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Author Topic: Mescaline via smoke?  (Read 228 times)

no1uno

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Mescaline via smoke?
« on: September 15, 2009, 09:48:32 AM »
Righto - looking into what is and is not available is kinda disheartening... Way too much can be restricted and it just plain sucks... :'( How to stick it to THEM? Find a route to psychoactive drugs from non-restricted (and unrestrictable) precursors...

Here's one now.... Syringol

Yup, you read right.... It's presence in smoke is characteristic for wood smoke...

OK - how easily is it going to be restricted... Not one fucking hope in hell, that's how...

How easily is it going to be got at... There's the rub...

Cos insofar as what to do with the shite.... look at this for a simple route to syringaldehyde... Yeah, no fucking nitrobenzene oxidation of lignin here, just react hexamine with syringol and boom, we is cooking with gas.

Now, just to kick around some ideas...

 :-*

* Worked out the bug - did somebody change the code for what the PHP Script does when it sees URL= "", seems we no longer need inverted commas around the url... Not huge, but makes a fucking big difference;)

** By the way, to extract from smoke requires making smoke then drawing it through water :o You know, like the really cool looking water pipes for "tobacco"? ;)
« Last Edit: September 15, 2009, 12:06:00 PM by no1uno »
"...     "A little learning is a dang'rous thing;
    Drink deep, or taste not the Pierian spring:
    There shallow draughts intoxicate the brain,
    And drinking largely sobers us again.
..."

2bfrank

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Re: Mescaline via smoke?
« Reply #1 on: September 15, 2009, 09:49:56 AM »
link dead by the way/ links alive now, and yes interesting for sure
« Last Edit: September 15, 2009, 05:13:16 PM by 2bfrank »

Douchermann

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Re: Mescaline via smoke?
« Reply #2 on: September 15, 2009, 04:21:50 PM »
Good find no1

At the grocery store, you can buy 'liquid smoke' which is a smoke flavor additive.  Rather than burning lots of wood and attempting to capture the smoke (and components of it) it may be possible to get it out of the flavoring.  And as you pointed out, a simple duff formylation will give us the desired aldehyde in the para (to hydroxy) position.

Sedit

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Re: Mescaline via smoke?
« Reply #3 on: September 15, 2009, 09:31:07 PM »
Burning wood would be a waste of time and it would be much better(and cleaner) to decompose the Lignin using Sodium Metabisulfite.

http://www.erowid.org/archive/rhodium/chemistry/syringaldehyde.spruce-maple.html

I have a much better reference then this page somewhere that I will look for. This is a bit removed from what im talking about but the products of the bisulfite leave one with pretty much the same componates as burning wood. It is supposed though if one has a wood stove they can extract these sort of things from then it could possibly be worth the burn.

The other paper the details the Lignin decomposition should either be in my library or sitting in the request section over at SM or WD.
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no1uno

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Re: Mescaline via smoke?
« Reply #4 on: September 16, 2009, 12:00:01 AM »
Yeah, or aq. acetone

Klason Lignin huh? Looks interesting...

Digest X g's of lignin with 15X mL 12M Sulfuric acid to remove the sugars, heat to 121C (some pressure is going to be generated), filter the black liquid and wash the filtrate with deionized water...

They then heat it to ~550C to burn off all the carbon - we don't want to do that obviously...

Then again, neither do we want to fuck around with nitrobenzene oxidation

How about destructive distillation (ie. pyrolysis) of the Klason Lignin? Shouldn't be any furans, etc. and the result should be nearly pure phenols, of which guaiacol and syringol apparently form the main products (also - there are articles on extracting the smoke condensate with ethyl acetate to get predominantly these two phenols - I can think of numerous uses for both:))

Then again - organosolv papers just got me thinking - could we maybe extract the Klason lignin by that route?

PS Wonder if the ubiquitous phosphoric acid from the parts store will do instead of sulfuric (it is a BITCH to get here)?
"...     "A little learning is a dang'rous thing;
    Drink deep, or taste not the Pierian spring:
    There shallow draughts intoxicate the brain,
    And drinking largely sobers us again.
..."

