LOL, my Cas would have to agree on that and just pour his double another cup. He doesn't sleep, so they also have that in common. He likes his caffeine and his booze. Sometimes together.
Nah, Norman doesn't have any of the drugs aboard. He's from the ending where he decided to quit cold turkey - meantime, the drugs were what was stabilizing the effects of the ARI device. Without it, he hallucinates all kinds of things and ignores them, pretending he isn't tripping out. He'd also try to caution Cas against the drugs because he'd be all "You realize I'm seeing tiny holographic tanks all over the room right now, right? Do you really want that?"
But yes, Anna would give him THAT look for all of that. She doesn't mince words, you silly thing.