Murphy - I was only able to get the 2nd of those papers (J Pharm Sci 1982, 71(10), p.1152). It doesn't mention an N-nitrosyl or an N-hydroxyl metabolites. I was under the impression that it was simply the fact that the 4-nitro gets reduced (which it doesn't in Rats) to the amine & since aromatic amines are ALWAYS suspect from a mutagenic POV - THAT was the group to blame. I was under the impression that N-nitroso was absorbed by food (cooked red meat) while hydroxylamines are actually used in the body? Shulgin certainly had no quarms making them.
I would gladly buy those papers if only I knew WHERE. Reaxys doesn't give a good link so basically, unless some Dutch chemist can help out.
The whole QSAR of this class is quite odd. An EWG ortho to an EDG seems to give the most potency. For example, in 1 table:
methaqualone 49
2-methyl-4-chloro 28
2-methyl-4-bromo 18
The scale is umol/kg
This pattern fits in with nitromethaqualone. Sadly, nobody seems to have tested 2-halo-4-methyl and once again, I think it's duration.
Sadly, all of the works of Klosa to produce 100s of analogues and registering physical constants was not turned into test compounds. I think a TFM would replace a nitro...
I would gladly buy those papers if only I knew WHERE. Reaxys doesn't give a good link so basically, unless some Dutch chemist can help out.
The whole QSAR of this class is quite odd. An EWG ortho to an EDG seems to give the most potency. For example, in 1 table:
methaqualone 49
2-methyl-4-chloro 28
2-methyl-4-bromo 18
The scale is umol/kg
This pattern fits in with nitromethaqualone. Sadly, nobody seems to have tested 2-halo-4-methyl and once again, I think it's duration.
Sadly, all of the works of Klosa to produce 100s of analogues and registering physical constants was not turned into test compounds. I think a TFM would replace a nitro...
Last edited:
