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N-methyl 6/5-apb

B

BLreturn11

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Joined
Oct 21, 2011
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I have a vague recollection of asking this before and the answer was a synthesis problem (please don't post any specific info) but then I can't find info.

Why hasn't the N-methyl been investigated, considering it would be the obvious (correct me if wrong) MDMA analogue?
 
No, on APB. So why are there no N-methylated APB derivatives?

Good question, I don't know.
 
skillet said:
No, on APB. So why are there no N-methylated APB derivatives?

Good question, I don't know.
Click to expand...

I understand now.

I'm assuming the extra bond existing on either end of the molecule might interfere with being active / MAT affinity. Possibly being the same reason why both of the oxygens at the 5 & 6 positions aren't both seen omitted as an analog together (a 5,6-APB) i.e. turned into extra bonds at once without one or the other oxygen remaining while on a cyclopentane configuration.
 
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sorry I have probably confused the issue:

N-Methyl 6-apb
or
N-Methyl 5-apb

I.e MDMA minus Oxygen + plus Hydrogen to make double bond

seems the obvious analogue but guessing there is a reason behind it.
 
From a SAR standpoint, we should expect reduced psychedelia (that is, reduced direct serotonergic agonism) and increased selectivity for SERT over DAT. I'm guessing that this would be mostly unwanted by most users, but they might be valuable compounds to have in our arsenals. I'm guessing that they're currently unexplored because 6-apb and 5-apb are relatively recent developments.

ebola
 
ebola? said:
From a SAR standpoint, we should expect reduced psychedelia (that is, reduced direct serotonergic agonism) and increased selectivity for SERT over DAT.
Click to expand...

If this is the case (I am ignorant of most of the SAR with these type of molecules) this would be a rather interesting point of venture. The subjective intensity of color and such (of which I am fully assuming as reason here) seems to me to do with serotonin agonism rather than its release (activity on SERT). To better act on SERT without doubling as an agonist to the receptor would be a plus subjectively, at least as far as I would be concerned. For wouldn't this result in a cleaner feeling serotonin releaser?
 
To better act on SERT without doubling as an agonist to the receptor would be a plus subjectively, at least as far as I would be concerned.
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Maybe. MDA and 5/6-apb are purportedly neato. For recreational compounds, cleaner isn't always better. Many people find selective SRAs a bit 'flat' or 'wanting' (I don't though :P).
 
It does seem odd these haven't been investigated yet. I'd guess the saturated N-methyl-6-APDB might be the most ecstasy-like, but probably all four compounds (i.e. N-Me-5-APB, N-Me-5-APDB, N-Me-6-APB, N-Me-6-APDB) would be recreational to some extent...
 
The 1993 5-APB/6-APB Nichols publication is a bit strange, as it starts off about MDA and MDMA both being neurotoxic but then goes into just the synthesis of molecules that have no N-Me without any reasoning. One possibility would be they just wanted a shorter chemical synthesis. But it's just a methylation and this is an Org Chem group so I don't see that as an issue. Perhaps maybe they did make them and they were inactive or poorly active, and could not explain it so they left it out or just left it out to keep the focus on the results that worked.

I just don't see why they would do the project as published, particularly when MDMA has always been the more popular drug.

J. Med. Chem. 1993,36,3700-3706
Synthesis and Pharmacological Examination of Benzofuran, Indan, and Tetralin Analogues of 3,4-( Methy1enedioxy)amphetamine
Aaron P. Monte, Danuta Marona-Lewicka, Nicholas V. Cozzi, and David E. Nichols
Click to expand...

I think you can read the first page for free without any access: http://pubs.acs.org/doi/abs/10.1021/jm00075a027
 
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I think Nichols, being ever so harm-reduction centered, simply shied away from developing the N-methyl versions knowing how similar they could be to MDMA and the resulting interest boom when the RC companies picked it up.
 
Thanks BLR11 I thought for a second to myself why doesn't 5-APB have the double bond in the Nichols paper figure, but must have quickly forgotten about it. I am not sure I agree with his group having less interest in MDMA-type drugs though. If you read the first page of the paper you will see the sole purpose of synthesizing 5-/6-APDB was to try and figure out why MDA and MDMA are neurotoxic.

