Pure Caffeine Frequently Unanswered Questions This is not a FAQ, it's a collection of messages about pure caffeine from coffee, tea and caffeine tablets. These questions were not answered by the official Usenet Coffee and Caffeine FAQ: 1. Why do you need pure caffeine? 2. Why not just buy pure caffeine? 3. Can you smoke pure caffeine? 4. Can you snort pure caffeine? 5. Can you shoot up pure caffeine? 6. How do you extract pure caffeine? 6.1 The commercial decaffeinating process 6.2 Extracting from coffee 6.3 Extracting from Vivarins 6.4 Extracting from tea leaves This is for information purposes only. I don't claim that the methods described in this file are safe or complete. As usual, don't do anything you're going to regret. I will not take any responsibility for your actions. With thanks to all those who have answered my and other people's questions. ----------------------------------------------------------------------- 1. Why do you need pure caffeine? Answer: why would anyone want to swallow all the nasty byproducts in coffee, tea, cola, caffeine tablets or guarana capsules? ----------------------------------------------------------------------- 2. Why not just buy pure caffeine? Answer: most chemical supply houses don't sell to individuals. If you know otherwise, let us all know by sending a message to the appropriate news groups: alt.drugs.caffeine. ----------------------------------------------------------------------- 3. Can you smoke pure caffeine? Answer: read the (edited) message below ======== Subject: Re: smoking caffeine From: [b w hite] at [oucsace.cs.ohiou.edu] (William E. White ) (+) From: [j--n--r] at [cello.gina.calstate.edu] (Jason Kennerly) (-) In article <46p45b$[o 0 h] at [lyra.csx.cam.ac.uk]>, Jon Coppeard <[jc 217] at [cam.ac.uk]> wrote: >ryanmcra <[r--nm--a] at [mi.net]> wrote: >>Just for curiosities sake! What would happen if you crushed up some >>caffeine pills into a fine powder and rolled it up in a marijuana joint. + It wouldn't work too well, since caffeine pills contain a lot of + miscellaneous other shit than caffeine. If you want to smoke caffeine, + you need to extract it from caffeine pills, and convert it to free base + form (using NaOH). - Caffeine is present in most pills as the freebase - the exception - typically being the citrate. Using NaOH on it is a bad idea in any case. + Alternatively, you can keep it as an acid salt (citrate, hydrochloride, + whatever) and mix it with sodium hydrogen carbonate (baking soda) and + expect it to basify "on-the-fly" as it were. I'd trust the former route + more than the latter. + Anyway, you'd need to smoke it in a vaporization pipe, of the form used + to smoke DMT and other free base alkaloids. - Yeah - caffeine vapor is _quite flammable_ and so it can't be smoked - with a direct flame hit without inhaling quite a bit of burnt caffeine. >And then smoked it, I presume? I'm not sure about this but the caffine would >probably just burn and turn into something else - + Which is one of the problems with smoking w/o a vaporization pipe. >I doubt it would actually make it to your brain. + If you managed to vaporize it, it probably would. Generally you *don't* + want to smoke vapors of acid salts of alkaloids; acid salts are for + ingesting, sniffing, injecting, and rectal insertion. - Actually, quite a few HCl salts are "smokeable" and often just that - happens, for example methamphetamine HCl among illegal drug users. >If it did though, then you would get some of the effects of both >drugs which, since they have fairly opposite effects, would be >rather strange. + Caffeine and marijuana don't have opposite effects. Marijuana is an + anandamide ligand (nobody knows if it's an agonist or antagonist); + anandamide receptors aren't well understood but may be coupled to + arachidonic acid; possibly involved in second-messenger processes. + Caffeine, on the other hand, is an adenosine antagonist, and by blocking + adenosine at presynaptic receptors, it increases neurotransmitter release + in the applicable neurons (catecholaminergic mostly, probably also some + glutamate). >I don't know why you would want to do this... taking combinations of drugs >which have opposing effects is never a good thing because you won't get the >full effects of either. + Not true. It *can* be dangerous, depending on the