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    Krokodil Chemistry 
    #1
    Bluelighter Kenaz's Avatar
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    I've seen the reports, and have even covered the Coaxil and Krokodil epidemics in Russia on Opiated Shamanism. I know that Krokodil is synthesized using crushed codeine tablets combined with a number of readily available (even in the poorest and most remote regions of Russia) household chemicals, and that the end product is supposed to contain some quantity of desomorphine, which is 8x as strong as morphine but shorter acting.

    Alas, I don't have any idea as to which household chemicals are used or what is done during the various stages of krokodil brewing. And I've noticed some interesting contradictions in the news coverage.

    One Russian rehab doctor said that krokodil withdrawal lasts for over a month and is more painful than typical heroin withdrawal. Yet I was under the impression that short-acting opiates tend to have front-loaded withdrawals as opposed to i.e. methadone: the suffering up front is more intense, but the duration is shorter as the stuff leaves your body faster.

    The reports suggest that iodine is one ingredient in the mix, and red phosphorus is another. I've heard bleach mentioned by some, and others have suggested lithium batteries may be used ala the "Birch/Nazi" synthesis of methamphetamine. (It's not clear if the lithium is used as a catalyst or if the batteries contain thionyl chloride). And if gasoline or paint thinner is involved, I'm guessing one of the steps requires a polar solvent. But as you can see, I'm no chemist: I'm sure there are other readers here who know far more than I.

    I'm sure this stuff does horrible things to users, I'm also aware that I'm getting most of my reports from English translations of Russian articles -- not exactly the most reliable of sources. (Something similar appears to have happened with the reports of "Paco" and "Oxi" as "horrible deadly new designer drugs poisoning south America" -- so far as I can tell, it sounds like both are crudely refined coca paste, a drug which has been used in the region for a very long time indeed... )

    If we had a rough idea of what was in a krokodil cook's toolkit, we'd have a better idea of what was going in a krokodil user's veins. One Georgian BLer mentioned seeing krokodil/coaxil users shooting up using 15-20ml syringes. 20ml of a solution of pill particles in suspension injected using a massive needle could explain a lot of the problems, like brain damage caused by microstrokes and rotting necrosis throughout the body. But I'd like to know what else is going on.

    I don't need exact recipes: I'm aware of BL's rules about synth discussion. (And I'm not planning on trying any of these recipes, being as how I rather like my brain and my extremities). But any available information would be greatly appreciated.
     

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    #2
    Bluelight Crew allium's Avatar
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    One Russian rehab doctor said that krokodil withdrawal lasts for over a month and is more painful than typical heroin withdrawal.
    Sounds like typical media bullshit.
     

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    #3
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    If the synthesis really is just a messed up port of the Birch / HI-RP reaction then it's going to be one of the most messy and fucked up reaction mixtures possible, comparable to "shake and bake" street meth. Stay far, far away. There's going to be lots of fun impurities like iodocodeine, iodomorphine, hydrogen iodide, etc.

    The actual literature syntheses use thionyl chloride, which I don't exactly class as a household chemical. It's still not nice stuff to work with.
     

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    #4
    the article i read about the stuff stated that administration is by needle via skin popping, injecting right under the surface of the skin and not iv or im. that's supposedly what leads to the skin becoming green and scaly which leads to the name. as usual initial reports are somewhat sketchy on facts.
     

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    #5
    Bluelighter Kenaz's Avatar
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    Quote Originally Posted by cocoabud View Post
    the article i read about the stuff stated that administration is by needle via skin popping, injecting right under the surface of the skin and not iv or im. that's supposedly what leads to the skin becoming green and scaly which leads to the name. as usual initial reports are somewhat sketchy on facts.
    In one article I read, they were pretty clear that they were IVing, since one user said "if you miss (the vein), it's an abscess for sure."
     

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    #6
    ok. i read the article again. i was incorrect in that first post. there was a mention of skin popping as being similar to what is being seen with these users. my bad.
     

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    #7
    *shudder*
     

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    #8
    So a "krokodil hunter" is one who seeks Krokodil and Coaxil is not related Coaxial cables.
     

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    #9
    Bluelight Crew B9's Avatar
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    Quote Originally Posted by allium View Post
    Sounds like typical media bullshit.
    If there's degree of long term poisoning involved then perhaps recovery may take quite a while, it's probably not like withdrawal from a clean opiate - speculation obviously
     

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    Bluelighter rakketakke's Avatar
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    I wonder why they don't go for 14-Cinnamoyloxycodeinone. It's straighforward chemistry and it's potency is 100 (116?) times that from morphine...

