Interesting 3-ringed PEAs

[Morninggloryseed]

I was looking at the DRAGONFLY analogues, as well as 2C-G and family. It seems the 2C-G family is 'forgotten' and I can understand with the length of action....I have had access to 2C-G for some time, yet never desired to taste it. I was also facinated with the correlation between G-3 and DMMDA. That the loss of oxygens does not change potency, but does change the nature of the experience from psychedelic to entactogenic.

Then I came up with the idea of a "G-3-HEMIFLY." Here, we have a three ringed PEA (just like dragonfly) but things are moved around, oxygens are absent, and a MeO is added. I'd love to know the activity.

 

[fastandbulbous]

If you take G-3 and remove one of the methoxy groups, you have the IAP analogue of MMDA, which should give a pretty good impersonation of MMDA as MMDA has a lot more affinity for the 5HT2a receptor and the trimethylene ring only buggers up the dopaminergic activity of IAP, not it's serotonogic actions

 

[tobala]

Are these purely intellectual exercises or have they actually been synthesized?

I ask only because some structures may be difficult or impossible to turn into an actual molecule.

 

[MattPsy]

No, a variety of these derivatives have been made. They can be made. Difficult in some cases, but certainly possible.

 

[tobala]

^^^^ Cool!

 

[notornotFMAN]

5-methoxy-3,4-dimethylamphetamine.
4-ethyl-5-methoxy-3-methylamphetamine.

 

[MattPsy]

Those are not 3 ringed :/ . (At least I now have an amusing vision of a robot which goes about it's business and occasionally utters chemical names much to the confusion of others)

 

[Morninggloryseed]

?

I don't think I've seen the G-3-hemifly or the DMMDA-hemifly before in any paper. Thus the point of this thread. I'd be very interested to see if I am wrong.

 

[MattPsy]

No no, i'm just saying the same sort of chemistry required to make them has been done before for close relatives.

As you were, continue .

 

[Reminisant B]

I like the idea of testing IAP analogues. G-3-hemifly looks cool.


On a similar but different topic what about the di-methylenedioxy-PEAs. Like bromo-dragonfly but with two extra oxygens. 8)

 

[vecktor]

I like the idea of testing IAP analogues. G-3-hemifly looks cool.


On a similar but different topic what about the di-methylenedioxy-PEAs. Like bromo-dragonfly but with two extra oxygens. 8)

unfortunately the lone pairs appear not to point anti to one another and therefore the interaction with the 2a receptor will be weak at best.
I also have no idea how they could be synthesised.

 

[Morninggloryseed]

How about this? This would be another neat 'crossover' between the PEAs and IEAs. And if it were active, it could throw a twist in to the current theory of activity (as so well outlined by F%B in the Acid/Dragonfly thread.

 

[Acyl]

Those compounds certainly do look interesting on paper, perhaps they would look better as a fine powder don't you think? Synthesis and bioassay anyone? heh :D

With all thats been done so far with phenethylamines/indoles/etc, the surface has still only been scratched. This gets me very excited and gives me plenty of hope for the future..

God I love chemistry.

 

[Morninggloryseed]

Or even making the dihydroindol to 4,7-dimethoxyindol-5-ethylamine...a true cross-over.

How about this? This would be another neat 'crossover' between the PEAs and IEAs. And if it were active, it could throw a twist in to the current theory of activity (as so well outlined by F%B in the Acid/Dragonfly thread.

 

[Acyl]

I was wondering about that 4,5-dimethoxyindole-5-ethylamine heh.

 

[Morninggloryseed]

Impossible. You cant have a 5-methoxy and an 5-ethyl-2-amine...they are at the same place.

 

[Acyl]

i know... it was in your post before you corrected it..

maybe i imagined the 5 but i couldve sworn i saw it before i refreshed the page :S

 

[Morninggloryseed]

Oh, I did do a boo-boo. Fixed it, but I guess not soon enough.

 

[Morninggloryseed]

Here are two more interesting 2C-G-3 analogues. This one certainly (to me) seems to be the best of the whole series. I wonder what these would do. No reason to assume they are not active.

 

[Vanadium]

hey !

Nice idea ; I thing the magic 3-alkylated coumpouds might be more expored. I was thinking about a Cyclic analog of 2C-T-2 : un cross between 2C-G-3 and 2C-T-2 ; i'm dreaming about a new phenethylamine with the long peaceful effect of 2C-G-3 (as descripted in PiHKAL) with the magic activity of sulfur-atom in position number four ; but this is just a dream, of course .

Shulgin talk about others 3-methylated known-2C-x such as 3-Me-2C-E (2C-G-12), 3-Me-2C-B, ...

I Imagine other FLY's and hemi-FLY's molecules such as a cross between MDA and the IAP. A sort of cyco-PMA, perhaps which dont have the horrible side effects of PMA/PMMA.

Morning golry, you talking about a nitrogen as hetero atom in position 4 (2,3-dihydroindole ring). Nitrogen atom has some similarities with oxygen atom : good H-bond donnor but I would place it in the 2th or 5th position instead of a methoxy group.
I remeber a bluelighter tall he's ever seen an analog of DMT with an sulfur atom instead of the nitrogen in the indole ring (Benzothiophene ring), wich has psychedelic effects !