combo. Methamphetamine + and diacetylmorphine (heroin), for example, is not inherently that much + more dangerous than the sum of its parts, but people tend to be stupid + and don't take into account that A) the effects of one drug can alter + the perception of the other, leading people to take more of the other, + and B) they don't metabolize at the same rate, so you can "run out" of + one and still be high on the other. ----------------------------------------------------------------------- 4. Can you snort pure caffeine? Answer: still a part from the previous message: + A friend of mine snorted pharmaceutical grade caffeine once; he said it + was extremely harsh on the nasal lining and not worth the buzz. - Because caffeine isn't all that potent - its difficult to get 600mg of - anything up into your nose without discomfort!!!! - 1,3,7-triproparagylxanthine might produce a more pleasant effect. - I prefer oral admistration of caffeine myself, and at that prefer the - slightly slower acting vivarin over NoDoz (which contains benzoic acid - and speeds its spread thru the body even if its just a preservative...) ----------------------------------------------------------------------- 5. Can you shoot up pure caffeine? Answer: It's probably not a good idea to put something directly in your veins unless it will not work orally. Even minor contaminations can be fatal. However, I'm not speaking from experience. If you have, or know someone who has, let us know in alt.drugs.caffeine. ----------------------------------------------------------------------- 6. How do you extract pure caffeine? Answer: Several solvents van be used, like aceton, ethyl ether, ethanol, chloroform or methylene chloride. Some of these substances are dangerouos to ingest. Carefully read the messages below. ----------------------------------------------------------------------- 6.1 Commercial decaffeinating process ======== Newsgroups: rec.food.drink.coffee Subject: Re: Decaffination processes From: [t w little] at [interserv.com] (Lazlo Toth) Date: Wed, 18 Oct 1995 20:42:52 GMT Here's how the direct method works: you soak the beans in water, and, while they are soaking, you flush the bean bath with methylene chloride, which bonds with the caffeine and is then removed from the water. The beans are left in the water to reabsorb any lost flavor elements. Now, there are those who say that the meth remaining in the beans is carcinogenic, etc. The meth, being volatile, is present in small quantities as the beans reach the roaster; once there, the intense heat of roasting burns off virtually all traces of the chemical. Fact: beans are roasted at temperatures in excess of 400 degrees F. Methylene chloride evaporates at 102 degrees. You be the judge. For those people who aren't sure, I'd be more concerned about the lead and heavy metals in my drinking water before I'd worry about meth in my coffee. Really. Where taste is concerned, I have had decaf by both processes, and I find that the Swiss Water Method removes some flavor from the beans. Water processed beans Many coffee lovers claim that decaf is unquestionably inferior to regular with regard to flavor, but, in reality, few can tell the difference when the playing field is otherwise level. I'll take my favorite coffee company's Sumatran Mandheling decaf and zing the tastebuds of anyone who says otherwise. Happy Cupping, Lazlo ======== Newsgroups: rec.food.drink.coffee Subject: Re: Decaffination processes From: [s--au--s] at [ix.netcom.com] (John Werner ) Date: 19 Oct 1995 11:20:05 GMT >>If exotic solvents are used is there really enough toxic residue >>to worry about? Inquiring minds want to know. in agreement with Barry: you'll find less than 1 part per 1.3 billion, you'll get more problems from your tap water in most parts of the country facts and general knowledge gained from sleeping on bags of decaf green coffee bags and the World Health Organization volume 51 detailing "Coffee, Mate, Tea, Methylxanthines and Methylglyoxal printed in 1991 in Lyon France which promotes the IARC Monographs on the evaluation of carcinogenic risks to humans. IARC is International Agency for Research on Cancer imho - worry more about getting struck by lightning or winning the lotto (you do have to buy a ticket, however) -- John Werner Stauf's Coffee Roasters Columbus OH 43212 USA 614.637.6828 