Capsiacin is the active chemical in chillis and is a irritant for humans and most mammals. Its formula is C18H27NO3 and in its pure form is a white crystalline solid.

To give a comparison between the strength of pure capsiacin and commen items, tabasco sauce has a piquancy (hotness rating using the scoville scale) of around 8.000. Pure capsiacin has a piquancy of 15,000,000.

It has potential for a agent to clear buildings, but also as a medicine. A pre 21st century application was to help tooth aches by rubbing some capsiacin oil on the sore tooth. I have read from one source that capsiacin powder can be smoked to produce a euthoric feeling. Not to sure on this one, as normally people to handle it have to use it in tox-rooms and wear aspirators/suits.

I'm trying to extract it from chillis. Capsiacin is soluble in oils, non-polar solvents such as diethyl ether, and polar solvent such as alcohol and acetone. It is sparingly soluble in water. Yesterday I sperated the skins and the seeds of about 750g of chillis and submerged both into as little 95% ethanol as I could. After about 10 minutes the liquid was and amber colour, and today the liquid is orangy/red. I think I might leave it for a week (occasionaly shaking it) before filtering it and letting most of the alcohol evaporate. The resulting liquid should be oily and very hot. I'll try burn some and see what effect is has. I'm not sure if heat destroys the capsiacin compound.

Interesting thread. I plan to grow some habeñero peppers this summer (along with my other crops) for some testing and basic food flavouring...

The seeds are what I was told by a friend are the hottest part of a pepper and contain the most capsiacin, and eating some of his homegrown habeñero pepper's seeds alone sort of proved that to me a few years ago.

For those who don't feel like going through the hassle of growing your own to experiment with, he also showed me a brand of hot sauce bought locally called "Spontaneous Combustion" which should be potent enough for any expedient needs of experimentation. I put a drop of this Spontaneous Combustion sauce on a chicken thigh he had just grilled, spread it about as best I could with my fingertip, and completely ruined the chicken portion as it was completely inedible by a mere mortal such as myself (without, of course, working yourself up to it at a very slow pace. Read: months of hotter and hotter peppers, which I finally did). I was told this sauce rated a cool 50 on such a scale you mentioned... Now imagine that in your lungs and eyes!

Burning it will have some effect if the smoke gets to you, but it's not as profound as having it sprayed as a liquid directly into the face. I should think that the orange-red liquid you have should suffice or if left to evaporate the alcohol out of it and are left with a paste, it could even be diluted with water and work well if simply applied with a squirt bottle or administered by presurized container (reloadable aerosol-type can from Harbour Freight?).

P.S. I'd be willing to bet that instead of diluting it with water, horseradish juice would add a wonderful effect as well. After all, isn't that the stuff they make that green paste they often serve with sushi so potent? I'm at a loss this minute what that shit is called, but I once had my sinus cavity completely drain on my plate in a resteraunt before with a moderate overdose (in one bite!) of the stuff. MOST embarrassing!

Wasabi is the name of the sushi dip. It has a different effect than chillis, more of a nasal thing than the chilli mouth burn. Ok now I'm on the search for some horseradish, that sounds like a great combo that will make you fold over.

I have tasted the red liquid and all mighty it is hot. It would certainly burn if in contact with eyes. But I am looking for a more passive way of doing things. Something that would travel through the air and make the room unlivable. I think for that effect I need to produce a stronger solution.

The ultimate would be to produce actual capsiacin crystals. But I think just by evaporating the alcohol you are left with an oil, because of the other compounds the alcohol dissolves. Maybe a less polar solvent is needed.

Festergrump - Ahead of you there my friend. Currently there are about 15-20 habeñero sitting on my bush, aching to inflame my stomach and various other sphincters.

I have had moderate success in using acetone to extract capsaicin but as evilgecko just snuck in there, it does leave a kind of oily grease at the bottom of the evaporation container.

Evilgecko, if you are looking for something to clear a room, get a frying pan and heat some oil up in it. Throw a few sliced up chili in it and get ready for irritation.

I think that you might have some success with a fairly cold (relatively anyway) burning smoke mix that utilized motor oil or olive oil impregnated with capsaicin. There are a few mention on other smoke treads about making it volatile enough to come across in the smoke.

