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Salvinorin Analogues; Beyond Salvinorin A

Migrated topic.
this is actually even more interesting now that i think about it..becasue I dont even think that the mazatecs chew quids RIGHT after they pick the leaves..I am preaty sure that they gather the leaves(sometimes they have to hike to get to them even), and then just use them later that evening..so maybe there is something even they are missing.
 
If you noticed, they normally wrap the leaves within fresh banana leaves or something similar to help preserve them. Maybe that prevents them from oxidizing?
 
I have 7 already going now..but I have a good supply of dry leaf and am letting my plants grow for the summer..than take some cuttings. I will prob do my fresh leaf experiments then:d
 
[quote='Coatl]
Also its very likely that salvia contains other diterpenoids similar to salvinorin A and B just because of the way these molecules are biosynthesized. Infact there can be really no doubt that other diterpenoids with a similar skeleton are in the plant.
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THAT is what I am interested in... does anybody have a FULL list of the compounds in Salvia divinorum?[/quote]
What burnt meant was that there are of course other diterpenoids which are precursors to Salvinorins A and B. Salvinorin B is a precursor to Salvinorin A. And of course, there is some other "salvinorins" that are precursors to Salvinorin B. There is not an enzyme in the plant that takes simple carbon chains and folds them like legos into salvinorins. It goes something like that (this is hypothetical of course!):

Simple carbon molecule --enzyme 1--> more complex molecule --enzyme 2-->even more complex molecule --enzyme 3 -->terpenoid molecule --enzyme 4--> more complex terpenoid molecule --enzyme 5 --> Salvinorin B --enzyme 6--> Salvinorin A

It is like a production line in a factory. Say a car factory; It is the final product (i.e. finished car) that does the job, but in the factory lie all sorts of half-finished cars (precursors). Some may find that a half-finished car may be more suited to one's needs and preferences, e.g. the precursor car that doesn't have its roof installed yet.

Same goes with biosynthetic pathways and active molecules.
 
it would be great if there was an analog for those that do not have the salvia sensitivity swim being one of those...
 
SWIM had posted some papers in another thread, the link to the post in question is here. It basically involved making salvinorin A orally active by using plants that inhibit the carboxylesterases (CE) in the body.

According to the papers the most promising plants are Arenaria serpyllifolia, Thapsia garganica and Rhamnus alaternus. All three are plants that have been used for medicinal purposes in Arabian countries.

According to the papers the "best" is A.serpyllifolia extracts that can inhibit both rat intestinal and porcine liver CEs, with T. garganica extracts coming second best and R. alaternus being third best and only capable of inhibiting only rat intestinal CEs. Of course rat and pig carboxylesterases are not 100% same as humans' neither the metabolism of these substances is the same. These results however indicate that A.serpyllifolia and T. garganica can also inhibit human CEs and possibly make salvinorin A orally active.

Unfortunately not much information can be found in the web about these plants...
 
Do you think Salvinorins get absorbed via Rectal Administration ?

Could be just like chewing , but even stronger and without the intense taste .
 
Observant said:
Do you think Salvinorins get absorbed via Rectal Administration ?

Could be just like chewing , but even stronger and without the intense taste .
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hm....

I'm sure I cannot chew with my butt and I wouldn't put that much leaf material up there! But an extract may work, actually it is a good idea for the fans of this route!
 
har har . Those who tried this route seem to like it . I think its a bit complicated .

I wasn't thinking of Leafes , but some ultra high potency extract , made into a suppository .
Better make sure you trip in the Bathroom .
 
69ron said:
If you noticed, they normally wrap the leaves within fresh banana leaves or something similar to help preserve them. Maybe that prevents them from oxidizing?
Click to expand...

would freezing the fresh leaves work also then?
 
Kathlene Harrison said that they(the mazatecs) put the leaves out on they'er alter and let them wither for a while bfore the ceremony, and that they are easier to quid this way..Could never find anything about them wrapping them in bananna leaves..but different shamanic families probabily have slightly different methods of working with them.
 
