Open questions in psychedelic chemistry.. What to test?

[benzyme]

It would be interesting to see the whole LSA adducts discussion put to rest.

I bet I could solve that puzzle with charged aerosol detection. Any adduct formed would have a larger droplet size.
It's not like MS, where molecules may fragment at the source. I can run a non-ionic mobile phase, like a pure alcohol (ethanol), and inject intact molecules.

 

[_Trip_]

That would be interesting benzyme, there seems to be a few possible candidates for LSA adducts and much talk over the years but nothing concrete. There also may be nothing to find but it would be good to see the discussion come to an end. (Or open up more questions).

What are your thoughts on other ergot alkaloids LSH etc?

 

[8-Serpent-Wind]

I know the question was not directed towards me but I will mention the alkaloids of Ipomoea and allies that I think are worth taking a closer look at:

Elymoclavine
Agroclavine
Penniclavine
Isopenniclavine
Chanoclavine
and lysergol.

Early animal studies mentioned some of these causing animals to react as if they were seeing things that weren't there.

I'm attaching a PDF that is one of the reasons I think this should be looked at.

And my favorite quote from it:

It was observed that, particularly in ELY well-trained dogs tried to avoid from inspector's eyes

Note that this is for Elymoclavine and that well trained dogs normally have no issues making eye contact with humans. However if said canines were "tripping balls" it makes sense...

Clavines have also been identified as present in ergot fungal sclerotia employed in Kykeon, and even present in some of the blue cheese molds that were used to make some forms of Kykeon instead of Ergot!

Also from a structure and function point of view the clavines look right while LSA does not, at least to me.

 

[benzyme]

That would be interesting benzyme, there seems to be a few possible candidates for LSA adducts and much talk over the years but nothing concrete. There also may be nothing to find but it would be good to see the discussion come to an end. (Or open up more questions).

What are your thoughts on other ergot alkaloids LSH etc?

I think they are interesting on paper, but I also think they function as pro-drugs (like 4-AcO-DMT, 1p-LSD, etc). I know it's been discussed extensively here, acetaldehyde forms a very unstable adduct. Any acid is going to cleave it right off, leaving LSA.

I'd certainly be willing to analyze adducts anyway, using CAD; there's no data out there for this method.
Since this counts as research, I'd also skip testing fees.

 

[RhythmSpring]

How much DMT is in kale?

And wheatgrass.

EDIT: I'm not joking.

 

[endlessness]

Endless, I'd love to collab at some point, to verify/compare data. I'm in a much more favorable state of mind than a decade ago, and have fully embraced the focus of data reprodcibility. That is what makes the science so robust, and manifests facts. What you and your peers do is fantastic, and I'd love to contribute.

Benz, your collab is most appreciated and wanted, im very glad for your offer

In august when im back home I'll check this thread again for other people's suggestions and we'll get this.going

 

[benzyme]

Endless, I'd love to collab at some point, to verify/compare data. I'm in a much more favorable state of mind than a decade ago, and have fully embraced the focus of data reprodcibility. That is what makes the science so robust, and manifests facts. What you and your peers do is fantastic, and I'd love to contribute.

Benz, your collab is most appreciated and wanted, im very glad for your offer

In august when im back home I'll check this thread again for other people's suggestions and we'll get this.going

:thumb_up:

 

[_Trip_]

I'm not well versed in chemistry but do any LSA adducts on paper pass Lipinski's Rule of Five?

 

[benzyme]

Lysergic acid alpha-hydroxyethylamide

Lysergic acid alpha-hydroxyethylamide | C18H21N3O2 | CID 134553 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more.

pubchem.ncbi.nlm.nih.gov

A quick glance at section 3 would indicate yes.

 

[downwardsfromzero]

AFAIK, nutmeg has no alkaloids (and no tryptamines, they require an indole base), as there are no amine groups. The primary active compound is myristicin, and to a lesser extent, elemicin.

Just to make it absolutely clear, I'm not suggesting that I believe alkaloids to have anything to do with the active compounds within the context of what is typically understood as being a nutmeg intoxication. To re-iterate, I'm specifically interest in following up the claims of detection of alkaloids in nutmeg as presumptively detected with, e.g., Dragendorff's and an alkaloidal fraction that displayed an analgesic action tested on rodents. None of the claims for alkaloids in nutmeg were ever backed up with an analysis on isolated, confirmed, alkaloidal material and certainly nothing was ever done to give any hint of what kind structures might be involved. For all I know, the researchers may have misidentified lignans or something but nevertheless, there's enough of a hint of interest to want to take one more look in that direction and either put the idea to rest or come up with an interesting snippet of new data.

The 5-MeO claim for mace is even more apocryphal (I can't even cite a source) but given that there is precedent from other myristicaceous plants, particularly Virola spp., I think it would be fun to have a look if only to dispel another case of Chinese whispers (if we're still allowed to use that term - I wouldn't know what else to call it).

And I fully accept that myristicin and elemicin are the main actives in nutmeg with the proviso that it is understood that certain lignans and neolignans in nutmeg will have a profound effect on the particulars of the metabolism of those phenylpropenes which gives rise to the vast unreliability of nutmeg as an intoxicant. But that is an almost entirely separate matter from the question of the putative alkaloids.

(I've been away for a while, otherwise I would have replied sooner.)

 

[benzyme]

:thumb_up:

 

[_Trip_]

I think it would be interesting to see if wild lettuce contains any hyoscyamine as reported and if this is having any effect on its reported benefits.

Only claim I've found was from a paper done in the late 1800s and a article quoting some Italian study I can't find.

 

[acacian]

I've always wanted to know more about the alkaloid profile of acacia floribunda as it often feels like it has a lot more going on than just DMT

+1 for more info on desmanthus illinoensis

.. and I'd also like to know more about the alkaloids in Delosperma

I've also always been curious about whether the davesia (a native pea with orchid like flowers) species in australia contain tryptamines

 

[downwardsfromzero]

It would be very interesting to find out if there are any intramolecular cyclisations going on in the psilo/baeo type mushroom indoles, specifically between the 4-OH and the sidechain N, via hydrogen bonding. Diagram attached.

I'm thinking solvent effects on spectroscopic (IR + NMR?) results might be a way into this but it would be most pertinent to look what happens under simulated physiological conditions which emulate the interaxonal space.

Espurrr mentioned that some components of psilo mushrooms might block neuronal uptake of DMT and that this uptake is reliant on a close match to serotonin which also suggests to me that some aspect of the 4-hydroxylated analogues from the mushrooms might be worth examining for their role in this phenomenon.

The the question extends to: do 4-hydroxylated indoles inhibit neuronal uptake of serotonin and/or DMT? Or is the observed uptake inhibition a product of the trace betacarbolines recently confirmed to be present in some psilocybin-bearing species, or perhaps from something else entirely?

Any further methodological suggestions for the 4-OH cyclic hydrogen bond examination would be most welcome!