Chemistry Contribution

[ChemicalEnthusiast]

Hello, everybody! I have known about this site for quite a while now and I have used and read a good bit of the information provided in the wiki and the forums. Everything from trip reports, extraction teks, and general information on the safety of using entheogens. I just recently performed my first DMT extraction from acacia confusa. I looked at almost every tek provided in the wiki and I ended up doing an acid-base extraction using information from many different teks. Before the extraction I have never smoked DMT, I was waiting until I extracted my own (partially because I didn't trust anyone else's ability to extract themselves or the sources that it came from). I have been interested in DMT for about 8 years now and now that I have experienced the wonder I am even more interested. I just recently received my undergraduate degree in biochemistry and I am currently applying for graduate school for medicinal chemistry programs. I have been doing research on the extraction, characterization, and synthesis of natural products for the last two years. I presented my research at the national conference for undergraduate research for the past two years and I have received numerous grants and stipends to help fund my research. I want to become a member of this forum because I think I have valuable information to provide and also I like engaging in discussions with others that have valuable information. Thank you for your consideration!

 

[Entheogenerator]

Welcome to the forum, CE!! Sounds like you will be a very valuable member to have around!

What kind of experience do you have with other psychedelics?

 

[benzyme]

welcome to the board. maybe you could help me develop a charge-based method (IEX) to separate gramine and hordenine from other alkaloids in phalaris spp. Separation science is my specialty, been at it for 8 years.

 

[ChemicalEnthusiast]

What kind of experience do you have with other psychedelics?

I don't have a whole lot of experience with extractions of other psychedelics from a clandestine prospective (yet). I plan to start messing around with LSA and psilocybin extractions when I get the time. Although I have gained a great amount of knowledge from my research about extracting, isolating, characterizing, and synthesizing compounds from natural sources, it is a lot different doing things with very limited equipment. During the duration of my research I had lots of equipment at my disposal including a brand new 400 MHz NMR, HPLC, lots of chromatography equipment, and basically any starting compounds (for synthesis) under $100/g.

maybe you could help me develop a charge-based method (IEX) to separate gramine and hordenine from other alkaloids in phalaris spp. Separation science is my specialty, been at it for 8 years.

I would definitely be interested in helping you with this. I don't know a whole lot about the alkaloid content in phalaris spp. But I could definitely do a little research. To be honest, I have limited experience with ion exchange chromatography, especially if you're trying to separate large amounts. In my research, I only used small columns as a means to separate milligram quantities when recrystalizing wasn't an option. Are you using IEX to separate large amounts?

 

[ChemicalEnthusiast]

I guess I've never heard of clandestine chemists using ion exchange chromatography as a means to get good quantities of substances.

 

[benzyme]

once you develop a working method, why couldn't you?
i'm used to working with 2mm i.d. columns...but the chemistry is the same.

if you're considering separations of the compounds you mention, clearly IEX, namely SCX, has its advantages.
I already have a procedure for separating LSA using amberlite 120Na.

 

[ChemicalEnthusiast]

once you develop a working method, why couldn't you?

No doubt it's possible but from my understanding most pharmaceutical companies avoid having to use chromatography as a means to isolate compounds; they prefer recrystalization. From my understanding it is more often used in a research setting where quantity and the massive waste of solvent isn't a concern. I'm no process chemist though.

 

[benzyme]

neither am I, but that says nothing. there's more than one way to skin a cat.

and i rotary evap my solvents.

 

[benzyme]

with some grass sources, a re-x will not isolate gramine and hordenine, thus, either IEX or solvent partitioning may be considered.

 

[ChemicalEnthusiast]

and i rotary evap my solvents.

Damn, you got all the bells and whistles. I guess what I would do if I was you is try to figure out the isoelectric points of both gramine and hordenine from the literature (or at least get an educated guess), and then buy a resin that is designated to work well for compounds with those pI's.

As far as separating the other alkaloids, I would try to separate them by any other means possible and then leave the chromatography to the 'hard to separate' compounds.

 

[benzyme]

precisely what I had already figured, which is why I asked for assistance developing the method
(Phalaris, as they like to say here, is the future)

you'll need to consider those things if you plan to isolate the psilo compounds, because a simple re-x won't cut it.
LSA (from the S&H strain), same applies...it's a good bit of column work, I've done it for a couple years, scouring patents and
papers, then applying it.

 

[ChemicalEnthusiast]

Actually, give me a day or so, I might be able to get those pI's for both gramine and hordenine. I have access to some pretty cool prediction software. A license I was granted still hasn't expired even though I'm not doing my research anymore, don't tell anyone, I was supposed to stop using it once I was done with the research . If the pI's are not listed anywhere in the literature, the software was developed to make predictions on things like chemical shifts for NMR, physical properties, etc. Not sure if it has one for predicting pKa's or pI's but I'll check and get back to you.

On a side note, alpha aesar fucked me over (on accident) and unintentionally wasted a good amount of my time. They sent me the wrong compound and I couldn't figure out what the hell was going wrong lol. I finally ran an NMR on what they sent me (probably should have done that to begin with) and it wasn't what I ordered. I ordered 3'4'-methylenedioxyacetophenone for an enolate alkylation step in the preparation of a compound called piperodione. I still have no idea what the hell they sent me (I didn't want to waste the time to figure out what it actually was). It definitely wasn't 3'4'-methylenedioxyacetophenone though.

Alright, I'm done ranting lol.

Btw, what's S&H strain?

 

[benzyme]

stevens and hall.

I look forward to your ambition. You're where i was four years ago
I'm just lazy, with a lot of knowledge, and experience (and equipment); been lurking since the hiveboard days.
I messed with all those progs, still do occaisionally. ChemAxon Marvin Sketch, in fedora (linux).


oh and btw...my background is nLC-MS/CE-MS. my avatar is an octupole/electron multiplier...mass analyzer.

 

[Spiritofspice]

I have the whole hive boards saved on my computer.

Man I miss those days.
So much ground was broken on there in the early days.

 

[ChemicalEnthusiast]

I was gonna ask what that was in your avatar, looks awesome!

I definitely have the ambition and much of the knowledge. I am gaining the experience (slowly but surely). I've been fairly passionate about entheogens for quite awhile and my knowledge is finally up to the point where I can start embarking on many adventures on my own.

The only source of knowledge is experience - Albert Einstein

 

[expandaneum]

i'm sorry, a bit of topic,

benzyme you probably know this one already but it works wonders for larger separations.

click here

And then the article; Dry Column Vacuum Chromatography (DCVC) - revisited

 

[benzyme]

sexy. :thumb_up:

looks like they topped the silica with bentonite, a nice touch, if they did.
IIRC, bentonite has microplatelet structure, with positive and negative charges.
I've used it in columns, vac filtration, and agar doping.

I also have a bottle of adogen 464, which can be used to dope silica, for use as an anion-exchange resin

 

[ChemicalEnthusiast]

Alright benzyme, here are the estimated pI's for gramine and hordenine.

pI - gramine - 12.61
pI - hordenine - 9.72

I can get a LOT of chemical information about these compounds (and any others for that matter). I'm not sure when the license I have expires so the sooner the better.

 

[ChemicalEnthusiast]

I can get logP and logD values as well and I can specify the pH at which the logD value is calculated.

 

[ChemicalEnthusiast]

At pH 12.5 hordenine has a charge of -.99 and gramine has a charge of 0. If my understanding is correct running an anion exchange column at pH 12.5 would elute the gramine and retain the hordenine.