The best (and worst) supplements for sleep

I didn’t sleep well last night.

This happens to me sometimes, especially when it’s hot out1We don’t have A/C., when I’ve just traveled through through multiple time zones, or when my upstairs neighbor is having a meeting of the Democratic Socialists of America in his living room, or, like last night, all three.2I like the DSA, but not when they are chanting and stomping around above my bedroom at 10PM. Yes, we are moving.

After tossing and turning for a bit, getting kicked out of bed by my partner, and staring at the ceiling above the couch well past midnight, I eventually turned to chemical assistance — both last night, to finally get to sleep, and this morning, to get myself going after what couldn’t have been more than four hours of sleep.

This experience is familiar to most of the frequent travelers I talk to, thanks to jet lag, early flights, and unfamiliar beds. My first recommendation is always to get the basics right: make sure your room is cold, dark, and quiet; turn of the tv, and get as little bright or blue light as possible.3Apps like f.lux and Night Shift can help with this.  But when all else fails, there are a number of chemicals (some prescription, some non-) that can help.

Some help you trick or retrain your biological clock, some help your relax enough to knock off, some simply knock you out, and some help you stay awake and alert after a bad night. Almost none should be a regular habit, but many are very useful in targeted circumstances — I personally rely on a number for few days to a couple of weeks at a time, depending on the situation.

They all have their own pros and cons, though, depending on the problem you’re dealing with and your own personal biochemistry — so before just telling you what I do, I’m going to explain a few of the most popular ones.

One other thing. If you don’t like the idea of “unnaturally” altering your sleep, I have some bad news for you: you already are. The modern world is full of things that mess with our sleep cycles, including street lights, the blue light from computers, sleeping in one uninterrupted block instead of two or more, spending all day inside, shifting time zones, when you eat, what you eat, etc. If you’re looking for “natural” sleep, give up the advances of modernity and live in a cave. If you’re unwilling to do that: chemicals.


Perhaps the most ubiquitous OTC sleep aid these days, Melatonin is a hormone that our bodies naturally synthesize towards the end of the day. Throughout the evening, melatonin levels build, and eventually high enough levels signal to our brains that it’s time to fall asleep. (It’s also critical for a number of biological systems that we associate with sleep — it’s a powerful antioxidant and metabolic signal, and plays a role in triggering a number of the body’s nighttime repair systems.)

When your sleep cycle is knocked out of whack — whether because of time zone shifts, inconsistent bedtimes, or too much exposure to blue light late in the day (which halts melatonin production) — your brain won’t produce melatonin naturally. Supplemental melatonin can help levels get back to normal, increasing time-to-sleep, quality of sleep, and length of sleep in healthy people. It’s also proven to work quite well in fixing jet lag and other time-related sleep disorders like shift work syndrome, although it’s not totally clear if it helps by actively manipulating your biological clock4This “clock” is not a metaphor. There is a central timekeeper in your brain, called the Suprachiasmatic Nucleus, or SCN, and a number of ‘peripheral’ timekeepers. You can read more about it on wikipedia., simply pushing the “reset” button on it, or some other mechanism entirely.

When you’re shopping for melatonin, pretty much any brand is fine; get the lowest dosage available. At least one study has shown that high doses (more than 3 mg) can lead to elevated melatonin levels 10 hours later, making it hard to wake up; another study has shown that a .5 mg dose helps sleep just as much as a 5 mg dose. I expect that this is highly person-dependent, so just try it out: buy the smallest pills you can easily find; if they don’t work, take more than one; if you wake up groggy, take half. (I personally buy these 1 mg pills and cut them in half).

Doxylamine (Ultra Sleep, Unisom) & Diphenhydramine (ZzzQuil, Tylenol PM, Sominex)

These are both antihistamines —Diphenhydramine is also marketed as allergy medication under the brand name Benadryl — but unlike some of the more recently-discovered antihistamines like Loratadine (Claritin), they also act as a mild nervous system depressant, which can cause sleepiness. This depressant effect doesn’t actually help you reset your biological clock, but sleep does, and the drowsiness they provide can still be still useful for that reason.

I also find they help slow my mind down a little bit when I wake up in the middle of the night — a mild grogginess that means I don’t immediately go into mind-racing-can’t-get-back-to-sleep mode. Again, be careful with dosage here: it’s easy to overdo it and not just feel groggy when you wake up in the middle of the night, but all the way through lunchtime the next day. I can only tolerate between ¼ and ½ of the listed dose (0.5–1 pills’ worth, depending on the brand) without prolonged grogginess.