I might have a bit of a session when I get home tonight. I'll pick my chili and save a few for eating purposes, the rest shall be condemned to acetone/oil or something and turned into a smoke mixture.

I'll get back to you all with the results.

Festergrump, Habeñero peppers have a rating of 100,000 - 300,000 on the scoville scale. I ordered some chili the other day that (reputably) have a rating of 1,040,000 scoville units. Ouch...... See the wikipedia (http://en.wikipedia.org/wiki/Scoville) entry about it.

I know that I have some documents somewhere regarding what techniques are used to extract capsaicin. For other forum members interest, the Naga Jolokia chili has a rating of 1.04 million SHU (scoville heat units) and police grade capsicum spray has a rating of 2-5million SHU.


Hmmmm, a cause for thought thinks me.

If you are using a volatile solvent for your extraction, just spray it into the target area and let the solvent do the job of dispersing the oil into the air as it evaporates. :)

What about ball-milling the peppers with some solvent? Mechanical grinding and mixing in solvent has to be more efficient than mere sitting. Use non-sparking media if the solvent is flammable, of course.

Speaking of inflaming.....

As I'm typing this, I have a bowl of water and ice cubes sitting next to me that I need to dip my left hand in every couple of minutes to stop the pain. When cutting chili, remember to wear gloves. You might think it doesn't matter but it really does. If they are only 300,000 SHU, I'd hate to so pig pepper (police spray).

I cut up enough habeñeros to fill a fair sized jar and they are awaiting the addition of acetone.

I'm planning on filling the jar with acetone, leaving it for a week, pouring off the acetone and repeating another 2 times. Hopefully this will remove most of the capsaicin without being too wasteful on solvent.

If you eventualy what to try and get pure isolated product maybe you could try using its low solubility in water to your advantage?

Try something like this:
Dry the material (seeds or chilies) grind and extract with water. Discard water, dry left over solids then perform a non polar (pet ether 40-60C would be good) soxhlet extraction take the nonpolar solvent wash in a separator funnel with water 3 times.

Evaporate nonpolar solvent and recrystilse in solvent of choice.

Or something along those lines depending of said solubility of product and solvent choice.

If you really wanted to purify even more try running the extacted washed product through a column of your choice with increasing eluting ratio of non-polar and polar solvent, in your choice of stationary phase.

Ultma - I don't really know you that well, and I'm not overly familiar with your posts, so forgive me if I'm talking out of my ass.

Personally, I don't see how water (a polar solvent) is going to dissolve Capsaicin (non-polar). I'm extracting it with acetone at the moment (which it is going to be doing for the next week). I'll repeat that twice, then evaporate off the acetone to leave me with a crude extraction.

I'll test that a bit (I'm hoping that it will dissolve in glycerine and possibly be used in smoke compositions). I'll either store it (fridge in acetone) or use it as it. If I store it, I'll attempt a low pressure distillation of the volatiles in it (when I have the gear, which will be a while).

I know that some form of capsaicin boils off at over 100*C (found out by frying chili). I'd assume that that oil was about 200*C, so I'll try for there. Low pressure because I don't want it to decompose as I'm trying to extract it. I've got some time to research the extraction before I attempt it in about 3 weeks.

Get back to you then, fiat accompli.

Ultma - I don't really know you that well, and I'm not overly familiar with your posts, so forgive me if I'm talking out of my ass.

Personally, I don't see how water (a polar solvent) is going to dissolve Capsaicin (non-polar).

The point of using water, is to get rid of anything that is polar before you try to extract it with acetone. This way anything that dissolves in both is taken in the begining.

Ahhh, I see now. Ooooh, there is actually something called a soxhlet. I know barely anything about extraction and I thought it was a typo. Damn.

Ignore my previous post as an extension of UTFSE (as in, I should have)

Sorry all.

I'm actually growing some habaneros myself, in addition to some hot banannas, sweet banannas, anahiems, and some cayennes. I planted some zimbabwe bird's eyes, tepins, and some other seeds a month ago, but they havn't came up. The seed pods the seeds were from looked like they were dried without excessive heat, so they should be viable. I'll have to try them again in a while.

