Trace Compounds in Salvia divinorum

['Coatl]

Abstract:
Background: Salvinorin B ethoxymethyl ether (Symmetry) is a novel and unusually potent salvinorin that has not previously been tested in humans. Methods: Symmetry was synthesized and given in doses of 10 µg to 400 µg to four test subjects. Effects were measured through semi-structured interview and administration of the Peak Experience Profile. Results: Symmetry was extraordinarily potent, psychoactive at the minimum doses taken. It produced geometric visions and ego loss at higher doses, and also induced a feeling of foreboding. Conclusions: Symmetry is a salvinorin derivative of unusual potency that is worthy of further investigation but nevertheless is unlikely to become popular.

See Article from Erowid

Thread at Salvia Source

 

[SKA]

Bump!

Great topics like this shouldn't be left catch dust.
Salvinorin B ethoxymethyl ether ( AKA "Symmerty" ) is a fascinating,
barely explored substance. Human bioassays have shown it to be psychoactive
to humans in doses as miniscule as 50 μg !!! That makes it many times more
potent than LSD, doesn't it?

Stunning potency. I was surprised to see Wikipedia had any info on Symmetry,
because I thought it was more obscure, but they have a pretty decent article:

Salvinorin B methoxymethyl ether - Wikipedia

en.wikipedia.org

Any more info on this compound would be most welcome.
But I'm specifically interrested in how it's made.
First step, Wikipedia sais, is deacetylation of Salvinorin A to turn it into
Salvinorin B. From there it is somehow converted into Salvinorin B ethoxymethyl ether.

So does anyone know how this deacetylation of Salvinorin A is performed? And does anybody
know what to do with Salvinorin B to turn it into Salvinorin B ethoxymethyl ether?







PS: Wikipedia describes 2 other interresting Salvinorin analogues.
Herkinorin: Herkinorin - Wikipedia &
Salvinorin B Methoxymethyl ether: Salvinorin B methoxymethyl ether - Wikipedia
The latter, is ALSO nicknamed "symmetry", just like Salvinorin ethoxymethyl ether. Most confusing.
But appearantly none is more potent than Salvinorin B ethoxymethyl ether.

 

[jamie]

soo..I am confused..I have read about symmetry before a couple times but I was not aware it was present as a trace salvinorin in salvia divinorum..I thought it was only synthetic?

 

[SKA]

It's not a trace compound in Salvia. It's synthesized from Salvinorin B, which IS
a trace compound in Salvia. But deacetylating Salvinorin A, the compound found in
the highers %-ages in Salvia, yields Salvinorin B too.

This Salvinorin B is then synthesized into Symmetry.


I found a PDF on the synthesis of "new C(2) modified salvinorin A analogues":

http://www.sagewisdom.org/leeetal2.pdf

Not sure if Symmerty is included or not.

Does anyone know anything about the synthesis of Salvinorin B Ethoxymethyl Ether?

And if so, could anyone devise an alternative, kitchen-chemist method
of modifying Salvinorin A into Salvinorin B and then Salvinorin B
into Symmetry? Would it be possible with more readily available chemicals or processes?

 

[gibran2]

...And if so, could anyone devise an alternative, kitchen-chemist method
of modifying Salvinorin A into Salvinorin B and then Salvinorin B
into Symmetry? Would it be possible with more readily available chemicals or processes?

I’m not sure, but I think Salvinorin B is what you get when you expose Salvinorin A in solution to UV light.

Also, Salvinorin B occurs in more than trace amounts – my extracted Salvinorin contained 18% Salvinorin B. (see salvia analysis thread)

 

[SKA]

Yeah I know it's not a Trace amount, but Salvinorin B is known to be the compound
present in smaller quantities than the main, active compound Salvinorin A.
I guess I don't know what the "Trace Compounds" in this topic's title is getting at...
I thought it was referring to Salvinorin B as a starting point for the synthesis of
Symmetry? Hell I don't know.

So Gibran, was that extract like 18% Salvinorin B, 72% Salvinorin A & 10% fats/oils?
Perhaps some Chlorophyl too? Was it a clean extract?