Sedit

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Re: Mescaline via smoke?
« Reply #5 on: September 16, 2009, 12:11:47 AM »
guaiacol and syringol sulfonate esters (IIRC on the sulfonate thing as its been atlest 6 months since I read this) are the main products from the digestion of Lignin with Sodium MetaBisulfite. The text im attempting to find for your right now shows exactly how to perform this and get the free form syringol and guaiacol from this tar of decomposed wood. Look into how they use to synthesis Vanillin back in the day because that is how they would go about it and how I came across the text.
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Sedit

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Re: Mescaline via smoke?
« Reply #6 on: September 16, 2009, 01:52:48 AM »
Heres a little something to think about no1uno. The oxidation of the lignin sulfonates yeilds primarily vanillin but also syringaldehyde...
This has typicaly been reported to yeild 8% vanillin by weight from the starting sulfonate.

Attached is a process for the seperation of the vanillin after oxidation of the sulfonates in a KOH solution feed with an oxygenated gas(air for fuck sake, gotta love patent speak).


Quote
It is known that vanillin can be made by oxidizing a lignin or lignosulfonate material, such as results from the kraft and sulfite cooking processes for producing pulp. The oxidation is carried out at elevated temperatures and pressures in thepresence of an oxygen-containing gas in an alkaline solution. The resulting alkaline aqueous solution contains in addition to the desired vanillin, the unwanted contaminants, such as orthovanillin, acetovanillone, para-hydroxybenzaldehyde and syringaldehyde, which must be removed from the vanillin if the vanillin is to be of high purity and quality.

Yeilds are shit but materials are cheep and one could picture a large wine processing jug full of saw dust. But even though possible non of it is really feasible or cost effective so academia is about all of this best use. Vanillin to trimethoxy benzyldahyde would be far more economical with no chances of it ever becomming watched.

Personaly I feel if anything your best bet would bee to look into obtaining wood creosotes which is the black tars they put on telephone poles(there is also coal tar creosotes so careful). That is mostly the type of products you want such as
« Last Edit: September 16, 2009, 02:06:49 AM by Sedit »
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no1uno

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Re: Mescaline via smoke?
« Reply #7 on: September 16, 2009, 04:03:48 AM »
Here's another option - Canola Seed Meal (such as is available by the ton) is 1-2% Sinapine...

Sinapine is the choline ester of Sinapic Acid - hydrolysis of which gives the Sinapic acid free & clear, ready for methylation, reduction to the propionic acid, followed by esterification, formation of the amide and then a Hoffman to the psychoactive amine...

Cheap as chips and you can still use the canola meal for stockfeed

By the way Sedit, IIRC the method you are talking about is only useful POST-Oxidation of the Kraft Lignin... That is what forms the aldehydes that react with the bisulfite... I'm only trying to dodge the oxidation step as it is the touchiest of the process.
"...     "A little learning is a dang'rous thing;
    Drink deep, or taste not the Pierian spring:
    There shallow draughts intoxicate the brain,
    And drinking largely sobers us again.
..."

Vesp

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Re: Mescaline via smoke?
« Reply #8 on: September 16, 2009, 04:33:11 AM »
Is this feed available cheaply in say 50lbs quantities, or is it mostly used only for industry?
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Sedit

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Re: Mescaline via smoke?
« Reply #9 on: September 16, 2009, 11:37:38 PM »
Quote
By the way Sedit, IIRC the method you are talking about is only useful POST-Oxidation of the Kraft Lignin... That is what forms the aldehydes that react with the bisulfite... I'm only trying to dodge the oxidation step as it is the touchiest of the process.
 