I have had a few habaneros seeping in alcohol for a month or so now. I need to really get on that, i have been meaning to start another batch seeping for a while now.

Anyone thinking of DMSO?

Just a thought on this, but it seems to me that the simplest way to extract the oil would be to grind up chillies with a little vodka in a blender, drain the juice out of the resulting good, and boil it in a double boiler (which won't let the temperature go above @100C) until you drive off all the water from the oil. And if it dosn't work add the oil to chili. :)

Using a Soxhlet extractor would be very efficient. Similar continuous extractors can be improvised. Acetone would be a pretty good solvent. If food grade ethanol was used it would be relatively cleaner. More consumption safe.

You might be able to get crystals through sublimation, though it would be pretty insane to even try.

Swany at APC has done some work on this:
http://www.apcforum.net/forums/index.php?showtopic=262
(pics on page 2,3)

There is also a thread at Sciencemadness:
https://sciencemadness.org/talk/viewthread.php?tid=5329

(For completeness)

I have done this extraction. It is very simple.

Use 1lb chopped and dried habeneros, mix with 500mls of denatured alcohol and let settle in sealed jar for one day. The orange solution is boiled off and a black oily substance is left that is painful to even smell.

I let it boil too long the first time I did it, and was greeted with a white vapor that caused throat pain, choking, coughing and running for the gas mask. I did not bother weighing it because more handling is not worth it. With concentration by sublimation, it should be white and crystalline.

Dilute black stuff with more alcohol and have fun with dipped toothpicks, etc...

Could you crash the precipitate in, say, 1*C ice water?

I think the problem that we face after getting the raw product from the solvent is how to separate the different forms of capsaicin. There is

Capsaicin and Dihydrocapsaisin - This is the stuff we want.

Nordihydrocapsaicin, Homodihydrocapsaicin, homocapsaicin - only rates about 8-10 million on the scoville scale (boo hoo, have a cry *grin*).

No idea why you would want to remove the second group, unless its just for the wank factor. The effort involved would far outweigh the benefits.

Brainstorming on a suitable solvent to use as a possible chili spray? There is acetone, eth/methanol, and any other non-polar(ish) solvent.

Soon, I'm going to run a test as to its solubility in glycerol (glycerine). If it is soluble, it would have certain application as an irritant in smoke mixtures. From past experiments, smoke compositions such as KNO3 sugar decomposes the Capsaicin (I expected as much).

*grin* Imagine, you've installed a nozzle in your exaust (car/motorbike) linked to a pump that pumped Capsaicin laden oil/glycerine into the exhaust. Piggies pull you over, just before you stop, you start the pump as if you're car had a problem.

Escape under the cover of the smoke/irritants you've put into the air.

I've also been interested in extracting pure capsaicin, since I visited a local restaurant where I was discussing hot sauces with the owner. He brought out an imported sauce called 'endorphin rush', and even though I had no more than a drop on the end of a toothpick, the effect was noticeable on the way in and out :-).

You can buy it, and heaps of other hot sauces on the following site:
http://www.firegirl.com/1331-02.html

The link is to a product called 'the source', which is apparently 7.1m scoville units. Interesting, considering that normal pepper spray is about 2-3m (http://en.wikipedia.org/wiki/Scoville).

Unfortunately its $95, but there are heaps of other good hot sauces there if you actually like hot food or want a cool sauce to show up your friends when they think they're Mr Hardcore for being able to eat a few chillies.

The website has several products which seem to contain synthetic capsaicin as well, I'm not sure how they synthesise it. Looks like you can buy the pure stuff, but its pretty expensive, US$100/g at this place, and you'd prob need a license.
http://www.sciencelab.com/page/S/PVAR/10410/SLC5212

Soon, I'm going to run a test as to its solubility in glycerol (glycerine). If it is soluble, it would have certain application as an irritant in smoke mixtures. From past experiments, smoke compositions such as KNO3 sugar decomposes the Capsaicin (I expected as much).

The glycerine idea sounds like a good plan, but how do you mix the glycerine with the KNO3? Do you use the glycerince as the replacement for the sugar? Maybe mix the glycerine with a little potassium permangante and the mixture would be self igniting.

