C30-NBOMe

[blueberries]

This chemical's just popped up, absolutely no information but already talks about vending. Seems like Mescaline attached to 2C-C but in the wild it could behave very differently. What do you think about it?

http://i.imgur.com/urBiSRz.jpg

 

[cannibalsnail]

I'd imagine some of it at least being hydrolysed to 2C-C and Mescaline. I seriously doubt it would be active as is.

 

[Solipsis]

I'd imagine some of it at least being hydrolysed to 2C-C and Mescaline. I seriously doubt it would be active as is.

You can say the same thing about other N-benzylated PEAs, yes they would partially hydrolyse to the parent PEA and some benzylaldehyde but let's not forget that quite a number of them are psychoactive and at extremely low doses at that.

Could you please define "popped up", blueberries?

There is a thread on this compound in PD here: http://www.bluelight.ru/vb/threads/675323-Trimethoxy-substituted-N-benzylPEAs

Although I don't think I put it as harshly there at this point I don't see what the fuss is about. There are more N-benzylated 2C-X derivatives that I can think of (probably ;P ), some of which may be active and at doses that are a little less extreme. I don't particularly trust these N-benzyl PEAs but if we must have them, it might be a good idea to focus on the compounds that are a little less potent, because there are more important factors than economics like effects moderated to be - hopefully - interesting / enjoyable in a little less extreme and more "responsible" way.

Yes, again this compound could be an example - but what about the countless other examples, like all sorts of permutations of halo-, hydroxy, methoxy, or cyclized ether substitutions on the N-benzyl....?

 

[King Kong]

You can say the same thing about other N-benzylated PEAs, yes they would partially hydrolyse to the parent PEA and some benzylaldehyde

I have heard several times this hypothesis, but is there any evidence to approve it?
Because, an imine would hydrolyse to the parent PEA and a substituted benzaldehyde, but not a secondary amine! An enzyme are required to metabolize N-benzylated PEAs to the parent PEAs... But I doubt that we have an enzyme able to do that.

Seems like Mescaline attached to 2C-C

There is no mescaline in these molecule. One carbon is missing.

 

[sekio]

I have heard several times this hypothesis, but is there any evidence to approve it?

This is the reaction catalysed by MAO, isn't it?

 

[Solipsis]

I have heard several times this hypothesis, but is there any evidence to approve it?
Because, an imine would hydrolyse to the parent PEA and a substituted benzaldehyde, but not a secondary amine! An enzyme are required to metabolize N-benzylated PEAs to the parent PEAs... But I doubt that we have an enzyme able to do that.

I can't find anything on the subject, you're probably right, in which case good call. It wasn't really my argument to begin with, I just responded to it in a matter like "so what if it does?", thinking that it might be in some equilibrium (forgetting that the acidity would very much matter).
And on that note: it is hardly pertinent to the rest of my post i.e. what I really tried to say.

Also, I just realized that if it were true that these secondary amines would hydrolyse, not only the parent PEA could form but also the benzylamine. If that carbon wasn't missing in the trimethoxybenzyl moiety, it could yield mescaline because it would be a sort of PEA palindrome - say a PEAEP.
Might be funny to stick it to LEO conjoining 2C-B and mescaline or something like that... well at least if it is active. Then again, minute quantities of unreacted mono-PEAs could make you especially liable legally a.k.a. the 4-AcO-DMT problem.

This is the reaction catalysed by MAO, isn't it?

MAOs gobble on monoamines which I think are all primary amines. Though it seems the 'mono' part refers to these neurotransmitters having one amino function (indoles and stuff not included I guess). I am not sure about that, but it can be confusing especially if indeed all monoamines are primary amines.

 

[sekio]

Doesn't MAO eat DMT - a tertiary amine? (and presumably N-methyltryptamine?)

Epinephrine is considered to be a monoamine, too. It's N-methylnorepinephrine.

 

[blueberries]

Could you please define "popped up", blueberries?

There is a thread on this compound in PD here: http://www.bluelight.ru/vb/threads/675323-Trimethoxy-substituted-N-benzylPEAs

Yeah, I meant it appeared fairly recently and there's quite a buzz hence the other thread, which I didn't manage to see, sorry!

There is no mescaline in these molecule. One carbon is missing.

Yeah I realised but thought I'd write it out a little simpler since I'm not too familiar with the chemical term; 2C-C n, (3,4,5 methoxy-phenylmethylamine)??

 

[Solipsis]

Yeah, I meant it appeared fairly recently

As in: the substance has been synthesized or the idea has been suggested?

Doesn't MAO eat DMT - a tertiary amine? (and presumably N-methyltryptamine?)

Epinephrine is considered to be a monoamine, too. It's N-methylnorepinephrine.

Ah, now we are getting in some interesting territory...

You are absolutely right, those are not primary amines but apparently MAO does not metabolize them.

Epinephrine is metabolized to NE by catechol-O-methyltransferase and even then MAO doesn't get its hands on it.

DMT is indeed demethylated, but I would be very surprised if it was by MAO. Then again, if MAOIs potentiate DMT, wouldn't a lot of DMT first be demethylated by another enzyme? Could it be that DMT is mostly a prodrug for NMT or even high levels of tryptamine itself? Do we have information on NMT or tryptamine being taken with MAOIs?

 

[sekio]

I was under the impression that MAO was the primary enzyme responsible for inactivating DMT when it is absorbed orally (or smoked).

