Interesting compound in mimosa

The above shows the library match I obtained on the GCMS I did of an acid/base extraction of MHRB. It was a component of about 10% by weight.

moecat

Cool!

Very interesting. This kind of sheds some light on this

I guess this was wrong?

...and at least five phytochemical analyses of Brazilian jurema preta [mostly unpublished] have failed to show presence of ßcarbolines nor any other category of potent MAO...

Click to expand...

hydrobromide said:

Very interesting. This kind of sheds some light on this

I guess this was wrong?

"...and at least five phytochemical analyses of Brazilian jurema preta [mostly unpublished] have failed to show presence of ßcarbolines nor any other category of potent MAO..."

Click to expand...

Thanks for the link! Well, it would seem in this case, a ß-carboline was found. Interestingly, Shulgin makes the comment that this tetrahydro-beta-carboline is a natural metabolite of DMT.

Tihkal #44

*clap clap clap* You take the prize for one of the best posts made in Advanced Drug disucssion... I hope you make more posts of this nature/calibre!

Meanwhile, I geuss this would explain mimosa's activity in the absense of a secondary MAOI.

moecat, why don't you repost all of your results from this extraction (assuming this is the same that was posted and then taken down)? I think those results would generate more disucssion here.

Interesting! Phalaris grass is rumoured to obtain activity through the oral route as well via the same alkaloid. Keep up the good work.

ref:
Gander, J. E.; Marum, P.; Marten, G. C.; Hovin, A. W. (1976) The occurrence of 2-methyl-1,2,3,4,-tetrahydro-beta-carboline and variation in alkaloids in Phalaris arundiacea. Phytochemistry 15(5):737-738

Fragbait said:

moecat, why don't you repost all of your results from this extraction (assuming this is the same that was posted and then taken down)? I think those results would generate more disucssion here.

Click to expand...

I suppose I can fill in a few details of the other work, although the GCMS data seems sufficient.

The extraction followed the QT extraction for the most part. Typical acid/base work up, but using pentane to defat and dichloromethane for extraction of the basified phase.

Gas chromatography with flame ionization (FID) detection of the residue gave this chromatogram:

GC-FID chromatogram

HPLC analysis on a C18 column with diode array detection gave:

HPLC chromatogram

The UV spectrum of the component of interest (from the HPLC run) is here:

UV/VIS spectrum

This was very similar to a reference UV/VIS spectrum I found of tryptamine at pH 4:

Tryptamine's UV/VIS spectum

Thus, I felt somewhat confident I had an indole chromaphore in the unknown.

With a desire to ISOLATE the unknown, I ran a reverse phase TLC plate on the residue (note, doing the reverse phase HPLC run pointed to the best solvent system for the reverse phase TLC). Here, the resulting TLC plate is shown under UV light on the right:

Reverse phase TLC

The camera has a hard time picking out the subtle differences in spot color. The unknown of interest was more bluish depending on the angle of the light:

TLC Spots under UV light as 2 different incident angles

My desire to isolate the unknown was due to my desire to obtain a pure sample for infrared spectroscopy. I made up a short flash chromatography column using the TLC solid support. I eluted 30 fractions with what looked like a separation. These are the fractions under UV light:

Preprative chromatography fractions under UV light

This seemed typical of carbolines based on this paper.

However, repeating the GC-FID analysis on the chromatography fractions showed too poor of a separation for a definitive infrared spectrum of the unknown.

So I said screw it, and answered the question at hand with the GCMS analysis, ...which seems correct.

If you used dichloromethane, it could be possible that the beta-carboline is an artifact produced by the extraction process. Dichloromethane in contact with aqueous alkali will cause a substitution recation to take place, the final product being formaldehyde. From what I remember, formaldehyde and acetaldehyde very easily react with tryptamines to form beta-carboline structures via a variation of the Mannich condensation reaction (the 2,3-double bond being the active methylene bond).

I wouldn't bet money on it, but if you carried out the extraction without the use of methylene chloride as the non-polar solvent, you wouldn't see significant amounts of the beta-carboline

PS Did you use any reagents that could have contained small/trace amounts of (or could form) formaldehyde/acetaldehyde for your T. peruvianus extraction, as phenethylamines are also susceptable to the same modified Mannich condensation, to form substituted isoquinolines?

Sounds very reasonable to me. Both the tryptamines and PEAs' appear to do this....Pictet-Spengler Rxn .





Also:

Callaway JC, Gynther J, Poso A, Vepsäläinen J, Airaksinen MM. The Pictet-Spengler reaction and biogenic tryptamines: formation of tetrahydro-beta-carbolines at physiological pH. J Heterocycl Chem 1994:31:431-435.

