L-Tartrate version of 1P-LSD

[BanE]

1P-LSD L-Tartrate, saw this on a website. Has anyone tried it?? Any differences to 1P-LSD?


Thanks guys,
Happy Trials and Happy Trails~~~~~~~~~~~~~~

BanE

 

[sekio]

They're the same thing. All the commercially sold LSD analogs are tartrate salts.

 

[babooon87]

1P-LSD L-Tartrate, saw this on a website. Has anyone tried it?? Any differences to 1P-LSD?


Thanks guys,
Happy Trials and Happy Trails~~~~~~~~~~~~~~

BanE

As far as I know lysergamide RC's have always been sold in that form. I guess it must be the most stable salt like fumarate for tryptamines.

 

[Hodor]

1P-LSD L-Tartrate, saw this on a website. Has anyone tried it?? Any differences to 1P-LSD?

As the posters above already stated, the L-tartrate form is just the standard salt form that LSD and its analogues are almost exclusively used as. It is no different from "1P-LSD" because what's sold as "1P-LSD" has always been "1P-LSD L-tartrate".

Let me explain:
Many substances are much more stable and/or easier to handle in their salt forms, and are consequently sold as such. So when people say "methamphetamine", what they mean isn't the pure methamphetamine freebase (which is a volatile, unpleasant smelling liquid - not exactly ideal for an illegal substance you want to smuggle past drug-sniffing dogs), but "methamphetamine hydrochloride" ( or "methamphetamine HCl" for short).
Ditto for cocaine, which is commonly traded as "cocaine HCl". Or MDMA in fact being MDMA HCl. DXM is sold as its hydrobromide form ("dextromethorphan HBr"). Amphetamine and morphine usually come as their sulphate salts.

While rarer than HCl salts, the tartrate salt is still the most preferred salt form for a number of pharmaceutical agents - notably the sleep aid zolpidem tartrate ("ambien"), the beta blocker metoprolol tartrate and of course the anti-migraine medication (and LSD precursor) ergotamine tartrate.

 

[DrumTripper]

Thanks Hodor, clearly explained as always!
So, what is the hemi-tartrate form?
Thanks,

 

[Hodor]

So, what is the hemi-tartrate form?

From what I understand, "tartrate" and "hemitartrate" are pretty much used interchangeably.

Tartaric acid has two carboxyl groups, meaning it can form a salt with two amine groups. Each lysergamide molecule only has one amine nitrogen basic enough to be protonated by tartaric acid.
Consequently, one equivalent of e.g. "1p-LSD hemitartrate" includes 2 equivalents of 1p-LSD for 1 equivalent of tartaric acid. Hence "hemi-tartrate" - half a tartrate for one 1p-LSD.

Even though LSD-25 and ergotamine are generally referred to as "tartrate salts", I am fairly certain they are actually hemitartrates, since (as I said) only one of their nitrogen atoms is actually basic enough to form a salt with tartaric acid.

I guess people will have different ideas of which sounds more intuitive to them: Is it "1p-LSD tartrate" because that's what you get if you fully neutralize one equivalent of tartaric acid with 1p-LSD? Or is it "1p-LSD hemitartrate", because said neutralization only requires half a molecule of tartaric acid per molecule of 1p-LSD?

 

[sekio]

Tartrate and hemitartrate/bitartrate are different things entriely, they are not interchangable, and it is not obvious what it means, its usage is archaic and actually means the opposite of what you'd think

Tartrate = 2 amines, 1 tartaric acid, "neutral salt"

Noun. hemitartrate (plural hemitartrates) (organic chemistry) Any salt of tartaric acid in which only one of the carboxylic acid groups is neutralised.

so, hemitratrate aka "bitartrate" = 1 amine, 1 tartaric acid, "acid salt"

LSD tends to form 2 LSD : 1 tartartic acid as a salt so we call it a tartrate salt. Hydrocodone pairs off 1:1 so we call that a bitartrate.

 

[Hodor]

Noun. hemitartrate (plural hemitartrates) (organic chemistry) Any salt of tartaric acid in which only one of the carboxylic acid groups is neutralised.

so, hemitratrate aka "bitartrate" = 1 amine, 1 tartaric acid, "acid salt"

Pubchem shows the structure for "zolpidem hemitartrate" to be "2 zolpidem : 1 tartaric acid". The European bioinformatics database "CheBi" goes as far as to state that "Zolpidem tartrate is the hemitartrate salt of zolpidem."

Zolpidem Tartrate

Zolpidem Tartrate | C42H48N6O8 | CID 441338 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more.

pubchem.ncbi.nlm.nih.gov

Ditto for alimemazine hemitartrate

Trimeprazine Tartrate

Trimeprazine Tartrate | C40H50N4O6S2 | CID 441236 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more.

pubchem.ncbi.nlm.nih.gov

Here's Caymanchemical's page on the hemitartrate salt of ifenprodil. Likewise, we've got 1 ifenprodil per 0.5 tartaric acid (i.e. a 2:1 ratio of ifenprodil:tartaric acid).

Ifenprodil (hemitartrate) (CAS 23210-58-4)

An NMDA receptor antagonist

www.caymanchem.com

The NMR spectra of various RC lysergamide hemitartrate salts in the "Return of the lysergamides" series of papers also show the same peak integral (1H) for the sp3 protons on tartaric acid as, for example, the protons on the benzene ring of the lysergamide. Seeing as how tartaric acid acid has two equivalent sp3 protons whereas each position on the benzene ring only has one proton, this implies a "lysergamide:tartaric acid" ratio of 2:1. (edit: I meant the protons attached to the secondary alcohol's carbon atom, not the actual alcoholic hydroxyl protons).

So despite what Wikipedia says, the way the term "hemitartrate" is commonly used in chemistry seems to be "2 amines, 1 tartaric acid", and it is unfortunately generally used synonymously with "tartrate" rather than "bitartrate".

Is it an archaic, confusing and rather stupid nomenclature? Absolutely, yes. But unless IUPAC sends in their inquisitors, that is unfortunately the way it is commonly used

 

[heatlessbbq]

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