would tianeptine free acid react with potassium bromide to form tianaptine bromide?

[1ledzepplin1]

Firstly, I want to know if Tianeptine bromide can be prepared from free acid and potassium bromide?

I was also wondering if tianeptine sodium has neurotoxic potential by being able to cause hypernatremia if administered rapidly at a large dose, or multiple large repeated doses on a diet that does not replete chloride anions quickly enough?

 

[asecin]

im curious of tianeptine's neurotoxic potential in general. is there such thing when it comes down to it??

 

[1ledzepplin1]

It hasn't been studied for causing any form of neurotoxicity to my knowledge. I have looked over a lot of information regarding it, but the tianeptine sodium may deliver too much sodium to those who abuse it and curiously there aren't any studies done on that. If neurologists and those who take care of patients presenting with tianeptine abuse could connect the dots between repeated hypernatremia and a form of brain damage that said patients could have, then it could be spurred by reading our little post here, haha.
I really do want to know why not tianeptine bromide pharmaceutical preparations though; like they Rx tianeptine in some countries. I think the indications that tianeptine is prescribed for could be tailored to its formulation better like that. Like potential studies of tia-bromide vs. tia-sodium if it's possible, and if there are any reproduceable and efficacious properties of one over the other for certain mental health conditions.

 

[g0to]

Didn't it used to be labelled a novel SSRE (Selective Serotonin Reuptake Enhancer)? Because of it's ability to alleviate depression whilst at the same time lowering serotonin. I know that that's how it was before, when I first heard of it, around ~2010-2011. I first saw it as Stablon pills, and then the cheaper powder form versions became more readily available as demand increased. It would be alot like ketamine, this drug, if it weren't for the fact of the extremely debilitating physical addiction.

With all this bullshit out nowadays, U-47700, extremely potent synthetic cannabinoids that feel nothing like weed/hash, fentanyl and all its analog forms, tianeptine (obviously..) it makes any pill or powder purchased on the street of questionable/lethal nature..

 

[asecin]

how did you come to the idea that tianeptine is working similar way to ketamine? as far as i know they are completely different drugs with various different mechanisms

 

[Hodor]

I don‘t think Tianeptine is going to react with a neutral salt (especially since tianeptine free acid only has a very low solubility in water (think regular cocaine HCl vs freebase cocaine).

Also, „tianeptine bromide“ isn‘t really a thing. There is „tianeptine hydrobromide“ that would presumably result from reacting tianeptine free acid with hydrogen bromide (hydrobromic acid).

At the same time, you could also try mixing tianeptine free acid with a base. While KBR is neutral, the highly basic potassium hydroxide („KOH“) would give you the potassium salt, while adding sodium hydroxide (NaOH) would result in the sodium salt (tianeptine sodium is the form used in the original Servier „Stablon“ pharma tianeptine Tablets). Sodium carbonate should also suffice... probably even sodium bicarbonate.

All in all, the Na/K-salt route seems like the easier approach, since I don‘t think hydrogen bromide is all that easy to acquire, whereas nobody is going to bat an eye at you for trying to acquire NaOH (plenty of soccer moms using this stuff for home-made soap).

 

[g0to]

how did you come to the idea that tianeptine is working similar way to ketamine? as far as i know they are completely different drugs with various different mechanisms

I was moreso comparing them in terms of acute antidepressant effect via a novel mechanism. Not so much that they work the same inside the brain.

 

[Hodor]

Re: Hypernatremia: Tianeptine Sodium is 95% tianeptine and only 5% sodium by weight. So if you were to ingest a whole gram of tianeptine sodium, that‘s just 50 mg of Na+.

In other words, the sodium is the least of your worries if you‘re addicted to this stuff.

 

[asecin]

how addictive is it anyway, it has very weak opioid effect from what i gather

 

[Hodor]

how addictive is it anyway, it has very weak opioid effect from what i gather

That also comes down to how you dose it: It's hard to get addicted when you've only got a prescription for a normal dose of 3x12.5 mg per day. However, when someone can easily buy grams upon grams of this stuff from a nootropics vendor, the risk for addiction is much greater, especially if that person had issues with opioid abuse in the past.

