Eudibamus cursoris, a bolosaurid from the Early Permian of Germany (~284-279 mya).
Although very lizard-like in appearance, this animal was actually part of a completely extinct group known as parareptiles – a diverse group of early sauropsids who were once thought to be the ancestors of turtles, but are now considered to instead be the evolutionary cousins to the true reptiles.
With a total length of about 25cm long (8-10″), the structure and proportions of its limbs suggest it could run fast on its hind legs, making it one of the earliest known examples of bipedal locomotion. Since its teeth were adapted for a herbivorous diet, it wasn’t using its speed to chase down prey but was instead probably sprinting away from predators.
But unlike the sprawling running of some modern lizards, Eudibamus may have been capable of holding its legs in a more upright position directly under its body, convergently evolving a more energy-efficient posture similar to that of later bipedal animals like dinosaurs.
Colobomycter pholeter, a parareptile from the Early Permian of Oklahoma, USA (~289 mya). Although known only from partial skull fossils, its full size was probably around 30cm long (1′).
It had huge fangs at the front of its jaws, along with a few other enlarged teeth further back, all with serrated edges that show it was clearly a predator. What exactly it was feeding on with this unusual tooth arrangement is unknown – but proposed ideas include piercing through hard-shelled arthropods, or stabbing into smaller vertebrate prey.
Bunostegos akokanensis, from the Late Permian of Niger (~260 mya). About 2.5m long (8′2″), similar in size to a modern cow, it was a member of a group known as the pareiasaurs – stocky herbivorous reptile-relatives with osteoderm armor in their skin and knobbly bony nodules on their skulls.
The anatomy of its limb bones suggest it walked fully upright, with its legs held vertically under its body. This sort of posture has independently evolved multiple times in different tetrapod lineages, but Bunostegos is one of the earliest known examples.