Question about 3C-x

[Synaps3]

I was wondering why only 3c-e and 3c-p exist. I have never heard of 3c-b, 3c-i, 3c-c. Would they be active?

 

[Solipsis]

Well,

3C-B is actually not called that but 4-Br-3,5-DMA, rat reactions were 'mescaline-like' from 5 mg/kg with deaths at 10 mg/kg.

http://bitnest.ca/external.php?id=%7DbxUgZ%5BC%40X%04txw%02TWYW

And:

[...] This model has new been used successfully for predictive purposes . For example, 3,5-dimethoxy-4-bromophenylisopropylamine, compound 27, was predicted to have high potency based on its log P value and in vitro activity in this preparation for its 2 carbon homolog 5 . Subsequent testing revealed that this compound elicits central effects in man at a dose in the range 3-6 mg [...]

Also interestingly:

As suggested by Nichola and Dyer (2) 3,4,5-substituted compounds are about as active in this preparation ae 2,4,5-aubatituted compounds of comparable log P . Thin work however, shore that this is independent of
whether or not the compound possesses an alpha methyl group. (Ia contrast an alpha ethyl destroys hallucinogenic activity, reduces 5-HT agoniat activity and imparts 5-ST antagonist activity to the molecule (9)

http://bitnest.ca/external.php?id=%7DbxUgZ%5BC%40X%04txw%02TWYW

Names for the 2-carbon homologue of 4-Br-3,5-DMA would be 3,4,5-MBM or 4-Br-3,5-DMPEA.

It doesn't seem like other halogen analogues of 3C-X were explored but logically they would be called 4-Cl-3,4-DMA and 4-I-3,4-DMA.

 

[sekio]

Given the similarity of Cl and OMe groups in vitro, is it possible that 4-Cl-3,5-DMPEA "chloromescaline" would be somewhere between mescaline and 2c-c?

 

[cryptix420]

y'all are so smart, it makes me want to take a chemistry class

 

[Incunabula]

Solipsis, I can't say I agree with you there. Shulgin named the 3C's in advance of their "discovery", as I understand it.

Very few of the homomescaline phenethylamines have been synthesized as their three-carbon chain counterparts, the corresponding analogues of amphetamine. And only three of them have been explored in man (four, if you count the amphetamine analogue of mescaline itself, TMA). The obvious names for these compounds have, unfortunately, already been used. It would be logical to use the letter M for a methoxy, and the letter E for ethoxy, etc. and simply read the groups from around the ring. But this is the naming system for the 2,4,5-trisubstituted amphetamines. MEM is, for example, 2,5-dimethoxy-4-ethoxyamphetamine (in sequence, methoxy, ethoxy, methoxy reading around the ring, and a fascinating compound talked about at length in this book), so this term cannot represent 3,5-dimethoxy-4-ethoxyamphetamine.

A truly simple code employs the length of the carbon chain. The phenethylamine chain is two carbons long, and the amphetamine chain is three carbons long.

If a drug has been initially developed (and initially named) as an amphetamine derivative (three carbon chain) then the two-carbon chain analogue will use the original name (or a symbolic part of it) with the term 2C ahead of it. The two-carbon analogue of DOB (a three-carbon chain compound) will become 2C-B. DOI becomes 2C-I, DON becomes 2C-N, and DOET becomes 2C-E. Each of these is a substituted amphetamine derivative lacking one carbon atom, thus becoming a phenethylamine derivative. Most of these have 2,4,5-substitution patterns.

And if a drug has been initially developed (and initially named) as a phenethylamine derivative (two carbon chain) then the three-carbon chain analogue will use the original name with the term 3C ahead of it. The three carbon analogue of E (escaline, a two-carbon chain compound) will become 3C-E. P becomes 3C-P and CPM becomes 3C-CPM. Most of these have 3,4,5-substitution patterns.