Assuming it’s legal where you are, and that you’re not prone to anxiety or paranoia when you use it, cannabis can be helpful to help you calm down and fall asleep. The research on the effects of cannabis’ constituent compounds like Cannabidiol (CBD) and Tetrahydrocannabinol (THC) is fairly thin because of cannabis’ long history as Schedule I drug, but both seem to help with insomnia.

Specifically, the research indicates that THC helps you fall asleep faster, but also triggers a decrease in slow-wave sleep and an increase in REM sleep, making sleep less mentally restorative. It’s not great, but it’s also not nearly as bad as other intoxicants like alcohol. High-dose CBD, on the other hand, helps both sleep quality and length of sleep, and is conveniently legal every state.5With some caveats: hemp-derived CBD is legal everywhere, but marijuana-derived CBD is legal on a state-by-state basis. Before flying with the stuff, I would be sure to make sure that it’s clearly labeled as hemp-derived


ZMA (an abbreviation of its first ingredient, Zinc Monomethionine Aspartate) is just a specific formulation of zinc, magnesium, and vitamin b6, two minerals that are proven (to varying degrees) to promote calm and sleep, and a vitamin that is a precursor to melatonin, all wrapped up together and marketed as a sports supplement.6Amusingly, it was first developed by Victor Conte of the BALCO sports doping scandal. Like many vitamins and minerals, it seems to only have an effect on people who are deficient; conveniently, something like half of US adults are deficient in at least one of these compounds. If you suspect you might be one of those adults, take the ZMA; if you know you’re deficient in one of them, though, don’t bother — just take that specific one.

A word of caution: many people also report extremely vivid and colorful dreams when they take ZMA, and B6 has been shown to increase dream recall, so be prepared.

Herbal sleep remedies

There are a number of plants or herbal compounds like valerian root, california poppy, rosemary oil, violet oil, passionflower, chamomile, lemon balm and lavender that have been promoted as sleep aids over the years. Almost all of these have some amount of clinical evidence, many of which are double-blind and placebo-controlled studies in humans, the ideal kind of study for proving efficacy. While some (chamomile, lavender, california poppy) show promising results, for most you’d need doses that are considerably higher than you could manage with commercially-available capsules or tea bags, unless you were eating them by the fistful.

Still, if you’re interested in experimenting with one or several of these in combination, I’d recommend trying it and seeing if it makes any subjective impact on your sleep quality. With the exception of passionflower (which you can’t buy in the US anyway), they’re all completely safe at any reasonable intake.

Chemicals to avoid

There are also a few categories of sleep inducing chemical that I’d strongly suggest you avoid, mostly because they don’t actually promote real, restful, restorative sleep — they just promote unconsciousness.

Alcohol, while enjoyable, messes with sleep in a number of negative ways. As a general nervous system depressant, it makes you drowsy; it also leads to an increase in adenosine levels — adenosine is the sleepiness-promoting hormone that caffeine works to block — leading to quicker sleep onset. But: booze also blocks melatonin production, and so once the sedative effects wear off, you end up sleeping more lightly, waking up more frequently, and generally getting poorer quality sleep.

Benzodiazepines (Xanax, Valium) are potentially addictive and impair memory formation and consolidation, even at prescribed dosages. They’ll help you relax and be unconscious for a while, sure, but say goodbye to all of that late-night reading you did to prepare for your new client.

Hypnotics (Ambien, Sonata, Lunesta) are what doctors prescribe when you really can’t sleep. The problem is that they actually work too well — if you hook someone on a hypnotic up to an EEG machine, their brainwave patterns look like someone who’s been knocked out with a blow to the head, not someone who’s asleep. Your brain does a lot of important work while you sleep, and when you’re on hypnotics, it can’t get much (if any) of it done.

The other chemical assistance

As much as I would prefer that you fix the negative impacts of too little sleep by sleeping more, that’s not always possible. It takes time to establish the habits and routines that quality sleep is built upon, sometimes you spend a whole night staring at the ceiling for unknown reasons, and occasionally events conspire to make it so you just can’t avoid a sleepless night. Which is to say, I would be remiss if I didn’t at least talk about the other kind of chemicals that affect sleep: those that will help you both postpone sleep and operate better on too little sleep.

Time to talk about stimulants.


We’ve talked about caffeine and coffee a number of times already on this website, but it’s worth bringing up as it’s by far the most ubiquitous stimulant used in the US, and the one that most people consume daily (or at least have daily access to). As great as caffeine is at promoting alertness, it also has a number of fairly nasty side effects, especially at the higher doses that a regular drinker might need to make up for poor sleep — anxiety, nervousness, jitters, and digestive issues, just to name a few.

