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3,4-Methylenedioxycathinone

MagickalKat777

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Joined
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Okay so I found very very little on this substance. It isn't available that I know of but I'm curious what people think as to whether it would be promising to explore or not.

MDA is definitely superior to MDMA in my mind so the cathinone analog could prove to be superior to methylone, if my logic means anything.

Anyone have any idea as to the pharmacology of this one? I'm very very curious about it.
 
MDMA has both serotonergic and dopaminergic actions. Methylone does as well, but the dopaminergic activity is much more pronounced. MBDB is another closely related chemical, but its activity is mostly serotonergic. Some people have interpreted this situation as meaning that methylone and MBDB are "split halves" of the effects of MDMA, and have taken the two chemicals together in an attempt to recreate the pharmacology of MDMA. Whether or not the pharmacology of this mixture is comparable to MDMA is unknown, as is the safety of such mixtures.

-quoted from wikipedia

I'm not completely sure if this is accurate, but I hope this info helps.
 
Ohhhhhh crap, I'm sorry. I misread your post as 3,4 -Methlenedioxymethicathinone. I'll try to pull up some info if I can.
 
3,4-Methylenedioxycathinone would be just as instable as cathinone. it would dimerize if left standing or heated too much. synthing it is not something i would want to try. i think we would hear much more about it if it was easy to handle.
 
(I had to delete my previous post because for some reason, it freezes when I try to edit it)

I found something that looks fairly interesting.

http://www.drugs-forum.co.uk/forum/local_links.php?action=jump&id=559&catid=18

If you look at Table 1, it seems as though MDC (3,4-MDC) was the only chemical that caused a disruption in reporting behavior in the animals once 3mg/kg was tested. They even did it twice and a separate 3.5mg trial and couldn't get the animals to report right. Sounds like intoxication to me, wouldn't you agree?

‡Disruption of behavior; majority of animals failed to make $5 responses during the entire 2.5-min extinction session. The 3.0 mg/kg dose
was evaluated twice; in one case the three responding animals made 0, 75, and 90% of their responses on the drug-appropriate lever with response
rates of 3.6, 3.2, and 4.0 responses/min, respectively, whereas in the second case, the three responding animals made 43, 0, and 80% of
their responses in the same manner with response rates of 2.8, 4.8 and 8.0 responses/min, respectively.

Also in the same article, it says this:

Results with the
methylenedioxy derivatives of cathinone are quite interesting.
The cathinone counterpart, 3,4-methylenedioxycathinone or
MDC, failed to completely substitute for (1)amphetamine or
DOM (Tables 1 and 2). Thus, introduction of the carbonyl
group has changed the properties of the molecule so that it no
longer seems to function in the same manner as its parent (i.e.,
MDA). This represents a qualitative divergence in the structure–
activity relationships of amphetamine and cathinone.
The N-monomethyl derivative of MDA, MDMA, possesses
amphetamine-like character but lacks DOM-like properties
(10). N-Monomethylation of MDC affords an agent,
MDMC, that behaves in a similar fashion. That is, a (1)amphetamine
stimulus (Table 1), but not a DOM stimulus (Table
2), generalized to MDMC. In terms of amphetamine-like
activity, MDMC (ED50 5 10.1 mmol/kg) is similar in potency
to MDMA (ED50 5 7.5 mmol/kg) (Table 3). In this instance
then, the effect of introducing the carbonyl oxygen was simply
to slightly reduce amphetamine-like potency.
From the foregoing discussion it would seem that MDC no
longer behaves like MDA but that MDMC retains the amphetamine-
like character of MDMA. Interestingly, both
MDC and MDMC retain MDMA-like character (Table 2) in
that they completely substituted for MDMA
(i.e., they produced
.80% MDMA-appropriate responding) in MDMA-trained
rats. Because MDMC (ED50 5 1.6 mg/kg; 6.9 mmol/kg) was
about half as potent as MDMA itself (ED50 5 0.76 mg/kg;
3.5 mmol/kg) (12), it would seem that here, too, the effect of
carbonyl-oxygen introduction is to decrease potency
 
Black said:
3,4-Methylenedioxycathinone would be just as instable as cathinone. it would dimerize if left standing or heated too much. synthing it is not something i would want to try. i think we would hear much more about it if it was easy to handle.

What leads you to believe it would be unstable like cathinone? Wouldn't the methylenedioxy ring add some stability to it?
 
as the methylenedioxy ring does not sterically hinder the dimerization it comes down to whether the -I effect or the +M effect of the methylenedioxy group has a stronger effect on the carboyl-group. i've been trying to look that up but so far to no success. my org. chem. book says determining the reactivity in case like that is difficult, and i have not been successful in finding the pKa of piperonylic acid. if it were lower then the pKa of benzoic acid (which is a possibility), i would assume MDC to be even more prone to dimerization than cathinone due to lower electron density at the carbonyl-C.

or have i overseen anything?
 
From another paper:

"This activity, and the relative ease of synthesis, suggest a possibility of future clandestine laboratory production."(refering to MDCATH)

No mention of MDCATH dimerization.
 
MagickalKat777 said:
What leads you to believe it would be unstable like cathinone? Wouldn't the methylenedioxy ring add some stability to it?

Primary amines in close proximity to ketones tend to form dimers, eg, two stuck together copies of the same molecule (polymerization). The ketone group of the one cathinone gets stuck to the amine of the other cathinone, and vice-versa, rendering them inactive.

Cathinone dimer:
chemistry14.gif
 
^^how long does this reaction take to occour under ideal circumstances (frozen, protected from light and stored in an inert gas)?
 
MagickalKat777 said:
So what about methylone then? What makes methylone so much more stable?
The methyl on the nitrogen, making it not primary amine. And thanks for the explanation above, have seen Dr. Shulgin quoted that primary amines would be unstable next to a keystone, but the why I hadn't a clue.
 
But when it is in salt form it will of course not dimerize or degrade, only when it is in its freebase form. (Methcathinone will also degrade as the freebase.)
 
As I've been doing a fair amount of reading regarding various cathinones & MDMA analogues lately, this substance came to mind. Couldn't really find too much info on it aside from this thread. So would a 3,4 methylenedioxy-cathinone hcl, or similar salt dimerize or degrade at relatively low temp? Seems like there must be some probs with it, or we'd see it somewhere...
 
Yes, I know exactly what you mean. I would love to have the beta ketone analogue of MDA and even went looking for info on it a while ago.

All I ever came up with is that it is unstable and can't be formed or kept for a usable period. The beta ketones have to have an N-methyl to be stable I guess.

Kinda sucks though; I bet it would be a great material.
 
me too... I haven't totally lost hope yet though, there are plenty of good substances that just aren't available, and as the bk's are relatively recent, its entirely possible that its slipped through the cracks somehow. May ask about it over in ADD...
 
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