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Several members of the group Theriocephalia - a group of therapsids, or “mammal-like reptiles*”, related to both gorgonopsids and modern mammals - are believed to have been venomous!
Euchambersia, a theriocephalian from Late Permian South Africa, had large openings behind each canine tooth that are believed to have held venom glands. Grooves on each tooth would have routed the venom into the bitten prey’s body.
(Above: Dmitry Bogdanov’s restoration of the animal in question.)
Another African theriocephalian, Ichibengops, had similar grooves on its teeth, and may have been venomous as well. Euchambersia and Ichibengops belonged to two different families of theriocephalians, implying that many more of these animals may have been venomous as well.
*”Mammal-like reptiles” is not a scientifically accurate term, as even pre-mammalian therapsids cannot be called “reptiles”. It’s used here for clarity’s sake.
