• N&PD Moderators: Skorpio

Hydrochloride or Terephthalate salts?

the better green

Bluelighter
Joined
Oct 30, 2006
Messages
237
Location
203
I was looking up oxycodone on the pill identifier, and came across a pill containing:

oxycodone hydrochloride 4.5 mg, oxycodone terephthalate 0.38 mg

I know most, if not all, contain the hydrochloride salt, but ive never heard of the terephthalate salt being used. Whats the difference, if there is one?

I know very very little in the field of chem., so i only understand its a salt formed from a chemical other than hydrochloric acid.

Mods feel free to move if I posted in wrong forum.
 
I'm assuming it's there because of some synthetic abnormality- it's not hurting anything, so they leave it.
 
'the better green', could you elaborate or link to the answer that you found.? There is no thread talking about the differences between the different neutralized acid-base salt intermediates and how they are used for the systemic delivery of molecular drug compounds into the body, how such salts would look on a 2 dimensional molecule image (if that's possible: you see the bases all the time, but never anything pointed out to be the attached HCl or sulfate, etc. makes me think it's either very unimportant to what information is trying to convey or can't be added on that scale of where the salt encompasses the molecule) and all such things...

Is hydrochloride the most generally water soluble or just the easiest and cheapest to make? Saccharides, for example, aren't better as one of the most water soluble of the sugars? Wikipedia doesn't have a cohesive page on these kind of salts generally which is disappointing to me as it greatly interests me...

Is there a comprehensive list anywhere of every commonly used salt? I wrote down about every one I found in the 2009 GBR / Generic Brand(s) Reference from Mylan pharmaceuticals (which is free and can be ordered sent to you online if you do a simple google search; all it is, is a ton of brand names to generic names and generic names to brand names, with full color pictures of the pills/tablets/capsules of the Mylan brand in the middle), and around 50% of them differed from the list given for the freebase conversion ratios table that is nested on the wikipedia page for Morphine currently.

Those being: acetate, citrate, bitartrate, stearate, phthalate, hydrobromide, hydrobromide (2 H2O), hydrochloride, hydrochloride (3 H2O), hydriodide (2 H2O), lactate, monohydrate, meconate (5 H2O), mucate, nitrate, -phosphate (1/2 H2O), phosphate (7 H2O), salicylate, phenylpropionate, methyliodide, isobutyrate, hypophosphite, sulfate (5 H2O), tannate, tartrate (3 H2O), valerate, methylbromide, methylsulfonate.

...If someone knows if the GBR '09 is online anywhere I could list what ones are commonly commercially prescribeable and so have some kind of human bioavailability. Many encyclopedic dictionaries have them listed throughout every letter too because there are so many. Though to find a exhaustive list with their general effects & effects in combination with what bases would be an infinitely important resource for a website such as bluelight and I am aghast that none has been even attempted in a thread yet that I know of (if it exists point me in that direction)
 
I once worked for a pharm company that made tannates of diphenhydramine just to have a new product.

Hydrochloride salts are the most common, obviously, but sometimes different salts of the same compound will engender differing pharmacological effects as well, so like many things in chemistry, the answers to your ? are both complex and not always clear cut.

For example, when taken orally amphetamine sulfate salts are said to be smoother and longer lasting than the hydrochlorides.

One thing I've never heard of is mdma.sulfate appearing on the illicit market or anywhere else for that matter, but of course, it could happen.

And then, of course, don't forget about chirality, or how tightly a pill has been pressed and bound with. All of these factors can make a real difference in effects.
 
OK, found the GBR list I made (these are all attested to as used in human pharmaceuticals):

Acetate
Acetonide
Alfa
Aminobenzoate
Aspart
Aspartate
Besylate
Bicarbonate
Biphosphate
Bitartrate
Bromide
Butoxide
Butyrate
Carbonate
Carbonyl
Chloride
Citrate
Decanoate
Detemir
Dextran
Diacetate
Dihydrochloride
Dimesylate
Dinitrate
Diphosphate
Dipotassium
Dipropionate
Dipvoxil
Disodium
Docusate
Estradiol
Estolate
Ethylsuccinate
Fumarate
Glargine
Glubonate
Guaiacoisuifonate
Hydrate
Hydrochloride
Hydroxide
Hyelate
Iodide
Iodine
Lactate
Liposome
Lispro
Lysine
Maleate
Mesylate
Methoxycinnamate
Monohydrate
Mononitrate
Napsylate
Oxide
Nitroprusside
Pamoate
Peroxide
Phenpropionate
Phenylbutrate
Phosphate
Polysaccharine
Polystyrene
Potassium
Probutate
Propionate
Protannine
Rinfabrate
Saccharate
Salicylate
Sodium
Succinate
Sucroso
Subcitrate
Subsalicylate
Sulfadiazine
Sulfate
Sulfide
Sulfonate
Sulfoxide
Tannate
Tartrate
Thiomalate
Triflutate
Trisalicylate
Tromethamine
Trioxide
Valerate
Versenate

