Dissociatives Arylcyclohexamines - Proper naming conventions?

[Didgital]

Hi so I've been doing large posters of different molecules (all the different molecules of Pihkal and Tihkal for example), and am about to start a poster detailing aryclolohexamine analogues.

However, I am bit confused on the naming conventions. The main arylcyclohexamine Wikipedia page states that phenyl ring substitutions should be designated with a ', for example 3'-Meo-PCP. Cyclohexane substitutions shouldn't have anything besides a number, and any substitutions on an N ring should be indicated with a ".

My understanding is MXE would be designated as 3'-Meo-2-Oxo-PCE, however all over the internet I am seeing conflicting examples.

Ketamine would technically be 2'-Cl-2-Oxo-PCM?

If anyone could confirm or deny the nomenclature or point me to the original literature that came up with these conventions that would be really helpful!


I actually just thought of another question, is why do we not see hardly any examples off n,n disubstituted compounds. The only one I've seen is PCDM (Phenyl Cyclohexyl DiMethyl amine. How come there are no methyl ethyl amines like 4-HO-MET or MIPT (I know they tryptamines, I'm just talking about amine substitutions..)

 

[Xorkoth]

Everything I have ever seen in terms of notation refers to MXE as 3-MeO-2'-oxo-PCE, not the other way around. And likewise, 2'-oxo-PCE for O-PCE. And simply 3-MeO-PCP, not 3'-MeO-PCP.

 

[Mjäll]

My only gripe is with the name DMXE, a glaring error that has been noted by others in this forum i think.

"desOXY methOXY -etamine" wtf no :D ...as much as i respect the legacy of MXE... Why mention the OXY if it's not only absent but also was an add-on in the first place?

 

[Xorkoth]

Well, because MXE was called MXE, and desoxy-MXE makes sense to label as DMXE... desoxy is often abbreviated as D in drug abbreviations.

 

[ecstacylover]

See here

Other hydrocarbon ring assemblies are named by selecting one ring system as the base component and considering the other systems as substituents of the base component. Such substituents are arranged in alphabetical order. The base component is assigned unprimed numbers and the substituents are assigned numbers with primes.

53.2 - The base component is chosen by considering the following characteristics in turn until a decision is reached:

(a) The system containing the larger number of rings.

(b) The system containing the larger ring.

(c) The system in the lowest state of hydrogenation

Clearly the deciding factor for ketamine analogues will be (c). Since the cyclohexyl ring is in a higher state of hydrogenation, it should be assigned primed numbers. So ketamine would be 2-Cl-2'-Oxo-PCE, etc.

I assume it's different for PCP analogues as one of the rings contains a nitrogen.

 

[nepalnt21]

i'm super interested in the last question.

what if (i'm gonna botch this, go easy on me) diisopropyl-phenylcyclohexylamine had some crazy effects like dipt lol just tossing wild ideas, someone way smarter than me please lay it all down!