would this be psychoactive at all?

[N3XU5]

I've been playin with some ideas for different phenylethylamines and i haven't found anything on this arrangement, but it does exist. Does anyone know if IUPAC 2-(2,4,5-trimethylphenyl)ethanamine has psychoactive properties, why or why not?

[N3XU5]

Or possibly if this structure is even stable: 2-(2,5-dimethyl benzyloxy0-oxamine?

[psychomanthis]

Interesting structure, it looks to me though that you are missing two carbons as compared to the phenylethylamines known to be psychoactive.

Adding those to this structure would make 1-(2,5-diethylphenyl)-2-aminoethane i think. I could very well be wrong though i really need to brush up on my organic chemistry.

[N3XU5]

Originally Posted by psychomanthis

Interesting structure, it looks to me though that you are missing two carbons as compared to the phenylethylamines known to be psychoactive.

Adding those to this structure would make 1-(2,5-diethylphenyl)-2-aminoethane i think. I could very well be wrong though i really need to brush up on my organic chemistry.

well suppose we just skip the methoxy in the whole phenylethylamine setup, i guess what I'm asking is if omitting those two carbons in the methyl groups affect the psychoactivity of the base setup? I want to imagine that it would considering by shape alone it's even closer to serotonin, and the R2 isn't occupied which has been known to severely reduce the potency of psychoactives.

[Hydroponichronic]

I get the impression that it doesn't have enough heteroatoms on the ring to really bind to much. I'm given to understand that to really work those 5HT₂ receptors we all know and love you need some nucleophiles on the ring. Might act as a monoamine reuptake inhibitor (mostly DA, by the looks of it) but I don't see direct agonism at any fun receptors.

EDIT: That said, I am a fan of chucking methyl groups on the ring. It seems to promote BBB crossing and more selectivity. You'd just need a methoxy or something on there to really give it "bang".

[N3XU5]

Originally Posted by Hydroponichronic

I get the impression that it doesn't have enough heteroatoms on the ring to really bind to much. I'm given to understand that to really work those 5HT₂ receptors we all know and love you need some nucleophiles on the ring. Might act as a monoamine reuptake inhibitor (mostly DA, by the looks of it) but I don't see direct agonism at any fun receptors.

EDIT: That said, I am a fan of chucking methyl groups on the ring. It seems to promote BBB crossing and more selectivity. You'd just need a methoxy or something on there to really give it "bang".

methyl groups seem to be able to have good altering effects and are not the hardest of reactions to get. so i suppose my question is does the third attachment on the aromatic ring inhibit the binding to 5-ht2? or is it just the lack of a methoxy group? if so could you make it 1-(2,5 dimethyl-4-methoxy)phenylethanamine? is that enough to give it a "bang" so to say?

[N3XU5]

Originally Posted by Kipohippo

I love it when Zoklet gets all sciency on me. Shit like this happens.

dude there's no way humans have discovered more than 10% of psychoactives. There's way too many combos...who's the next shulgin?

[yawanur]

Originally Posted by N3XU5

dude there's no way humans have discovered more than 10% of psychoactives. There's way too many combos...who's the next shulgin?

[litefire]

Originally Posted by Kipohippo

Zoklet apparently lol.

Hah..yeah right.

[N3XU5]

Originally Posted by litefire

Hah..yeah right.

why not? information has never been available like this. if a kid in a garage and become a famous musician then a clandestine chemist most certainly can discover and entirely new class of psychoactive...why shouldn't it start here?

[litefire]

Originally Posted by N3XU5

why not? information has never been available like this. if a kid in a garage and become a famous musician then a clandestine chemist most certainly can discover and entirely new class of psychoactive...why shouldn't it start here?

There have been many clandestine chemistry forums before Zoklet. MANY..most of them much better too. Most of them now are gone, IE The Hive(probably the best) and WetDreams. Zoklet has a very poor userbase, we have some very talented, very knowledgeable chemists here, but most of them rarely post and when they do it's rarely original content.

