I think medication for Dean only falls along the lines of 'self medication'. Hell drink to ease the pain, or maybe take some kind of hard-core painkiller to knock himself out for a while, but 'care' for himself is pretty close to beyond him, I think, and something the would probably consider...wimpy. I don't doubt he sees it as part of his 'duty' to take care of Sam (and Kevin and Bobby) that way, because that's what a good leader does for his soldiers, that's what you *do* for everybody else.

I think the nurturing 'mom Dean' stuff is buried so far under that he barely realizes it, and yet... It comes out, and he lets it, so long as it's leavened with 'suck it up' bravado.