Thus, R2-CS implies that a known amphetamine drug has been shortened to a phenethylamine, and R3-CS inplies that a known phenethylamine has been lengthened to an amphetamine. A great number of the former have been made and have proven to be most rewarding. Only a few of the latter are known, but most of them will eventually prove to be potent psychedelics.

So, actually Shulgin as already asigned trivial names to the halogen analogues of 3C-X. That is 3C-C, 3C-I and 3C-B etc ad nauseam.

Also, not as clear or logical, but I would also argue concerning the 2-carbon homomescaline phenethylamines (as Shulgin calls them). that if propoxy is Proscaline, and ethoxy is Escaline, then it would also follow that the Chloro analogue would be named Chloroscaline, and the Brom analogue would be called bromoscaline, Iodo analogue would be Iodoscaline.....etc

right?

 

[Solipsis]

No, the answer is right here in front of us.

And if a drug has been initially developed (and initially named) as a phenethylamine derivative (two carbon chain) then the three-carbon chain analogue will use the original name with the term 3C ahead of it. The three carbon analogue of E (escaline, a two-carbon chain compound) will become 3C-E. P becomes 3C-P and CPM becomes 3C-CPM. Most of these have 3,4,5-substitution patterns.

This couldn't be true of 2C-B to 3C-B (+ same for other halogens), because I'm pretty sure the 2-carbon homologues of these were developed first (i.e. 2C-B, 2C-C, 2C-I ) and alpha-methylating these yields the names DOB, DOC and DOI as chosen by Shulgin, and consequently not 3C-B, 3C-C and 3C-I which were not chosen.
And it is not the case either that he gave these compounds multiple names as he sometimes does (DOB has a whole list, including 4-Bromo-DMA for example), but I have just checked PIHKAL and the Shulgin Index and 3C-B is not another name for DOB.

In the case of halogens, these 3C-X names are not fit for 4-X-3,5-DMPEA either because then the names would implicate the 2,4,5 substituted analogues and not the 3,4,5 substituted ones. That is where it would get hairy indeed, and as you say not clear or logical. You are right to say that it could be possible for 4-chloro-3,5-dimethoxyphenethylamine to be named chloroescaline, chlorescaline, chloroscaline or chloromescaline and the amphetamine homologue could indeed be called 3C-C, but this is not the case i.e. I cannot find anywhere that Shulgin actually gave these names and I recommend against it (if I may be so rude). It would give confusion, like I pointed out starting this paragraph. If anything I'd say, let's name chloromescaline like Sekio says or otherwise chloroscaline (omitting the E at least does not imply any ethyl moiety involved) CM for short and the amphetamine 3C-CM... doing the same with other halogen analogues. Let me check the Shulgin Index if CM is taken. Well not that it'd matter since it is not up to me to name compounds, but just for fun?
(Maybe chloromescaline implies 4-chloromethyl instead of 4-chloro, but this is really getting into moot nitpicking, sorry)

edit: just checking the Shulgin Index, and it seems that 2-CM and 2,6-CM are indeed chloromescalines although the chloro's are not substituting for methoxy's. Also under the 2C-C entry it seems a lot of other substitution patterns with chloro and methoxy were tried but I am missing plain "CM" everywhere. Maybe I am missing something but my guess is that CM is not taken by something else.

Considering 3,4,5-MBM is a way for Shulgin to designate 4-bromo-3,4-dimethoxyphenethylamine along the same lines of 'MEM' it is quite likely the chloro analogue would be 3,4,5-MCM or plain MCM. Let's also not forget that bromomescaline is a name for 2C-B and not actually the 3,4,5-subbed MBM. To add to the confusion 8(

Qualitatively perhaps chloromescaline could fall in between mescaline and 2C-C, who knows really? (I'd try it) but I think the substitution pattern is very important and it seems likely that it is closer to mescaline. There is probably very few people who would be interested in synthing it (not counting novelty-related motive) because it is harder to make than mescaline and there is no reason why it would be significantly more potent, offering no improvement on that like the amphetamine counterpart would. N-benzylation would probably be a disappointment as well.