Amazing thread! 😁 would it be possible for someone to create these analogs at home?
SalvinorinTIC.jpg
 
Infundibulum said:
SWIM had posted some papers in another thread, the link to the post in question is here. It basically involved making salvinorin A orally active by using plants that inhibit the carboxylesterases (CE) in the body.

According to the papers the most promising plants are Arenaria serpyllifolia, Thapsia garganica and Rhamnus alaternus. All three are plants that have been used for medicinal purposes in Arabian countries.

According to the papers the "best" is A.serpyllifolia extracts that can inhibit both rat intestinal and porcine liver CEs, with T. garganica extracts coming second best and R. alaternus being third best and only capable of inhibiting only rat intestinal CEs. Of course rat and pig carboxylesterases are not 100% same as humans' neither the metabolism of these substances is the same. These results however indicate that A.serpyllifolia and T. garganica can also inhibit human CEs and possibly make salvinorin A orally active.

Unfortunately not much information can be found in the web about these plants...
Click to expand...


Anyone ever try this or have more info? I got A.serpyllifolia seeds and am going to try and grow them. Any tips or insights welcome.

9/17/2017 Edit: I'll start a thread in the ethnobotanical garden section about growing A.serpyllifolia (after I triple check with Google that I indeed need to start a new thread). I'll (hopefully) report results when combining it with salvinorin back in this thread. This is just to try to keep the threads clean and organized. Feedback welcome (thanks).
 
Question coming up, but please be patient with me as I'm learning about chemistry.

Could salvinorin-b get converted to salvinorin-a? The way I understand it, there is only one esterification step needed. Could this be done with vinegar (acetic acid)? Sounds too simple to be true, but wouldn't the reaction be:

OH-S + H3CCOO-H -> H3CCOO-S + H2O, where S is the common structure of Salvinorin a and b.​

Is this the Fischer–Speier esterification or the Steglich esterification depending on the catalysts/dehydration used? Is there a way to get this reaction going by a low tech kitchen alchemist?

I ask because there is an interesting salvia recently discoreved (S. potentillifolia, paper attached)that has 0.24% by leaf dry-weight of salvinorin-b. It grows in turkey and should be hardy to frost (but I'm not sure), propagate from seed, etc. Also, if this esterification is simple enough it could be done during salvia d. extractions to maximize yield/purity of salvinorin a.

Any thoughts? Many thanks on any insights/corrections. Planning to work on this, so if anyone knows why it will not work, please let me know so I can move on to other things.
 

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Update: Mindlusion pointed out in the chat area that while esterization of Salvinorin b is possible it would not happen with acetic acid due to the kinetics of the reaction. Acetic anhydride would work, but that is a controlled chemichal since it is used to make heroin from morphine (boooo). Adding catalysts would either destroy the salvinorin (Fischer esterification), or requires difficult to procure chemicals beyond the reasonable expectation for a kitchen alchemist (Steglich esterification).

There may be a path to esterify salvinorin b using aspirin. That remains an open question for another day.
 
What about doing this to Salvinorin b:

https://www.researchgate.net/post/How_to_synthesize_aspirin_without_using_acetic_anhydride said:
It is possible to produce aspirin by reacting salicylic acid with acetic acid & sodium acetate by heating one and half hr. & pouring the reaction mixture in ice-water mixture to get solid aspirin.
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Could it be that simple? Make a vinegar/baking soda volcano (sodium acetate), mix with acetic acid and salvinorin b under heat, them get salvinorin a. It can't be that easy, right?
 
Or how about this? Esterification with ethanol and boric acid? Both household grade?


Abstract:Ethyl salicylate is synthesized, isolated, and characterized in a three-step process using simple equipment and household chemicals. First, acetylsalicylic acid is extracted from aspirin tablets with isopropyl alcohol, then hydrolyzed to salicylic acid with muriatic acid, and finally, the salicylic acid is esterified using ethanol and a boric acid catalyst. The experiment can be directed towards high school or university level students who have sufficient background in organic chemistry to recognize the structures and reactions that are involved.

Edit: after reading the paper it seems like the original SA -OH group is not being esterized, a different part of the SA molecule is. Therefore, this may not work of our purposes.
 

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