N,N-dimethyl-phenethylamine

[Ham-milton]

I was thinking about the dimethylamphetamine /dimethylcathinone disparity in potency, and I think Hussness is right.

I assume it has to do with the one being a VMAT2 ligand and the other a DARI, so being a tertiary amine doesn't impact it as much, at all. Accurate?

 

[neuwelt]

The SAR of amphetamines and cathinones seem to differ quite much.
For example lengthening of the alkyl chain reduces potency for amphetamines, but increases the potency for cathinones (compare MDPV to methylone for example, although the qualitative expects may be lowered). And cathinones seem to accept a wider array of N-substituents and tertiary amines are more potent as far as I can see.

I wonder how the activity of "N-pyrrolidiniomethylone" is... And as beta-keto analogs of phenethylamines are rumoured to be just as active maybe it is possible to subsitute the amine in those cases!

 

[Ham-milton]

That'd be subbing the propyl for methyl on MDPV, right?

Sounds like a winner to me.

 

[LockFlimsy]

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!

This is old but there’s a plant called Eria Jarensis an it contains N,N-dimethylphenethylamine. It’s a euphoric stim used for workouts.

 

[Phobos]

This is old but there’s a plant called Eria Jarensis an it contains N,N-dimethylphenethylamine. It’s a euphoric stim used for workouts.

There may be traces of NN-DMPEA in Erja Jarensis, but the NN-DMPEA found in PWOs is 100% synthetic.

It's listed as a plant extract to go around the FDA rule that says that only plant extracts can be sold as dietary supplements while synthetic chemicals cannot.
I tried it and there it has a mild but decent activity, nothing recreational IME, but can be useful as a performance enhancer and an anorectic.

 

[LockFlimsy]

Interesting, Idk what pwo mean. Besides that this one site i tried gave me some pretty euphoric experiences(they sell it purified from the plant.) same with their club mixxx 3.0, felt like I was rolling fr. Listed as all natural ingredients too

 

[Phobos]

Interesting, Idk what pwo mean. Besides that this one site i tried gave me some pretty euphoric experiences(they sell it purified from the plant.) same with their club mixxx 3.0, felt like I was rolling fr. Listed as all natural ingredients too

PWO= Pre Work Out.
None of the NN-DMPEA or DMAA available for sale is actually extracted from a plant.

 

[LockFlimsy]

PWO= Pre Work Out.
None of the NN-DMPEA or DMAA available for sale is actually extracted from a plant.

makes sense shoulda figured that one out. Seems paranoid, Do you have links to studies?

 

[AlsoTapered]

I was thinking about the dimethylamphetamine /dimethylcathinone disparity in potency, and I think Hussness is right.

I assume it has to do with the one being a VMAT2 ligand and the other a DARI, so being a tertiary amine doesn't impact it as much, at all. Accurate?

Neurotoxicology of Synthetic Cathinone Analogs

The present review briefly explores the neurotoxic properties of methcathinone, mephedrone, methylone, and methylenedioxypyrovalerone (MDPV), four synthetic cathinones most commonly found in “bath salts.” Cathinones are β-keto ...

www.ncbi.nlm.nih.gov

 

[Phobos]

Seems paranoid, Do you have links to studies?

These plants only have trace amounts of these psychoactives meaning you'd need to process multiple tons of plants material to extract a kg and the price doesn't reflect that.

Look at that study in the citation: https://en.wikipedia.org/wiki/N,N-Dimethylphenethylamine#cite_note-1
They extracted 5mg of NN-DMPEA from 10kg of fresh plant, meaning you'd need 200 times as much to get a gram, so 2 metric tons for 1g, which is between 10 to 4 doses of NN-DMPEA.

If you instead have a look at Chinese raw chemical web shops you'll find prices that make it possible for a supplement company to sell you PWOs.
Still sound paranoid?

 

[LockFlimsy]

These plants only have trace amounts of these psychoactives meaning you'd need to process multiple tons of plants material to extract a kg and the price doesn't reflect that.

Look at that study in the citation: https://en.wikipedia.org/wiki/N,N-Dimethylphenethylamine#cite_note-1
They extracted 5mg of NN-DMPEA from 10kg of fresh plant, meaning you'd need 200 times as much to get a gram, so 2 metric tons for 1g, which is between 10 to 4 doses of NN-DMPEA.

If you instead have a look at Chinese raw chemical web shops you'll find prices that make it possible for a supplement company to sell you PWOs.
Still sound paranoid?

What I’m talking about ain’t pwo. Besides that I can’t find where you found those rates or numbers. So yes you still seem paranoid

 

[Phobos]

What I’m talking about ain’t pwo. Besides that I can’t find where you found those rates or numbers. So yes you still seem paranoid

May not be a PWO, it's still sold as a dietary supplement.

Click on the link, you'll get a Wikipedia page, the citation part.
Click on citation 1, then click download PDF and read, it's one page.
You'll find that they extracted 5mg of NN-DMPEA from 10 kg of Eria Jarensis.
I am not making this stuff up mate.

 

[sekio]

Pretty sure that phenethylamine and its N-methylated btetheren are all inactive as stimulants because MAO eats em up.

 

[Didgital]

^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)

Who would turn good dmt into anything else. Phenethylamine is dirt cheap and could easily be methylated with standard reductive amination.

 

[Phobos]

Pretty sure that phenethylamine and its N-methylated btetheren are all inactive as stimulants because MAO eats em up.

When used in OTC products sold as legal stimulants you'll usually find something with mild MAOI activity in there, like Hordenine.

 

[G_Chem]

When used in OTC products sold as legal stimulants you'll usually find something with mild MAOI activity in there, like Hordenine.

Yup not too hard to make these phenethylamines active by MAO inhibition.

Also I seriously doubt the legitimacy of a vendor that also sells a product called “Club Mixxx 3.0”

-GC

 

[AlsoTapered]

Oh, classy, 'Club Mixxx 3.0' for me every time.

Someone got ripped off and is now attempting to pass on the rip off. Maybe it DOES have MAOI activity so if taken with something else, it increases the activity of the second compound? Not in a safe way, mind.

Amazing to think that it's just cost them far more than it would cost to employ a consultant medicinal chemist to design a legal DET homologue. I mean, they are known.

 

[sekio]

Too bad hordenine is probably inactive orally:

In experimental animals, given sufficiently large doses parenterally (by injection), hordenine does produce an increase in blood pressure, as well as other disturbances of the cardiovascular, respiratory, and nervous systems. These effects are generally not reproduced by oral administration of the drug in test animals,

... also, curiously:

Using the sulfate salt (see "Chemistry"), Heffter gave a subcutaneous dose of 0.3 g to a 2.8-kg cat (about 107 mg/kg), and observed no effects besides violent vomiting; the cat behaved normally within 45 mins.

Poor cat.

OTC "legal stimulants" have a lot of these sort of things, active in binding assays but with pharmacokinetics that are garbage.