I Like to Draw Pictures of Random Molecules

[Solipsis]

The difference is Nitrogen forms more stable bonds with oxygen and carbon then Phosphorus does - look at the rapid metabolism of psilocybin.

That is not really a fair comparison is it? In psilocybin it is a phosphoryl ester, and it is one in 3C-PO as well. In 2C-N there is no oxygen and certainly no ester.
The point is that other esters like acetoxies are also readily cleaved but it says nothing about the carbon that is there in the acetoxy, which would bind quite strongly to another carbon.

By the way that phosphate is missing an oxygen

 

[DL-ark]

How about this ether of 2-cb molecules? Am I correct in think that this should be metabolized into two 2-cb molecules?

And how about a giant thread of these hooked together as ethers (kind of)

http://i.imgur.com/cd02f5q.png

I'll let you click the link to see it, as it is pretty giant and ISN'T an ester as I thought.
We can weave this stuff into clothing, or make 2-cb blotter paper. Paper that is actual 2cb.

 

[black53]

if this actually gets split in to 2x 2c-b it would be legal here since it's not a classic ester

 

[N0 W4RN1NG]

That is not really a fair comparison is it? In psilocybin it is a phosphoryl ester, and it is one in 3C-PO as well. In 2C-N there is no oxygen and certainly no ester.
The point is that other esters like acetoxies are also readily cleaved but it says nothing about the carbon that is there in the acetoxy, which would bind quite strongly to another carbon.

By the way that phosphate is missing an oxygen

I think you misunderstand me - I was simply telling him that, like you said, 3C-PO would rapidly be cleaved into 3C-OH. I never questioned carbons' ability to bind to carbon, haha.

Also, 2C-N *does* have two oxygens...it is a nitro group, not an amino group:

An amino group would be too hydrophobic to bind to 5HT2x, and therefore probably be inactive.

In addition, I believe in "3C-PO", it would be an ETHER, not Ester.

And technically his 3C-PO is ok without an additional oxygen, note the 2 double bonds, not single bonds - all orbitals are used correctly.

EDIT: @ DL- ark and black53, those are not esters actually, DL-ark yours is an ether, Black53 yours is a simple ketone(I know black, you didn't say yours WAS an ester), and both of them would have less-than-ideal conversion into 2C-B...and who knows what the parent compound would do inside the body.

THIS would be an ideal pro-drug into 2C-B, although you would have to be very careful to keep it out of the heat, etc:

Incidentally, that IS an ester, lol.

EDIT2: Actually, yours would not convert into 2C-B at all, you joined the structures at the alpha carbon instead of at the amine. If you wanted to bridge them that way, you could do this:

^Also an ETHER, not an ester...It would break down into 1 (2C-B) and 1 (alpha-hydroxy-2C-B), though.

 

[DL-ark]

I think you misunderstand me - I was simply telling him that, like you said, 3C-PO would rapidly be cleaved into 3C-OH. I never questioned carbons' ability to bind to carbon, haha.

Also, 2C-N *does* have two oxygens...it is a nitro group, not an amino group:

An amino group would be too hydrophobic to bind to 5HT2x, and therefore probably be inactive.

In addition, I believe in "3C-PO", it would be an ETHER, not Ester.

And technically his 3C-PO is ok without an additional oxygen, note the 2 double bonds, not single bonds - all orbitals are used correctly.

EDIT: @ DL- ark and black53, those are not esters actually, DL-ark yours is an ether, Black53 yours is a urea(I know black, you didn't say yours WAS an ester), and both of them would have less-than-ideal conversion into 2C-B...and who knows what the parent compound would do inside the body.

THIS would be an ideal pro-drug into 2C-B, although you would have to be very careful to keep it out of the heat, etc:

Incidentally, that IS an ester, lol.

Woops, sorry.. Guess I got the oxygens confused with carbons.

Because 2cb is already relatively stable by itself, would this 2cb ester be more or less as stable as LSD?

 

[N0 W4RN1NG]

...would this 2cb ester be more or less as stable as LSD?

Less, I think. :/

 

[DL-ark]

Less, I think. :/

But then wouldn't it just break down to 2cb or would be it be something else like N-Hydroxy 2cb

 

[N0 W4RN1NG]

It would break down into N-Hydroxy-2C-B (HOB), which in turn would be quickly metabolized in the gut to regular 2C-B.

A fair portion of it would probably break down directly into 2C-B as well, actually.

 

[DL-ark]

It would break down into N-Hydroxy-2C-B (HOB), which in turn would be quickly metabolized in the gut to regular 2C-B.

A fair portion of it would probably break down directly into 2C-B as well, actually.

Sooo.... Problem solved?

edit: also I wasn't completely wrong for once, hooray!

 

[N0 W4RN1NG]

^ Yeah, but the problem here could be that small amounts could degrade into 2C-B before you want them to, and that could get you in legal trouble.

I wonder if cyclizing the structure would gain more stability...*looks at sekio quizzically*

I.e:

...Shit, here's one that will metabolize into 2C-B *AND* GHB!