    I don't think there is anything wrong with desomorphine and that all the media around is due to the iodine and other chemicals that are left behind because of sloppy synthesis. (most known are hydrogenation of a-chlorocodide (made with thionyl chloride and codeine) and subsequent demethylation of the dihydrodesoxycodeine-D to dihydrodesoxymorphine-D)

    I've looked into this chemical for quite a while but RP/I synthesis supposedly also leaves a mixture including the 2-iodo compound, methyldesorphine & all sorts of 3-deoxy relatives so that explains...

    http://www.springerlink.com/content/w763n75n05574561/

    I could upload this if you want...
    Last edited by rakketakke; 03-07-2011 at 13:07.
     

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    #11
    I guess it's because they can do it with available chemicals, cinnamoyl chloride might be a bit hard to come by. I agree there's probably nothing wrong with pure desomorphine as a drug, and the chlorination, hydrogenation, demethylation route probably gives pretty clean product, so I guess that's not how they're doing it.

    I wonder what happens in an HI reduction of an allylic alcohol, would HI add across the double bond after deoxygenation? I can't remember the mechanism of the benzylic deoxygenation, after conversion of OH->I... Wouldn't you also get some rearrangement to apocodeine with the hot HI? I guess free iodine is responsible for the 2-iodo derivative, it sounds like a mess.
    Last edited by skillet; 03-07-2011 at 14:54.
     

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    #12
    Bluelighter adder's Avatar
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    I got interested myself how they actually think what they get is desomorphine.

    But firstly, I must deny that desomorphine withdrawal lasts a month unlike morphine's or heroin's. I have injected >99% pure desomorphine HCl and the main difference is that it lasts shorter than either (morphine and heroin). I have heard and read a lot of misinformation about desomorphine and it really irritates me how this drug is seen now. It really is no different than pure morphine or pure heroin concerning addiction, tolerance, and toxicity if it's also a pharm grade product. What makes people taking "krokodil" literally rot and decay are substrates used in the crude process of synthesizing desomorphine along with a lot of side products (I haven't counted all possible but it goes into tens if you count in all 7,8-dichloro, 7,8-diiodo, 6-chloro etc. combinations and they possibly open the tetrahydrofuran ring so...).

    Chemicals they use (taken from a case info against a "drug dealer" of this) are: <brand name> tablets (1 tablet contains: 0.3g methamizole, 0.1g naproxen, 50mg caffeine, phenobarbital 10mg, codeine 8mg) or <brand name> (all the same but without naproxen), iodine, formic acid ethanol solution (all of these are OTC in Russian pharmacies), or <brand name> (0.3g paracetamol, 0.15g methamizole, 50mg caffeine, phenobarbital 15mg, codeine 10mg), or others (there are many), petroleum, and red phosphorus (and some chlorinating agent? but what? I don't think SOCl2 lies on the street...).

    And shoot me but even being a chemist I couldn't really synthesize desomorphine and PURIFY it having any tablets containing codeine + something and chemicals I listed. This calls for pure codeine salt to start with.

    What I think is they don't really get rid of 6-OH in high %, most is probably 6-Cl and the drug they get high off is mainly α-chloromorphide. Yet, where's the chlorinating agent? There's nothing about thionyl chloride. In this case, then they get high off α-iodomorphide and numerous other side products that have some opioid activity.
    Last edited by adder; 06-07-2011 at 11:03. Reason: I decided to delete medicines names.
     

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    #13
    Bluelight Crew allium's Avatar
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    Quote Originally Posted by B9 View Post
    If there's degree of long term poisoning involved then perhaps recovery may take quite a while, it's probably not like withdrawal from a clean opiate - speculation obviously
    You may be right, but media tend to say that every drug is worse than heroin.
    Smoking blends? As dangerous as heroin.
    Bath salts? 5x more addictive comparing to heroin.
    Poppy seeds? Junkies can make dangerous drug from it by mixing them with acetic anhydride. Sure, we need prohibit them.

    Sorry for this offtopic.
     

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    #14
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    I agree the media are sensationalist but just thought that it is possible that the illness resulting could take some time to get well from - I mean if the reports are actually true I think that you'd feel unwell for a fairly long time. Knee jerk reactions at each end of the spectrum aren't that useful stereotypical media breeds stereotypical drug aficionado - sometimes.
    You could well be correct tho.
     

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    #15
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    Yet, where's the chlorinating agent? There's nothing about thionyl chloride. In this case, then they get high off α-iodomorphide and numerous other side products that have some opioid activity.
    I think that's what the iodine is for - who needs chlorine as a leaving group when you have iodine?
    It would be trivial to add some table salt to the rxn broth (containing, among other things, HI) and generate HCl in the right conditions, methinks. (-> PCl3 etc)
     

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    #16
    It's the double bond that gets me, if it is actually possible to produce desomorphine by this route, can the double bond be fully reduced with HI? I mean I can see that HI could add across the double bond, and the alkyl iodide could possible be reduced by whatever mechanism HI reduces benzyl iodides (someone help me out here with the mechanism).