Noooo..... The MetaBisulfite is the process. The Sulfite liquor containing Lignin sulfonates left from the Kraft pulping process is whats oxidised to the aldahydes by putting the sulfonates into a pressure reaction vessle containing KOH and feed oxygen to form the aldahydes. They use the MetaBisulfite in order to break down the Lignin and leave with clean pulp as I understand it.
« Last Edit: September 16, 2009, 11:44:37 PM by Sedit »
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no1uno

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Re: Mescaline via smoke?
« Reply #10 on: September 18, 2009, 07:12:54 AM »
Vesp, the feed is available in 25, 40 & 50kg bags - also by the pallet / bulk (1 ton) bag... Cost is pretty fucking good too (Actually it is dirt cheap... people try and shave costs by feeding excessive qty's to stock and the sinapine fucks things up apparently)

Sedit -

Quote
From the first paragraph of the Erowid article you cite: 

It has recently been reported1 that a yield of 25% of vanillin based on Klason lignin can be obtained by treatment of spruce wood with alkali in the presence of nitrobenzene. Employing the same technique, we have confirmed this result by digesting spruce wood meal (35.0g, 28.6% Klason lignin), sodium hydroxide solution (400 mL, 2 N), and nitrobenzene (24 mL) in a stainless steel bomb with good agitation at 160°C for three hours.

The nitrobenzene is used as an oxidant - the procedure oxidises the lignin phenylpropanoids/phenylpropenes to aldehydes/etc. The bisulfite addition products allows for facile separation of these from the other components (phenylpropenes, various acids, etc)... The aldehydes themselves don't exist naturally - they are too prone to oxidation - they only exist after being released by either (1) Hydrolysis (from sugar esters mainly) or (2) cleavage.

"...     "A little learning is a dang'rous thing;
    Drink deep, or taste not the Pierian spring:
    There shallow draughts intoxicate the brain,
    And drinking largely sobers us again.
..."

Sedit

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Re: Mescaline via smoke?
« Reply #11 on: September 18, 2009, 12:40:42 PM »
I must quote myself to clear up the misunderstanding.

Quote
This is a bit removed from what im talking about but the products of the bisulfite leave one with pretty much the same componates as burning wood.

What they demonstrated in the link is not the Kraft process but another means one can take to decompose the lignin. I mearly included it to demonstrate the structure of the decomposition products. When done in an alkaline sodium pyrosulfite enviroment the product is a liquor of Sulfonates that can be oxidised to the corrisponding aldahyde. Read the patent I attached a post later that discribes the purification and oxidation of the Sulfite waste liquid from the Kraft process. I have another reference someware that I am looking for that discribes how to convert the sulfonates into Guiaiacol and other corrisponding benzenes.
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no1uno

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Re: Mescaline via smoke?
« Reply #12 on: September 25, 2009, 05:03:55 AM »
This paper (Props to Java & Timecube) claims a fucking magic result - from Birch Bark/Wood pyrolysis they got a pyrolysis oil, upon steam distillation of that they got 16 light fractions... Extracting one with pentane, removing the pentane then extracting with toluene gave the claimed yield of 92% Syringol after being shaken with water and the toluene removed.

Ok - kind of interesting isn't it?

Yeah, the specific fraction would be a headfuck, but I'd have to wonder about what would happen if we got the Pentane/X insoluble, toluene soluble fraction, that didn't extract into water of the steam distillate per se
"...     "A little learning is a dang'rous thing;
    Drink deep, or taste not the Pierian spring:
    There shallow draughts intoxicate the brain,
    And drinking largely sobers us again.
..."

timecube

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Re: Mescaline via smoke?
« Reply #13 on: September 26, 2009, 08:30:49 PM »
Quote from: no1uno on September 25, 2009, 05:03:55 AM
Yeah, the specific fraction would be a headfuck, but I'd have to wonder about what would happen if we got the Pentane/X insoluble, toluene soluble fraction, that didn't extract into water of the steam distillate per se

Looking at Figure 7 and Table 2 in the paper, it's clear that the useful fractions are mainly from around 90 - 105 C.  Table 2 shows what else you're going to pick up along with it at those fractions.  They focus on the fraction from 95 - 100C where you get the most syringol.  There appears to be quite a bit of it in the 90-95 and 100-105 fractions too, but they also have more methyl syringol, isoeugenol, and some other substances not present in the 95-100 fraction that may be harder to separate out.

The main problems would probably come from the pyrolysis setup, particularly in creating a strong enough vacuum.  The reactor could be scaled down to accommodate a not so strong pump, but then it would probably take forever to process a usable amount of material.

I don't quite understand what you're asking about extracting into the steam.