I've soaked about 200g of dried short chillis (sorry I don't know the correct name) in as little of 95% ethanol as I can for a week. I then filtered of the solution and have left it on a plate to evaporate. Every day the liquid level drops quite substantially and oily deposits have started to form on the surface.

The Chilli And Ethanol Mix
http://i5.photobucket.com/albums/y171/evilgecko_nz/BottleFullOfChilliAndEthanolWebVers.jpg

The Oily Substance Starting To Form As Ethanol Evaporates
http://i5.photobucket.com/albums/y171/evilgecko_nz/CapsiacinOilPrecipitatingWebVersion.jpg

Ahhh, I mustn't have made that clear then.

If the capsaicin does dissolve in glycerine, then it can be sprayed into the hot exhaust of a vehicle, causing an irritating smoke screen.

There is a way to have it (glycerine/oil/etc.) work with KNO3 kinds of smoke mixtures, but until I get it working properly, I'm going to keep it to myself.

Why not try motor oil as well as glycerin? It would cause the same effect and chances are that capsaicin is more soluble in motor oil than glycerin (non-polar vs polar).

At a chili research institute, the professor explained that the base of the chili is the spiciest. If you dice the habaneros pepper and place it in an atomizer (turns it into gas), you can then place it in a canister under pressure. For this I suggest going to a scuba or paint ball shop. I haven't done this, but it is an idea.

Could you extract using 99% Isopropyl Alcohol? I'm weary to use denatured alcohol because I'm planning on usning this in some food for human consumption, don't want to poision anyone....:(

*whistle* I just looked at the specs. for denatured alcohol. Fuck using that for anything related to food (Aviation Gasoline anyone?).

I'd go the Isopropyl Alcohol if I were you. Otherwise, If you have a distillation kit and some time, brew up a 25L batch with some yeast, and after distillation, this will give you about 4L of 78% ethanol.

Maybe I'll just bite the bullet and buy some 190 proof at the liquor store.

I have a bottle of 99% isopropyl, but I don't what else might be in it (nothings listed...)

What do you think, would there be anything else in it?

Forgot to ask, whats the purpose of dehydrating the peppers first?

The 99% most likely only contains water as the extra 1%. I still wouldnt use it though, isopropyl aclohol is converted into acetone by the liver.

isopropyl aclohol is converted into acetone by the liver.
Extracting it with isopropyl alcohol means in no way drinking the stuff....:confused:

But I agree, the one percent should only be water.

Not to start an argument or anything here, but can't the same be said for the denatured alcohol?

If you aren't concerned about using the isopropyl because you will evaporate it off, then why is there such a great concern about the denatured? I mean I don’t know about you, but to me, having acetone in my body is just as bad or worse than aviation gas.

Now before I post this, I am pretty confident that someone here will make a complete fool of me for what I just said, but I'm okay with that, if I am wrong, please enlighten me oh great ones.

Well, see, I think the deal with it is this. 99% Isopropyl is just that. No one is going to drink it (unless you're a nigger), so there shouldn't be any nasties in it.

On the other hand, fuck knows what in denatured alcohol. Who knows what is going to evaporate off and what isn't?

Personally, if you are going to use it for human consumption, use the Isopropyl and make sure you heat it gently when you are evaporating it off. You won't be eating a lot of it (it will be damn hot) and even if you do, there will only be minuscule amounts left, if any.

Has anyone here drunk isopropyl alcohol? If so, what were its efects?

Bugger - From our mate, Wikipedia *sigh*.

Isopropyl Alcohol -
Isopropyl alcohol is oxidized by the liver into acetone. Symptoms of isopropyl alcohol poisoning include flushing, headache, dizziness, CNS depression, nausea, vomiting, anesthesia, and coma. Use in well-ventilated areas and use protective gloves while using. Poisoning can occur from ingestion, inhalation, or absorption.

Isopropyl alcohol is about twice as toxic as ethanol. Isopropyl alcohol does not cause an anion gap acidosis (like ethanol or methanol). It produces an elevated osmolal gap, but generally no abnormal anion gap (though this may be seen as a result of hypotension and lactic acidosis). Overdoses may cause a fruity, acetone-like odor on the breath.