 

[Bagseed]

Firstly, I want to know if Tianeptine bromide can be prepared from free acid and potassium bromide?

I was also wondering if tianeptine sodium has neurotoxic potential by being able to cause hypernatremia if administered rapidly at a large dose, or multiple large repeated doses on a diet that does not replete chloride anions quickly enough?

no, you can definitely not prepare an acid chloride from an acid and KBr. Br- is not a strong nucleophile at all and has no tendency to react with a carboxylic acid.

 

[1ledzepplin1]

Thanks for the info, got a source? re: 95:5 ratio.
And I'm fairly sure tianeptine bromide can be made. I recognize that trying to obtain large quantities of Hydronium bromide is not going to go unnoticed as it is a very hazardous substance. I can produce my own if I need to. I would just really like to see what 37.5mg of TIabromide if possible, would do.

 

[Bagseed]

of course it should be possible to make, but just not with either HBr or KBr..... if you don't know this, and also what reagents might actually apply, you lack basic knowledge in organic chemistry.

ps I would not ingest any acid chloride or anhydride. strong electrophiles (as is the terminal carbon in an acid chloride/anhydride) are usually bad news for your body and DNA... after all you basically introduce a R-C+=O group in your body, but maybe it gets immediately hydrolysed in your gut to the corresponding acid, which would make the whole thing totally futile anyway.

but now it came to me tha maybe you are talking about the bromide salt? protonation at the basic N?

 

[Hodor]

Thanks for the info, got a source? re: 95:5 ratio.
And I'm fairly sure tianeptine bromide can be made. I recognize that trying to obtain large quantities of Hydronium bromide is not going to go unnoticed as it is a very hazardous substance. I can produce my own if I need to. I would just really like to see what 37.5mg of TIabromide if possible, would do.

Tianeptine + HBr wouldn‘t give you tianeptine bromide (as in the bromide salt) though. It would give you the HYDRObromide salt.

 

[Hodor]

but now it came to me tha maybe you are talking about the bromide salt? protonation at the basic N?

He‘s obviously talking about Tianeptine HBr, yes.

Atleast I doubt he‘s trying to halogenate the free acid into an acyl bromide... atleast I can‘t think of any reason to prepare a „tianeptinyl bromide“.

Unless you were some sort of mad prodrug scientist (DiTianeptinyl-morphine! 4-TianeptinylOxy-DMT! 1-Tianeptinyl-LSD!)

 

[sekio]

Tianeptine can form a salt of either form, because it has both a carboxylic acid and an amine... its a "zwitterion" where both the amine and acid are charged but they balance it out... it can form a hydrochloride salt in acid conditions, or if it gets paired with a base like sodium it can be a salt that way too.

in any case i dont think it would react with potasssiumm bromide though. youd just have a mixture of tianeptine and KBr then...

 

[asecin]

sekio, i dont understand chemistry on such advanced level, but can you tell me, do you think by its formula tianeptine has any toxicity?

 

[sekio]

You'll have to be a little more specific with respects to dosages, routes of administration, and other context-sensitive aspects. Even using table salt to "cure depression" could be considered toxic if you take it in irresponsibly large doses


Taken in moderate dosages and paying attention to development of any side effects, it shouldn't be harmful though.

 

[1ledzepplin1]

Lol, I was just curious. I was mainly fishing for people with information related to the sodium to tianeptine ratio because I don't have a clue what it is. But anyways ty for ur replies.

 

[Hodor]

Lol, I was just curious. I was mainly fishing for people with information related to the sodium to tianeptine ratio because I don't have a clue what it is. But anyways ty for ur replies.

Ah, sorry. Re: sodium-to-tianeptine, you just have to divide the molecular weight for sodium (Na) by that of tianeptine sodium.

M(Na) = 23.0 g/mol
M(C21H24ClN2NaO4S) = 458.9 g/mol
=> 23.0/458.9 = 0.05 = 5% Na in tianeptine sodium