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It’s the middle of the night, and you can’t sleep. Time to choose your own adventure: 1. Toss and turn all night, thinking about all the sleep you aren’t getting. 2. Make a steaming cup of something warm and try to sip yourself to sleep.3. Pop a Xanax you got the last time you flew cross-country, and thank modern medicine for all it’s good for.

If you’re anything like us, when you go against doctors’ orders (we can hear our M.D.’s voice in our head: “Only take one for anxiety before a flight”), you rationalize: It’s not like this is going to kill me, right?

No, it’s probably not, says Margo Farber, a pharmacist and the director of the Drug Information Services at the University of Michigan Health System. But while it might not be a life-threatening choice, it’s definitely not the best option for most people today.

What Xanax Actually Does

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Xanax is part of a class of drugs called benzodiazepines, along with Valium, Ativan, and Klonopin. Doctors and psychiatrists usually prescribe them for anxiety, as they mimic the brain’s GABA (gamma-aminobutyric acid) neurotransmitter for a sedating effect, Farber says. This basically calms you down and can make you sleepy, which is why some people reach for it at night.

But that’s kind of a roundabout way of doing things. In comparison, Farber says that the “Z drugs,” or non-benzodiazepines, specifically made for sleep (think Lunesta, Sonata, Ambien) don’t mimic GABA, but activate the receptor that GABA would normally trigger. Same endgame—glorious sleep—but they’re faster acting and without many of the side effects.

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And those side effects of benzodiazepines, ranging from temporary amnesia to grogginess to reduced motor function, are nothing to mess around with. Farber says people taking them adapt to their dosage, so they don’t experience “the hangover effect” quite as strongly. But if you’re only prescribed Xanax for occasional use and pop a one-off in the middle of the night—then you’ll likely feel the effects in full force.

And they can persist from eight to 12 hours, meaning you may actually feel more tired in the morning than you would normally (irony at its worst). So if you take the Xanax at 2 a.m. and wake up at 7 a.m., you’ve still got seven more hours’ worth of those side effects—bad news for getting to work on time, basically.

Plus, Xanax was made to treat anxiety. Say you’re a nervous flier—when you take one before boarding, the medicine goes up against the chemicals surging in your body, reacting to them and counteracting some of the drug’s effect, says Joseph M. Ojile, M.D., medical director and chief executive officer of the Clayton Sleep Institute. So if you take it when you’re actually calm and relaxed—for instance, about to go to bed—there’s none of that counteraction, and the grogginess and potenial amnesia is going to hit you more severely.

Still, It’s 2 a.m.

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Basically, yes, there are better options—namely, sleep medications and setting up your bedroom for sleep success (sorry, laptop). But if sleeplessness hits, and you have a Xanax left over, Ojije says it’s fine to take one once or twice a week (if you haven’t been drinking)—just try half your normal dosage first. The risks are dose-related, so if you take less medicine, you run a lower risk of that dreaded hangover.

But definitely stick to just once or twice a week. Any more and you increase your chances of building tolerance, says John Mendelson, M.D., a internist who researches commonly abused drugs at California Pacific Medical Center Research Institute’s Addiction and Pharmacology Research Laboratory. “Tolerance happens pretty easily—just taking it [every night] for a week or two, a very short period of time. Then once you’re tolerant, the drug can have less of an effect,” Mendelson says.

In that same vein, you’ll also become dependent—meaning you need it to fall asleep, and may go through withdrawal symptoms, like rebound anxiety or insomnia, when you try to stop, Farber says.

The Takeaway

One Xanax (or even better, half of one) is fine to take once in a while, if you can’t get to sleep and you have a leftover on hand. But don’t expect to be firing on all cylinders the next morning, and keep in mind that there are way better options. Upping your sleep hygiene can help, as can prescription and OTC medicines—anything that makes it possible for you to go to bed relaxed and able to catch plenty of zzzs without turning into a zombie the next morning.

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