Fortunately, there’s a way to mitigate some of those side effects: l-theanine, an amino acid that occurs naturally in tea. When taken in combination with caffeine, it can improve attention, cerebral blood flow, cognition, mood, and “modulate the more acute effects of higher doses of caffeine” like anxiety and post-caffeine energy crashes.7Theanine does not, however, help with the bathroom stuff. Try some good old-fashioned Pepto for that.

To get it, you can simply drink tea instead of coffee, or buy supplemental l-theanine capsules and take them with your coffee. It seems to work best at a 1:1 coffee and l-theanine ratio, similar to the ratio found in tea, so try to find 100 mg pills and take one for each 8oz cup of coffee.


Modafinil and related -afinils like adrafinil and armodafinil aren’t stimulants, technically speaking, they’re “wakefulness-promoting agents.” Traditional stimulants overclock your central nervous system by getting it to either release more neurotransmitters or by making the neurotransmitters that are released more effective, leading to an increase in nervous system activity. Modafinil works differently, although—here’s the kicker—scientists are not strictly sure how.

What they are sure of, though, is that it works with fewer side effects and less addictive potential than many traditional stimulants, making it the prescription of choice for people with narcolepsy and other sleep disorders. There, also, lies the rub: while it is generally regarded as safe, has few side effects, and can be helpful, it is a Schedule IV drug, which means you technically need a prescription to buy it. Without getting into too much detail on this, I will say that it’s relatively easy to obtain in the US through gray-market online pharmacies and in other countries where it’s legal as an over-the-counter drug.

Modafinil is also a nootropic — a mental performance enhancer.  It helps cognitive performance and alertness impressively in sleep deprived individuals, but even on a full night’s rest, some improvements still exist. Because of this (and the non-insignificant cost), modafinil is the chemical equivalent of breaking out the big guns: I’ll only use it when I’ve both slept poorly and really need to perform well the next day; usually less than once per month.

Practically, modafinil can be used to reduce needed sleep by about two-thirds for a few days in a row (making it possible to operate normally on 2-3 hours of sleep), or to skip a single entire night of sleep with few side effects and very little need to make up for the missed sleep. There is a lot of anecdotal evidence that we quickly build tolerance to modafinil; in my experience trying to use it to skip a full second night of sleep in a row or to run on 2-3 hours of sleep for more than a handful of days usually just isn’t possible. Also because of that potentially quick tolerance, I personally recommend 1) starting with just half a pill (100 mg) and only increasing to full pills if you’re not feeling the effects, and 2) taking a two or three day break between uses to redevelop tolerance.

Amphetamines (Adderall, Ritalin, Vyvanse)

Unlike modafinil, amphetamines are highly-regulated and enforced Schedule II drugs. There are only a few documented modafinil convictions, almost always with confounding circumstances, but people are convicted of felony possession for less than a handful of Adderall all the time. That being said, prescriptions are common and it is generally available, so it’s worth mentioning.

Because of the way that amphetamines overclock your nervous system, they actually don’t work particularly well for global stimulation and wakefulness-promotion. Unlike many other stimulants, they don’t add stimulation to thought processes equally; they instead stimulate proportionally — so the loud bits get louder and the quiet bits stay quiet.8This is because caffeine works by blocking adenosine receptors (adenosine makes you feel tired); that blocking means you’re generally less tired across the board and all mental processes uptick evenly. Amphetamines instead get your brain to release more neurotransmitters for every signal and also re-absorb them more slowly, which means that small signals stay small but big signals get much, much bigger.  I find it useful to think about this from a math perspective: signals with caffeine = signals + caffeine; signals with amphetamine = signals x amphetamine.

For this reason, they’re best used as amplifiers to increase focus on the object of attention and make everything else seem less important by comparison rather than as general stimulants. (This amplification is also why they tend to be really excellent drugs for people with attention disorders — they help the important things seem seem important and the unimportant ones seem less important). Also, unlike modafinil, they often require quite a lot of ‘make-up’ sleep when used to function on less sleep or skip sleep all together.

Taking both the legal risks and the mismatch of action and desired effect into account, I don’t recommend amphetamines to counteract lack of sleep. If you really need something beyond caffeine, get modafinil instead.

My personal strategy

What I ended up doing last night was taking .5 mg of melatonin and making some tea with california poppy in it. I eventually got about four hours of sleep, and then it was time to wake up and get to work. To stay moving this morning, I’m following a souped up version of the Henry Rollins coffee schedule (a 16oz cup in the morning, followed by a couple of ounces every hour or so from a Zojirushi thermos) — I also took about 200mg of l-theanine to attenuate the negative side effects of slamming that much caffeine first thing on an empty stomach.

But that’s what works for me. Most of this stuff varies greatly from person to person, and the only way to find out what’s going to work is to try it.

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