Dragendorff reagent: test for the presence of piperazine?

[Pans-Advocate]

I was browsing pillreports.com when I found this report:

http://www.pillreports.com/index.php?page=display_pill&id=22439

In the comments, someone makes a note that "Dragendorff reagent has only one reaction and produces an orange precipitate in the presence of secondary and tertiary amines. Both BZP and TFMPP are both 2* and 3* amines."

I did a quick YouTube search and came up with this video, in which a prepubescent kid with some chemistry know-how manufactures this reagent out of Pepto-Bismol, hydrochloric acid, and potassium iodide.

Is it reasonable to believe that using Dragendorff reagent to test pills can tell us whether or not the pills have piperazines in them? It looks like perhaps the presence of caffeine in a pill could confound this result, but I think there might be something important here ...

(Mods, please move if this isn't the right forum for this thread)

 

[socalthizzn]

i personally think that kid of full of shit.

 

[socalthizzn]

im going to make it right now, and i am going to test a bart simpson cut out and a purple biohazard both pipes, ill letu know.

 

[TearItDown]

im going to make it right now, and i am going to test a bart simpson cut out and a purple biohazard both pipes, ill letu know.

I'm really interested in the results. Post back soon

 

[AylaV]

Here's the issue

http://www.friedli.com/herbs/phytochem/alkaloids/alkaloid1.html

Dragendorff's reagent (solution of potassium bismuth iodide) gives orange coloured precipitate with alkaloids.

and

Alkaloids are basic - they form water soluble salts. Most alkaloids are well-defined crystalline substances which unite with acids to form salts.

The question isn't so much whether it will turn orange -- it should (as piperazines are very similar to piperadines -- a subclass of alkaloids). Dragendorff's reagent tells you whether something contains an alkaloid.

 

[LSDMDMA&AMP]

no no no. wouldnt it TELL you if its a secondary or tertiary amine? thats the point. so you could (after testing with other reagents) determine that its not just a few mg of MDxx to fool the tester and an active dose of pipes.

 

[AylaV]

hmm.. was doing a little more research on this =)

http://www.ncbi.nlm.nih.gov/pubmed/11793881

The sensitivity of this new CAR method is 2.5 to 15-times greater than that of conventional detection with Dragendorff reagent for some of the tertiary amines dimethylamphetamine, methylephedrine, levomepromazine, chlorpromazine, caffeine, theophylline, theobromine and nicotine. This present method provides rapid TLC detection of abused tertiary amino drugs such as phenethylamine, phenothiazine, xanthine derivative, nicotine and narcotics.

This may be talking about a newer method, but it references the "old" method of using Dragendorff to detect tertiary amines such as the ones listed above (one of which, theobromine happens to be the active substance in chocolate ).

As far as primary and secondary amines..

http://books.google.com/books?id=gA...onepage&q=dragendorff secondary amine&f=false

Primary and secondary amines are not (or only at high concentrations) detectable with Dragendorff's reagent. However treatment of such compounds with dimethyl sulfate . . . enables detection with Dragendorff's reagent to be achieved.

The thing is, though, that if you're adding dimethyl sulfate you're suddenly detecting everything.

 

[LSDMDMA&AMP]

dont add dimethyl sulfate then? THIS could completely kill off piperazines as a cut. or at least decrease the number. dont be so skeptical. have you ever been piped? it fucking sucks.

 

[AylaV]

dont add dimethyl sulfate then? THIS could completely kill off piperazines as a cut. or at least decrease the number. dont be so skeptical. have you ever been piped? it fucking sucks.

Quite honestly, we need to find out what kind of amine piperazines specifically are. If they're tertiary, then this will be great for testing for pipes. If they're secondary, we need to find something else.

 

[RGB]

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.

Quite honestly, we need to find out what kind of amine piperazines specifically are. If they're tertiary, then this will be great for testing for pipes. If they're secondary, we need to find something else.

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.

 

[Pans-Advocate]

There's another video on YouTube in which it is demonstrated that Dragendorff reagent reacts to the presence of alkaloids in concentrations as low as 5-10 parts per million.