Ford Prefect and Beaker are really the only two guys that ever (consistently) brought anything new to the table. Hydroponichronic is extremely knowledgeable and experienced and so is Bunghole, but both of them rarely post here anymore. This forum is dead compared to how it was when Zoklet first started up.

Joe Pedo is another user to mention except he randomly dissapears as well. He rarely posts.

[N3XU5]

Originally Posted by litefire

There have been many clandestine chemistry forums before Zoklet. MANY..most of them much better too. Most of them now are gone, IE The Hive(probably the best) and WetDreams. Zoklet has a very poor userbase, we have some very talented, very knowledgeable chemists here, but most of them rarely post and when they do it's rarely original content.

Ford Prefect and Beaker are really the only two guys that ever (consistently) brought anything new to the table. Hydroponichronic is extremely knowledgeable and experienced and so is Bunghole, but both of them rarely post here anymore. This forum is dead compared to how it was when Zoklet first started up.

Joe Pedo is another user to mention except he randomly dissapears as well. He rarely posts.

i could not agree more. i wasn't saying that zoklet is the latest and greatest, but compared with say, 25 years ago? the internet in general has not only provided troves of information for any clandestine operation but has allowed for the connections to be made as well....hard to imagine without computers

[Gun Lover]

I spend too much time pondering these types of questions.

Originally Posted by N3XU5

I've been playin with some ideas for different phenylethylamines and i haven't found anything on this arrangement, but it does exist. Does anyone know if IUPAC 2-(2,4,5-trimethylphenyl)ethanamine has psychoactive properties, why or why not?

Immediately makes me think of 2C-G.

I mean, us amateurs mostly just have SARs to base judgment off of. Pros like Nichols, et al. have fucking pharmacophores -- 3D models of the active sites of a damn 5-HT2AR itself. I thought I saw pictures once but I could never find them again.

That said, the pros have been designing ever more selective agonists for years now and you've gotta start with a 2,5-dimethoxyphenethylamine, really. Your compound, as hydro said, is probably lacking affinity to any of the active residues of the receptor.

Also keep in mind that this shit would almost literally last forever in your body. Shit takes fucking ages to get metabolized (see 3,4-dimethylcathinone)

And not to mention that even though you might have a new 5-HT2A agonist, it is likely that it might not even possess the ability to cause PLA2 activation, which is utterly crucial to psychedelia. Serotonin itself is a full agonist at the 2AR but SSRIs don't make you trip because they lack the ability for PLA2 activation.

Just something to keep in mind.

Originally Posted by N3XU5

Or possibly if this structure is even stable: 2-(2,5-dimethyl benzyloxy0-oxamine?

I think you need to work on the nomenclature a bit. You talking about an oxime or 2,5-dimethyl-4-methoxyphenethylamine? Oximes are pretty interesting but hard to get across the BBB.

So the verdict on your compounds: My semi-educated guess says no central activity in either compound.

Keep thinking, but stick with teh methoxies

[Hydroponichronic]

Originally Posted by N3XU5

does the third attachment on the aromatic ring inhibit the binding to 5-ht2? or is it just the lack of a methoxy group?

Lack of methoxy (or other heteroatom group), as I understand it.

if so could you make it 1-(2,5 dimethyl-4-methoxy)phenylethanamine? is that enough to give it a "bang" so to say?[/quote]

Possibly. I, for one, would be interested to find out.

[N3XU5]

Originally Posted by Hydroponichronic

Lack of methoxy (or other heteroatom group), as I understand it.

if so could you make it 1-(2,5 dimethyl-4-methoxy)phenylethanamine? is that enough to give it a "bang" so to say?

Possibly. I, for one, would be interested to find out.[/quote]

well i've got two hypothetical structures. one would be 1-(2,5 demethyl-4-methoxy)phenylethanamine. basically a 2c-g with the methyl and methoxy groups switch in place and number.
the second molecule i've been thinking of is 1-(2,5 methoxy but with a methoxy group replacing the ethyl groups attached to the amine?
so would an oxygen atom replacing the first carbon attached to the amine fuck the whole thing up? or is that possibly a new class of psychs?
if that structure is inactive on the right parts of our brains then could adding various methoxy groups to the aromatic ring help promote BBB crossing as mentioned earlier in this thread?