The dose of GHB you got would be pretty low, because you would only want to take so much 2C-B, but still...just a cool novelty haha.

 

[DL-ark]

^ Yeah, but the problem here could be that small amounts could degrade into 2C-B before you want them to, and that could get you in legal trouble.

I wonder if cyclizing the structure would gain more stability...*looks at sekio quizzically*

I.e:

...Shit, here's one that will metabolize into 2C-B *AND* GHB!

The dose of GHB you got would be pretty low, because you would only want to take so much 2C-B, but still...just a cool novelty haha.

Your first structure has a triple bond which will not work in that place (carbons cant accept 5 bonds) god damn I am dumb

 

[N0 W4RN1NG]

Your first structure has a triple bond which will not work in that place (carbons cant accept 5 bonds)

I know carbon can't accept 5 bonds! (well, technically it can, but I'm not going to get into that)

It's only a quaternary carbon my friend, take a second look at the picture.

 

[blueberries]

...Shit, here's one that will metabolize into 2C-B *AND* GHB!

The dose of GHB you got would be pretty low, because you would only want to take so much 2C-B, but still...just a cool novelty haha.

I was thinking of this earlier. I noticed throughout the world of compounds that adding a benzene group *somewhere* would create a much more potent version of that compound, as in the case of Bromadol, Etonitazene, NBOMe's, PPOM etc.

So, I give you this on the offchance of it being workable:

That benzene ring could be modified in a way similar to the aforementioned potent compounds, depending on whether or not it would be workable or not. I tried to make it para, as is the custom but being a 7 sided ring, there are dual options. This is pure SAR theory based on what little I know, so be brutal, as this theory has plagued me for ages now and I want an answer!

 

[adder]

^ Where do you have an additional benzene ring in your modified 2C-B? Making a more potent analogue is not as simple as adding a benzene ring somewhere to a molecule. The reason why this works for various drugs (like bromadol or NBOMe's) is because that additional benzene ring is capable of interacting with another portion of receptors making binding stronger. The N-(2-methoxybenzyl) added to phenethylamines makes NBOMe's look more like LSD if you try to make them overlap like this.

Then we could modify NBOMe's substituting 2-methoxybenzyl with some bioisosteric functional groups and end up with analogues from the second row. I'll make an exception and share this.

---

It's no brainer here, but I've been wondering why we haven't seen 1-(thiophen-3-yl)propan-2-amine popping out and its N-methyl analogue.

It should resemble dopamine more than MPA does and perhaps its oxidized metabolites would be even more active.

 

[N0 W4RN1NG]

It should resemble dopamine more than MPA does and perhaps its oxidized metabolites would be even more active.

Adder, I believe that the a-propyl, N-pyrrolidine deriv of that is available, under the name "a-PVT-2" and it is indeed more potent than a-PVT (the 2-thiophene variant). Meaning you are probably right, and that homologue of MPA should be explored.

What do you think of my "N-dioxazole"(?) 2c-b 2 posts up? Would it be ridiculously unstable?

 

[DL-ark]

I know carbon can't accept 5 bonds! (well, technically it can, but I'm not going to get into that)

It's only a quaternary carbon my friend, take a second look at the picture.

Oh my god I am such a dumbass...

 

[N0 W4RN1NG]

All good, happens to the best of us

 

[DL-ark]

All good, happens to the best of us

Well, sorry for trying to call you out anyway.

 

[DL-ark]

Here is a chemical designed to be a psychedelic... It is based off of efavirenz, the FLY series of compounds and.... mescaline(kinda)!

 

[adder]

What do you think of my "N-dioxazole"(?) 2c-b 2 posts up? Would it be ridiculously unstable?

First of all, 2C-X-NBOMe's doesn't seem to tolerate too many changes to their structure. DOX's drugs don't really benefit from adding NBOMe part as 2C-X's do. So you really need to be careful when you add bulk to a compound's structure.

Also, cyclohexane has completely different chemical properties from benzene. In benzene there is a lot going there, because you've got a delocalized pi system there, so its electrons are capable of creating interaction based on charges and partial charges, especially when it's also substituted. E.g. that's how dopamine interacts with DAT, its 3,4-dihydroxyphenyl part interacts with the same site as the ester part in cocaine and phenyltropanes. And that's also how, I think, the analogues of NBOMe's that I posted yesterday would substitute for LSD/LSZ and 2C-X-NBOMe's. Of course when you change one functional group to another, you have to remember that it may not have exactly the same properties even if it has the same size.

In your compound, you don't have a secondary amine there. You've got a dioxazepanone fused into the ethyl side-chain, too many oxygens there and that nitrogen won't be able to interact in the way amines in 2C-X's and 2C-X-NBOMe's interact with the 5-HT(2A) receptors. Perhaps it would be metabolised into some amount of 2C-B, but that's just about it. The 4-methylcyclohexyl part (the one that you mistook for phenyl, I guess) certainly won't substitute for 2-methoxybenzyl in NBOMe's. Generally I don't think that your original compound would be stable, also, I don't really think that it would pay off to synthesize it. But above all I think that your molecule is too big to fit in as NBOMe's fit into the receptor's cleft.