Acetone -
Acetone is an irritant and inhalation may lead to hepatotoxic effects (causing liver damage). The fumes should be avoided. Always use goggles when handling acetone; it can cause permanent eye damage (corneal clouding).

Small amounts of acetone are metabolically produced in the body, mainly from fat. In humans, fasting significantly increases its endogenous production (see ketosis). Acetone can be elevated in diabetes. Contamination of water, food (e.g. milk), or the air (acetone is volatile) can lead to chronic exposure to acetone. A number of acute poisoning cases have been described. Relatively speaking, acetone is not a very toxic compound; it can, however, damage the mucosa of the mouth and can irritate and damage skin. Accidental intake of large amounts of acetone may lead to unconsciousness and death.


Now, someone is going to ask why not just use acetone in the first place? - Anti rust agents that they put in it (someone said that, and I would be inclined to agree).

It's like Hansel and Gretel - Follow the bread crumbs.

And instead of drinking ethanol, why not simply drink acetaldehyde instead? It does not attract any excise tax. (It is further metabolized to acetic acid, unlike isopropanol which cannot be easily oxidized beyond acetone, a ketone, to a carboxylic acid).

While I know this thread is a little old (about 2 months) I found this on my computer.

I can't remember if I got it from the forum (a link) or if I found it via searching, but here is something for everyone interested in capsaicin.

Name says it all; it's a short description by a couple of Korean chemists on the synthesis of a bioisoester of capsaicin.

From what I can glean from the "technobabble", capsaicin affects dopamine receptors, and hence, this bioisoester of capsaicin has been altered to make it more effective. This conclusion that the alteration makes it more effective stems from research into the effectiveness of 1-hydroxy-2-pyridone on dopamine.

Hopefully someone will be able to try this, and from reading what they need, it will be someone who lives in a country where you can still own most of the precursors for the fatalities of the "War of Drugs"

Without further procrastination -

You would definitely need a well stocked lab to perform this synthesis. I am concerned the yield vs. the rather high cost of performing this synthesis would not be justified unless the effect of this capsaicin derivative is considerable. This compound might be a little stronger compared to naturally derived capsaicin, but is it worth it? Plus, is this compound actually safe for topical application without blinding or disfiguring someone?

I would have thought compound 9, 4-aminomethyl-2-methoxypyridine-N-oxide, may actually be commercially available, but I didn't find it. Starting from here would make things a lot easier.

This reaction scheme would have to be considerably optimized and improved to make it cheaper before N-hydroxy-2-oxopyridyl-8-methyl-6-trans-nonenamide (the name of the capsaicin derivative) could be used. If this stuff is 10,000 times more powerful than natural capsaicin then I would say go for it.

I checked some of the principle authors other works to see if there was a follow up article. This journal was published 8 years ago after all. I was unable to find anything more about this compound.

Have a look at this (http://appft1.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.html&r=1&f=G&l=50&s1=%2220050085652%22.PGNR.&OS=DN/20050085652&RS=DN/20050085652) Mega and tell me what you think. Seems to start from a relatively basic precursor (3-methyl-butyne). I can't find the patent number for it though.....

Abstract:
Preparation and purification of synthetic capsaicin

The present invention provides methods for synthesizing the trans isomer of capsaicin and/or capsaicin-like compounds by utilizing a process wherein the trans geometry is set from the beginning of the synthesis reaction and carried through the entire synthesis process.

Your link don´t work. The patent number is US 2005/0085652 A1.
I have uploaded it here (http://rapidshare.com/files/42297580/US020050085652A1.rar.html)

I would think that using peppers would be one of the least efficient ways to extract capsaicin. Many medicines contain capsaicin as an active ingredient. It would stand to reason that capsaicin could be extracted from said medications via HCl without damaging the capsaicin. It would not be anywhere near as protracted as many of the pepper-based extractions mentioned earlier, and you wouldn't even have to worry about removing excess HCl. That could clear a room all by itself. My only concern is that such medication might not be over-the-counter or really expernsive.

