I understand that it has something to do with throwing a benzene ring into the fires of Mt. Doom, but you might want to consult with Gandalf on that one...
(I also thought the name was pretty amusing at first.
)
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Dragendorff reagent: test for the presence of piperazine?
- Thread starter Pans-Advocate
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I understand that it has something to do with throwing a benzene ring into the fires of Mt. Doom, but you might want to consult with Gandalf on that one...
(I also thought the name was pretty amusing at first.
) 
Jewel
Greenlighter
Good work, Pans-Advocate; I wasn't aware of this reagent until you mentioned it. This is definitely pretty exciting stuff. :D Makes me wish that I had a formal education in chemistry so that these things would be more obvious than amazing, heh. Oh, and yes, this will also raise a positive for caffeine, but I suppose that's not too terrible.
Alkaloids often contain multiple amine groups. In the case of the recreational piperazines, most contain both a secondary and tertiary amine group, but DBZP and MBZP only contain tertiary amine groups. I doubt those ones will show with the Dragendorff reagent, but at least BZP, TFMPP, and mCPP (the most common pipes afaik) will show up. By the way, you can tell if a compound has an amine group by looking for any nitrogen atoms. If the nitrogen has two hydrogens on it, it's a primary amine group. If it has one, it's a secondary amine group. No hydrogens means it's a tertiary amine, in which case the group's only contribution to the compound's chemical properties is the lone pair off of the nitrogen atom.
(By the way, if any of you chemists out there see anything wrong with this, please correct me -- I was taught chemistry by Wikipedia and constant pestering of my ex-chem. engineering girlfriend. 8))
To any of you who're thinking about trying this out, I recommend dissolving a crushed piece of a pill (doesn't have to be huge) in a test tube of distilled water, then adding 1mL of Dragendorff reagent. The reagent should change from its normal golden/golden-brown color to a more reddish tint, and in the presence of sufficient reactant will form an opaque precipitate. Also, the kid in the video is absolutely correct -- you can indeed make it that way.
The names primary, secondary and tertiary actually refer to the number of Carbon atoms the Nitrogen is bonded to, not the Hydrogen atoms. Amines are essentially ammonia + 1, 2 or 3 hydrocarbon groups in place of Hydrogen atoms. What makes the amine are the carbon groups, so they are what the naming is based on. For a primary one of the H's is removed from ammonia (NH3) and replaced with a C, for secondary 2 of the H's are replaced with C's, and in tertiary there are 3 C atoms attached to the N (and no hydrogen- N will usually have a maximum of 3 bonds). It's easier to remember and makes a little more sense to think of it as: Primary = 1 C, secondary = 2 and tertiary = 3.
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ShAYZoN
Bluelighter
magic beans
Greenlighter
now someone should market it and make it easy to obtain!
misterpicky
Bluelighter
- Joined
- Feb 4, 2010
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- 102
So, to summarize, will dragendoff reagent be able to test for piperazines in pills? Along with other tests of course, such as mecke, marquis, etc.
Jewel
Greenlighter
I could be wrong, but the problem here that I see is that it tests for 2nd and 3rd degree amines- but MDEA and MDMA both fall into that category (2nd degree)- MDA is a primary amine. So, if you have a pill that has both pipes and MDMA in it, and you test it with the usual reagents, and the Dragendorff, both will show up positive- but you won't know for which. Since a lot of pipes contain a little MDMA, most of the time this could lead to inaccurate results- you'll only be sure if all of the other reagents test negative for MDxx- though there are other drugs that are secondary and tertiary amines that could also show up and cause a reaction with this reagent. It's still a cool thing if it works at least somewhat, but it leaves a ton of room for error since it can't specifically test for piperazine and piperazine alone.
Roujaxian
Bluelighter
I think jewel wraps it up well. It is indeed very helpful but not the be all end all pipe test.
I am the one who posted the pill report in question. (lumptal)
<br>
Ok here we go: This is going to be long
I have been using Dragendorff reagent in the lab for years and it is one of the most useful and versatile reagents out there it’s been around probably for over 100 years. It is normally used for TLC plates to visualize spots after a run but since most ppl on here can’t just quickly run a TLC plate at home I’ll leave it at that.
