new MDMA homologs

[wungchow]

anyone ever tried making MDMA but with the benzene ring replaced by a thiophene ring? there's two possible places for the sulfur atom to be located. this could give rise to a whole range of substitutions.

see the attached picture

 

[Helios.]

Believe it or not, we are trying to mimick dopamine
(DA; 3,4-dihydroxyphenylethylamine) here.

Five-membered rings are poor substitutes for any DA receptor.

If you wan't to go heterocyclic, your only 6-membered option is pyridine which is long lasting but not as good as the phenyls.

I don't think pyrrillium is terribly stable. It certainly doesn't look that way.

 

[bigmac74]

Believe it or not, we are trying to mimick dopamine
(DA; 3,4-dihydroxyphenylethylamine) here.

Five-membered rings are poor substitutes for any DA receptor.

Surely all we care about is the DAT though, not the receptors.

If you wan't to go heterocyclic, your only 6-membered option is pyridine which is long lasting but not as good as the phenyls.

I don't think pyrrillium is terribly stable. It certainly doesn't look that way.

I'm not sure what pyrillium is, but what about MDMA with a pyrole substituted for the phenyl?

 

[Helios.]

DAT requires a 6 membered ring for optimal efficacy.
Pyrrilium is a 6 membered, aromatic ring with an oxygen with a plus charge on it.
I don't see how it could be stable as a methaphetamine, but stranger things have and will continue to happen.

 

[hussness]

anyone ever tried making MDMA but with the benzene ring replaced by a thiophene ring? there's two possible places for the sulfur atom to be located. this could give rise to a whole range of substitutions.

see the attached picture

I believe those are actually the same compound.

 

[BigBenn]

^^^Heh, true true

Turn the first one upside down and what do you get? The second one!

 

[MattPsy]

Why just DAT? We aren't going for a pure stimulant...
Aren't we aiming for SERT too?
(as well as NErT)

 

[Smyth]

Yeah, all helios meant though is that when we modify dopamine in a way that enables BBB penetration and helps by-pass MAO clearance we end up with MDA. The fact that this also has 5HT and NA activity is just part of the parcel I guess.