ph 614.486.4475 fax ======== Newsgroups: alt.drugs.caffeine Subject: Re: commercial caffeine production From: [o cha] at [cnj.digex.net] (matthew e. harbowy) Date: Sun, 26 Nov 1995 18:52:32 GMT [jol t x] at [west.net] (Jolt-X) wrote: >Have you heard of any places that sell their leftover caffeine for >peanuts? Is there any way for John Doe to get 10 grams of caffeine for >himself? Technical caffeine (not for human consumption) is available from any chemical supplier. Food grade caffeine is available from some chemical companies, but they're not likely to sell to individuals. I understand that GF makes food-grade caffeine. >Also, is this decaffeinating process hard? Can some home chemist do it >or does it requie a lot of time and effert and it would be cheaper to buy >vivarin? It's actually easy, but *not* safe. Commercial caffeine is typically extracted using supercritical carbon dioxide, which is CO2 under high pressure such that it can become a liquid (regular CO2 only comes as a solid, very cold, or as a gas). Caffeine can be extracted using any of the solvents which dissolve caffeine well, such as ethyl acetate, chloroform, methylene chloride, carbon tet, etc. But do you really want such carcinogens in your body or air? Yep- it looks like vivarin is cheapest. matt Matthew E. Harbowy "I'm the bear that went over the mountain" http://www.cnj.digex.net/~o-cha/index.html ----------------------------------------------------------------------- 6.2 Caffeine from coffee, using alcohol From: [c--ig--m] at [ix.netcom.com] (Colin Bigam ) Date: 7 Oct 1995 18:55:47 GMT Okay, I guess I'm the only practicing (legally folks :-) chemist around here. You should be able to use almost any organic solvent to extract caffeine, but ethanol (drinking alcoho) is probably your best bet at home. Someone suggested ether, but even if you can get it, DON'T DO IT! It's too dangerous of a solvent to be playing with at home. (fumes knock you out, highly volotile, *extremely* flammable, forms explosive peroxides upon sitting, etc.) If you can buy it, use everclear which is 95% ethanol. Add it to your ground (finely) coffee and mull together, then filter off the solvent. Evaporate it down (carefully and slowly --EtOH is fairly flammable too) and you have crude caffeine extract. Don't use this stuff! Dissolve it up in a minimum of boiling vodka, (40-50% EtOH in water) reduce it to ~80% volume, and then let it cool. With luck you should be getting nice white crystals falling out of solution. (may take as much as a day or two, depending on how pure the extract was to begin with) If your crystals aren't _really_ white, filter them off, dissolve in hot vodka again, and recrystallise them again. Anything less than white (or clear, if you have really good crystals) means impurities, and you don't want impurities. ***WARNINGS (and a disclaimer): 1)Straight ethanol is flammable and dangerous, and the fumes can find their way to open flames if there are any around. They can also make you giddy and incapable of caution. (as can be seen at any local bar :-) 2) Other solvents can be used, but it's hard for the average guy on the street to get them in pure enough states to be safe. Industrial acetone (like you buy at auto stops), for instance, contains residues you don't want to put in your body. 3) For all I know, setting up a lab to extract legal substances with readily available materials and equipment may be illegal where you are. I don't even know if it would be legal here, although I can't imagine why not. 4) Caffeine, as others have pointed out, is dangerous in quantity, and can kill you in a _most_ unpleasant way. 5) I take absolutely *no* responsibility for what happens to you if you try any or all of the above. None! Really, though, it's probably both cheaper, easier, and more convenient to buy something like no-doz, unless it's illegal. (which it is in some places) Colin Bigam [c--ig--m] at [ix.netcom.com] [c--ig--m] at [signalpharm.com] ======== Subject: More extraction chemistry! From: [c--ig--m] at [ix.netcom.com] (Colin Bigam ) Date: 10 Oct 1995 06:02:42 GMT In <45a1fg$[1 kp] at [news.xs4all.nl]> [REDACTED] at [xs4all.nl] (Pierre Gielen) writes: >Do you have any idea what the residues in them are? One would expect >no harm of a little bit of coffee in the end product. Or is this >something else? While