[Hydroponichronic]

Originally Posted by N3XU5

one would be 1-(2,5 demethyl-4-methoxy)phenylethanamine. basically a 2c-g with the methyl and methoxy groups switch in place and number.

No idea, but it sounds feasible.

Originally Posted by N3XU5

the second molecule i've been thinking of is 1-(2,5 methoxy but with a methoxy group replacing the ethyl groups attached to the amine?

Wait, what molecule are you referencing? What ethyl groups attached to the amine?

Originally Posted by N3XU5

if that structure is inactive on the right parts of our brains then could adding various methoxy groups to the aromatic ring help promote BBB crossing as mentioned earlier in this thread?

Methoxy groups actually hamper BBB crossing, since they add heteroatoms to the structure, which decreases lipophilicity.

[N3XU5]

alright the molecule I'm talking about is the basic 2c-h molecule but instead of and ethyl chain could one remove the first ethyl group off the chain attached to the ring and replace it with an oxygen atom? i mean i really don't know jack shit about this but i'm just throwing ideas out there. not to mention it would be stupid hard to make. so basically what i think would be 1-(2,5 methoxy)phenoxylamine? my nomenclature may be off but i splained it best i could.

secondly hydroponichronic, what i'm not really understand here being the super noob i am with my organic chem. what is it specifically that promotes BBB selectivity, reaction with the 5ht2a receptor as well as pla2 activation?
so with your response, cut the methoxy and just create a basic 2c structure but with ethyl groups instead of methyl groups. would that possibly do the trick?

[N3XU5]

Originally Posted by Hydroponichronic

No idea, but it sounds feasible.



Methoxy groups actually hamper BBB crossing, since they add heteroatoms to the structure, which decreases lipophilicity.

So it's lipophilicity that accompanies the proper PLA2 activiation? What exactly accompanies lipophilicity? Is it the creation of a hydrophobic wall on one side of the molecular structure? If so I assume the differentiation of the ring is one that would have to be inactive in affecting the lipophilicity. And is it sPLA2 activation that we're after?

[BungHole]

Originally Posted by N3XU5

alright the molecule I'm talking about is the basic 2c-h molecule but instead of and ethyl chain could one remove the first ethyl group off the chain attached to the ring and replace it with an oxygen atom? i mean i really don't know jack shit about this but i'm just throwing ideas out there. not to mention it would be stupid hard to make. so basically what i think would be 1-(2,5 methoxy)phenoxylamine? my nomenclature may be off but i splained it best i could.

secondly hydroponichronic, what i'm not really understand here being the super noob i am with my organic chem. what is it specifically that promotes BBB selectivity, reaction with the 5ht2a receptor as well as pla2 activation?
so with your response, cut the methoxy and just create a basic 2c structure but with ethyl groups instead of methyl groups. would that possibly do the trick?

You mean like this?

I don't know anything about the pharmocological activity of O-aryl hydroxylamines, but the ethylamine chain is an essential aspect of the compounds of this class (phenethylamines).

[N3XU5]

well no, not exactly, just an oxylamine chain. ring->oxygen->ethyl->amine and whatever other components could be conjured...

[EDIT] now looking at it yes, but with an ethyl in the chain but that about hits it on the money

[BungHole]

Originally Posted by N3XU5

well no, not exactly, just an oxylamine chain. ring->oxygen->ethyl->amine and whatever other components could be conjured...

[EDIT] now looking at it yes, but with an ethyl in the chain but that about hits it on the money

Honestly man, I don't know what the fuck you are saying. I know you confirmed that you agreed with my drawing, but if you can't just look at a structure and recognize it, you are absolutely lost and need to start from the beginning.

Anyway, I suppose this is what you mean.


I have no idea what the activity of this molecule is. But I highly doubt it acts in a way similar to phenethylamines. Stick to a C-C bond.

By the way, when you see something on this forum you don't understand, that means you're pretty much obligated to research it. It's like a rule of the internet.

[N3XU5]

of course. but i feel like i need to work on my nomenclature like i said. i couldn't find that certain structure name.