Understanding Tryptamine Chemistry

[thethinice]

Hey all, I love this forum! I'm new here, simply had to join up and post something.

My questions are regarding the specific chemical properties of N,N Dimethyltryptamine. I noticed that lots of people protonate this molecule by use of acetic acid. I know that acetic acid, being a carboxylic acid, will readily protonate amines. DMT contains two nirtogen atoms for potential protonation. However, one of these atoms is sterically hindered, and the other, attached to an aryl group (being a part of the indole structure) I have read is NOT readily protonated by weak acids and that this indole structure is only protonated by a strong acid such as HCl. I noticed that most times the protonation of DMT is apparently achieved by CH3COOH, boiling is involved. Is this because the heat catalyzes a reaction that would not happen at room temperature?

I have also noticed that many, in efforts to deprotonate a DMT salt, add, what to my calculations appears to be, an unnecessary amount of sodium hydroxide.

And, lastly, I'm curious about the best media for recrystallization of DMT and DMT salts, respectively (if there is any consensus). I have read that DMT can be readily recrystallized from acetone. Just looking for thoughts and ideas.

Thanks to anyone who reads this! Again, happy to be on this forum.

 

[benzyme]

hexane, but many people use the more commonly available heptane. acetone is more suited to recrystallizing dmt salts.

check the pKa distribution chart on chemicalize for the pyrrole nitrogen's pKa. it's calculated as 17.15. for the purpose of extraction using commonly available chemicals, the pyrrole nitrogen is not easily manipulated.

 

[endlessness]

As far as sodium hydroxide excess, notice it's not being used solely to deprotonate DMT but also to break down the bark material, so having plenty of it is useful in that sense.

As benz said, acetone is good for DMT salts crystallization. For example FASA crystallization yielding DMT fumarate, one of the lovely methods to crystalize/purify DMT, courtesy of DMT Nexus researchers

When extracting, in theory you wouldnt even need to add an acid if you do an A/B extraction because DMT is already in salt form in the plant, so its already water soluble. Acid will help down breaking plant material too, and also if you use tap water which is too basic, this will help further lowering the pH. You could really use almost any acid, vinegar is used because of it being cheap and easily available. Some people use HCl but there are really no practical benefits, just increased safety issues.

 

[thethinice]

DMT exists in salt form in the plant? So in theory one could use water to extract (with no purity) DMT from plant material?
Good to know about HCl. I don't really have the budget to experiment, otherwise I'd order kilo after kilo of ACRB and hypothesize and experiment myself. This is why I love this site. It's like what is said about science, you "stand on the shoulders of giants". The nexus is quite the giant to be standing upon.

 

[endlessness]

Yeah, if you think about ayahuasca, that's exactly what it is: an acqueous extraction of alkaloids from plant material. And there is no acid used traditionally, just boiling (or cold soaking) in water.

Of course, other things are also extracted in the process, so it's not "pure", but whatever else is extracted from such plants is perfectly safe to consume orally (which might not be the case if you were extracting from other lesser known 'experimental' plants).

Then you can proceed to purify and crystallize in any number of ways as explained in our wiki. Not sure if you had time to check that, but there's plenty of good info there.

While ordering plant materials may certainly get what you want, ideally we want to help people growing their own and/or finding dmt-containing plants in their area which they can sustainably harvest from.

Stick around, keep posting and I'm sure you'll learn a lot, and so will the Nexus also gain from your presence, in a mutually beneficial relationship....

And if your path is anything like what happens with some of us, you may just have found your second home

 

[thethinice]

Thanks! regarding the growing of plants, there is a specific plant I am very interested in. I'm wondering where in the forum or wiki I should go for guidance. It is known as canary reed grass, or phalaris arundinacea and it is one of few that can grow in my area.

 

[endlessness]

You should look into Acacias, there might be some which can grow in your area and which have DMT-containing phylodes that can be harvested sustainably. What zone are you in? Maybe you can get some Acacia acuminata growing.

As for Phalaris, it's a bit of a tricky plant, since alkaloid content can be so variable. I suggest clicking my signature link and checking the phalaris analysis thread (and links therein) for more info.

Good luck!

 

[thethinice]

Thanks for the pointers! also, in what salt form is DMT assumed to exist in the plant? This would mean you cannot extract DMT with DCM from planet material?

 

[endlessness]

I'm not sure if it's known which specific salt form. Possibly DMT tannate due to tannic acid in some plants but this may depend on plant. I'm really unsure, just guessing here.

Either way you can always base the plant material before extracting, in an acqueous solution (whether you're doing an A/B or STB), or doing a dry-tek style such as amorfati/q21's tek or the ethanol tek, so the fact that it's in salt form shouldn't be a problem.

Regarding DCM, if you plan on using that, please be sure to work in a well ventilated area (ideally with a flowhood ) due to it's possible health dangers. Also, don't let DMT standing in DCM for too long due to it reacting with DMT to form a chlorinated tryptamine by-product

 

[thethinice]

Good info! So as far as the plants go, I'm in zone 5b/6a technically. I could grow certain plants outdoors in the summer and indoors in the winter. What acacia strains are best for this climate?

I was also considering growing some anadenanthera colubrina or peregrina as indoor/outdoor plants. Any thoughts/comments greatly appreciated. I love plants.

 

[thethinice]

I would like to move my plant discussion to an appropriate section, but I'm a noob and cannot. Inasmuch as I've written an essay and a couple topics that were well received, I'm sure it's just a matter of time. 'Til then, thanks for sticking with me on this thread

 

[downwardsfromzero]

Make quality posts and show the right attitude and you'll get promoted soon enough.

Jamie has done some good work on phalaris, there's plenty of great information to absorb here.


PS Welcome!