Methaqualone, para isomer

[Everlasting Reign]

Does anyone have any pharmacological information on the p-tolyl analog of methaqualone? Google scholar returned little in the way of psychoactivity.

Regards.

 

[mad_scientist]

Pretty sure its a selective convulsant.

 

[Everlasting Reign]

How do you know?

 

[mad_scientist]

Because the o-methyl group or equivalent is absolutely required for sedative activity, and the p-chloro compound is a convulsant 8)

 

[MurphyClox]

...as is the para-bromo derivative. I'm afraid mad_scientist is right in this respect. - Murphy

 

[Everlasting Reign]

Reference?

Typically, aromatic quinazolinones display anti-convulsant activity.

 

[mad_scientist]

From this paper

"Boltze von KH, Dell HD, Lehwald H, Lorenz D, Rüberg-Schweer M. Substituierte Chinazolinone-(4) als Hypnotica und Antikonvulsiva. (German). Arzneimittel Forschung. Drug Research. 1963; 13(8):688-701."

and I think we may have gone through some of the related papers also, was a long time ago we discussed it.

Anyway stop wasting our time n00b, this compound is not what you are looking for.

 

[Hammilton]

Hell, many of these are convulsants even when they're sedatives.

 

[Everlasting Reign]

From this paper

"Boltze von KH, Dell HD, Lehwald H, Lorenz D, Rüberg-Schweer M. Substituierte Chinazolinone-(4) als Hypnotica und Antikonvulsiva. (German). Arzneimittel Forschung. Drug Research. 1963; 13(8):688-701."

I see. Does that paper mention specifically the p-tolyl isomer, or just the p-chloro isomer?

 

[vecktor]

I see. Does that paper mention specifically the p-tolyl isomer, or just the p-chloro isomer?

methyl is isosteric with chlorine, so madscientist's prediction is sound.

 

[MurphyClox]

I see. Does that paper mention specifically the p-tolyl isomer, or just the p-chloro isomer?

The para-isomer is not specifically mentioned in the cited paper but as Vecktor said, both residues are bioisosteric.

 

[fastandbulbous]

If you fiddle about with the structure of either barbiturates or benzodiazepines, you end up with convulsant compounds, so why the surprise at the same being true for methaqualone?

 

[Everlasting Reign]

Thanks for the information.

 

[Hammilton]

If you fiddle about with the structure of either barbiturates or benzodiazepines, you end up with convulsant compounds, so why the surprise at the same being true for methaqualone?

With benzos, anyway, the modifications neccessary to produce a convulsant are quite large. With barbiturates, however, it's quite small. I guess these are closer to benzos structurally, but with the issues of methyl methaqualone being a convulsant, it's no surprise that this is.