p-methylacetophenon

icecool · Insistent Chemist

What do you think about this?
Can the acetophenon be substituted with methylacetophenon and thus also become methylphenylethylamine insted of phenylethylamine?
It is para-methylacetophenon which SWIM want's to start out of insted of acetophenon.

And is this a drug, I guess it was and was a replacement for amphetamine...

Lief · Wed Mar 16, 2005 5:11 am

Its not a drug.

icecool · Insistent Chemist

What is it then?
I somewhere read it was related to amphetamine and used to stop migraine...

IndoleAmine · Dreamreader Deluxe

phenethylamine is the "active" compound in chocolate, it produces increased serotonin release, but is not considered a drug... Very Happy

4-methylphenylethylamine may be a migraine medication, but certainly no drug in the common sense.

But if you would replace acetophenone with phenylacetone in the above synthesis, you would maybe get phenylisopropylamine (or phenylisopropyl-n-methylamine when methylammonium formate or n-methyl formamide are used), which is indeed a drug.

But the Leuckart reaction is not a very good route to choose when one would want to dream about anything like phenylisopropylamine - it makes a lot of tar and the workup can be quite messy. Can be scaled up to enormous amounts though.

It was the method of choice in the past times, but has been replaced with other, cleaner and more efficient methods, like hydrogenation with RaneyNi under pressure..

i_a

Lief · Mon Mar 21, 2005 4:06 am

There's a big difference between alpha-phenethylamine and beta-phenethylamine.

IndoleAmine · Dreamreader Deluxe

Not really. Very Happy

Vitus · Psychoscientist

alpha-phenethylamine has been found in street samples containing amphetamine and caffeine.

http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=9013285&dopt=Abstract

http://dx.doi.org/10.1016/0379-0738(95)01852-2

Some cook probably diluted his P2P

IndoleAmine · Dreamreader Deluxe

Or made it from phenylacetic acid and didn't purify properly, and thus had some phenylacetaldehyde impurities...

Nicodem · Tue Apr 26, 2005 12:55 pm

No, phenylacetaldehyde contamination would give beta-phenylethylamine instead, though I can't imagine what kind of clandestine method would reduce phenylacetic acid or any of its derivative to phenylacetaldehyde.

Alpha-phenylethylamine is probably used to dillute amphetamine (on purpose) only because it tastes similar. It is simply cheap and it suits this purpose. It is not to be exclude what Vitus sugests, that it is the P2P that was dilluted with the cheap acetophenone for the same reasons, as any method used to make amphetamine from P2P also gives alpha-PEA from acetophenone.

IndoleAmine · Dreamreader Deluxe

Can you please clarify on the difference between alpha- and beta-phenethylamine? ChemDraw gives the same structure for both, merck doesn't differentiate - I doubt theres any difference...

Nicodem · Tue Apr 26, 2005 3:19 pm

alpha-phenylethylamine: Ph-CH(NH₂ )-CH₃ {the Ph group is on the alpha carbon; two enantiomers exists}

beta-phenylethylamine: Ph-CH₂ -CH₂ -NH₂ {the Ph group is on the beta carbon; no optical isomery}

The PEA compounds that bees like are the beta-PEA.

IndoleAmine · Dreamreader Deluxe

Ah, I see.

"a-phenethylamine" is commonly called a-Methylbenzylamine where I com from, sorry.

b-phenethylamine is the neuroactive form found in man, but a-phenethylamine is derived from acetophenone/ammonia reduction...

Kinda clears up the confusion which evolved in another thread (about phenethylamine derived from 1-phenyl-2-nitroethene reduction and its psychoactivity), I would say! Very Happy

(I don't know for sure; but I BET there are many p2p routes leading to PAAldehyde impurites and subsequent b-phenetlylamine formation upon reduction - imagine just a few hundred ppm P2P molecules being teared apart under violent reductive conditions..)

IndoleAmine · Dreamreader Deluxe

Or imagine someone accidentally bought phenylacetaldehyde instead of phenylacetic acid..... Very Happy