5-/6-APB came from a patent, you can see the link in the wiki. It is surprising neither of them (Nichols or Briner et al) covered N-methylation then.

sekio said:
I think Nichols, being ever so harm-reduction centered, simply shied away from developing the N-methyl versions knowing how similar they could be to MDMA and the resulting interest boom when the RC companies picked it up.
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The paper came out in 1993, long before any RC company ever existed hence it could not have been a concern then. Also he has published many papers detailing novel molecules that were most likely psychedelic such as the NBOMe series, which if he were really worried about this sort of stuff, he never would have done.
 
long before any RC company ever existed

Hm? I'm positive there were RC companies in the 70's and 80's. Just not ones as we know them.
 
Shulgin & Nichols may well have had there own agena for not looking in to N-Methyl variants. They were looking for non-neurotoxic MDA/MDMA analogues and of the two MDA is more neurotoxic so would logically be the one to explore.
 
sekio said:
long before any RC company ever existed

Hm? I'm positive there were RC companies in the 70's and 80's. Just not ones as we know them.
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In the early 90s, there were many mail order vendors on BBS, IRC, that sold chemicals from MBDB, MDEA all the way to various tryptamines. They weren't known as research companies as we know them today.

I was wondering why we havent seen n-methyl 6-apb yet. Through my searching, I found one experience report.


Oral:
Weak: <50mg
Mild: 50-100mg
Strong: 100-130mg
Very strong: 130mg+

These doses are extrapolated from the 4 doses I have heard of people taking. I took 130mg which was perfect for me (will write a proper report soon), my friend took 120mg (after the initial come-up he was fine but for a while looked like he had taken too much will include his stats in my report), another fellow researcher I've talked to took 100mg and found that more than enough and his friend took 125mg and found that to be the best dose for him.

Very similar to MDMA doses and a tiny bit more potent than 5-APB and 6-APB
No info so far on any other ROAs

Come-up: 60-90mins
Peak: 3-4hours
Duration 6-8hours


Main effects: Euphoria, increase in music appreciation, increased energy, slightly trippy, empathogenic qualities
Side effects: Usual euphoric stimulant type things i.e. dilated pupils, gurning/jaw tension etc. No nausea present although one of my mates who took it with me almost passed out on the come up at 120mg (I had 130mg) He had been drinking more than me though. I found the come-up pretty strong but not quite ‘eyes rolling into the back of your head’ strong
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AlmostFamous said:
I was wondering why we havent seen n-methyl 6-apb yet. Through my searching, I found one experience report.
Click to expand...

I'm sorry - is this for 6-APDB, 5-APDB, or the n-methyl 6-APB? It was my impression that no one had gone that direction yet. Also, there was a thread on here a long while ago with a tiny bit of speculation: http://www.bluelight.ru/vb/threads/...n-hydrochloride-first-trial-of-a-new-compound

Nichols did MDMAI, but I have no idea what that would do to the benzofuran analogue. Your guess is as good or better than mine. :/
 
persianslipper said:
I'm sorry - is this for 6-APDB, 5-APDB, or the n-methyl 6-APB? It was my impression that no one had gone that direction yet. Also, there was a thread on here a long while ago with a tiny bit of speculation: http://www.bluelight.ru/vb/threads/...n-hydrochloride-first-trial-of-a-new-compound

Nichols did MDMAI, but I have no idea what that would do to the benzofuran analogue. Your guess is as good or better than mine. :/
Click to expand...


It was a report for n-methyl 6-apb. Poster said it was a custom synth.
 
^Very interesting.

Things being done "underground", you never know the reasoning (which is in some way the most interesting part - think PIHKAL etc, such a shame).

I know there are a LOT of MDA fans out there (particularly on bluelight!) - so yeah logical reason why 6-APB has taken off (as the legal MDA analogue). Still RC companies deal with the masses (+profit): Surely MDMA is the stereotypical (less psychadelic) stimulant/empathogen that people would go for. It's also not exactly that different chemically (1 x methyl) and it seems the production of RC's is on the increase. Which leave the question of why?

I'm not in any way recommending or suggesting it should be done (could well be a disaster compound waiting to happen but that is the case with most of these things) - just very curious as to the reasoning. The elephant in the room so to speak.
 
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