Oh pretty cool I found a thread on it:

http://www.bluelight.ru/vb/threads/...imethoxyphenethylamine-And-Other-Obscure-PEAs

Where Dondante lends a hand:

From the PIHKAL entry for DESOXY:

"A mescaline analogue with a bromo atom in place of the 4-methoxyl group is an analogue of mescaline in exactly the same way that DOB (a very potent am-phetamine) is an analog of TMA-2 (the original trisubstituted amphetamine). This analogue, 3,5-dimethoxy-4-bromoamphetamine, has been found to be a most effective serotonin agonist, and it is a possibility that it could be a most potent phenethylamine. But, as of the present time, it has never been assayed in man."

And also the name 3C-C came up in the OP
OK I lolled.

 

[Incunabula]

^I'm sure you have a much better grasp of chemistry than I do, but we're discussing naming, and I must say that I don't agree with you on your interpretation of that Pihkal quote on naming of amphetamine's.

But I think we can both agree that Shulgin kind of made a mess here

This couldn't be true of 2C-B to 3C-B (+ same for other halogens), because I'm pretty sure the 2-carbon homologues of these were developed first (i.e. 2C-B, 2C-C, 2C-I ) and alpha-methylating these yields the names DOB, DOC and DOI as chosen by Shulgin, and consequently not 3C-B, 3C-C and 3C-I which were not chosen.
And it is not the case either that he gave these compounds multiple names as he sometimes does (DOB has a whole list, including 4-Bromo-DMA for example), but I have just checked PIHKAL and the Shulgin Index and 3C-B is not another name for DOB.

I'm absolutely not saying DOB should be called 3CB, and I'm not saying they have double names. No, I'm pretty sure the DO's were developed before the 2C's, think DOM! which was first synthesized by Shulgin in 1964.
And DOB which was made in 1967! (source is erowid and pihkal) Clearly the 2C's came later.

secondly, if it was as you say, then Shulgin would be setting up a naming system for the amphetamines and 2C's, and then start out by breaking it...?! of cause the DO's were made first.

In the case of halogens, these 3C-X names are not fit for 4-X-3,5-DMPEA either because then the names would implicate the 2,4,5 substituted analogues and not the 3,4,5 substituted ones. That is where it would get hairy indeed, and as you say not clear or logical. You are right to say that it could be possible for 4-chloro-3,5-dimethoxyphenethylamine to be named chloroescaline, chlorescaline, chloroscaline or chloromescaline and the amphetamine homologue could indeed be called 3C-C, but this is not the case i.e. I cannot find anywhere that Shulgin actually gave these names and I recommend against it (if I may be so rude). It would give confusion, like I pointed out starting this paragraph. If anything I'd say, let's name chloromescaline like Sekio says or otherwise chloroscaline (omitting the E at least does not imply any ethyl moiety involved) CM for short and the amphetamine 3C-CM... doing the same with other halogen analogues. Let me check the Shulgin Index if CM is taken. Well not that it'd matter since it is not up to me to name compounds, but just for fun?

First of all, in the naming system of amphetamines he describes in the first quote from Pihkal that I quoted, he specificaly says it's not about wether the compound in question has the 2,4,5-substitution pattern or the 3,4,5-substitution pattern. It's about what was developed first ! The 2c or the amphetamine.

second, you are right that he didn't specificaly designate the name 3C-C to the compound 3,5-Dimethoxy-4-Chloro-Amphetamine. But I think that's only because he never went that far with the 3,4,5-substituted amphetamines, and their 2C analogues. But he did write the above quote about naming of amphetamines under escaline in Pihkal, AND.....it's how he's named the few compound's that he synthezised, named and wrote about in Pihkal, after the DO's. As I see it he named these posible compounds in advance with out saying so in a way.

let's have an overview of what I'm talking about:

Allyl ->Allylescaline ~ 3C-AL
Cyclopropyl -> CPM ~ 3C-CPM
Ethoxy -> Escaline ~ 3C-E (not 3C-EM)
isopropoxy -> Isoproscaline ~ 3C-iP (not 3C-iPM)
propoxy -> proscaline ~ 3C-P (not 3C-PM)

So following how Shulgin already named these 3,4,5-substituted phenethylamines, then the names would go like this:

Chloro -> chloroscaline ~ 3C-C (not 3C-CM)
Bromo -> Bromoscaline ~ 3C-B
Iodo -> Iodoscaline ~ 3C-I
etc etc...

