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Melatonin

C13H16N2O2 organic

Properties

StateSolid (white to off-white crystalline powder)
ColorWhite to off-white
SolubilitySlightly soluble in water (1 g/L); soluble in ethanol and DMSO
Melting Point116-118°C
Boiling PointDecomposes before boiling

About Melatonin

Melatonin is the indoleamine the pineal gland makes from serotonin every night when the suprachiasmatic nucleus tells it that the lights are out. The biosynthesis is a two-step trim from serotonin: aralkylamine N-acetyltransferase (AANAT) acetylates the primary amine to N-acetylserotonin, then HIOMT methylates the 5-OH to give the 5-methoxy group. Pineal output peaks somewhere around 2-4 a.m. at roughly 60-70 pg/mL plasma in a healthy adult and falls back to ~10 pg/mL by sunrise. The on/off switch is light at 460-480 nm hitting melanopsin in the intrinsically photosensitive retinal ganglion cells, and the pathway runs retina → SCN → paraventricular nucleus → superior cervical ganglion → pineal. That's why a glance at a phone screen at 11 p.m. delays melatonin onset by 60-90 minutes in most people. Pharmacologically, melatonin binds MT1 and MT2 receptors with Kd around 100 pM, and unlike a benzodiazepine it does not sedate by enhancing GABA — it shifts the circadian phase, which is why it works for jet lag and shift work but is hit-or-miss for ordinary insomnia. The over-the-counter US market sells about 3 mg per pill on average, which is roughly 30x the physiological peak; clinical sleep medicine increasingly recommends 0.3-0.5 mg taken 4-6 hours before target bedtime for circadian phase-shifting.

Where you'll encounter it

If you have ever flown JFK to Heathrow on a redeye, landed at 7 a.m. local with the sun blasting, and wondered whether to take the 5 mg melatonin gummy in your bag — you have run into the dosing problem nobody tells you about. The high doses sold in the US (3-10 mg) raise plasma melatonin to ~1000x physiological levels for hours, which is more about hitting receptors hard than about restoring the natural curve. Sleep researchers like Charmane Eastman have shown 0.3-0.5 mg works as well or better for phase-shifting, with less morning grogginess. In the lab, melatonin shows up in dim-light melatonin onset (DLMO) assays — researchers measure salivary melatonin every 30 minutes under <30 lux red light to find each subject's true circadian phase, the gold-standard chronotype measurement.

Common Uses

  • OTC supplement for jet-lag phase shifting (0.3-0.5 mg dose, 4-6 h before target bedtime)
  • Adjunct treatment for delayed sleep-wake phase disorder and shift-work disorder
  • Dim-light melatonin onset (DLMO) assays for circadian-phase research
  • Free-radical scavenger in oxidative-stress and neuroprotection research
  • Adjuvant in chemotherapy clinical trials for solid tumors

Safety Information

Not classified as hazardous under GHS. Common side effects at 1-5 mg supplement doses include daytime sleepiness (~15% of users), morning grogginess, vivid dreams, and headache. Long-term safety data beyond ~6 months are thin. Drug interactions: warfarin (additive bleeding risk via CYP1A2 inhibition), fluvoxamine (8x plasma melatonin from CYP1A2 inhibition), nifedipine (reduced antihypertensive effect), and immunosuppressants. Pediatric use only with sleep specialist oversight — case reports of seizures in children with neurological conditions. Pregnancy category not established; avoid. The supplement is unregulated by FDA in the US, so independent assays have found 70-470% of labeled dose across brands.

This safety summary is for educational reference only and may not be complete. It is not a substitute for Safety Data Sheets (SDS), medical advice, or professional chemical safety guidance. Always consult appropriate SDS and qualified professionals before handling chemicals.

Constituent Elements

Frequently Asked Questions

What is the molar mass of melatonin?
C13H16N2O2 works out to 232.278 g/mol: 13 C (156.143) + 16 H (16.128) + 2 N (28.014) + 2 O (31.998). For dosing math, a 3 mg tablet is 12.9 micromoles — and given a healthy adult's endogenous nighttime peak corresponds to roughly 0.0003 mg circulating in 5 L of plasma, the typical OTC pill is dosing supraphysiologically by orders of magnitude.
Why does looking at a phone before bed actually delay sleep?
The melanopsin-containing retinal ganglion cells peak in sensitivity at 480 nm, smack in the middle of where LED screens emit. About 30 minutes of phone use at typical brightness (50 lux at the eye) suppresses melatonin onset by 60-90 minutes. Night-shift mode and amber-tint glasses help — they cut the 460-490 nm band where the suppression is strongest. Total darkness or dim incandescent (<10 lux, no blue) is what the SCN reads as 'night.'
Why doesn't melatonin work like a sleeping pill for everyone?
Melatonin is a circadian signal, not a sedative. Z-drugs and benzos potentiate GABA-A and knock you out by suppressing the wake system. Melatonin binds MT1/MT2 in the SCN and shifts the phase of your internal clock — it tells the system 'it's nighttime now,' not 'go to sleep right now.' For someone whose clock is already running on time and who simply cannot fall asleep, melatonin often does little. For jet lag, shift work, or DSPS where the clock is misaligned, low doses (0.3-0.5 mg) timed correctly work well.