Ive read a couple posts and im still a bit confused. I get that dmt fumerate is in salt form, and it is taken orally or insufflated. It also has a longer shelf life than its freebase brother. But is it easier or safer to make?

It would actually be more work...

During your extraction, the plant matter is exposed to a base, let's say NaOH for this example, the purpose of using this base is to degrade plant cell walls, but more importantly it converts the DMT tannate and/or DMT oxalate salts into freebase DMT.

So when you extract you are obtaining the free-base, the non-protonated version of the molecule, and converting this free base to a salt would be extra work...

*The term "free-base" refers to the conjugate base form of an amine...the deprotonated form of an amine.

When an acid and a base are combined, they neutralize, creating a salt.

So if you have free-base DMT, and react it with Fumaric acid, you will obtain DMT fumarate, if you use hydrochloric acid with free-base DMT you will yeild DMT hydrochloride, if you use acetic acid you will get DMT acetate, and so on...

DMT free-base is not water soluble, and is more vulnerable to degradation than the salt forms of the compound, however DMT salts are not smokeable, and are much more suited for storage, injection, or oral consumption with an MAOI, or for infusing into decoctions containing MAOI compounds.

Shulgin comments on DMT salts:


-eg

Just remember, that when an acid and a base are mixed, they neutralize, losing their acidic/basic properties, forming a salt.

a free-base is the non-protonated form of an amine, and as its name suggests, serves as the organic base in the acid/base neutralization reaction, the acid used determines the acid salt formed, so HCL gives the hydrochloride salt, fumaric acid gives the fumarate salt, acetic acid gives the acetate salt...and so on.


Below is a link which goes into greater detail:

---

(A little off topic, but:
THC does not contain any nitrogen atoms, it is not an alkaloid or an amine and does not possess strongly acidic or basic qualities, because of this, it has never been possible to use THC in an acid base neutralization, and thus THC salts have been non-existent...however tetrahydrocannabolic acid or "THCA" is an acid, and thus can be reacted with a base to form a salt...
http://www.google.com/patents/US20050049298
http://summit-research.t...ystallization-technique/


-eg

Dude eg you are the bomb!

It's called fumarate, not fumerate. When an alkaline substance (a base), such as dmt freebase, is reacted with fumaric acid, it forms a so called fumarate salt of the base. This is similar to acetic acid -> acetate, hydrochloric acid -> chloride etc.

Salts of dmt are indeed a bit more stable than the free base form. Another difference is that salts of dmt are generally soluble in water, whereas the free base isn't. So if you want to ingest dmt orally, a salt form is most convenient. (A salt form is not absolutely necessary, because your stomach acid will turn any swallowed free base into a soluble chloride anyway. But before the dmt freebase gets to your stomach, it will burn a bit in your mouth and esophagus, because it is such an alkaline substance.) Fumarate salts are preferred over other salts, because they are easy to crystallize and are not very hygroscopic - unlike many other dmt salts. It is difficult to handle and weigh a substance that tends to melt into a sticky goo from exposure to atmospheric moisture.

On the other hand, the free base of dmt has a much lower melting point and boilig point than its salts, which explains why it is the preferrable form for vaporization ("smoking" ).

There are different routes to dmt fumarate. Sometimes it is the direct result of an extraction tek, sometimes the result of a tek is dmt freebase and a separate procedure is needed to convert this into a fumarate salt. Search the forum and browse the nexus wiki to get an idea of the teks that you can use.


*Cough* This is actually incorrect. It is the fumarate part of the salt that is the conjugate base. The protonated dmt is the conjugate acid. The free base is not conjugated to anything, as the term "free" implies.

Great info, i make salts at work all the time, so im kinda familliar with the chemistry, but this took it another mile. Thank you all for the help and for putting up with my begginner questions

(Equally off-topic, but...) Well, THC is a phenolic compound, which makes it weakly acidic. This means it can be dissolved in a strong base like sodium hydroxide and then precipitated out of aqueous solution with even a fairly weak acid. I'm not saying this will necessarily be an effective process although I'd like to try it one day just for the giggles.

When it comes to thc ill stick to co2 and butane. In reference to the differences between fumerate and freebase, i have a more solid understanding.

Still slightly off topic: what plant matter is best for a begginer's first extraction? Whats a good begginner tek?

My understanding is that THC is not acidic enough, even as a weak acid, for an acid/base neutralization to be effective, but by all means, it wouldn't hurt to experiment.

-eg

Hmmm...

Not sure quite how I got that mixed up, "mea culpa"

Isn't it counter-intuitive how the conjugate acid was the base that become protonated, and that the conjugate base is what's left of the acid after protonation?...

I feel obligated to clarify below:

A conjugate acid is a base that has had a hydrogen ion connected to it, a base that has become protonated.

When forming the fumarate salt of DMT, the DMT-freebase is the base that is receiving a proton from the fumaric acid, the fumaric acid and DMT base react and neutralize, forming the fumarate salt of DMT, and the conjugate base is what's left of the fumaric acid acid after it has protonated the DMT.

·An acid readily gives up a proton (H+)
·A base readily accepts a proton

The conjugate acid is the protonated base, and the conjugate base is what's left of the acid after its donated it's hydrogen ion (proton)

-eg