Vigilant, watchful (5)
I believe the answer is:
alert
I believe this is a double definition.
'vigilant' is the first definition.
(similar in meaning)
'watchful' is the second definition.
(similar in meaning)
(Other definitions for alert that I've seen before include "Lively" , "On one's toes" , "Wide-awake and watchful" , "In state of watchfulness" , "Watchful, sharp" .)