I Like to Draw Pictures of Random Molecules

[Transform]

Aye, but ergolines are at least a bit special, having chemical features of both tryptamines and phenethylamines?

 

[sekio]

Not neccesarily.

Even Shulgin himself pointed out, SAR is not always as simple as "Compound X plus group Y makes super potent compound XY, so compound Z plus group Y makes super potent compound ZY".

There is also the problem of diminishing returns one runs into. Compounds can only be made to bind so tightly before any changes you make to them decrease activity.

A huge part of LSD's activity comes not from the fact that it's "both a phenethylamine and a tryptamine" - that's mostly just fun trivia - but from the fact that the whole molecule is almost entirely flat and planar.

Another curio is that any modification of the amide seems to greatly decrease activity.

Another other thing to notice is the "phenethylamine" in LSD is a tertiary amine, a sure sign of doom in the traditional PEA world.

 

[countyourculture]

These were posted to Sasha's facebook page.

Thoughts?

 

[Sturnam]

These were posted to Sasha's facebook page.

Thoughts?

If I'm reading those letters correctly, none of those are even phenethylamines....not a single one has a nitrogen. And without that, no activity. Plus, for the second one, tert-butyl groups in the 4 position makes it inactive, and having hydroxyl groups instead of methoxies greatly reduces activity, although a 2-hydroxy might be ok.

So, no, no, and no. For several reasons.

 

[countyourculture]

I don't see an amine either. I'm interested simply because of the source.

 

[Epsilon Alpha]

Maybe they're prodrugs? I know he mentioned some compounds in nutmeg being activated by that mechanism. Or, they're just some random reagents he had laying around.

 

[sekio]

Jar on the far right is trans-isoapiole.

Other two are substituted hydroquinones

 

[F1n1shed]

um , que?

 

[sekio]

trans-isoapiole is a precursor for DMMDA
The other two are closely related to antioxidants like BHT & the quinones

 

[Limpet_Chicken]

Hydroquinones can also serve as start points in preparing such things as the 2Cs, etc.

 

[Transform]

If I recall, The Shulgin Index has information about quinones so it may be related to that.

 

[cannibalsnail]

Didn't he theorise about a new structure for hallucinogenic drugs derived from tetrahydroquinolines?

 

[2CBCB]

2c-b-fly-bro(madol)
I doubt it'd be active, but oh... if it were :3

 

[cannibalsnail]

You could create an unstable peroxide group by the amine which would cleave to an oxygenated amine leaving bromadol behind. The 2C-B-FLY-OH would metabolize to 2C-B-FLY. But the synthesis would be near impossible and for what reason?

 

[Transform]

So that you could OD while you enjoy your threshold dose of 2C-B-FLY, of course.

 

[2CBCB]

You guys had to ruin my fun

here's something a little more do-able, and potentially actually quite interesting.

 

[sekio]

Fairly sure the hydroxymethyl-BOMamines aren't active.

The FLY-NBOMe compounds, if I remember right, are actually less potent than the plain NBOMes.

 

[cannibalsnail]

Correct. The NBOMes were chosen BECAUSE they were the most active.

 

[2CBCB]

I screwed up and tacked the oxygen in the wrong place, meant for it to be NBOMe. I've had a severe lack of sleep this past week (broken mains-attached fire alarm bleeping every minute of every night and day, I cant rip it off the wall because the fucking thing will alert the local fire dept).

Didn't realize the FLY-NBOMe's were less potent though. Seen a few people attempting to put in for 2c-b-fly-NBOMe recently, their reasoning now eludes me if 2c-b-fly would simply be more potent and cost-effective... and it's legal, so its not an issue like that.

 

[irobeth]

I'm not good at SAR but I get impulses when I see molecules to make others

I don't know why I wanted a fluorine here

A symmetric conformationally restricted pregabalin?