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2,5-Dimethoxy-4-Hydroxyphenethylamine (2C-OH?)

hydrobromide

hydrobromide

Ex-Bluelighter
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I was thinking about possibly active compounds that weren't listed in PIKAL. It's your basic 2C-x compound with a hydroxy group in the 4 position. I searched pretty much everywhere and only found that it is found naturally in a few psychoactive cacti (including San Pedro).

Anyone have any more info on this?

Do you think it would be active?

How easy would this be to synthesize from 2C-H?
 
Well, to synthesize you need something which has hydroxy group... like NaOH or something other. I don't think it's that simple and this need more knowledge, lab supplies and skilled chemist who know's what he or she is doing. Maybe there something in pihkal about it or similar? Dunno... I don't help here so I quit. Allthought it would be interesting to know about it's activity.
 
I think adding NaOH to 2C-H would just convert the 2C-H into the freebase (if it was a salt to begin with). I'm not sure if it would affect the 4-position...I could be wrong though, I'm still leaning a lot.
 
hydrobromide said:
I was thinking about possibly active compounds that weren't listed in PIKAL. It's your basic 2C-x compound with a hydroxy group in the 4 position. I searched pretty much everywhere and only found that it is found naturally in a few psychoactive cacti (including San Pedro).

Anyone have any more info on this?

Do you think it would be active?

How easy would this be to synthesize from 2C-H?
Click to expand...

I am more than skeptical that you have seen an 2,4,5 compound occur naturally in cacti. Most likely what you saw was the 3,4,5 equivalent, ie 4-demethylmescaline.

As far as activity goes, my gut feeling tells me than this compound would be inactive. Normally -oh groups should be protected on a benzene ring to promote activity, but then that would give us TMPEA.
 
Re: Re: 2,5-Dimethoxy-4-Hydroxyphenethylamine (2C-OH?)

Keret said:
I am more than skeptical that you have seen an 2,4,5 compound occur naturally in cacti. Most likely what you saw was the 3,4,5 equivalent, ie 4-demethylmescaline.
Click to expand...

actually you're right...sorry, i misread. 3,4-dimethyl-5-hydroxyphenethylamine was the one found in the cacti.
 
does anyone know of any more 'possibly' active compounds that could be synthed from 2C-H (other than the ones listed in PIHKAL, i.e. 2C-B, 2C-C, 2C-I, etc.)?

it seems like there's quite a few possible combos...I just don't know much about chemistry as I would like at the moment.
 
Well nearly an infinite amount man, so long as you've got long enough, and enough chemicals and equipment.
 
According to two chemists I've talked too (one very respected in the field of psychedelic chemisty), this molecule would not cross the BBB as the OH group would be sensitive to being torn apart by MAO system. Of course, no one knows this for sure until the compound is made and tested.
 
Well dopamine has 2 hydroxy groups so there's a chance
it can be psychoactive. (If you can call dopamine psychoactive?)
 
Last edited:
hydrobromide said:
does anyone know of any more 'possibly' active compounds that could be synthed from 2C-H (other than the ones listed in PIHKAL, i.e. 2C-B, 2C-C, 2C-I, etc.)?
Click to expand...

You can go down one step further with halogens and get 2,5-dimethoxy-4-astatophenethylamine. Astatine though is radioactive and the isotope
with longest half-life is at 8 hours. You can read more
here.

And as all 2C-T's has 1 sulfur atom you can go two steps further down
and get 2,5-Dimethoxy-4-methyltelluridophenethylamine. (2C-TE). There's not
much info about it. One more step down in the same group and you can get
2,5-dimethoxy-4-methylpoloneophenethylamine. (2C-PO). Polonium
is radioactive and emits alpha particles so eating this compound could
burn holes in your brain. Read more here.
 
morninggloryseed said:
According to two chemists I've talked too (one very respected in the field of psychedelic chemisty), this molecule would not cross the BBB as the OH group would be sensitive to being torn apart by MAO system. Of course, no one knows this for sure until the compound is made and tested.
Click to expand...