And if it's true that Salvinorin B can be deacetylated in a solution under
UVlight, that is a piece of cake. The Salvinorin-Analogue PDF I posted earlier
mentions solving Salvinorin A in 0 degrees Celcius(I believe) Methanol in the presence of
Potassium Carbonate. Didn't seem too hard either, but then again I am still uncertain
which Salvinorin Analogue this synthesis intends to yield...

It's kind of a vague document if you ask me. Needs decyphering.

 

[gibran2]

...
So Gibran, was that extract like 18% Salvinorin B, 72% Salvinorin A & 10% fats/oils?
Perhaps some Chlorophyl too? Was it a clean extract?
...

It’s a very pure extract. See The Salvia Analysis Thread for details: 80% Salvinorin A, 18% Salvinorin B, 2% probably assorted other salvinorins. No fats, oils, or chlorophyll.

 

[SKA]

So have you, Gibran, or anyone else here got even the slightest idea of how
to convert Salvinorin B to Salvinorin B Ethoxymethyl Ether?

A bioassay that circulates the web mentions a couple of researchers' names who may have written papers
on the synthesis of Salvinorin B Ethoxymethyl ether:

INTRODUCTION
Many readers of The Entheogen Review will be familiar with the largely legal psychedelic Salvia divinorum, an entheomedicinal sage originally used by the Mazatec Indians of Oaxaca, Mexico. This plant's active compound, salvinorin A (Ortega et al. 1982), is the most potent naturally occurring psychedelic known, producing clear effects at doses of one milligram or less when vaporized (Siebert 1994). Salvinorin A acts at the kappa opioid receptor (Roth et al. 2002), and since most previously known potent opioids have been alkaloids, not diterpenoids, this discovery has excited scientists considerably. In recent years, over a hundred derivatives of salvinorin A have been synthesized in hopes of producing new medicines (Prisinzano & Rothman 2008). A few of these derivatives have had interesting properties, but most are simply disappointing, less-potent imitations of salvinorin A itself. Other salvinorins and related compounds have also been extracted from the plant (Shirota et al. 2006), but again, these compounds are less potent at opioid receptors than salvinorin A.

Roth, Prisinzano, Rothman & Shirota. It seems these are the researchers who's papers we'd need to read
through if we want to find information on the Synthesis of Salvinorin B Ethoxymethyl Ether.

I found this PDF by Prisinzano & Rothman:

http://www.sagewisdom.org/prisinzanoandrothman.pdf

I'll go through it looking for any info on "Symmetry" & it's synthesis.

I'll read through any PDFs of these people I can find, but I sure could use a hand. Anyone?

 

[Mindlusion]

well, addition of an ether is fairly simple in theory, but, these salvinorins are complex diterpinoids, I don't know what method was used in the .pdf, and what possible side reactions could occur.

Salvinorin A (ester) is hydrolyzed to the inactive component Salvinorin B (with -OH alcohol group)

The ether can be added on with deprotonation of the alcohol, followed by the addition of the desired ether (ethylmethoxyether) with the appropriate leaving group (usually halides).

---

Thanks for the .pdf

 

[SKA]

well, addition of an ether is fairly simple in theory, but, these salvinorins are complex diterpinoids, I don't know what method was used in the .pdf, and what possible side reactions could occur.

Salvinorin A (ester) is hydrolyzed to the inactive component Salvinorin B (with -OH alcohol group)

The ether can be added on with deprotonation of the alcohol, followed by the addition of the desired ether (ethylmethoxyether) with the appropriate leaving group (usually halides).

---

Thanks for the .pdf

Could you explain this process more specifically, in lay men terms?

Hydrolizing Salvinorin A into Salvinorin B can be done by exposing
Salvinorin A in solution to UV light, according to Gibran. Easy enough.
Or do you propose another method of doing this?

Furthermore; Could you explain in practical terms how deprotonation of the alcohol(on the Sally B molecules I assume?) would be performed? And could you explain the subsequent step of adding ethylmethoxyether with the appropriate leaving group?

This is Chinese to me, being the chemistry noob that I am.

 

[Infundibulum]

^
ppl, isn't this discussion going towards (disallowed) synthesis talks already?

 

[SKA]

Ah I guess that's right. I kind of ventured into synth talk without realising.
My bad.
Forget I asked for it.