Hello Nexians,
It's been some time since I've been regularly active on the forums but I have some recent work to share with you all. Some may find it useful, the information on the alkaloidal makeup of D. sanguinalis or "Hairy Crabgrass" available online seems to be few and far between, with only a couple of people contributing information and bioassay results, but it has been reported to contain appreciable amounts of 5-MeO-DMT and perhaps N,N-DMT.

Anyways, while browsing the forum and boning up on local plants in the area where I've recently moved I was introduced to a species I was not familiar with, Digitaria sanguinalis. So I looked at a bunch of pictures and learned how to identify it and came to the conclusion that this plant grows absolutely EVERYWHERE in this city, including my front yard (and now part of my garden). My curiosity was piqued, and I decided to see what was in it.

An unknown amount of fresh D. sanguinalis blades were collected from a spot that recieves full sun most of the day. I intend to collect large samples from different parts of the city, at different points in the season, to continue the study of this species. It is an invasive weed here so I don't think anyone will mind.


Although this was not deliberate, the fresh grass was sealed with as little air as possible and refrigerated at about 40°F for about four to five days.
The fresh grasses cut into smaller pieces and added to a 3qt cooking pot. 2qt of water was added, along with the tiniest splash of vinegar. This was brought to a low boil and simmered, stirring occasionally for one hour.


The grass was filtered out, saving the tea and putting it on medium heat in a separate pot to reduce. Another 2qt water/splash of vinegar was added to the grass, the mixture was brought to a low boil and simmered for one hour again, stirring periodically. This was then filtered and the two aqueous grass tea solutions were combined and reduced over several hours on medium heat. I tried to keep it at a low simmer rather than a full rolling boil.

Once reduced to a more manageable amount, the mixture was dried further in the microwave until it was a thick soupy texture. To this, excess calcium hydroxide was added until the mix had changed brown, released a pungent odor and had a pasty texture. This was left to dry completely overnight.

100mL heated 70% isopropyl alcohol was added to the dried residue/CaOH mixture and swirled around a bit. The dried paste was not crushed or broken up, just soaked for a few minutes until the alcohol had a yellowish color and then decanted off, then placed in a double boiler to reduce. This was repeated once more with another 100mL heated 70% isopropyl alcohol, leaving it to sit for just a little longer (20 minutes maybe), then the alcohol was decanted off and combined with the first pull to reduce the volume.

After reducing to approx. 100mL or so, the alcohol solution was placed in the freezer overnight to precipitate any less desirable plant waxes or oils. The alcohol was decanted off and then placed back into the double boiler to reduce.

Once the solution was almost completely evaporated, it was removed from heat and left to evaporate slowly at room temperature. A layer of crystalline substance began to form on top of a liquid oily layer underneath as it dried. These were mixed together to ensure full evaporation of solvent.

A very small amount was vaporized off the end of a pin.. It had a very odd smell. Almost like N,N-DMT, but not quite. Not as indole-y. Smelled similar to the flavor of a wide-spectrum bufotenine extract I made years ago. But the smell was hopeful, at the very least.

A small amount of both the crystalline substance and the oily part were subjected to TLC testing using materials provided by Bunk Police and TLConscious, a project I was thrilled to see came together finally (Thanks endless and everyone else who contributed!!). I will preface by saying I have a fair amount of extraction experience, but I am completely new to TLC testing. User error is not unlikely beyond this point. I will also add that some of my reagents may have surpassed their shelf life.

When dissolved in the testing solution, a strange precipitate formed after a couple minutes. I tried to mix it well enough to get uniform samples.

And here are the results so far: inconclusive. Ehrlich's reagent came out rather orange and stayed pretty much the same orange.. Not the purple I was hoping for. The Mecke reagent gave me a little more hope, turning brown, and then slowly red. The Liebermann reagent sizzled but did not change color much. Another hopeful Ehrlich's test still did not show any purple. Again, this may be due to the age of my reagents.

So no conclusion as of yet. If I were to bioassay a minute dose of this, the results would be posted. I would like to utilize a service like ecstasydata.org or something similar to get a GC/MS result but those services can be rather pricey. I may also try to recrystallize in petroleum ether or benzene, as the alkaloids I am hoping to find should all be reasonably soluble in their freebase form if I’m not mistaken. I will keep the thread updated. Obviously if this plant contains any amount of an illegal substance the whole extraction will be discarded, the end product will be incinerated and the author will immediately alert the authorities..

Thank you to the few of you who have encouraged work with this plant, you know who you are. Questions, comments, criticisms are all welcome. This plant is way too prevalent to not explore its chemical makeup.

Nice work, keep it up!

But damn, it looks like all the dmt leaked out onto the pavement

Hello friend,

This week I'll post here to help regarding how to interpret the TLC.

That being said I just want to offer you this. Let me know and we'll get it lab-tested for free!

Be well!

Awesome, thanks so much!

After another night left out to dry it's become slightly more crystalline rather than fluid and smells quite strongly of indole. I just can't imagine what the problem is other than expired Ehrich's.. I will have to order more. In the meantime I will definitely be preparing a sample for testing.

Microdose bioassays may be attempted but concerns about gramine and other potential toxins may force me to be cautious.

Thank you for doing this work

The info in the link below may be of interest/relevant.

https://books.google.com...%20alkaloids&f=false

It claims that D. Sanguinalis tested negative for alkaloids. Just a heads up on their result, I think this worthwhile testing further.

Very interesting, thank you! So far I have found only two isolated reports of active alkaloid detection but very limited info. My extract smells quite a lot like indole + some other plant-y smell. But definitely like indole.. I will keep you posted!

Regarding the TLC...

You have to be careful that the solvent line rises evenly in the plate, try to set the plate carefully on the developing chamber, because if it rises unevenly then spots get together and it's hard to compare things.

Another idea is not to put so many different reagents in the same plate because as the solvent expands it will cross contaminate the other spots that you want to visualize.

One thing that isn't clear from your pics, it seems the 3 lanes in the plate are the same substance? If possible, run at least one of those lanes with a known DMT-containing plant, some DMT extract or something similar if you can. If you dont have any tryptamine-related plant or extract to compare, then use something else you might have like caffeine or harmalas and use this tlc calculator

Yet another idea for you to have in mind, is to take a pic of the plate under UV light so we can see the spots before the reagents are added. If the spots are too small/soft, then do another plate with a more concentrated sample. If the spots are too large, dilute a bit. If there are multiple spots in the sample, some large spot and some smaller, you can do a couple of different plates, one with more concentrated samples, one with more dilute. This will help you get a decent resolution and also a large enough spot in case of the minor spot, so that you can see if there is any reaction with the reagent later on.

Considering the most important thing you want to find out is whether it has tryptamines like DMT or similar, then ehrlich is your best bet first. Ehrlich reagent does spoil reasonably fast, you gotta get some fresh one if you can, and store it well, like in the freezer. You can run another plate and use another reagent or two later on.

Let me know if you have any questions or need help interpreting TLC results now or in the future.

Hey great work!

This is not Digitaria Sanguinalis though

This is most likely Bromus Diandrus, or "Ripgut Brome" grass.

I see this everywhere, it's very pretty with the purple tinges.
It grows around Crabgrass, but this is not the crabgrass.

Hey everyone,

Was considering running a quick extraction and submit for testing on what I think is Digitaria cilaris. Could anyone assist with an ID? (there's usually more leaf foliage but it's November now so it was hard finding one still flowering)

Thanks in advance!