N&PD Moderators: Skorpio
2c i isomers1?
sackynut
Bluelighter
Im just grasping exactly how analogues work and trying to completely grasp isomers and racemic mixtures. Does 2ci or any of the 2c drugs have isomers? I have not heard anything on this subject and would just like to be enlightened! Thanks! -sacky
atara
Bluelighter
The DOx drugs have isomers, the [R] isomer is always more potent.
MDMA is an exception; here the isomer is more potent.
The 2C drugs, except for 2C-T-17, are all achiral.
sackynut
Bluelighter
Thanks for the info it quenched my thirst for knowledge much appreciated!
Astavats
Bluelighter
No other 2C-I isomers exist to my knowledge however they could. Atara gave an example of stereoisomers but you could also switch the iodine and methoxy positions and have a structural isomer.
Take a look at the TMA series for a visual. They all contain the same chemical formula though posses unique positioning of substitutes.
http://en.wikipedia.org/wiki/Trimethoxyamphetamine#TMAs
A simpler example would be butane; http://en.wikipedia.org/wiki/Butane#Isomers
pofacedhoe
Bluelight Crew
^^^nah isomer based potency varies from one drug to the next... you cant be that certain
MurphyClox
Bluelighter
Sackynut should Wiki's definition for the term "isomer".
Are you asking for conformational, constitutional or configurational isomers? These terms sound all quite similar, don't they?
Peace! - Murphy
melange
Bluelighter
levo-dextro
MurphyClox
Bluelighter
^...errrr, what are you referring to, Melange?
melange
Bluelighter
I am sorry - I am not quite on your level yet murphy
--edit--I am drunk disregard
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<pyridinyl_30>
Bluelighter
I'm pretty sure he means stereoisomers (dextro/levo, R/S, +/-). If that is the case, then no 2ci has none, like atara said.
LivingOnValium
Bluelighter
i too believe the op asks about enantiomers.
<pyridinyl_30>
Bluelighter
An enantiomer is a 50/50 mix of R/S stereoisomers at a single carbon. 2ci cannot exist in as an enantiomer.
<pyridinyl_30>
Bluelighter
That should say a racemic mixture is a 50/50 mix of enantiomers. 2ci cannot exist as a racemic mixture of enantiomers.
dread
Bluelighter
I think you're talking about diastereomers.
dread
Bluelighter
2c-t-17 and 2c-g-5 have stereoisomers.
Zapa
Bluelighter
sackynut
Bluelighter
sorry i took a little road trip for a few days. yeah I guess I meant stereoisomers, R, S etc. I dont quite fully understand the spacial aspects of molecules yet really and Im just finally completely grapsing how two chemicals can be considered analogues. I appreciate the responses thanks.
Do the 2c drugs (besides t-17 and g-5) not have stereoisomers because they cant exist stably, or because its just impossible to flip the molecule? thanks. I tried Wiki-ing isomers (long before I posted this thread) and it made sense but at the same time, the "rules" (if THAT makes sense) of molecular spaciality [haha] I did not understand.
Interesting stuff I love chemistry!
dread
Bluelighter
They don't have stereoisomers because they are symmetrical - ie. there is no chiral center - which is what makes chiral compounds asymmetrical, thus able to exist as two mirror images (stereoisomers.)
When you add the alpha-methyl group, giving a DOx compound, the molecule becomes asymmetric because the alpha-carbon becomes a chiral center. Let's look at the alpha-carbon specifically: in a 2C, it is connected to the amine nitrogen, the beta carbon, and two hydrogens. The two hydrogens being the same, it has a symmetry - even if you swap the hydrogens with each other, the structure stays the same. Now in DOx, one of those hydrogens is replaced with a methyl group. Naturally, you have two distinct places where you can stick that methyl on, therefore, you have two stereoisomers of the same compound.
As for the two 2C-compounds that are chiral: both 2C-T-17 and 2C-G-5 are chiral because their para-substitution (or 3,4-disubstitution in case of G5) contains a chiral center.