this is generally true, you may have something that reacts with ethanol to form nasties, etc. The basic rule of chemistry is if you don't know *exactly* what you have, (to <0.1%) don't eat it! :-) >Hm, with luck... I always thought of chemistry as an exact science :-) >Anyway, I still have two questions: See the bit about compounds oiling out below. Recrystallisation is definitely a luck-based art! >1. The alcohol will evaporate if you boil it. In the end you'll only >have boiling water. So why bother using wodka in the first place? Actually, if you boil vodka to half (or 1/4 or 1/32) volume, you'll have...vodka! Water and ethanol coevaporate, so the mixture remains constant. (within certain limits) >2. If caffeine is soluble in water (it is of course, or else we >wouldn't drink coffee), why do caffeine crystals fall out? I've never >noticed caffeine crystals falling out of cold coffee... The answer is that caffeine isn't all _that_ soluble in water, and is much more soluble in EtOH. What you want is to get something that is soluble enough to get all of the caffeine (and impurities) just into solution when hot (i.e. saturated), but won't hold it when cold. The caffeine falls out, but the impurities generally stay in solution because there's so little of them that they're not near a saturated solution. (This isn't precisely right, but close) Also, I never thought about it before, but it's possible (unlikely, but...) that caffeine _does_ fall out of solution in cold coffee. However, in a chemical witches brew like coffee is, it would almost certainly oil out, rather than crystalise, and it would just join with the scum and oils floating on the top. Hmmm... >I'll try the extraction, of course, but I'd also like to know what it >is that I'm doing. By the way, do you have any idea of the yield? >Let's see: about 50 grams of coffee per pot, gives you 10 cups x >100mg, that's 2%, a very inexact estimate indeed. I really have no idea, but at an absolutely wild guess, I'd say there's probably about 200mg to 250mg of caffeine in the grounds that produce a normal cup of coffee. I have no basis for this, other than a gut instinct, based on ~100mg soluble caffeine per cup. Some other notes: A few others have mentioned some ideas, some good and some bad. 1) Mix the solution of crude extract with decolourizing charcoal and filter it off. Great idea! I haven't used charcoal for a while because of my compounds, which is why I forgot it. 2) Do the extraction with industrial acetone. As I originally said, I really don't like this idea too much, for the same reason as I don't like the idea of using crude extract for human consumption. There's just no telling what's in the tar that gives the colour. (N.B. Even if you use acetone for the extraction, use vodka or water/everclear in some proportion to do the recrystallisation--it will almost definitely not work from acetone/water) 3) Methylene Chloride. Biggest complaint is that the stuff is nastier to our bodies than ethanol. (or acetone, for that matter) In the lab, this is generally a ways down in the list of desirable solvents to choose. 4) For the guy who ran an IR to prove purity, I'm afraid you didn't prove anything except that you got the stuff. IR is about the single worst indicator of purity there is. Chromatography, NMR, Mass Spec, are all valid to within certain limits, (some are very good) but IR is almost unique in being effectively useless at detecting less than 40% impurities. 5) Finally, the real LD50 of caffeine is 150mg/kg body weight, which for an average person comes to 10 or 12g. Weigh out ten grams of salt or sugar some day to get an order-of-magnitude idea of how much compound you're dealing with, and then realize that (very roughly) that much caffeine can kill you. Good luck, don't start a fire, and don't kill yourself. Colin [c--ig--m] at [ix.netcom.com] P.S. I _still_ don't take any responsibility for any of this! :-) ----------------------------------------------------------------------- 6.3 Purifying caffein from Vivarin tablets From: [z--y--x] at [bighorn.accessnv.com] (ZZYZX) Date: 8 Oct 1995 16:57:39 -0700 This isn't an extraction from coffee or tea, but (IMHO) it will give better yields and higher purity caffeine than any of the other methods I've seen posted to Usenet. A few years ago I did a project on caffeine