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shugenja said:
Bull

There are loads of trip reports identifying purple goo from bk-2c-b (dimerization) especially upon insufflation

here is one from BL

http://www.bluelight.org/vb/threads/694585-The-Big-amp-Dandy-K-2C-B-Thread-Part-1/page3
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Yes, because all the recreational users who snort the drug can tell if it's dimerised. I mean, yeah, definitely, they've got an NMR machine in their nose, or maybe their eyes have the world's best microscope which can view up to the angstrom. Definitely.

Also read that post carefully. "Storage in water seems to lead to polymerisation into a purple substance."

Stuff like this can definitely happen if stored in solution (especially for a long time). Once in solution, the crystal lattice breaks and the molecules are not fixed in an ordered structure anymore. They are free to move and collide with each other, and if they collide in the right orientation with the right energy, you will get a reaction. Even so, I'm doubtful as to whether the purple substance is the aldol self polymerisation product. Since bk-2-CB is basic itself, it might catalyse its own reaction (enamine type aldol catalysis) but still I think the bulky aromatic ring would slow down this reaction significantly.
 
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aced126 said:
Yes, because all the recreational users who snort the drug can tell if it's dimerised. I mean, yeah, definitely, they've got an NMR machine in their nose, or maybe their eyes have the world's best microscope which can view up to the angstrom. Definitely.

Also read that post carefully. "Storage in water seems to lead to polymerisation into a purple substance."

Stuff like this can definitely happen if stored in solution (especially for a long time). Once in solution, the crystal lattice breaks and the molecules are not fixed in an ordered structure anymore. They are free to move and collide with each other, and if they collide in the right orientation with the right energy, you will get a reaction. Even so, I'm doubtful as to whether the purple substance is the aldol self polymerisation product. Since bk-2-CB is basic itself, it might catalyse its own reaction (enamine type aldol catalysis) but still I think the bulky aromatic ring would slow down this reaction significantly.
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A nice archived discussion:

http://www.bluelight.org/vb/archive/index.php/t-694537-p-4.html

BTW -- tap water makes the dimerization reaction go fastest (a minute or 2)

reportedly vinegar reverses the dimerization


Lastly, my proposal was not that a possible reaction would result in a major product, but that a minor product could occur -- resulting in 5-10% of the dose converting to the hydroxy.

sp hybridization can result in (temporarily) 5 bonds at the beta-carbon --

if those 5 bonds are hydroxy (O), hydroxy (O) , Cl, carbon, carbon (as in the gem diol with a nucleophilic attack by the HCl) -- all I have to do is find a substitution that replaces the Cl with a Hydrogen (perhaps a simultaneous hydride shift with ejection of the halogen), and also where one hydroxy is lost as water (reacting with H3O+), but one is retained.

There is another possible pathway through the conjugate acid of the enol as well.
 
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Black said:
i already factored in the resonance stabilisation in my estimate above. all my points from that post above still stand, as well as the challenge for the corresponding equation that actually leads to an alcohol.


exactly what i was thinking.
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Because the ketone is a Lewis Base and H3O+ (H+) is a Lewis acid -- you can calculate all you want, and the ketone will still want to accept that H+ and break that pi bond regardless of pka (especially in an aqueous acid)

Perhaps you should do a little research regarding the special cases of electron donation and acceptance between Lewis acid-base pairs.
 
you do know that you have a simple brønsted acid when the electrophile is a H+? the lewis acid/base theory is a generalisation that's not needed here.

regardless of pka? wtf? the pka is exacly the equilibrium constant that describes that reaction!

this is really basic organic chemistry. it's certainly not me who has to do research here...
 
shugenja said:
sp hybridization can result in (temporarily) 5 bonds at the beta-carbon --

if those 5 bonds are hydroxy (O), hydroxy (O) , Cl, carbon, carbon (as in the gem diol with a nucleophilic attack by the HCl) -- all I have to do is find a substitution that replaces the Cl with a Hydrogen (perhaps a simultaneous hydride shift with ejection of the halogen), and also where one hydroxy is lost as water (reacting with H3O+), but one is retained.

There is another possible pathway through the conjugate acid of the enol as well.
Click to expand...

That could be the most illiterate paragraph I've read about organic chemistry (sorry). I strongly advise you actually spend time learning about it properly rather than wasting your time "finding a substitution that replaces the Cl with a hydrogen". And Black is correct, this is really really basic, stuff you learn in school even, let alone university.
 
aced126 said:
That could be the most illiterate paragraph I've read about organic chemistry (sorry). I strongly advise you actually spend time learning about it properly rather than wasting your time "finding a substitution that replaces the Cl with a hydrogen". And Black is correct, this is really really basic, stuff you learn in school even, let alone university.
Click to expand...


Are you denying that a ketone will form a gem diol in water?

Are you denying that a 5 bonded transitional state exists for carbon based on sp hybridization?

"In an SN2 there is simultaneous formation of the carbon-nucleophile bond and breaking of the carbon-leaving group bond, hence the reaction proceeds via a TS in which the central C is partially bonded to five groups.

Once again the leaving group is a water molecule formed by protonation of the -OH group." (that would be the OH reacting with an H3O+)

http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch04nucle.html


maybe you just forgot ....
 
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I'm all for the idea of not accepting what you're told and demanding evidence, but this, well this is a new level of stubbornness. Trust me when I say that what you're writing makes you look like a fool to anyone with a good grounding in chemistry, and it's obvious that you're trying to look smart by pulling out some random reactions you found on the internet which you obviously have no clue about. First get to grips with basic concepts like oxidation and reduction, and pKa. I couldn't be bothered to explain the plethora of reasons for why your recent posts simply aren't chemically coherent.
 
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