http://rhodium.lycaeum.org (http://rhodium.lycaeum.org)
http://www.fortunecity.com/westwood/storey/116/ (http://www.fortunecity.com/westwood/storey/116/)
Lilienthal's Reference #305:I know of no active compounds with an amine function on the benzene ring.
benzodiazepines?
paracetamol?
fentanyls?
Okay, let's rephrase: "I know of no entheogens/entactogens with an amine or amide function on an aromatic ring". The 4-amino and 4-acetamido derivatives of 2,5-DMA is for example fully inactive.
"Entheogenic" is such a subjective term! And surely you would agree that there are many non-entheogenic biologically active compounds worthy of interest. Perhaps you may find the following articles interesting:
European Journal of Medicinal Chemistry (1996) 31 133-142.
European Journal of Medicinal Chemistry (1999) 34 137-151.
Journal of Medicinal Chemistry (1963) 6 519-524.
Journal of Medicinal Chemistry (1978) 21 1 56-63.
Journal of Medicinal Chemistry (1980) 23 2 154-162.
Journal of Medicinal Chemistry (1986) 29 8 1406-1412.
Each of the them is a study of biologically-active 4-amino phenethylamines. Of particular interest to this discussion is the article from '86, in which the indole homolog of MDA is studied, which turns out to be, among other things, a potent MAO inhibitor at serotoergic, norandegenergic, and dopaminergic receptor terminals.
Also worth reading is the JMC article from '63, in which 4-dimethylaminoamphetamine was found to be a more potent anorexigenic compound than phenmetrazine (albeit somewhat weaker than amphetamine itself.)