extraction for chemistry class, and I eventually came up with a pretty good method. I used crushed Vivarin tablets as my starting material, and was able to get good yields (>80%) and very pure caffeine. The reason I chose to use Vivarin rather than some other OTC stimulant (e.g. No-Doz), is that No-Doz contains mannitol, which is really tough to separate from caffeine. The main inert ingredient in Vivarin is dextrose, which has different solubility characteristics than caffeine. Here is the procedure: Thoroughly crush 80 Vivarin tablets (two family packs if I remember correctly). You should crush/grind them until they are in a powder form. Not crushing them well enough will result in lower yields. Put this powder (which should be yellow) into a 1000mL beaker or other large glass container and to it add 800mL of acetone. Make sure it's at least technical grade acetone. The kind you can buy at the hardware store for thinning fiberglass resins works fine, just make sure there are no other ingredients. DO NOT use nail polish remover, as this often contains perfumes and other garbage. Never allow the acetone to come in contact with plastic, because it dissolves most plastics, and you probably don't want your product to be contaminated with plastic. Stir this mixture for about 20 minutes. It's wise to do this outside or in a fume hood, because besides not being great to breathe, acetone vapor is EXTREMELY FLAMMABLE! I accept no responsibility if you kill or injure yourself in any way because of this procedure. Allow the mixture to stand (preferably covered) for about an hour. During this time, the dextrose, which is insoluble in acetone, will settle to the bottom of the container, and the caffeine and food coloring will remain disssolved in the acetone. After an hour, CAREFULLY pour off (decant) the transparent yellow liquid into a suitable container, being sure not to allow any of the undissolved solid matter to go with it. A pipette works well for this, but it takes quite a bit longer. Add another 400mL or so of fresh acetone to the solid sludge in the bottom of the original container. Mix, allow to stand, and decant as before, and add the decanted liquid to the same container as the first stuff that you poured off. You might even want to do the mix-settle-decant process a third time with 400mL of fresh acetone, but it's not necessary. By this time most of the caffeine will be in the transparent yellow solution anyway. Discard the solid sludge in the bottom of the first container, as this is mostly dextrose. Filter the yellow liquid through filter paper, if available, or at least through 3 layers of coffee filters. Remember, NO PLASTIC! Allow the (completely transparent) solution, which looks very similar to urine, to evaporate entirely (outside). This can take a few days. Be careful not to put it close to any sources of ignition, and it's a good idea to shield it from leaves and twigs that might fall into it. You could also use a steam bath to evaporate it much more quickly, but that could be dangerous if it's not done right. After the acetone has evaporated completely, there should be a yellow solid in the bottom of the evaporation container. This is primarily caffeine, but contains some other compounds as well. You can quit at this point, if you don't mind "fairly" pure caffeine. If you want it more pure and/or the yellow coloring bothers you, then go on. Dissolve the above solid in room temperature, distilled, water, using as little water as possible. Filter this mixture. Add to the above solution a SMALL amount of powdered, activated charcoal. You can get this quite easily at any store that sells fish supplies, because it's used in aquarium filtration systems, but you will probably have to crush it up yourself. Stir it for about five minutes. If there is still any yellow in the solution, add more and stir, but try not to add too much, as it will adsorb the caffeine as well as the impurities. Add only enough to get rid of the yellow tint. When the solution has no more yellowish coloring to it, filter it (this needs to be done with filter paper to get all the charcoal out). Evaporate the resulting caffeine-water solution and you should have very pure caffeine. When I had perfected this process, I took a sample of the finished caffeine to school and tested it on the IR. It produced