...and one I couldn't read my own handwriting no matter how hard I looked or how many other people I showed it too. It looks maybe like "Ghaditine", someone else said "Gluiligine", another said "Gloditine", so there's one missing that is something like that. The "Alfa" one had many permutations which I didn't even record because I wasn't sure it was a salt. Also, the insulins had some odd ones that didn't end properly but they had enough instances that I re-recorded them. This same reference, GBR '09, had Bi-'s & Di-'s, I didn't think bi- or di- were any different. I also heard that, mono, bi/di, tri, tetra, aren't supposed to take priorty when alphabetizing though I have done so here since I am trying to learn the nomenclature and for those who are too. There is no where near exhaustive as there are as many as there are chemical permutations, like when I read that the naphthalenedisulfonate salt is also used besides just the hydrochloride for this or what, which I guess is, or is related to tosylate or toluenesulfonic acid. Then this article title Terephthalate: but effective on humans, nontoxic or with some medical use, there is likely some form of exhaustive list for...

OK: Last post and this post, with the more proper ordering system, and the one or two other substances added, a sulfimide which looks promising to me. heh:

Acetate, Diacetate – Acetonide – Alfa – Aminobenzoate – Aspart, Aspartate - Besylate - Bromide – Butoxide – Butyrate - Carbonate, Bicarbonate – Carbonyl – Chloride – Citrate – Decanoate – Detemir - Dextran - Dipvoxil – Docusate – Estradiol – Estolate – Ethylsuccinate – Fumarate – Glargine –Glubonate – Guaiacoisuifonate – Hydrate - Hydriodide (2 H2O) - Hydrobromide, Hydrobromide (2 H2O) - Hydrochloride, Dihydrochloride, Hydrochloride (3 H2O) – Hydroxide – Hypophosphite – Hyelate – Iodide – Iodine - Isobutyrate - Lactate - Liposome - Lispro - Lysine - Maleate - Meconate (5 H2O) - Mesylate, Dimesylate - Methoxycinnamate - Methylbromide - Methyliodide - Methylsulfonate - Monohydrate - Mononitrate - Mucate - Napsylate - Nitrate, Dinitrate - Nitroprusside - Oxide, Trioxide - Pamoate - Peroxide - Phenylbutrate - Phenylpropionate - Phthalate - Phosphate, Biphosphate, Diphosphate, Phosphate (1/2 H2O), Phosphate (7 H2O) - Polysaccharine - Polystyrene - Potassium, Dipotassium - Probutate - Propionate, Dipropionate, Phenpropionate - Protannine - Rinfabrate - Saccharate - Salicylate - Sodium, Disodium - Stearate - Succinate - Sucroso - Subcitrate - Subsalicylate - Sulfadiazine - Sulfate, Sulfate (5 H2O) - Sulfide – Sulfimide - Sulfonate, Naphthalenedisulfonate - Sulfoxide - Tannate -Tartrate, Bitartrate, Tartrate (3 H2O) - Terephthalate - Thiomalate - Triflutate -Trisalicylate -Tromethamine - Valerate - Versenate
 
Last edited:
Still no one linking to the "answering" thread or answered question? I find salts of drugs to be highly interesting and am somewhat disheartened that this thread does not have more input in that direction either.
 
it is quite possible that the terephthalate salt is there to alter the dissolution characteristics of the formulation, there is a dark art in pharmaceutical formulation where the use of polymorphs, and amrphous compounds is used to control the rate of dissolution and the absorbtion of the formulation as well as to improve the mechanical characteristics of the formulation. Phthalates are also quite good stabilisers and it is equally possible it is there for stability, the short answer though is it is there because the formulation works and I doubt anyone outside of the manufacturer knows why it is there.
 
Top