Various β-aminoketones / phenylpropylamines

[Allylbenzene]

Whilst investigating the β-aminoketone metabolites detected after administering pure allylbenzenes (eg studies for elemicin, safrole, myrstricin) which look like this (for safrole):

​

— I found various β-aminoketone containing drugs with a range of activity including muscle relaxants, anaesthetics, opioids and 5-HT3 antagonists. For example:

​

roi posted about it here.
[edit]
@Smyth2 clarifies: "This is called Perisone, CAS Fb: [22385-99-5] HCl: [6281-80-7]". It's a muscle relaxant like other related structures (see below).

2-methyl-1-phenyl-3-(piperidin-1-yl)propan-1-one
...
Summary: Substance dissolved incredible easy in water. 50mg rectal seems to be a nice recreational dose, however too euphoric to get work done. Not much of a body high though, seems to be rather mental, no crazy amounts of energy, feels really clean. Comedown is not unpleasant at all, not much of a urge to redose. Short duration (2-3 hours), but pretty enjoyable.

So yeah, if you go the oral route it'll probably take around 100mg. Decent stim, nothing to rave about though.

Here's some other related drugs that came up:

- Proroxan, non-selective alpha-blocker (α-adrenoreceptor antagonist)
- Propipocaine, local anaesthetic
- Lanperisone, muscle relaxant
- Eprazinone, mucolytic and bronchospasm relieving drug

- Inaperisone - muscle relaxant (inc Tolperisone, Eperisone below)

- Ondansetron, 5-HT3 antagonist

- Lobeline

Lobeline has multiple mechanisms of action, acting as a VMAT2 ligand, which stimulates dopamine release to a moderate extent when administered alone... It also inhibits the reuptake of dopamine and serotonin and acts as a mixed agonist–antagonist at nicotinic acetylcholine receptors. It is also an antagonist at μ-opioid receptors.

A series of tertiary amine drugs based on this structure (below) which interact with serotonin & dopamine receptors including SERT, 5-HT2A, D1, D2, D3, D4. Designed to be antagonists at these receptors.

Dimethylaminopivalophenone is an opioid analgesic with a potency ½ that of morphine

Based on the indole derivative Ondansetron, here are some simpler ß-aminoketone variations inspired by the allylbenzene metabolites found by Oswald. Ondansetron is a highly selective serotonin 5-HT3 receptor antagonist with low affinity for dopamine receptors.

> Ondansetron (top)
> simple ß-aminoketone variations based on the yellow sub-structure (below)

...including those based on N-(dimethyl / piperidyl / pyrrolidyl) and the classic 4-hydroxy / 5-methoxy (or 7-methyl) substitutions.

​

Context - aminoketone metabolites from allylbenzenes, here for safrole:

​

There's also interesting overlap between the aminoketone metabolite of methyl chavicol (top) and 6-methoxy-DMT (bottom).

The allylbenzene aminoketone metabolites in their dimethylamine form are chemically more like DMT than phenethylamines.
If you took the pyrrolidine section off of the indole group of 6-methoxy-DMT and replaced it with a keto group, you would have 1'-oxoestragole-DMA, which is the dimethylamine metabolite of methyl chavicol (estragole).​

In this context, the equivalent indole substitutions for allylbenzene aminoketone metabolites would be as follows:

Allylbenzene​	​	Indole equivalent
Estragole​	= 4-methoxy​	= 6-methoxy indole​
Methyl Eugenol​	= 3,4-dimethoxy​	= 5,6-dimethoxy indole​
Safrole​	= 3,4-methylenedioxy​	= 5,6-methylenedioxy indole
Myrstricin	= 3-methoxy-4,5-methylenedioxy	= 7-methoxy-5,6-methylenedioxy indole

A comparison between myrstricin's equivalent indole substitution and myrstricin's aminoketone metabolite that forms in-vivo (the dimethylamine one):

This type of modification could be explored with any indole-based psychoactive.