a very clean spectrum, which matched almost exactly with the textbook IR of caffeine. If you don't get the same kind of yields I did, try: 1. Crushing the tablets more thoroughly 2. Doing more extractions with the acetone 3. Using less activated charcoal I accept no responsibility for any damages incurred by this procedure or misuse of it's product. If anyone has any suggestions about how to improve this procedure, please let me know. I am interested to see if others get the same good results that I did, so if you try it, please e-mail me or post a followup. Have fun! ZZYZX ([z--y--x] at [accessnv.com]) ----------------------------------------------------------------------- 6.4 Extracting caffeine from tea This description is in German. If you don't understand this, read the summary towards the end of the message. From: "Torsten Otto" <[OTTO TORSTEN] at [erzicip.erzwiss.uni-hamburg.de]> Date: Thu, 2 Nov 1995 10:18:32 +100 Extraktion von Coffein aus Teeblaettern Ansatz: 25 g Teeblaetter 150 ml Ethanol (H3C-CH2OH) 12 g Magnesiumoxid (MgO) 50 ml Dichlormethan (H2CCl2) 15 ml Schwefelsaeure (H2SO4), c = 1 mol/l 5 ml Natronlauge (NaOH), c = 1 mol/l Vorschrift: Die zerkleinerten Teeblaetter werden in die Huelse eines Heissextraktors gegeben und 5 h mit dem Ethanol bei kraeftigem Rueckfluss extrahiert. Der alkoholische Auszug wird mit einer Aufschlaemmung des Magnesiumoxids in 75 ml Wasser versetzt und in einer Porzellanschale unter haeufigem Umruehren auf dem Dampfbad zur Trockne eingedampft. Der Rueckstand wird einmal mit 125 ml, dann noch dreimal mit 65 ml siedendem Wasser aufgekocht und heiss abgesaugt. Die vereinigten waessrigen Auszuege werden abgekuehlt, mit 15 ml Schwefelsaeure versetzt und im Vakuum auf etwa ein Drittel eingeengt. Wenn noetig, wird von einem sich bildenden flockigen Niederschlag heiss abfiltriert. Nach dem Ab- kuehlen wird fuenfmal mit je 10 ml Dichlormethan ausgeschuettelt. Die organischen Phasen werden gemeinsam zur Entfaerbung mit 5 ml Natronlauge, dann mit ebensoviel Wasser geschuettlet. Nach Entfernen des Loesungsmittels im Vakuum wird der Rueckstand aus wenig heissem Wasser umkristallisiert. Ausbeute : ca. 1,0 g Bemerkungen: Zur Reinigung kann auch im Wasserstrhlvakuum sublimiert werden (89 C, 15 mm Hg), da das Umkristallisieren auf Grund der nur erforderlichen geringen Wassermenge haeufig Schwierigkeiten bereitet. Gefaehrdung: Dichlormethan ist mindergiftig (Xn), Einatmen der Daempfe und Kontakt mit dem menschlichen Koerper vermeiden. Ethanol ist leichtentzuendlich (F), von offenen Flammen, WAErmequellen und Funken fernhalten. Entsorgung: Dichlormethan in Sammelbehaelter fuer halogenhaltige, organische Loesungsmittel. Die waessrigen Reaktionsloesungen sind vor der Entsorgung zu neutralisieren. Zeitaufwand: Apparaturaufbau 0,5 h Reaktionsdauer 5 h Aufarbeitung 4,5 h Well, there you go, that's it in German. Basics in English: Don't do it outside a lab. And you'll get 1 g out of 25 g tea leaves. If you're lucky. Put the crushed tealeaves in the extractor. Extract for 5 h with ethanol. Disperse the MgO in water and add to what you got. Dry. Boil with water (1x 125 ml, 3x 65 ml), and suck out. Let the liquid you got cool, add sulfuric acid, under vacuum get rid of two thirds. If necessary, get rid of solid stuff by filtering. After cooling, shake 5x with Dichlormethan (dichloromethane?). Shake organic phase with first NaOH, then water, so it's colorless. After destilling the solvent off, recrystallize from a little hot water. This is no way technical English. I don't know much of that, so I write it in a definitely colloquial style. You have the exact stuff in German, if it helps you. Again, I think this is more interesting than practically useful unless you have a lab at hand and know how to use it. And it's a lot of work for just a little result. And I wouldn't trust stuff I make myself to be really clean, not having the apparatus to test the purity, even if it SEEMS to be perfect. Actually, the stuff I got really looked like commercially bought caffeine and had the right melting temperature. I'll get a picture of the apparatus in separate mail. Hope this is of any use to you. ----------------------------------------------------------------------- Know anything that should be added to this file? Post an article to the Usenet news group alt.drugs.caffeine!