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The longest I've been awake was three days. I've known people that have been awake for 15 days before. I think you have to be awake for 4-6 weeks before it kills you, though your body usually makes you pass out before then.
If you have chronic insomnia, I would seriously go to a doctor and get some sleeping pills or go to a sleep clinic. There's usually a reason why you can't sleep, but untill you figure it out and correct it, takes some pills for a couple of nights just to sleep for awhile.
If you don't want to take pills, take Valerian root. I don't recommend eating it raw though, I would take it capsule form because it tastes disgusting. But Valerian will definitely relax you naturally and that's usually enough for your body to sleep for awhile.
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