(which is how I'm also sure he'd have named them had he continued with that particular research if he had, had the time)

So why is 3C-C misleading? it's not more misleading than, say 3C-E.
And no, 3C-CM isn't taken, but neither is 3C-C. So it could be 3C-C and it could be 3C-CM, as long as nothing is already called either..

Or maybe there's something I've completly missed here?

I'm also very surprised that he doesn't have 3,5-dimethoxy-4-X-phenethylamine and 3,5-dimethoxy-4-X-amphetamine 's in the Shulgin index?

I'd say, in the end, it's the inventor's prerogative to name an invented compound, but who invented 3,5-dimethoxy-4-Chlorophenethylamine and 3,5-dimethoxy-4-chloro-amphetamine? I'd say Shulgin did that. So somebody should ask him :D

Considering 3,4,5-MBM is a way for Shulgin to designate 4-bromo-3,4-dimethoxyphenethylamine along the same lines of 'MEM' it is quite likely the chloro analogue would be 3,4,5-MCM or plain MCM. Let's also not forget that bromomescaline is a name for 2C-B and not actually the 3,4,5-subbed MBM. To add to the confusion 8( [/I]

As I understand this comment from Pihkal, he actually talks against using that naming system because it's already in use for the 2,4,5-trisubstituted amphetamines:

The obvious names for these compounds have, unfortunately, already been used. It would be logical to use the letter M for a methoxy, and the letter E for ethoxy, etc. and simply read the groups from around the ring. But this is the naming system for the 2,4,5-trisubstituted amphetamines. MEM is, for example, 2,5-dimethoxy-4-ethoxyamphetamine (in sequence, methoxy, ethoxy, methoxy reading around the ring, and a fascinating compound talked about at length in this book), so this term cannot represent 3,5-dimethoxy-4-ethoxyamphetamine.

And also the name 3C-C came up in the OP
OK I lolled.

??? I don't understand?

 

[lastest]

This thread makes a series of high-pitched whistling sounds as each of the posts flies over my head.

 

[Solipsis]

Apparently you are comfortable with other names for the suggested compounds than I am. "Agreeing to disagree" tends to sound lame but considering this is about nomenclature that has a somewhat arbitrary element in it regarding the ultimate choices, and not about true or untrue facts, there is nothing else to be proven.

Why I (reluctantly) accept 3C-E but not 3C-C is because E already actually stands for escaline and 3C-E would mean: 3-carbon homologue of escaline.
C does not necessarily mean chloroscaline. It can, and I am a bit tired of arguing over it... but it can also designate other chloro-PEAs.
An argument why 3C-C would still be acceptable is that it could not be the 3-carbon homologue of 2C-C since that is already called DOC. Then again, alternative names are possible.

Also, with the DOX a resolution is offered: the ethyl and propyl are called DOET and DOPR, I think because DOE would suggest the 3,4,5-substituted compound following the E for escaline (i.e. 3C-E) and DOP that same way.
Calling them DOET and DOPR makes them exceptions that follow the typical DOX 2,4,5 substitution pattern.

So if we now go back: you might think that in 3C-E and 3C-P the E and P stand for ethyl and propyl in the same context as 2C-E and 2C-P but I don't think they do. Because the substitution pattern is different AND the 4-position substition is not ethyl and propyl but ethoxy and propoxy.