I think this means that Dragendorff is basically a one-shot test for the presence of adulterants, in that, if you see a reaction, the pill is not pure. A pill that doesn't cause a positive Dragendorff test might still be adulterated, but if it does, it definitely is.

Only problem is that MDxx/caffeine pills will throw up red flags with this test ... but this is still a pretty important test to have in your arsenal. A lot of pipe pills could get screened out with this reagent, I'm pretty sure.

 

[socalthizzn]

I'm really interested in the results. Post back soon

warning!!!!!! it smells like shit to make dragendorf!!!!!! made me cough voilently wen i mixed it!

cutout -instant red swirl. 5 seconds red/brown tint. 10 seconds, blood color orange hue.


pokeball - instant red swirl 3 seconds full red red, 10 seconds dark brown center red outter, orange hue.


this shit works yo!!!!! i put my foot in my mouth!!!!!!

 

[Coolio]

What happens when you put a legit, MDMA-only pill in the reagent, socalthizzn? That's also important.

 

[socalthizzn]

Here's the issue

http://www.friedli.com/herbs/phytochem/alkaloids/alkaloid1.html



and



The question isn't so much whether it will turn orange -- it should (as piperazines are very similar to piperadines -- a subclass of alkaloids). Dragendorff's reagent tells you whether something contains an alkaloid.

my reaction with dragendorf was more of a red/ brown with an orange hue, is that normal or do u think i mixed it wrong?

 

[socalthizzn]

What happens when you put a legit, MDMA-only pill in the reagent, socalthizzn? That's also important.

honestly i dont have a ""pure" mdma pill... cleanest bean in my collection is a pokeball ....... wen i come across a known "pure" pill or molly for that matter i will most definatly aquire test and post here.



also for some reason my BL acct is fucked up, i cant post pics but should be allowed to with as many posts i have. mods tell me my acct is ok but for some reason still cant post any attachments

 

[AylaV]

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.

I was trying to figure out exactly how to determine primary, secondary, tertiary Thanks for clearing this up!! This is exciting news ^^

So BZP (the second image) has one hydrogen attached to the nitrogen, making it a tertiary amine. MDMA, the top image, appears to have none (if i'm interpreting this all correctly). This would mean that BZP would show up, but MDMA wouldn't, right?

 

[Coolio]

MDMA is a secondary amine. The nitrogen atom has two non-hydrogen (carbon) atoms attached to it, and one hydrogen atom.

MDA is a primary amine. The nitrogen atom only has one carbon atom bound, and two hydrogen atoms.

 

[LSDMDMA&AMP]

somenoe needs to contact dancesafe or eztest and get the word out.

 

[RGB]

So BZP (the second image) has one hydrogen attached to the nitrogen, making it a tertiary amine. MDMA, the top image, appears to have none (if i'm interpreting this all correctly). This would mean that BZP would show up, but MDMA wouldn't, right?

The nitrogen in the middle of BZP is a member of a tertiary amine group, because there are no hydrogens bound to it. The nitrogen on the other side of that ring is bound to one hydrogen, making it a member of a secondary amine group. In total, I'm not sure if it's appropriate to call it anything but an alkaloid since it contains both groups.

MDMA is a secondary amine, because the nitrogen is bound to one hydrogen. This image might make it a little more clear:

(A little general info: each node is a carbon unless otherwise indicated, and hydrogens are implied to fill up any remaining valence electrons. For instance, the rightmost carbon has three hydrogens attached to it in order to bind its three remaining valence electrons.)

Thanks for the detective work, socalthizzn. Your hands-on contribution is greatly appreciated. Anyway, this all makes me wonder specifically what Dragendorff is indicating...does it react in the presence of a compound containing both secondary and tertiary amine groups, or does it just react to some other property of alkaloids (acidity or something)? If it's a way to identify a compound consisting of secondary + tertiary amines, then I think we're in luck. As Pans-Advocate said, a lot of other common cuts are going to match this description, but at least good old MDMA/MDA won't. :D

 

[ShAYZoN]

This is awesome how is frodo regent made?