I don't want to disagree with you or your friend MGS.. so are you sure this is what your friend said? The hydroxyl group might block blood-brain barrier transport because it makes the chemical too lipophobic, or hydrophilic... But the Hydroxy shouldn't effect either the affinity, or the activity of MAO on the PEA, and MAO attacks the nitrogen, and lots of PEA based compounds which very high affinity for MAOs have no substitution on the benzyl (deprenyl).
 
I agree with bilz0r, if this molecule can't make it thru the BBB, it's becasue the hydrxyl group is too polar to allow for its passing thru but not because it would be torn down by any MAO. Polarity issues and MAO issues are two different things.
 
hydrobromide said:
I was thinking about possibly active compounds that weren't listed in PIKAL.
Click to expand...

I was wondering the same thing about a month ago. I used the periodic table among other sources of information and wondered in 2c-Cl (using a chlorine atom) would be active.

Astatine, one atom below chlorine in the halogen group, would be too radioactive to consume, so that just leaves chlorine as a possibly active halogen when substituted into the 4th position.

Im sure that Bilz0r is right about what he said.

I would write more, but im hungover :\
 
Re: Re: 2,5-Dimethoxy-4-Hydroxyphenethylamine (2C-OH?)

Schizomanic said:
I was wondering the same thing about a month ago. I used the periodic table among other sources of information and wondered in 2c-Cl (using a chlorine atom) would be active.

Astatine, one atom below chlorine in the halogen group, would be too radioactive to consume, so that just leaves chlorine as a possibly active halogen when substituted into the 4th position.

Im sure that Bilz0r is right about what he said.

I would write more, but im hungover :\
Click to expand...

Actually, 2C-C does have the chlorine atom.
http://www.erowid.org/library/books_online/pihkal/pihkal022.shtml
They leave off the second letter for some reason (2C-B has Bromine, Br, not Boron, B)
 
^^^^^^^
You're thinking of 2C-C. All the halogens have been used in the 2C-x compounds except Astatine (for obvious reasons).

There's plenty of other things that could fit in the 4-position though not just halogens. So is it generally true, the heavier the group is on the 4-position, the more likely chances are for it being active. Take the inactive compunds 2C-H and 2C-F, a hydrogen atom and a flourine atom are very light. On the other hand with 2C-B and 2C-E, a bromine atom and a CH3CH2O group are heavier and they're active.

Do the heavier or longer longer things in the 4-position make the molecule less polar and easier to cross the BBB? This type of stuff is very interesting to me, but I know little about it.

Are there any websites, or other sources where I can learn more?

Also does anyone know when Shulgin's new book is coming out, or where I can find more info on it?
 
^^^^^^

No that's another book. AFAIK He's still working on the third book as of now.
 
Re: Re: Re: 2,5-Dimethoxy-4-Hydroxyphenethylamine (2C-OH?)

thepodman said:
Actually, 2C-C does have the chlorine atom.
http://www.erowid.org/library/books_online/pihkal/pihkal022.shtml
They leave off the second letter for some reason (2C-B has Bromine, Br, not Boron, B)
Click to expand...

Oh, excuse me, you're right. I do have another compound that I was wondering about. I even drew diagrams, lol. I'll dig it up and post it later.
 
alright, heres something interesting i thought of

2c-Na... sodium

and a hydroxy group should work, 2c-t (just a sulfur closed off with a hydrogen) is active and its not very different from a HO group
 
Actually 2C-T is the methyl sulfide compound, not the thiol. So it looks like the methoxy substituted compound, not the hydroxy.

Also 2C-Na ain't gonna happen, not to mention that organometallic compounds generally tend to fall apart in aqueous environments.

Though what might be interesting would be a mono- or di-substituted amine.
 
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