You'd need something on the sorts of injuries/diseases that 24th Century medicine still can't treat, to be sure of occasionally stumping your CMO (and giving them something to work on). There's a huge list of medicines and medical equipment in the Trek Encyclopedia. Perhaps a brief list of medicines and a quick summary of what each is used for (sort of a Treknobabble chart, so the players can immediately say "Get me a hypo filled with......" and know that it should be filled with hyronalyn if the patient has suffered radiation exposure).
"That might have been the biggest mistake of my life..."
"It is unlikely. I predict there is scope for even greater mistakes in the future given your obvious talent for them."
Vila and Orac, Blake's Seven