N,N-dimethyl-phenethylamine

[sodiumglow]

While pondering the fact that AMT is the Tryptamine homologue of Amphetamine, the idea of N,N-dimethyl-phenethylamine, the PEA homologue of DMT, popped into my head. A quick search turned up nothing that seemed to provide me with what I'm looking for. Is this compound active? Is it around? Has this thread been done x number of times? ...and if so, mods, please feel free to delete/merge.

Just curious about this I guess, and also, what about the amphetamine analogue, N,N-Dimethyl-Amphetamine? And to go a bit further (and a tad bit off course), why do some substitution patterns seem to be exclusive to the two structures? Why do para halogenated substitutions appear mostly on PEA's, and on Tryptamines you see things like 4 position Phosphorloxy and Acetoxy substitutions, and more mono and di substitutions on the amine Nitrogen?

I apologize if this has all been said and done before, but this all popped into my head as of two minutes ago while I was perusing the site and figured this would be the best place to ask, Thanks!

 

[branflakes]

There is no such thing because there is only one "N" position on the phenethylamine backbone. There are two only on the tryptamine one.

Tryptamine:

Phenethylamine:

 

[sodiumglow]

So why is DMT also known as N,N-DMT if both methyls are on the amine nitrogen?

I believe you are mistaken. I may not know much by the way of pharmacology but I'm pretty sure I've got my basic nomenclature down pat.

Edit: And yes, it does exist. Google it (N,N-dimethyl-phenethylamine). My problem is what I've found doesn't tell me much (that I can understand at least) about it.

Raspberries to you sir *pbbbbbbt*

 

[qwe]

^i dont have much chem background but is it possible to just do away with that H connected to the N in the phenethylamine and then you'd have RN1 and RN2 like the tryptamine? so you could add two methyls and you could get N,N-DMP (dimethylphenethylamine)

 

[DadeMurphy]

What? Of course you can make dimethyl phenethylamines. Nitrogen will take 3 single bonds. The nitrogen in phenethylamine can be dimethyl substituted.
dimethyl-pea and dimethylamphetamine have both been made and there is info out there on them if you search.

 

[MattPsy]

Correct. Nitrogen can indeed accept three bonds (or even four, in an ionized quarternary structure). The N,N designation is a bit unnecessary, but you can use it if you like. Dimethylphenethylamine is perfectly acceptable, as is 2-phenyl-1-dimethylaminoethane, or a variety of other similar naming schemes.

Um, as for your other points: Dimethylamphetamine is believe /has/ been made and assayed, but AFAIK it wasn't very nice at all, as in it wasn't pleasant recreationally.

As for the PEA & Trypt structures - it's to do with the orientation and position of relative areas of polarity/attraction of the different substituents so they can interact with the surface of the receptor(s) they're designed to fit with and activate. For example, a region of negative charge may interact with a region of positive charge to elicit effects. Or, vice versa, like with hydrophobic ("water-hating") regions.
Basically, the structure of them determines where these different regions will be places and as such some structure homologies for ach are not always successful on the other due to placing and orientation of the properties in the regions involved.

 

[Morninggloryseed]

So why is DMT also known as N,N-DMT if both methyls are on the amine nitrogen?

I believe you are mistaken. I may not know much by the way of pharmacology but I'm pretty sure I've got my basic nomenclature down pat.

No, you have it wrong. It is known as N,N-DMT because both Me are at the amine...which is "N." N,N-DMT means the methyls are on the amine (N).

 

[kidamnesiac]

Dimethyl amphetamine is reduced in potency from Meth, if I recall. Perhaps someone here knows exactly why, but I could speculate...

This actually makes me curious too, if, in the typical 5-HT ligand model, the N's end up in the same place, why are the N-alkyl PEA's of reduced potency while the N-alkyl TEA's generally retain potency? This was probably covered in the Dragonfly, etc. thread but I forget

 

[DadeMurphy]

Acting at different sites.
Hallucinogenic tryps are primarily targeting the 5-HT2A receptor, stimulating PEAs target the various membrane monoamine transporter (esp. DA, and NE).

 

[MattPsy]

Huh, what? The psychedelic PEA's primarily bind to the 5-HT2A receptor. They have low affinity for the monoamine reuptake transporters (with the exception of, say, MDA).

I'd say the PEA's and trypts target different residues. The ethylamine side chain comes out at a different angle afterall...
(then again, AMT is active, and it's a non N-substuted trypt :/ )

 

[DadeMurphy]

I said stimulating PEAs.
Dimethylamphetamine is not a psychedelic PEA.

 

[MattPsy]

Yes. But everyone else was not.

 

[sodiumglow]

No, you have it wrong. It is known as N,N-DMT because both Me are at the amine...which is "N." N,N-DMT means the methyls are on the amine (N).

lol.... ummm, that's exactly what I said.

But thanks for the replies all, and for humoring my uninformed queries. :D

 

[Riemann Zeta]

N,N-dimethyl-phenethylamine is inactive. It is simply destroyed by MAO just like PEA. The amphetamine analogue, dimethylamphetamine is also essentially inactive, but nevertheless is still considered a C-I compound. I always wondered why dimethylamphetamine is inactive--other bulky N-substituted amphetamines (such as ethylcathinone, bupropion, prolintane, etc...) are dopamine reuptake inhibitors.

 

[hugo24]

N,N-Dimethy-MDA is also down in activity,but for some reason Dimethylcathinon seems to be of good activity.

 

[hussness]

I would speculate that the common factor underlying these observations is that the SAR for transported stimulants doesn't work well with a tertiary nitrogen, whereas tertiary nitrogens are acceptable for non-transportable stimulants. This might explain the observations about NN-diMe-MDA, dimethylcathinone, bupropion, etc.

 

[kidamnesiac]

I dont know the molecular mechanism, but if they are 5-HT agonists and essentially substitute for each other in all experimental protocols, this ^ doesn't hold weight.
The DA NE story is probably close to this though.

 

[hussness]

You're right about 5-HT agonism not following that theory, but I wasn't meaning to include those effects. I'm not very familiar with the mechanism(s?) of 5-HT agonists, but they seem to be very different biochemically from the actions of stimulants.

 

[Acyl]

There is no such thing because there is only one "N" position on the phenethylamine backbone. There are two only on the tryptamine one.

...What.....?

You got it all wrong man.

 

[MurphyClox]

Old thread but I just encountered this compound I would like to ask the initial question again: Any definitive results/experience about N,N-Dimethylamphetamine?

What I found:

1. 6-12 times less active than Meth in behavioral assays with squirrel monkeys and rats (found here: J Pharmacol Exp Therap 1990, 253(2), p.466)

2. 10 times less active (but also less toxic) then Meth in behavioral asays with rats (found here: Brain Res 1997, 771(1), p.115)

3. Meth is made out of N,N-Dimethylamphetamine by metabolic means (found here: Klinische Wochenschrift 1955, 33(11_12), p.284 and here: Arzneimittel-Forschung 1956, 6, p.26)

Is this stuff active? Somebody (MattPsy) said, it was assayed in humans and worked but was not pleasant/recreationally useful. More details on this plz? I just encountered around 20 g for free and like to know more.

Peace! Murphy

Edit: Plz note that some of my refs are co-authored by a guy named Ricaurte. Not very trustworthy. So follow my implications with caution... (Thx for that hint goes to Vecktor)