Ok, well I have been thinking about this quiet a bit. I tried this method http://www.tomstrong.org/recipes/capsaicin.html and it worked to an extent. Anyways I was thinking of possibly making some kind of damaging gas with it. I've heard of people using cayenne powder, mixing with olive oil, and heating it. After heating it, add cold water, the resulting smoke/vapor is like tear gas.

Personally I haven't been stupid enough to try that. So how about an improvised weapon with capsaicin suspended in the olive oil ? Of course this is all assuming it's soluble in olive oil.

So I would think some kind of 2 layer design, the bottom layer containing something that burns really hot (I don't know many incendiaries). The top chamber would have a capsaicin/oil mix on top of a thin metal plate (thickness depending on the heating source). The heating source would go off, cook off the oil solution,and the fumes from that would probably be like being maced in the eye except all over your body, and by a gas.

Feel free to flame me, I think it's a feasible idea with some work.

Edit: I'm not the smartest person at 3am.

Of course this is all assuming it's not soluble in olive oil..i doubt it is because it's not soluble in water.

Do you mean soluble in olive oil?

If something was not soluble in water I would think it would be more likely to be soluble in oil.

I think I made a post about this somewhere....

I was making a stew and decided to fry some fresh, sliced habaneros in olive oil. To cut a long story short, the capsaicin in the chili's became air born, and then it made its way around the room, invading my eyes and lungs. Took about 15-20 minutes for the hacking and wheezing to fade after I left the room.

I ran a test to see if I could vaporise chili/capsaicin using just your usual KNO3/Sugar smoke mix.

The results were as I expected: The heat destroyed the capsaicin (it is organic after all)

My idea to prevent this from happening was basically this. You have a metal tube, with a metal sheet bisecting it in the middle (so if the tube is vertical, the sheet is horizontal). A small hole (or series of holes) are drilled in the sheet to allow the smoke to escape.

In the bottom chamber, pack in some of your preferred smoke mix. Personally, I'd use KNO3/Sugar with some bicarb to slow it right down. Then in the upper chamber, you have your capsaicin (that you've extracted using ethanol).

The main problem is here that as soon as the tube starts to warm up (or its just a hot day), it will melt and if there is any serious amount in there, it will just flow onto the bottom chamber, or out of the smoke device.

So thus, I propose this. The extracted capsaicin is mixed with candle wax then packed into the upper chamber, with a big hole through the middle (of the wax). This is to allow the smoke from the bottom chamber to pass by the capsaicin/wax mixture thus vaporising it without destroying it, and then pass out of the chamber. If done correctly, the smoke leaving the device would be cool enough that it doesn't auto-ignite and should be cool enough that it doesn't destroy the capsaicin as it passes by.

This device should produce clouds of white smoke that would be fairly unbearable to inhale.

That sounds like a good idea Alexires! I am going to test that out and take some pics. anyone know what this substance does when injected into the body?

Well, I don't have a digital camera, however I tested this. Instead of using the vertical chambers i tried a small one inside a large one. I had to improvise so I used 2 coke cans.

The larger on on the outside contained the capsaicin/oil mixture, while the one on the inside contained acetone, kerosene, and napalm (I did 3 trials). Another variable I tried was using vegetable oil, only olive oil worked.

Trial one (Napalm): The napalm didn't work, kind of expected that one. It was a weird config for it.

Trial two (Kerosene): The kerosene seemed to work and after about a minute and a half steam started coming out like oil on a skillet. I didn't inhale it..however I stuck the tip of my finger in it for around 15 seconds. I actually felt a little "buzz" on my finger but nothing painful. If inhaled i think it would be pretty painful, I'm debating on whether to use an animal for testing. I know sticking my finger in it was incredibly reckless and stupid, but I'll take some pain in the name of progression.

Trial three (Acetone): The acetone worked much the same as the kerosene, albeit a little bit better. Nothing bad just a little bit more of a "buzz". I really don't know how to describe the sensation.

Eventually I'm going to try the vertical chamber configuration, but only after I try working KN03/Saltpeter smoke bomb material into it, if anyone has suggestions please tell me. I used acetone to extract the capsaicin from habenero peppers.

A word of warning use gloves when handling capsaicin, even small amounts give away some pretty angry fumes (a few grams).