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Desmanthus illinoensis, leptolobus and spp. Workspace

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All of my measurements were on dry weight.
Assuming your yield was from 4 year old plants, it does sound like concentration increases with age, by a lot.
 
The ones I extracted were 7 and 8 years old, so age may have had an influence. I also waited until after fall freezing began so the roots would be richer in alkaloid.
The size of the roots impressed me. 870 Grams of root from 4 plants, I did not expect that from the above ground parts.
 

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Just a small thing regarding the mass spectra, sample 3 peaks are inverted, the DMT peak is the one at 5.5min, the other bigger one is the unknown (notice DMT always elutes at the same time in all tests using this system).

As for the purity, the DMT was quantified using UV photospectrometry and turned out really low %. For example sample 2 turned out with only 5% purity. I asked them to clarify if this was a mistake because it seems awefully low (and incarnation's bioassay didn't indicate such a low purity) but they said there is likely no mistake there. In any case the UV photospec is not their usual quantification method, they use HPLC-MS for that but the instrument is down for maintenance. When it is back up this quantification will be repeated and I'll post here.

In any case, tbh the fact that it's such a young plant makes me indeed think that low alkaloids may be normal, we should def test again with older plants too.

The unknown substance's spectra is this following:

Screen_Shot_2018-11-23_at_8.30.46_AM.png


What one can do is look at past publications of different desmanthus (or if that doesn't help, of other DMT-containing plants) and see if any of the substances already described have a similar mass spectra, which would be good indication. I'm too busy for that at the moment but I'd be curious if you guys find anything :)
 
Oxazolidinone has a MW of 87, and is capable of kicking out CO2 at m/z 44. The intervening fragments could correspond to loss of NH, CH, and/or CH2. But I'm pretty rubbish with MS interpretation, by my own reckoning.

Attached is an image of the structure of several oxazolidinones, oxazolidin-2-one being the most likely. It's the cyclic carbamate of ethanolamine.

Edit: Well, the EIMS for oxazolidin-2-one doesn't match, so we can probably scratch that one. Aziridine carboxylic acid seems a bit far-out as an alternative, though.

Edit2: Throwing in another suggestion we have 3-Isoxazolidinone but real (not predicted) MS data is harder to find.
 

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Going into this compound with (presumed) MW 87, a molecular weight search turns up the following list:
86.97 Chlorodifluoroamine
86.99 2-Propenenitrile, 2-chloro-
86.99 Trifluoroamine oxide
87.01 (Methylthio)-acetonitrile
87.01 Ethane, isothiocyanato-
87.01 Thiocyanic acid, ethyl ester
87.03 Oxazolidin-2-one
87.07 1-Aziridineethanol
87.07 Butanal, oxime
87.07 Morpholine
87.07 Propanamide, N-methyl-
87.07 N,N-Dimethylacetamide
87.07 Propanal, 2-methyl-, oxime
87.07 2-Propanone, O-methyloxime
87.07 3-Pyrrolidinol
87.07 Butanamide
87.07 Propanamide, 2-methyl-
87.07 Acetamide, N-ethyl-
87.07 2-Butanone, oxime
87.08 Guanidine, N,N-dimethyl-
87.10 1-Butanamine, 3-methyl-
87.10 1-Pentanamine
87.10 1-Butanamine, N-methyl-
87.10 N-tert-Butylmethylamine
87.10 2-Propanamine, N-ethyl-
87.10 1-Propanamine, N-ethyl-
87.10 Neopentylamine
87.10 2-Butanamine, 2-methyl-
87.10 2-Butanamine, 3-methyl-
87.10 3-Pentanamine
87.10 Ethanamine, N-ethyl-N-methyl-
87.10 1-Propanamine, N,2-dimethyl-
87.10 2-Butanamine, N-methyl-
87.10 N,N-Dimethyl-1-propanamine
87.10 1-Butanamine, 2-methyl-
87.10 2-Propanamine, N,N-dimethyl-
Click to expand...
This list contains only compounds for which the MS data exists on the NIST database. This would be EIMS? What ionization type was used for the mystery compound?

Next (after lunch :) ), I'll take a look through for the most likely culprits, and maybe work on a few other isomers that aren't listed. And I'll try not to spam out this thread. Is it OK to carry on posting this here?
 
endlessness said:
Just a small thing regarding the mass spectra, sample 3 peaks are inverted, the DMT peak is the one at 5.5min, the other bigger one is the unknown (notice DMT always elutes at the same time in all tests using this system).
Click to expand...

I changed and replaced the sample 3 peaks.
 