Maybe instead of "it is not called 3C-B", I could have said that it might be called that by some. But if you will just check isomerdesign and other references you will see it is called 4-Br-3,5-DMA. We can go on all day about agreeing to that or not, but who exactly are we to reject names that have already been given? That is why I was surprised that you 'disagreed' with me in the beginning: not because I couldn't be wrong, but because it was not my judgement call and I just basically quoted isomerdesign.

I could still be wrong of course.

Why 3C-C mentioned in that other OP was funny to me is because the provided formula is not even a 3-carbon compound so that couldn't possibly be it - yet similarly to your own suggestion, the name was being asked about. Just a funny coincidence to me. :D

 

[RhythmSpring]

Pd-->add?

 

[Solipsis]

lol. well it mostly got 'advanced' because respondents made it that way... but good call yeah.

Interested in their feedback.

PD >> ADD

 

[nuke]

I would guess they're all active with enhanced toxicity. Alpha-methylation converts partial agonists to full agonists in terms of 2c-? to DO? compounds.

 

[Incunabula]

No body else seems to have an opinion on the matter, very well

Apparently you are comfortable with other names for the suggested compounds than I am. "Agreeing to disagree" tends to sound lame but considering this is about nomenclature that has a somewhat arbitrary element in it regarding the ultimate choices, and not about true or untrue facts, there is nothing else to be proven.

I agree

Why I (reluctantly) accept 3C-E but not 3C-C is because E already actually stands for escaline and 3C-E would mean: 3-carbon homologue of escaline.
C does not necessarily mean chloroscaline. It can, and I am a bit tired of arguing over it... but it can also designate other chloro-PEAs.
An argument why 3C-C would still be acceptable is that it could not be the 3-carbon homologue of 2C-C since that is already called DOC. Then again, alternative names are possible.

I totally get your point. And I also understand why you dislike the whole "3C" naming structure, because they actually imply that it's a homologue of a 2C-X. Which it is not. One would think that 3C-P was the amphetamine homologue of 2C-P for instance. So yeah, as I said, Shulgin did make a mess of the names here.

Actually the more I think about it, I see that 3C-P and 3C-E are totally stupid names, because people keep comparing it too 2C-E and 2C-P.

I also understand how Chloroscaline doesn't specify which chloro-PEA we are talking about, except, as I saw it, that it is following the naming tradition how Shulgin had already begun naming the 3,4,5-substituted PEA's. So this is were the hint and "logic" is in the name concerning the structure. But I'm actually kind of changing my mind on that.

Also, with the DOX a resolution is offered: the ethyl and propyl are called DOET and DOPR, I think because DOE would suggest the 3,4,5-substituted compound following the E for escaline (i.e. 3C-E) and DOP that same way.
Calling them DOET and DOPR makes them exceptions that follow the typical DOX 2,4,5 substitution pattern.

it might be the case with DOPR, he doesn't say. But it's definitely not the case with DOET--->

The original code for this compound was DOE, which was completely logical based on DOM being the methyl member of this series (DO for the removal of the oxygen, desoxy, and M for putting a methyl in its place). And the putting of the ethyl thence should be DOE. This was fine until it was pointed out to me by a close colleague that DOE was a classic abbreviation for desoxyephedrine, a synonym for methamphetamine.

Maybe instead of "it is not called 3C-B", I could have said that it might be called that by some. But if you will just check isomerdesign and other references you will see it is called 4-Br-3,5-DMA. We can go on all day about agreeing to that or not, but who exactly are we to reject names that have already been given? That is why I was surprised that you 'disagreed' with me in the beginning: not because I couldn't be wrong, but because it was not my judgement call and I just basically quoted isomerdesign.

Sure, of cause I agree with that, and it's absolutely not my call either! I'm was just talking pro following the naming structure Shulgin had already begun naming the 3,4,5 PEA's with.

We both know what compounds we are talking about, what we're discussing is their trivial names. No ones going to go around calling something "four-bee-are-three-five-dee-em-a".

