acid, pH=1 at 100 degrees Celsius (Table 3). The latter is an interesting lead for advancing extraction methodologies. They also show that, on average vihno da jurema traditional preparations contain twice as much dmt compared to ayahuasca (Table 4) (even though this does not always correlate with how much dmt you take in a session)

I think that it is no surprise that dmt is in ayahuasca and in vinho da jurema, which makes this aspect of the study redundant. I would have liked them to expand on the vinho da jurema, as this is not supposed to have any added ingredients (as caapi is for ayahuasca) for MAO inhibition and our knowledge of why vihno da jurema is active as is, is very limited.



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nen888
#10 Posted : 2/13/2013 10:51:59 AM
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..i wish they'd expanded on the vinho de jurema too..a Maps report says it was actually Mimosa verucosa (see last paragraph) without an added MAOI plant..contacts tell me a 'mimosa' is ingested with caapi by african-brazillians in northern Brazil..

 
3rdI
#11 Posted : 2/13/2013 11:14:22 AM

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cool, cheers Infundibulum
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nen888
#12 Posted : 2/13/2013 10:03:02 PM
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Infundibulum wrote:
Quote:
They also fiddled with extraction parameters and show that 50/50 water:ethanol extracts very high amount of dmt at just room temperature, which is only marginally worse than using hydrochloric acid, pH=1 at 100 degrees Celsius (Table 3). The latter is an interesting lead for advancing extraction methodologies.

..before all these nexus folk-teks and similar, chemists advised me 'ethanol/water for DMT'..at room temperature DMT dissolves easily in ethanol, but put it in acetic or hydrochloric acid and it needs heat..the argument against using acid/ heat is that it could alter other compounds in the plant..i also wish they's analysed what other compounds were in there..
 
Infundibulum
#13 Posted : 2/13/2013 10:21:11 PM

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I was also surprised by the ethanol/water thing and I too believethat it is gentler compared to acid and/or heating.

I have used once only room temperature water to extractmhrb, which pulled roughly 75% of the spice in it. I wonder how much the presence of ethanol would had changed the yield.

Chemists out there, do you have an idea why the addition of ethanol makes extraction so much efficient?


Need to calculate between salts and freebases? Click here!
Need to calculate freebase or salt percentage at a given pH? Click here!

 
Vodsel
#14 Posted : 2/14/2013 12:18:13 AM

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I'm no chemist, but maybe ethanol will dissolve not only the alkaloidal salts but the free bases present in the plant material as well.
 
benzyme
#15 Posted : 2/14/2013 1:36:31 AM

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alkaloids don't exist as free bases in plants.

alcohol may partake in van der waals interactions because of the alkyl moiety, whereas
water only hydrogen-bonds. i'd be curious on how effectively butanol would
pull dmt. it's used in several tertiary solvent systems in TLC to analyze tryptamines
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Kash
#16 Posted : 2/14/2013 3:07:12 AM

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Well, ethanol is an astringent that likes to absorb water from cells, which can damage cells through shrinking ...Its antiseptic effect of denaturing proteins and lipids likely play into it as well. Those qualities in combination of ethanol being polar likely contribute to it being better at absorbing alkaloids from plant material than water during extractions.
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ymer
#17 Posted : 2/28/2013 5:10:10 PM

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Infundibulum wrote:
Layman summary:
The authors analysed both ayahuasca and vinho da jurema, and quantified dmt in it using admittedly fancy equipment. They also fiddled with extraction parameters and show that 50/50 water:ethanol extracts very high amount of dmt at just room temperature, which is only marginally worse than using hydrochloric acid, pH=1 at 100 degrees Celsius (Table 3). The latter is an interesting lead for advancing extraction methodologies. They also show that, on average vihno da jurema traditional preparations contain twice as much dmt compared to ayahuasca (Table 4) (even though this does not always correlate with how much dmt you take in a session)

I think that it is no surprise that dmt is in ayahuasca and in vinho da jurema, which makes this aspect of the study redundant. I would have liked them to expand on the vinho da jurema, as this is not supposed to have any added ingredients (as caapi is for ayahuasca) for MAO inhibition and our knowledge of why vihno da jurema is active as is, is very limited.


That sounds very interesting, would it be possible to do the following?

1. Soak in 50/50 ethanol/water for a few hours/days at room temperature.
2. Filter out plant material, discard plant material and keep the liquid.
3. Evaporate/distill the ethanol from the 50/50 filtrate until you reach azeotrope.
4. Perform FASW.
5. Yield Smile
 
 
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