    Like Adder said, who's to say this stuff actually contains desomorpine in any amount?
     

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    #17
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    It obviously contains enough active opiate to get an effect.
     

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    #18
    Bluelighter rakketakke's Avatar
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    Quote Originally Posted by adder View Post
    I got interested myself how they actually think what they get is desomorphine.

    But firstly, I must deny that desomorphine withdrawal lasts a month unlike morphine's or heroin's. I have injected >99% pure desomorphine HCl and the main difference is that it lasts shorter than either (morphine and heroin). I have heard and read a lot of misinformation about desomorphine and it really irritates me how this drug is seen now. It really is no different than pure morphine or pure heroin concerning addiction, tolerance, and toxicity if it's also a pharm grade product. What makes people taking "krokodil" literally rot and decay are substrates used in the crude process of synthesizing desomorphine along with a lot of side products (I haven't counted all possible but it goes into tens if you count in all 7,8-dichloro, 7,8-diiodo, 6-chloro etc. combinations and they possibly open the tetrahydrofuran ring so...).

    Chemicals they use (taken from a case info against a "drug dealer" of this) are: <brand name> tablets (1 tablet contains: 0.3g methamizole, 0.1g naproxen, 50mg caffeine, phenobarbital 10mg, codeine 8mg) or <brand name> (all the same but without naproxen), iodine, formic acid ethanol solution (all of these are OTC in Russian pharmacies), or <brand name> (0.3g paracetamol, 0.15g methamizole, 50mg caffeine, phenobarbital 15mg, codeine 10mg), or others (there are many), petroleum, and red phosphorus (and some chlorinating agent? but what? I don't think SOCl2 lies on the street...).

    And shoot me but even being a chemist I couldn't really synthesize desomorphine and PURIFY it having any tablets containing codeine + something and chemicals I listed. This calls for pure codeine salt to start with.

    What I think is they don't really get rid of 6-OH in high %, most is probably 6-Cl and the drug they get high off is mainly α-chloromorphide. Yet, where's the chlorinating agent? There's nothing about thionyl chloride. In this case, then they get high off α-iodomorphide and numerous other side products that have some opioid activity.
    Well the iodo compounds can be separated on a column of AC on alumina, elute the alks with ammonia in ethanol or methanol... I suppose to purify the desomorphine, you could dissolve the products in water, and heat the solution to 50 C until the water evaporates.

    You're not alone, I can get pretty frustrated at all the "krokodil" threads whilst there is nothing inherently wrong with desomorphine.hcl ... Could you elaborate a bit (out of personal experience preferably) on it's pharmacology. You say it's inbetween morphine/heroin, any diffirent effects that pronounce themselves more thoroughly?

    And tablets like that are OTC in Russia? Funny country

    Cheers
     

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    #19
    Bluelighter adder's Avatar
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    Yes, there are many brand names with similar set of active ingredients in Russia and post-Soviet countries (e.g. in Ukraine there are the very same medicines). To compare this with the most widely used brand name (I guess), I can say that the very same brand name in Poland consists ONLY of methamizole (and there are no options like "Plus", "Extra" or anything that would boost methamizole with codeine).

    I'm definitely not saying that one couldn't halogenate with some iodo compound instead of chloro compound and finish with desomorphine. But let's look at the few minutes before the start of "brewing" "krokodil". A person leaves the pharmacy with a drug containing minute amount of codeine, I2, and formic acid ethanol solution. Then goes to buy industrial grade petrol and eventually finds oneself in some apartment (I don't know about the red phosphorus, are they getting it from matches?). Anyway, the whole process includes putting it all on a gas cooker (no temperature control).

    Sure, they don't really need to goof around with some batteries. Having iodine, they can produce α-iodocodide and HI(aq) will definitely demethylate at position 3, so they also get α-iodomorphide. But the whole process also makes iodine add at 7 and 8 just like any halogen (not to mention they also get some 1-iodo and 2-iodo compounds but this doesn't make the compounds inactive). But they expect HI(aq) to do 3 things: 1) get rid of iodine atoms at 7 and 8 so they get a "dihydro" compound (the way they do it, probably puts back a double bond there, formation of methyldesorphine as a side product only proves that), 2) demethylate at 3 (and that's actually the only sure thing to happen but hot concentrated acid like that will easily open the tetrahydrofuran ring and this is all boiling! even hot conc. HCl(aq) will open this ring; so they lose the activity down to 10% if the opening happens), and 3) dehalogenate at 6. (this can happen, HI can exchange for HCl, but they use no catalyst so the yield for desomorphine is very low, I guess the compound was found in this red-brown solution they inject but still...). There's some overreduction, I think. And hot acid is probably both their friend and their foe in this process.