Sedit

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Re: Mescaline via smoke?
« Reply #14 on: September 26, 2009, 09:00:41 PM »
The suggestion that it would take forever to make a useable amount of material may not be so at all considering the amount of people that still have wood stoves. The flue pipe higher up away from where it can be overheated will be loaded with pounds of these materials ready for a steam distillation.

It all sounds kind of crazy but an old wood stove and pipe could make a decent amount in a very short amount of time if you put slightly damp birchwood into it and burned it. A strong fan on the flue pipe would air in collecting it and preventing further decomposition.
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no1uno

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Re: Mescaline via smoke?
« Reply #15 on: September 26, 2009, 10:05:24 PM »
OK, do we need a vacuum or a blower? Push enough air into the fire and it has to come out somewhere, no? Set up a furnace with a small blower on it - push the flue gasses through a water trap...

Separating the fractions would be painful to begin with for fucking sure, getting rid of all the organic acids - predominantly propionic/acetic to start with, then the various sugar condensates, etc. then sorting out the phenols....

Look at this paper too...

The authors extracted the smoke distillate/condensate with (1) ether after saturating the solution with NaCl, then evaporated the ether; (2) Extracted with a 5% HCl Sol'n saturated with NaCl (to remove the bases); (3) extracted the NP layer with 5% NaHCO3 Sol'n (to remove the acids); (4) then extracted with 5% NaOH (to grab the phenols)...

All we'd need to do is acidify the aqueous sol'n from step 4, extract with ether, evaporate the ether then extract it with toluene. That really should be all that is needed to fucking narrow down this shit quite dramatically.

Remember, the fraction we are after has the distinctive "smokey" smell and makes up about 0.5-1% (at a guess) of the weight of the starting wood. 2-300kg of wood is fuck all, winters coming there isn't it?

* Once it is extracted out to that extent - a Duff Formylation then extraction with bisulfite will finally separate the oat from the chaff.

PS Or given that the bit we want is toluene soluble - why not just extract the distillate in step 1 with Toluene (instead of ether), shake that with various solutions - ie. acid, weak base, plain water, then extract the remaining phenols from it with NaOH solution? Should be a fucking sight quicker and a lot more effective (not to mention toluene is a much nicer solvent for home use).
« Last Edit: September 26, 2009, 10:25:13 PM by no1uno »
"...     "A little learning is a dang'rous thing;
    Drink deep, or taste not the Pierian spring:
    There shallow draughts intoxicate the brain,
    And drinking largely sobers us again.
..."

timecube

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Re: Mescaline via smoke?
« Reply #16 on: September 27, 2009, 04:13:47 AM »
Quote from: no1uno on September 26, 2009, 10:05:24 PM
OK, do we need a vacuum or a blower? Push enough air into the fire and it has to come out somewhere, no? Set up a furnace with a small blower on it - push the flue gasses through a water trap...

See that's the thing with the wood stove... we don't want to burn the wood at all, we just want to heat it really hot under vacuum so the oils leech out.  The vacuum keeps oxygen away from the wood and of course lets us distill the oil at a lower temperature.  The smoke from burning the wood likely has some useful material in it, but vacuum pyrolysis like this as described in the paper should yield much more (because we're not burning it all up.)

I was thinking something along the lines of a large heavy walled metal can with a small opening at the top (like a metal can that looks like an oil drum, an empty propane tank, or the like.)  Something you could attach a pipe to and make airtight.  Then you would need a receiving flask or tank and a strong vacuum pump.

Vanillin is cheap enough that I'm not sure how practical all of this really is, but if you have a lot of birch trees where you live and some spare parts and time, then this is certainly an interesting route worth exploring.

Edit:
Something like a propane tank would actually be really difficult to load and then clean out.  Something would be needed that had a large opening that could be easily opened and sealed shut.  Those really large pipes that are held together by bolts (like on submarines) come to mind.  One end could have some end cap that's remove for easy loading and cleaning, then bolted back on, and the other side would adapt down to a smaller sized pipe to extract the oils through.  Those are probably fairly expensive though.  Just a thought.
« Last Edit: September 27, 2009, 04:31:34 AM by timecube »
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