It's like calling 2C-B 2,5-Br-4-DMPEA.

But, yeah, 4-Br-3,5-DMA is also in Pihkal too, under that name. But i think it's because it was found to be not a psychedelic or just really strange, so he didn't bother to give it a proper pronouncable name, because it was never distributed among his circle of friends.

But surely, even as he says, there must be some very interesting psychedelics among the PEA's with mescaline's 3,4,5 orientation. I just thought that following Shulgin's way of naming the ones we had so far could be continued, no matter how silly the names turned out 8(

 

[Hammilton]

I was wondering why only 3c-e and 3c-p exist. I have never heard of 3c-b, 3c-i, 3c-c. Would they be active?

Uh.. They do. They're DOB, DOI and DOC.

oh I see this was already pointed out and then got very complicated and confused for reasons I don't understand.

 

[Incunabula]

Uh.. They do. They're DOB, DOI and DOC.

oh I see this was already pointed out and then got very complicated and confused for reasons I don't understand.

No, they aren't.

3C-X is the name Shulgin gave to the amphetamine's that were developed after their 2C counterparts, kind of. Difficult to explain and I can't really be bothered, but it's all there in the Pihkal quotes

3C-P is 3,5-dimethoxy-4-propyloxyamphetamine

3C-E is 3,5-dimethoxy-4-ethoxyamphetamine

And the discussion is about wether 3,5-dimethoxy-4-Chloro-amphetamine, for instance, could be called 3C-C, or if it's too misleading.

 

[sekio]

Shulgin must have been stoned or something, the way he named the 3c's is silly.

2C-x = 2,5-dimethoxy-4-sub-phenethylamine
DOx = 2,5-dimethoxy-4-sub-amphetmine
3C-x = 3,5-dimethoxy-4-sub-amphetamine

 

[Solipsis]

And the discussion is about wether 3,5-dimethoxy-4-Chloro-amphetamine, for instance, could be called 3C-C, or if it's too misleading.

I don't really see a doubt that it is already all misleading. However you can certainly call that compound 3C-C, some might be confused and misled while others are not. It's fine really. The point is mostly: you're the first person using that name. Or you might be one of the first ones. Go right ahead, I will probably join you. Just wasn't quite as self-evident as you made it out to be.

Trivial names would be a trade-off, making things more practical. While 3C-C is very practical, for people who find it important to remain clear on the structure of the drug this may not be an ideal name. On the other hand, if that would make you mix up DOC and 3C-C, you probably shouldn't be handling these materials in the first place QED it's a little arbitrary anyway

 

[Hammilton]

The problem with using trivial names for research chems is the shear volume of compounds. That's the problem we saw with the beta-ketones that were oh-so popular. Methcathinone, mephedrone, methedrone, pentedrone, flephedrone, buphedrone, etc. It got a little ridiculous. The appearance and use of the name methedrone was most troubling and retarded. It made and continues to make me wonder if it was name in an intentionally confusing way. While we may all understand the difference here, there are almost certainly people who would mistake it for a typo or just misread it.

I do agree with Solipsis, no one using these compounds should be confusing the two.

Now, it may be retarded that the DOX's are 2,5 and the 2C's are 2,5 while the 3C's are 3,5 substituted. I would be willing to bet that Shulgin would agree with this, but we're not going back now.

It's interesting that 3C-B isn't known, but 3C-B-FLY is available for purchase already.

 

[FlippingTop]

This thread makes a series of high-pitched whistling sounds as each of the posts flies over my head.

Quite true. Fascinating reading mind you

 

[Synaps3]

Well, no matter what it's called, I still find it interesting that so many variations of 3,5 substituted phenethylamines/amphetamines (not sure what the difference is) have been synthed, but the ones that seem the simplest to me (iodoscaline - 3c-i, chloroscaline 3c-c, etc.) have not. I have pretty much no chemistry background, so maybe there is some reason that I am unaware of. Allylscaline, proscaline, jimscaline seem much more complex.