Melatonin

Melatonin
By Nikki

General Information:

 * Compound Name: ** Melatonintoc


 * IUPAC Name: ** N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide


 * Other Names: ** N-acetyl-5-methoxytryptamine, pineal hormone, 5-methoxy-N-acetyltryptamine


 * Molar Mass: ** 232.278 g/mol


 * Molecular Formula: ** media type="custom" key="22115500"


 * Melting Point: ** 118° C


 * Boiling Point: ** 512.831 at 760 mmHg


 * <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">Density in Natural State: **<span style="color: #404040; font-family: Verdana,Geneva,sans-serif;">No data found; the amount of melatonin varies in plants, animals, and humans through age and night/day (the older you get, the less melatonin is produced and, at night, melatonin production in the brain increases, while in the day it decreases).

<span style="background-color: #008080; color: #ffffff; font-family: Verdana,Geneva,sans-serif; font-size: 140%;">Historical Background and Discovery:
<span style="background-color: #ffffff; color: #404040; font-family: Verdana,Geneva,sans-serif;">For most of the twentieth century, the pineal gland was thought to be a vestige and lacked importance. <span style="color: #404040; font-family: Verdana,Geneva,sans-serif;">In 1917, Carey Pratt McCord and Floyd P. Allen first discovered melatonin by feeding extract of the pineal glands of cows to tadpoles, which lightened the tadpoles skin by contracting the dark epidermalmelanophores <span style="color: #404040; font-family: Verdana,Geneva,sans-serif;">. In 1958, Aaron B. Lerner, a dermatology professor, and his colleagues at Yale University extracted the hormone from rat urine in hopes of using this substance from the pineal gland to treat skin diseases. They named this substance produced by the pineal gland melatonin. The thought that melatonin regulated night/day patterns was first assumed in 1979, and in the 1980's, melatonin became thoroughly studied. A study that was done in 1984, in which people were given various dosages of melatonin before they went to bed, found that it <span style="color: #404040; font-family: Verdana,Geneva,sans-serif; line-height: 1.5;">made the people feel more tired. These studies helped to prove that more melatonin is produced in the glands at night, or in the dark, and is reduced during the day, or in the light, and that it could help regulate irregular sleeping cycles. Richard Wurtman, of MIT, first patented melatonin's use as a low dosage sleep aid in 1995. Melatonin is now sold in pill and liquid forms as a supplement to help people regulate sleeping patterns and treat illnesses, such as chronic headaches.

<span style="background-color: #008080; color: #ffffff; font-family: Verdana,Geneva,sans-serif; font-size: 140%;">Where It is Found/How It is Obtained:
<span style="background-color: #ffffff; color: #404040; font-family: Verdana,Geneva,sans-serif;">Melatonin is a hormone produced naturally in the pineal gland, a small gland in the brain. It is found in humans, animals, plants, and microbes. It is also found in many foods, like olive oil, tomatoes, carrots, nuts, and other common fruits and vegetables. Melatonin can be obtained by extracting it from urine, but it is mainly obtained from animal pineal tissue or it is made synthetically in a laboratory to sell as over-the-counter dietary supplements. These supplements are sold in the form of a pill or liquid at local drug stores without a prescription. <span style="background-color: #ffffff; color: #404040; font-family: Verdana,Geneva,sans-serif; line-height: 1.5;">Scientists remove the pineal glands from the brains of animals and extract the natural melatonin from the glands to produce natural melatonin supplements. Scientists produce synthetic melatonin in a lab using pharmaceutical grade ingredients that is identical to the molecular structure of natural melatonin produced in our bodies. You cannot find exactly how they produce it synthetically in the lab because the information and ingredients used are not open to the public. Synthetic melatonin is said to be much safer than natural melatonin supplements because it is very close to the molecular make-up of melatonin and is made with pharmaceutical ingredients. Natural melatonin supplements are obtained through the pineal glands of animals, which could possibly contain viruses or diseases.

