New Heteroatoms For 4-Substituted 2,5-Dimethoxyphenethylamines

[Morninggloryseed]

So I saw a picture of a crystal of bismuth (ingredient in pepto bismol) and noted how awsome they looked.

And then I thought it would be neat to incooperate that into a psychedelic. Sure enough I looked at the periodic table, and noted that nitrogen and phosphorus were in the same row. Both elements found in friendly, neighborhood psychedelics. So I thought about making a psychedelic with bismuth, because wouldn't it be awsome to trip on something so pretty!

Then just today, I was reading about 2C-T-13 and read Shulgin say....

Most of the synthetic adventures of putting a basic something aways out from the benzene ring, at the four-position, have involved subtle things such as unsaturated bonds or three-membered rings. This was the first try with the actual use of a different atom (an oxygen). What about other heteroatoms such as sulfur or nitrogen or silicon or phosphorus, or some-such?

Low and behold, phosphorus and nitrogen are in the same row as bismuth! So I am thinking, this may actually work.

Here are a few obvious bismuth analogues I came up with.....

Personally, I'd put my money on D and G being active. But you guys who have real knowledge of pharmocology, neuropharmocology, and chemistry...what do you think of the prospects of these?

 

[Dave]

They look interesting, but one thing of note from a chemical standpoint is that the larger an atom is the less likely it will form multiple bonds. In a nutshell, the filled non-valence electron shells are so fat, that the pi orbitals (which are required to overlap to form multiple bonds) will not sufficiently overlap. So either the pi bond will not be formed, or will be so weak that it would break at room temp. So D and G would be very unstable (if not impossible to synth).

Granted, this is not 100% certain. Personally I think that this would be the case, but that doesn't necessarily mean much from someone specializing in inorganic chem

Oh, and as a postscript-- chances are the final product would still be a white crystalline powder.

 

[fastandbulbous]

An atom the size of bismuth had chance to be so big that it wouldn't 'fit' into the space in the receptor. If you consider that a group bigger thyan propyl hcauses a rapid drop in potency, something the size of bismuth had chance to be inactive

 

[Morninggloryseed]

^^^^^^^^

That's a good point, but then again molecules like 2C-G-5, 2C-G-N, 2C-T-9, 2C-T-22, and others are pretty "big" at that end as well. I guess there is only one real way to find out.

 

[indelibleface]

By the way, that website is definitely incredible. If I won the lottery and had money to throw away, I'd definitely buy one of those displays. Being a chemistry nut like I am, it'd definitely be a cool art piece of sorts.

 

[Angelus]

i am def getting one of those when i have some $$ to throw around.

 

[fastandbulbous]

That's a good point, but then again molecules like 2C-G-5, 2C-G-N, 2C-T-9, 2C-T-22, and others are pretty "big" at that end as well. I guess there is only one real way to find out.

Still a lot smaller than an atom of bismuth