Well, I looked at all the EIMS spectra on the NIST database and none of them really matched. Were your team using a different ionization method?

Here's a list of compounds (and some ions) in the MW 87 range that also came up on the NIST search, but without MS spectra available:
87.0773 Propanamide, 2-oxo-
87.0977 nPrCO2 anion
87.0977 iPrCO2 anion
87.1204 Isoxazolidine,2-methyl-
87.1204 Formamide, N-propyl-
87.1204 Formamide, N-isopropyl
87.1237 N,N'-dimethylguanidine
87.1397 Tetrahydropyran, protonated
87.1397 3-Pentanone, protonated
87.1397 2-Methyltetrahydrofuran, protonated
87.1408 sBuCH2O anion
87.1408 nPrCH(Me)O anion
87.1408 iPrCH2CH2O anion
87.1408 Et2CHO anion
87.1408 iPrCH(Me)O anion
87.1408 nC5H11O anion
87.1408 tBuCH2O anion
87.1408 EtC(Me)2O anion
87.143 Thiazoline
87.143 2,5-Dihydrothiazole
87.1634 2-Pentanamine
Click to expand...

I would note that the large peak at m/z 44 could correspond to a dimethylamino- fragment.
 
I now have 3year old DI in my patch. My last test was with 1 year plants and the results were very low dmt content harvested late fall. No gramine but high hordenine. Reading through this thread i am trying to decide when to harvest. i saw mention of good results late spring early summer or possible early spring. I am certainly in no rush so if anyone has an opinion on which harvest window i should choose reply here or PM me. I am sure time of day plays as well. If i had a bigger patch and more time i would test all variables but alas, the life of a householder...
 
Elrik said:
Boy, now I'm looking forward to testing my extract. I had expected lepto to contain lots of NMT. I may have to rethink using 150 mg oral as my trial dose :lol:

I was surprised to see acetaldehyde in the water extract. If lepto does contain NMT we can expect some 1,2-dimethyl-ß-carboline too.

I assume the root bark yield was calculated on fresh weight?
I got 0,149% alkaloid base from whole root, fresh weight basis
Did you also get a severe emulsion on the A/B?
Click to expand...
Curiuos Elrik, did you bioessay?
 
Backtracking a little, my best guess for a likely culprit for the MW 87 compound is now N,N-dimethylisopropylamine. The dimethylamino- group corresponds to m/z of 44, but we should see a fragment at m/z 72 rather than the 73 & 74 experimentally observed. (I'm not that good at this stuff :oops: )
45525_1
 
endlessness said:
This one guy posted here he made several experiments and june/july were best, alkaloids reduced starting august, i edited my first post in this thread to include his quote.
Click to expand...
thx E
I may have found anothe Desmanthis strain. Leaves and seedpods look the same as Leptobulus but these are taller. Will try to get a snapshot and see if i can get a proper ID
 
hello i am BEZ ....
i am looking into desmanthus illinoisis. and woderd if any of you have done more work with this plantb ,those of you who did a simple AB extract or did you do a de-fat step ? did you try to cleanup with naptha and freeze persip also what have you found about grammine, content and if AB excluded it .
i remember a large field of it as a kid but that area has grown into trees no more bundle flowers . i am still looking
i orderd some seeds

thanks Bez
 
nen888 said:
Desmanthus illinoensis
>up to 0.34% DMT roots: Thompson, Alonzo C., Gilles F. Nicollier & Daniel F. Pope 1987 Journal of Agricultural and Food Chemistry 35: 361-365. "Indolealkylamines of Desmanthus illinoensis and Their Growth Inhibition Activity."
reports of lower amounts (e.g. 0.14%)

Desmathus leptolobus is said to be higher in tryptamine levels
>DMT/NMT: Appleseed, Johnny 1992-1996 cited by Shamanic Plants & Herbs, Natural Remedies | MAYA Ethnobotanicals
Click to expand...
I read that Desmanthus Leptolobus has lower DMT levels at around 0.14% in the root bark. This could be inaccurate information, and its possible that there are other tryptamines contained within it unaccounted for by the site I read from.
 
DMTeenager said:
I read that Desmanthus Leptolobus has lower DMT levels at around 0.14% in the root bark. This could be inaccurate information, and its possible that there are other tryptamines contained within it unaccounted for by the site I read from.
Click to expand...
The proof of the pudding is in the... extracting. My Desmanthus seedlings were destroyed by slugs and woodlice, though.
DMTeenager said:
site I read from
Click to expand...
Link?
 
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