Ah, I didn't know it had a specific name, just thought it was a variation on the Mannich condensation. Cheers for the specific reference

I have experienced quite strange effects after smoking DMT or taking it orally, if i got a dark "goo" from mimosa, vs white crystals. Smoking this goo, whatever else is in there seems to take effect slower, and last longer, and it really leaves a nasty ugly color to everything.. makes me feel "wierd" (not in a good way) too.

Anything new on this?

I'm really curious because, lately the DMT i've extracted from mimosa, if you smoke it in a bowl its fine, but if you vaporise it in glass, there's this STRANGE "underwater effect" - it really fucks with your perception of movement, there's definitely something else in my extract thats active.

I've heard from someone else that mimosa (and another type of bark) does contain this compound, but i'm really wanting to get as much of it as i can out..

Could anything be said about its solubility in different solvents, water, etc.. maybe there's some way I can separate a lot of this crap (i dont like it!). Maybe if i got the ph of the water too low it would end up extracting more of this? BTW, i acid/base extract it and just use naptha as the nonpolar solvent.

Also if this is a metabolite of DMT or what it could decompose into, that might explain why i have some that seems to have more of this - I was putting the dry extracted DMT in a glass vial and melting it down on a heating plate (then putting small amounts of naptha in etc) trying to purify it more (get all the NaOH out), possibly melting it down caused some to decompose into this strange one? Is that a possibility - that depending on conditions or whatever it could decompose into this other active molecule?

Someones famous

"Mystery alkaloid(s)"! Must be the season of the witch...

pinoline

Here is only something I recently asked myself:

It is known that ß-carbolines are metabolites of DMT (see anywhere in TIHKAL or "In vivo metabolism of alpha,alpha,beta,beta-tetradeutero-N, N-dimethyltryptamine in rodent brain. Barker S A; Beaton J M; Christian S T; Monti J A; Morris P E Biochemical pharmacology (1984 May 1), 33(9), 1395-400."
In the case of 5-MeO-DMT it is 6-MeO-THßC, better known as pinoline.
Pinoline is reported to be a very strong SSRI but also a MAOI. Rats behave like under the influence of an antidepressant, after feeding with pinoline. (no wonder!!)
My consideration is whether the pinoline or tryptoline (without methoxy-) might be participant in any way to the overall effect of the DMT´s? Are they propably responsible for the pleasant afterglow?

Any comments?

Difficult to say but I did notice that the compound shares some interesting similarities to one of my research interest: 3-substituted-4-aryl-N-methyl-piperdines as neuro-reuptake inhibitors of monoamines.

It's interesting that the compound at the top of the page looks quite similar to THP's also but that is BTW.

Im looking forward to Shulgins contribution in this area since cyclization of the amine tail to a fused piperidine is not something that I have seen that much of. I do recall seeing it in Mitragynine and am interested to know if it is possible to manipulate the tryptamine scaffold to make novel opioids.

Also, I didn't think it was considered Kosher to mix SSRI's and MAOI's together because of serotonin syndrome and hyperthermia/high BP. I think the drug p-thiomethylamphetamine which was sold as an MDMA analog also had this property.

fused piperidines, carbolines and quinolizines

I was always fascinated by the carboline world, which represent fused aryl piperidines. But I am always a bit anxious, doing real research in this field, since some of them can be metabolized to MPP+ analogues which do the same job in the body than MPP+ (uncoupling respiratory chain by inhibition of triosephosphate isomerasis) which soes not sound like fun! Nevertheless I have done some research, which was rarher disappointing. The cyclisized analogue of 5-MeO-MIPT with an carboline skeletton: 6-MeO-N-isopropyl-tetrahydro-ß-C. I tested it up to heroic 40 mg without any noticable effect. (maybe a little sleepiness). Concerning your mitragynin, which has a indolo-quinolizine skeletton, an other interesting compound comes into my mind: It is a dopamine D1/D5 antagonist, containing a tryptamine and PEA moiety in one molecule. I´ll try to paint it: and atach it, but I don´t know if it works.

Looks like you drew the 5-MeO analog. I'm not quite sure why you opted for the N-isopropyl analog either when N-Me would have sufficed.

Parallel to Mitragynine, i'm actually very interested in disrupting the indole aromaticity by oxidation with Pb(OAc)4.

I'm not going to be able to do this idea because of the laws in my country. I think it is an area that other researchers should look into however, since it looks like it could lead to some credible findings, atleast potentially.