Could it be that DMT is mostly a prodrug for NMT or even high levels of tryptamine itself? Do we have information on NMT or tryptamine being taken with MAOIs?

I've never heard of DMT being demethylated in vivo.

Epinephrine is metabolized to NE by catechol-O-methyltransferase and even then MAO doesn't get its hands on it.

This paper actually suggests the primary route of epinephrine metabolism is oxidation by MAO.

---

Now that I think about it more, it is unlikely MAO would split a PEA to the benzaldehyde and parent PEA. MAO apparently oxidises e.g. phenethylamine to phenylethanal. (amphetamine to phenylacetone) N-dealkylation (at least of e.g. benzphetamine) is controlled more by CYP enzymes.

 

[tryp2fun]

Of course DMT is a substrate for MAO! Why do you think that DMT is orally inactive, but orally active when consumed with harmaline, an MAO-A inhibitor?

 

[Solipsis]

I just explained my alternative notion: it seemed possible to me that an active demethylated metabolite was a MAO substrate. I guess that is untrue and would go against a lot we think and know about this... I just couldn't find any information about MAO being able to metabolize N-methylated compounds directly. So I was wondering out loud since IAA is a known metabolite of DMT. Sorry.

So instead, MAO is able to lop off an entire amine function including methyl(s) ? Then I guess I wonder how big the N-substitution would have to be to (possibly) sterically hinder MAOs active site? Does this happen gradually or not at all because it has a convenient tertiary structure?

I was under the impression that MAO was the primary enzyme responsible for inactivating DMT when it is absorbed orally (or smoked).



I've never heard of DMT being demethylated in vivo.



This paper actually suggests the primary route of epinephrine metabolism is oxidation by MAO.

---

Now that I think about it more, it is unlikely MAO would split a PEA to the benzaldehyde and parent PEA. MAO apparently oxidises e.g. phenethylamine to phenylethanal. (amphetamine to phenylacetone) N-dealkylation (at least of e.g. benzphetamine) is controlled more by CYP enzymes.

Yes, but if both N-substitutions are phenethylamines, you would always get a PEA and phenethanal..

 

[sekio]

So instead, MAO is able to lop off an entire amine function including methyl(s) ? Then I guess I wonder how big the N-substitution would have to be to (possibly) sterically hinder MAOs active site?

I believe that is the case. It's an oxidative cleavage. As you said, DMT is oxidised into HIAA.

I think that maybe the N-site is less important than other parts of the molecule for MAO activity. For instance, mescaline, a primary amine, is mysteriously not degraded by MAO as well as e.g. PEA is. But it does make sense that steric hindrance at the N-site would protect compounds from oxidation. It probably explains the relative activity of e.g. oral DPT compared to DMT.

Re: dmt demethylation in vivo: I believe that NMT actually does have effects if administered IV/smoked. I`m not sure if they are considered as pleasant or desirable as those of DMT though.

I'm pretty sure that if DMT was demethylated it wouldn't be "all the way" to tryptamine, though - as IV tryptamine seems to be essentially inactive compared to the N-methylated versions.

Yes, but if both N-substitutions are phenethylamines, you would always get a PEA and phenethanal..

Via the CYP enzymes, sure. Via MAO you would probably just get 2eq of an aldehyde/ketone.

 

[cannibalsnail]

Clearly the backside of 2A ligands is more important in determining enzymatic resistance than the actual amine. Tryptamine/DMT are rapidly destroyed by MAO, but a simple alcohol group in the 4th or 5th position GREATLY reduces the reaction rate. Similarly Phenethylamine, the addition of ring substitutions prevents MAO degradation.

Binding pockets in proteins are significantly more complex than simple amine interaction.

 

[blueberries]

As in: the substance has been synthesized or the idea has been suggested?

Oh right, yeah just the idea has been suggested but it was by one company offering it as a synth option. I'm guessing they haven't tried to yet because it seems to be the only mention of it, apart of course from people looking to do a group buy.

 

[mysticmusic]

Assumptions regarding the metabolic fate of this molecule are widely speculative at best.
It's seems as likely to me to face a similar pathway as super-potent 25-C-nbome, as to breakdown into something like a mix 2C-C and Mescaline. ROA possibly plays a significant role here; it could conceivably breakdown to a mix of 2C-C and Mescaline OS, yet have greater stability and potency like 25C-nbome with parenteral administration ,
Certainly extreme caution titrating the dose is in order, at least until more data is available.

 

[sekio]

It's not going to break down into mescaline; it's one carbon short.

Maybe into methylated gallic acids though.

 

[klondike_bar]

I am very interested in this compound, and have requested a sample from a custom synth lab, which was unable to provide very much information outside of pricing and availability.

 

[Solipsis]

Be careful, considering we don't even have binding assay data like with some other N-benzyl PEAs it could be much less specific and more dangerous, depending on what it actually is that makes N-benzyl PEAs potentially dangerous.

 

[klondike_bar]

Be careful, considering we don't even have binding assay data like with some other N-benzyl PEAs it could be much less specific and more dangerous, depending on what it actually is that makes N-benzyl PEAs potentially dangerous.

absolutely. Does anyone here have *ACTUAL* access to equipment that can somehow test or evaluate unknown materials like this? If i am able to procure a sample of the material i would be massively interested in sharing with someone who has the relevant pharmaceutical/organic chemistry expertise to provide more information