Dmt fumerate clarification

[Mike-ologist]

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?

 

[entheogenic-gnosis]

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:

As to salts, this last recipe above, taken from the literature, is the only claim of a valid hydrochloride salt of DMT. In the original synthesis, by Manske, the following description appears. "The hydrochloride could be obtained only as a pale yellow resin which, when dried in a vacuum desiccator over potassium hydroxide, became porous and brittle." I have found no attempts at its synthesis in the literature, and I have personally had no success at all. The picrate salt is well defined, used mostly for isolation and purification. The oxalate is used occasionally in animal studies. Early human studies involving the injection of solutions of the hydrochloride apparently made by dissolving DMT base in dilute aqueous HCl, and neutralizing this with base to achieve an end pH of appropriate 6. The fumarate is the salt specifically approved by the FDA for human studies, and this was the form used for human intravenous injection employed in the recent New Mexico studies. -shulgin ; TIHKAL; DMT entry

-eg

 

[entheogenic-gnosis]

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:

Neutralization

A neutralization reaction is when an acid and a base react to form water and a salt and involves the combination of H+ ions and OH- ions to generate water. The neutralization of a strong acid and …

chem.libretexts.org

A neutralization reaction is when an acid and a base react to form water and a salt and involves the combination of H+ ions and OH- ions to generate water. The neutralization of a strong acid and strong base has a pH equal to 7. The neutralization of a strong acid and weak base will have a pH of less than 7, and conversely, the resulting pH when a strong base neutralizes a weak acid will be greater than 7.

When a solution is neutralized, it means that salts are formed from equal weights of acid and base. The amount of acid needed is the amount that would give one mole of protons (H+) and the amount of base needed is the amount that would give one mole of (OH-). Because salts are formed from neutralization reactions with equivalent concentrations of weights of acids and bases: N parts of acid will always neutralize N parts of base.

Neutralization

A neutralization reaction is when an acid and a base react to form water and a salt and involves the combination of H+ ions and OH- ions to generate water. The neutralization of a strong acid and …

chem.libretexts.org

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(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...

US20050049298A1 - Production of Delta 9 tetrahydrocannabinol - Google Patents

Δ9 THC acid is obtained from plant material and extracted into an aqueous solvent under conditions of pH control. The acid is converted to a salt and the salt extracted into a polar solvent, yielding acid of high purity. The Δ9 THC acid is t5hen converted to Δ9 THC which is further purified and...

www.google.com

http://summit-research.tech/crystallization/thca-acidic-crystallization-technique/

-eg

 

[Mike-ologist]

Dude eg you are the bomb!

 

[pitubo]

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'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.

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

*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.

 

[Mike-ologist]

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

 

[downwardsfromzero]

(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...

(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.

 

[Mike-ologist]

(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...

(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?

 

[entheogenic-gnosis]

(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...

(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.

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

 

[entheogenic-gnosis]

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

*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.

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