    Concerning desomorphine subjective effects, well, they're not like in between morphine and heroin. It hits faster than morphine but I haven't noticed "the bang" to be of heroin's type (for me it's like being hit suddenly by a hammer in a few seconds after the injection and almost none peripheral effects). But at the same time it definitely lacked the feeling of being wrapped in some cotton-like cocoon morphine always gave me (I do/did like the "pins & needles"). Also, it felt less like "a key to the paradise", I don't mean it didn't sedate me and it didn't give me euphoria but it lacked some kind of character just as many stronger than morphine opioid drugs do (N-phenethylnormorphine is another example despite its power). IMO, it's a matter of MOR/KOR and MOR/DOR agonist ratios and those semi-synthetics get "speedier" and are less peripheral acting, morphine biases this perfectly IMHO. It's also shorter acting and that I can tell for sure because I was really addicted to morphine at that time and while morphine could leave me "satisfied" for like 6 hours, with desomorphine the change was like by 25% to its disadvantage. I don't think one can earn something here thanks to cross-tolerance or rather its partial lack. I felt it was like 1:8 morphine to desomorphine.

    Nonetheless, I can understand how people using this don't stop even if the main compound they get high off is something like α-iodomorphide, besides they get an effect of synergy. But one thing I can't understand why there's a second time. Rotting starts after the first shot after all because of substrates and solvents used. It's like the spot used is damaged right away. But really, even if heroin is cheap in Russia when the price is given in $, this is far from affordable for Russian people who are good if they monthly earn money 1g of heroin is worth there. And the price of 1g somewhere near Chelyabinsk may really be as low as 100 rubles for a shot (this means 0.25g but I don't know current situation, prices go up both in Russia and in countries to which heroin is delivered through "the Northern Path").
     

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    #20
    They have some really funky OTC and semi-OTCs over there don't they.

    I sometimes shop for nootropics from russki sites, not to get into source discussion, but their take on memory disorders and fatigue, etc, is quite progressive compared to here in the UK or other western european countries. Here there is nothing in the way of medication for memory disorders, nothing at all, unless you have advanced dementia or alzheimer's, even then its dependent on the primary care trust whos area you live in, if you get anything at all.

    As for SOCl2 not being available....that isn't the case. It wouldn't surprise me if they were draining it from batteries, as there is a kind of battery that uses Li and thionyl chloride, I've opened them up when I was younger and some happened to be found in a power supply in a long abandoned industrial complex of some sort. There is a fair bit of thionyl chloride in those batteries actually, or there can be, at least in the large ones I found (they were around the size of the big zinc-carbon cells that occur in 4-packs in those large batteries with the spring type contacts on the ends, the big bulky square things)
     

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    #21
    Bluelighter adder's Avatar
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    Yeah, I know about these batteries and I guess along with industrial petroleum they are the source of heavy metals found in the solution they use. What has been found in the greatest amounts seems to back up this theory. Some time ago I did a few sketches of possible reactions taking place (that's my source of the probable summary amount of side products) and knowing I2 won't dissolve in water, I'm rather leaning toward the usage of SOCl2 in this process. And the source of it given on some Russians sites is lithium batteries indeed (SOCl2 plays a role of a liquid cathode and some salt of lithium plays a role of an electrolyte). Anyway, like you stated above, you had found such batteries in an abandoned complex, such Li-SOCl2 batteries aren't rather found in some devices of daily use. So I'm guessing people who go through this process might get such batteries from some facilities. But here's another problem - there are a few varieties of lithium batteries and some contain toxic compounds like bromine (I) chloride.

    Concerning various OTC findings in Russia, well they also seem to keep quite a lot of drugs Western countries ceased to use long time ago. A lot of them are exported to Ukraine. The other thing is how prescriptions are important in "the Western world" and in the post-Soviet republics and Russia itself. One can easily get such drugs like phenazepam, gidazepam, or even a barbiturate - benzobarbital in 100mg or 50mg pills (terribly long-acting, something along the lines of phenobarbital) - without having a prescription. It's just a matter of the pharmacy you enter and the person who's behind the counter.

    But I have heard that methadone began to be used in Ukraine in detoxes a few years ago. It's definitely not the main target country, it's more of a transit country but in recent years drug market has grown. I wonder to what scale the substitution maintenance treatment is implemented now but it's a good sign. Nonetheless, I don't think all of the people in need for help will get it from the country. It reminds me a lot of the situation in Poland. We first got an experimental program in the neuropsychiatric hospital in Warsaw (10 participants at the very beginning?). Now, we've got 15 such centers but 1/3 of them are in Warsaw. I live not far from Warsaw so when I was turned down in my city I decided to give it a shot in Warsaw. Nothing, I still have to get it from the street from junkies who get it for free and drink the syrup only when they didn't manage to sell it and get enough money for heroin (and its price has gone up recently with the quality going down).
     

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    #22
    Too much synthesis discussion, I'm closing this
     

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