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This is very important: when making dragendorff reagent you must use at least ACS pure reagents to get sensitive and reliable results. The homeschool way will not cut it and will go bad very fast. The reagent should not smell unless you add a lot of GAA then it will smell like acetic acid but it shouldn’t smell bad. You can alternatively use citric acid at 1g/10mL. The addition of sufficient acid is important because some pill fillers will show a black or darker spot that can confuse people who don’t have a lot of experience with the reagent. And the reaction is very obvious if you drop powder in and the powder itself turns orange that is a negative to be considered positive it should be an obvious cascading precipitate.
<br>
Dragendorff reagent tests for secondary and tertiary amines (explained earlier) very sensitively and selectively. A molecule can have one or the other or both and it will work (does not have to be an “alkaloid”). There are some exceptions to this rule like caffeine and some others. Caffeine will NOT react with dragendorff reagent. I’ve heard explanations as to why but I’ve tried it dozens of times and it does not react. The way it’s most useful is when pill testing all reagent tests come up negative except for possibly sometimes fizzleing in H2SO4 based reagents. The procedure is the same as it is with other reagents just scrape off some of the pill into the dragendorff reagent and observe the cascading precipitation of an orangey color change. This reagent is also very useful when a pill comes up all good(clean) with the basic reagents but you want to know if you have MDA(1’) or MDXX(2’) because if a precipitate forms you know you have MDXX if not its presumptive MDA.
<br>
The issue of mixed pipes-MD compound: There is the fizzing in >90% H2SO4 (but that’s not reliable really many things do that) but you can do an over oxidation test that I have developed that isn’t 100% accurate but can really help determine what’s going on. Lumptal’s Oxidative Odor Test: Dissolve KMnO4 until saturated into RT acidified ddiH2O and filter off the remaining crystals (be sure to stir for 10-15 minutes). Place 1-3 drops of Acidified KMnO4 solution into a shot glass and scrape off a small amount of a pill into the liquid. When pipes are present an obvious brown precipitate will form stirring may be required (sometimes with bubbles forming) within around 20 seconds. One of the reaction products of this reaction is benzaldehyde which has a characteristic odor of almonds. This smell indicates that BZP is presumptively in your pill and can be smelled at very very low concentrations especially when u cup ur hands around the shot glass and smell (usually not necessary tho). MDXX compounds will likely oxidize into 3,4-methylenedioxybenzaldehyde much much slower and the reaction products have a distinct characteristic floral aldehydey odor. You will probably have to get “pure” samples of each and memorize the smells created by the reaction for this to help you and be reliable but it’s a nice easy to obtain reagent. I have never had pure tfmpp so I donno what trifloromethylbenzaldehyde (or the chloro or etc etc) smells like but the mix of bzp and tfmpp still smells like almonds so I assume as long as the pipe has a heterocyclic benzene ring attached with at least 1 carbon in between the Piperazine it should give off a benzaldehyde (or benzaldehyde like) odor. I find with practice it’s very reliable. Just know what 3,4-methylenedioxybenzaldehyde smells like and if u don’t smell that then you might have problems. It will be fairly obvious when there is a mix of benzaldehyde and piperonal cause the benzaldehyde overpowers. You will have to correlate these smells with other reagent tests obviously to be sure no other adulterants might have benzaldehyde as an oxidative product (meth, amphetamine, even ephedrine and its derivatives will all give off the benzaldehyde odor the thing is they all come up on the other reagents so it could be useful to know…
<br>
I have been working on this problem since June and have come up with a few good reagents for testing pipes. There is a reagent that I have that I think may be selective for pipes only (well in the current state of e adulteration), but it requires 2 steps and a nonpolar organic solvent. Test takes about 10 minutes to complete. I’m going to keep trying to find material to test it out on but it works very well so far. (for those out there who know just think about what I said about benzaldehyde and you may be able to figure out where I’m going. I would want to market it forshure if I can prove it works. Problem is I would need to find a bunch of different pipes to prove it works for all the pipe derivatives blah blah.
BTW word on the street is within the next 10 days someone may start selling lab grade dragendorff reagent for TLC and other reagents for testing on that place where you bid on things soon.
<br>
Ok here we go: This is going to be long
I have been using Dragendorff reagent in the lab for years and it is one of the most useful and versatile reagents out there it’s been around probably for over 100 years. It is normally used for TLC plates to visualize spots after a run but since most ppl on here can’t just quickly run a TLC plate at home I’ll leave it at that.
