Some sailed creatures of the Permian - the Pelycosauria Synapsids: Dimetrodon and its relatives.
illustration by Mario Lanzas
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Some sailed creatures of the Permian - the Pelycosauria Synapsids: Dimetrodon and its relatives.
illustration by Mario Lanzas

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Dimacrodon hottoni was a synapsid that lived during the mid-Permian, about 272 million years ago, in what is now Texas, USA.
Known only from incomplete skull material, it had a thin bony crest on its forehead and a long snout with unusually toothless jaw tips — which had a rough bone texture suggesting there was a small keratinous beak there.
Its full body proportions aren't known, but since its skull measured around 50cm (~1'8") it was probably at least 2.5-3m long (~8-10').
When its fossil remains were first discovered in the mid-20th century it was thought to be a dicynodont-like anomodont, but later examination in the 1990s suggested it was actually a more basal "pelycosaur-grade" synapsid, possibly a sphenacodont close to early therapsids. There hasn't been any further study on Dimacrodon since then, though, so its exact evolutionary relationships remain very murky.
Its ecology is equally unclear, but its beak-like jaws suggest it may have been somewhat herbivorous. It would have lived around a coastal river delta in a semi-arid climate, alongside herbivorous caseids like Cotylorhynchus and Angelosaurus, predatory sphenacodontids like Dimetrodon, small lizard-like parareptiles and captorhinids, and aquatic temnospondyl amphibians.
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How about some love for the less charismatic permian denizens?
Perhaps some varanopids, as the man of the monitors i am...
Varanopidae
An extinct family of Synapsid reptiles from the Late Carboniferous to Middle Permian. There is disagreement over whether they are more closely related to mammals or to other more reptilian synapsids. They are somewhat similar looking in appearance to Monitor Lizards, family Varanidae.
Varanodon agilis
Found in the Chickasha Formation of Oklahoma, USA, which dates to the Roadian stage of the Middle Permian. This could be an early growth stage of the much larger Watongia, and not in fact a separate and distinct species.
illustration by Dmitry Bogdanov
Watangia meieri
Found in the Chickasha Formation of Oklahoma, USA, which dates to the Roadian stage of the Middle Permian. This could be an later growth stage of the much smaller Varanodon.
illustration by Dmitry Bogdanov
Varanops brevirostris
From the Early Permian of Texas and Oklahoma, USA.
illustration by Dmitry Bogdanov
Elliotsmithia longiceps
Fromin the late Middle Permian of South Africa. The only Varanopid known from Africa. Named for the anatomist Sir Grafton Elliot Smith, and not the singer Elliiott Smith.
illustration by Seismic Shrimp
Dimetrodon
Height: 2.0 Meters
Weight: 250 Kilograms
Length: 2.0 Meters
Dimetrodon Is A Large Pelycosaurian Synapsid That Lived During The Early Permian (259 MYA). It's Diet Consisted Of Other Synapsids, Like Edaphosaurus. It Had A Sail Reaching Over 1.8 Meters
"During the latter part of the Early Permian in an upland forest, the primitive gorgonopsid, Watongia encounters four Cotylorhynchus, which were among the largest of all pelycosaurs. Watongia was about 1.6m (5 ft) long, and Cotylorhynchus reached lengths of 4 m (13 ft)."
From Dinosaurs: A Global View (1990) by Sylvia J. Czerkas & Stephen A. Czerkas. Illustrated by Douglas Henderson, Mark Hallett, John Sibbick.

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a long time ago youd have called her "mom" !
A small elliotsmithia tries to steal an egg from a trio of nesting moschops.