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The Nature of Salts and Freebases

Psychedelics_r_best

Psychedelics_r_best

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Oct 16, 2004
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I know the different properties of salts and freebases, I know how you can convert a compound from one form to another, but what I don't understand is where this change physically exists and how it corresponds to molecular weight. Where does the change occur physically that results in the different properties?

When something is a Hydrochloride salt, for example, how is this manifested in the structure of the compound that results in it having diminished mass compared to, for example, an acetate form of the same compound?

What I don't understand is how these changes are manifested without the actual chemical structure of the compound being manipulated.
 
http://en.wikipedia.org/wiki/Ionic_compound

^ it's as simple as this. The alkaloid molecule hasn't changed, it's just formed an ionic bond with the acid molecule. Covalent bonding is what keeps the atoms within each molecule together, they're sharing electron orbits. Ionic bonding is more like a magnet, with positive/negative poles that are attracted to each other. The geometrical pattern that the ionic compounds get folded into via these electromagnetic forces are what lead to crystallization.
 
The amine tails of a lot of psychdelic chemicals are slightly basic. When you introduce them to an acid, they form a weak bond and the acid (HCl, etc) and the base (eg, methamphetamine) 'stick' to eachother. This is often called an ionic bond.

The weight, if the chemical is properly washed and pure, is the original compound plus the weight of a molecule of the acid (except in some cases like fumaric acid, which has two acidic tails and allows two basic molecules to form a salt with it). In the case of the fumarate, the salt exists in a 1:2 ratio with the original slightly basic amine.
 
what would be the practical application of turning a salt into a freebase.

i understand freebases can be smoked and salts cant, anything else?
 
I used to think that the choice of a counter ion when making the salt of an organic compound was no big deal. However it seems that it is a big deal. It can alter pharmacokinetics, shelf-life, and absorption. It's not really an issue with your average recreational drugs but in the pharmaceutical industry I think they do their homework when decided upon which salt to use.
 
It can be useful for recreational drugs too, ie, if you wanted to make a longer lasting form of 2c-d, there are a bunch of salts which you can used to extend the half-life of the drug... I think F&B had done this.
 
compiling autumn, read the wikipedia entry on ionic compounds. Because of the ionic bond, the compound generally requires more heat to melt or boil than either the cation or anion would alone. This means freebase alkaloids can be heated to the point of a semi-controlled vaporization (boiling) with a lighter and a pipe/foil at a much lower temperature than their salt forms. At higher temperatures, the drugs become more irritating to the throat, lungs, nostrils. At a certain point, for some compounds around or perhaps even below the boiling point, an ionic compound will combust. This creates a whole set of unknown byproducts in the resulting smoke, and destroys the original alkaloid's molecular structure, leading to no drugs. During the process of combusting a salt form of an alkaloid drug, a lot will be vaporized, but a lot more can be lost to combustion, resulting in a waste of drugs.

This does not apply to ALL alkaloid drugs. Some drugs like methamphetamine you cannot use in freebase form, as it's caustic and flammable at lower temperatures than it vaporizes readily. Other drugs have low boiling points as an HCl salt and work just as well as the freebase form for vaporization.


http://energyconcepts.tripod.com/energyconcepts/combustionfluegasses.htm
 
thanks for the information, everyone! i understand this alot better now, my o-chem's a bit rusty.

that wikipedia entry cleared things up alot too. the stability of the ionic bond would cause most melting or boiling points to be raised. makes me wonder why people claim that theyre getting "sooo high" when theyre smoking the salt forms of oxy or xanax or something. i keep telling them that a conventional lighter probably wont be able vaporize the stuff, but its casting pearls before swine.

thats interesting, though, about the methamphetamine. i wouldnt have expected that.
 
Cigarette lighters can heat things in excess of the boiling point of any drug you could think of. I can't find any good references on the temperature the average cigarette lighter can heat things to, but it's at least 500'F to 1500'F.

You can definitely vaporize oxycodone, and even OxyContin if you crush it up and/or extract properly. I've never seen much evidence that alprazolam can be vaporized before it burns and becomes inactive combustion byproducts.
 
Yeah, freebase methamphetamine is a nasty oil. It'll burn your skin like lye (but not as bad, I don't think) when you touch it, and burst into flames when you try to smoke it. You can eat it in gelcap form safely though, as it'll become methamphetamine HCl upon contact with the acidic contents of your stomach.
 
A freebase is the non-ionic form of the compound.
By adding bases or acids, you can strip or add a proton (hydrogen ion) respecitively.

By altering the number of protons, when the compound is taken out of solution, it forms ion bonds and latices. These inter-molecular bonds are what increases the boilding point.
 
huh, so there is credence to people smoking the oxy then. are those lighter temps acheivable before you burn your fingers on the lighter though?

most freebases would be more unstable, right? hence why drugs are usually available in a salt form?
 
nuke said:
It can be useful for recreational drugs too, ie, if you wanted to make a longer lasting form of 2c-d, there are a bunch of salts which you can used to extend the half-life of the drug... I think F&B had done this.
Click to expand...

Link please, please?
 
So, in freebase form then a compound is the lightest it can be because nothing is bonded to the amine chain, but when you change something to a salt the HCL or whatnot bonds ionically to the amine end of the molecule, correct?

So when one says 4-Ho-MIPT HCL there is actually an HCL bonded to the amine end of the molecule? Howcome altering the acid on the bond only changes molecular weight and doesn't change the neuropharmacology of the drug?

And last thing. Is psilocin and psilocybin that naturally is naturally synthesized by enzymes in mushrooms freebase or a salt? I would think a freebase, right?
 
So, in freebase form then a compound is the lightest it can be because nothing is bonded to the amine chain, but when you change something to a salt the HCL or whatnot bonds ionically to the amine end of the molecule, correct?
Click to expand...

Yes.

So when one says 4-Ho-MIPT HCL there is actually an HCL bonded to the amine end of the molecule? Howcome altering the acid on the bond only changes molecular weight and doesn't change the neuropharmacology of the drug?
Click to expand...

Yes. The reason it does not affect the pharmacology of a compound (hydrochloride anyway), is because the bond is weak and the body lops it off before it gets into your blood stream. Some salts are bonded more strongly or uniquely and will effect the pharmacology of a molecule, but for the most part, sulfates, fumarates, acetates, phosphates, citrates, ascorbates, hydrochlorides, and hydrobromides are all the same. And even if you ingest the freebase of a chemical, it will turn into the hydrochloride of the compound once it gets to the stomach (which is filled with HCl acid).

And last thing. Is psilocin and psilocybin that naturally is naturally synthesized by enzymes in mushrooms freebase or a salt? I would think a freebase, right?
Click to expand...

Sort of -- psilocybin is a zwitterion itself and actually forms a salt internally (the amine bonds weakly to the phosphoroxy group), so it's automatically a salt. Psilocin usually remains in the mushroom as a freebase (iirc). This is why mushroom tea is effective, but the best mushroom teas will also incorporate a little ethyl alcohol in order to get the psilocin in addition to the psilocybin.
 
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