<br>
This is very important: when making dragendorff reagent you must use at least ACS pure reagents to get sensitive and reliable results. The homeschool way will not cut it and will go bad very fast. The reagent should not smell unless you add a lot of GAA then it will smell like acetic acid but it shouldn’t smell bad. You can alternatively use citric acid at 1g/10mL. The addition of sufficient acid is important because some pill fillers will show a black or darker spot that can confuse people who don’t have a lot of experience with the reagent. And the reaction is very obvious if you drop powder in and the powder itself turns orange that is a negative to be considered positive it should be an obvious cascading precipitate.
<br>
Dragendorff reagent tests for secondary and tertiary amines (explained earlier) very sensitively and selectively. A molecule can have one or the other or both and it will work (does not have to be an “alkaloid”). There are some exceptions to this rule like caffeine and some others. Caffeine will NOT react with dragendorff reagent. I’ve heard explanations as to why but I’ve tried it dozens of times and it does not react. The way it’s most useful is when pill testing all reagent tests come up negative except for possibly sometimes fizzleing in H2SO4 based reagents. The procedure is the same as it is with other reagents just scrape off some of the pill into the dragendorff reagent and observe the cascading precipitation of an orangey color change. This reagent is also very useful when a pill comes up all good(clean) with the basic reagents but you want to know if you have MDA(1’) or MDXX(2’) because if a precipitate forms you know you have MDXX if not its presumptive MDA.
<br>
The issue of mixed pipes-MD compound: There is the fizzing in >90% H2SO4 (but that’s not reliable really many things do that) but you can do an over oxidation test that I have developed that isn’t 100% accurate but can really help determine what’s going on. Lumptal’s Oxidative Odor Test: Dissolve KMnO4 until saturated into RT acidified ddiH2O and filter off the remaining crystals (be sure to stir for 10-15 minutes). Place 1-3 drops of Acidified KMnO4 solution into a shot glass and scrape off a small amount of a pill into the liquid. When pipes are present an obvious brown precipitate will form stirring may be required (sometimes with bubbles forming) within around 20 seconds. One of the reaction products of this reaction is benzaldehyde which has a characteristic odor of almonds. This smell indicates that BZP is presumptively in your pill and can be smelled at very very low concentrations especially when u cup ur hands around the shot glass and smell (usually not necessary tho). MDXX compounds will likely oxidize into 3,4-methylenedioxybenzaldehyde much much slower and the reaction products have a distinct characteristic floral aldehydey odor. You will probably have to get “pure” samples of each and memorize the smells created by the reaction for this to help you and be reliable but it’s a nice easy to obtain reagent. I have never had pure tfmpp so I donno what trifloromethylbenzaldehyde (or the chloro or etc etc) smells like but the mix of bzp and tfmpp still smells like almonds so I assume as long as the pipe has a heterocyclic benzene ring attached with at least 1 carbon in between the Piperazine it should give off a benzaldehyde (or benzaldehyde like) odor. I find with practice it’s very reliable. Just know what 3,4-methylenedioxybenzaldehyde smells like and if u don’t smell that then you might have problems. It will be fairly obvious when there is a mix of benzaldehyde and piperonal cause the benzaldehyde overpowers. You will have to correlate these smells with other reagent tests obviously to be sure no other adulterants might have benzaldehyde as an oxidative product (meth, amphetamine, even ephedrine and its derivatives will all give off the benzaldehyde odor the thing is they all come up on the other reagents so it could be useful to know…
<br>
I have been working on this problem since June and have come up with a few good reagents for testing pipes. There is a reagent that I have that I think may be selective for pipes only (well in the current state of e adulteration), but it requires 2 steps and a nonpolar organic solvent. Test takes about 10 minutes to complete. I’m going to keep trying to find material to test it out on but it works very well so far. (for those out there who know just think about what I said about benzaldehyde and you may be able to figure out where I’m going. I would want to market it forshure if I can prove it works. Problem is I would need to find a bunch of different pipes to prove it works for all the pipe derivatives blah blah.
BTW word on the street is within the next 10 days someone may start selling lab grade dragendorff reagent for TLC and other reagents for testing on that place where you bid on things soon.
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of coarse I must note that other active compounds (ketamine) and many more have the nessisary ring that will produce the benzaldehyde like smell (2 chlorobenzaldehyde for ketamine which is described as smelling like benzaldehyde) so its kinda not that specific for pipes. but it does help.