You'd probably have a "wet brain" already for that shy an amount to black you out. On the drugs: yes, certain drugs leave no hangover.
If you gulp down a bottle of wine, you might. But by the glass, over time, it is unlikely. If you do not metabolize wine well, then the next morning will bring a stomach ache and more.
5 Six once glasses of Wine? Only if you're a Lightweight and you would be looped not pass out.
Oh please, enough of the Imperial system.<br />
5 glasses of wine you say, well if you were drunk you wold at least feel groggy but that is not a lot anyway.
No. You cannot.