novel chemical with MDMA-like action

[wungchow]

take a look at the hypothesized compound. the ring is planar and there's an oxygen in the 3-position (which I believe to be the requirement for MDMA-like activity.) plus it should rapidly cross the BBB.

 

[Riemann Zeta]

7 membered rings are generally not too stable. In this case, I would think a reaction would occur at the 5- or 7-position, giving an enol addition product. Also, the tropolone ring might prevent the compound from being a DAT/SERT substrate altogether.

 

[LuxEtVeritas]

Is that 3-oxo-methamphetamine?

 

[vecktor]

Is that 3-oxo-methamphetamine?

no its 3-2-methylaminopropyl tropolone (7 membered ring)

it would exist in equilibrium with the hydroxy enol form, the tropolone ring itself is really quite stable and is found in a large number of natural products, however one issue with the proposed molecule in addition to reaction at the position alpha to the keto group would be addition of amine across the ring, a well documented reaction which would majorly complicate any synthesis. I would expect the primary amine to dimerise.

I also thought that having the oxygen or nitrogen hydrogen bond acceptor para to the side chain was the SAR for mixed DA and SE releasers.

 

[kidamnesiac]

not really a para position on that thing is there?

you're also begging for Nu attack on that ketone/enol in a solution of h2o, that ring wouldn't stand a chance, as others have mentioned.

 

[vecktor]

not really a para position on that thing is there?

you're also begging for Nu attack on that ketone/enol in a solution of h2o, that ring wouldn't stand a chance, as others have mentioned.

I suppose the 'para' equivalent position would be one to the left (anticlockwise) of the current keto?? difficult with an odd number??

The tropolone ring is aromatic

 

[hussness]

Tropolones also have a pKa of about 7, so at physiological pH a lot of the molecule would be present as the zwitterion, which would impede absorption.

 

[LuxEtVeritas]

no its 3-2-methylaminopropyl tropolone (7 membered ring)

it would exist in equilibrium with the hydroxy enol form, the tropolone ring itself is really quite stable and is found in a large number of natural products, however one issue with the proposed molecule in addition to reaction at the position alpha to the keto group would be addition of amine across the ring, a well documented reaction which would majorly complicate any synthesis. I would expect the primary amine to dimerise.

I also thought that having the oxygen or nitrogen hydrogen bond acceptor para to the side chain was the SAR for mixed DA and SE releasers.

thanks ...duh...i had a spell, LOL

any idea if N,a-dimethylisobenzofuran-ethananmine (or benzofuran) would be at all an MDMA 'mimetic'?