<span style="background-color: #008080; color: #ffffff; font-family: Verdana,Geneva,sans-serif; font-size: 140%;">Uses and Importance:
<span style="background-color: #ffffff; color: #404040; font-family: Verdana,Geneva,sans-serif;">Melatonin is secreted in the pineal gland at night, or in the dark, to help the body to sleep. It is reduced in the pineal gland during the day, or in the light, to help the body to stay awake. It is naturally produced in our bodies as an internal clock to give humans and animals a regular sleep/wake cycle. In plants, melatonin is used to regulate plant growth by slowing root formation, while promoting above ground growth. It is also used to regulate plants' responses to night and day, defend against harsh environments, and function as an antioxidant. For humans, melatonin is used as a dietary supplement, sold in stores, to help regulate sleeping patterns in humans. These supplements are believed to cure problems such as jet lag, <span style="background-color: #ffffff; color: #800080; font-family: Verdana,Geneva,sans-serif;">seasonal affective disorder <span style="background-color: #ffffff; color: #404040; font-family: Verdana,Geneva,sans-serif;">(also known as "seasonal depression"), insomnia in the elderly, sleeping disorders in children with autism or mental retardation, sleeping patterns for those who work night shifts, sleeping disorders in blind people, cluster headaches, and sleeping problems/confusion after surgery. Studies have shown that as you get older, the amount of melatonin produced decreases, showing that supplements are most beneficial to insomnia in the elderly rather than in children or adults. Some other studies show that melatonin plays a crucial part in the aging process and taking supplements can reduce aging and increase longevity. When small amounts of melatonin were given to lab mice, it reduced the oxidative damage done by aging and delayed the inflammatory process, which increased the longevity of the mice. Some other studies concluded that melatonin may reduce the risk of some cancers, like breast cancer, but those studies are still being done and are not proven. Melatonin supplements may not work for all patients with sleep disorders, such as insomnia, because the body may already be producing enough melatonin. Melatonin is important because without it being produced in our brain, we would not have the sleep cycle of day and night. Another importance of melatonin is that many people suffer from sleeping disorders and they sell melatonin as an over-the-counter sleep aid. It is also important because melatonin is being linked to reducing the risk of cancer, reducing aging/increasing longevity, fighting illnesses, such as headaches, and strengthening the immune system. If studies continue, melatonin could be, or lead to, a cure for supposedly incurable illnesses and diseases.


 * = [[image:melatonin.jpg]] ||= [[image:melatonin3.jpg width="300" height="300"]] ||
 * <span style="color: #404040; display: block; font-family: Verdana,Geneva,sans-serif; text-align: center;">Purified Melatonin (white-tan powder) || <span style="color: #404040; display: block; font-family: Verdana,Geneva,sans-serif; text-align: center;">Melatonin Over-the-Counter Supplement ||

<span style="background-color: #008080; color: #ffffff; font-family: Verdana,Geneva,sans-serif; font-size: 140%;">Structure:
<span style="color: #404040; font-family: Verdana,Geneva,sans-serif;">Melatonin includes the elements of Carbon, Hydrogen, Nitrogen, and Oxygen. It contains one benzene ring, one carbonyl, one pentagonal ring containing 4 carbons and a nitrogen to complete it, and an oxygen branching off of the benzene ring. As seen in the picture below, there are two amine groups, one carbonyl group, one oxy group, and five double, covalent bonds.


 * [[image:melatoninstructure.png]] ||
 * <span style="color: #404040; font-family: Verdana,Geneva,sans-serif;">Structural Formula for Melatonin ||

<span style="background-color: #008080; color: #ffffff; font-family: Verdana,Geneva,sans-serif; font-size: 140%;">Percentage Composition:
<span style="color: #404040; font-family: Verdana,Geneva,sans-serif;">The percentage composition of each of the four elements in melatonin are explained in the table below:


 * <span style="color: #800080; display: block; font-family: Verdana,Geneva,sans-serif; text-align: center;">Element || <span style="color: #008080; display: block; font-family: Verdana,Geneva,sans-serif; text-align: center;">Percent Composition by Number of Atoms || <span style="color: #808000; display: block; font-family: Verdana,Geneva,sans-serif; text-align: center;">Percent Composition by Mass ||
 * <span style="color: #800080; display: block; font-family: Verdana,Geneva,sans-serif; text-align: center;">Carbon || <span style="color: #008080; font-family: Verdana,Geneva,sans-serif;">13/33 = 39.39% || <span style="color: #808000; font-family: Verdana,Geneva,sans-serif;">(156.1391 / 232.28) x 100 = 67.22% ||
 * <span style="color: #800080; display: block; font-family: Verdana,Geneva,sans-serif; text-align: center;">Hydrogen || <span style="color: #008080; font-family: Verdana,Geneva,sans-serif;">16/33 = 48.48% || <span style="color: #808000; font-family: Verdana,Geneva,sans-serif;">(16.12704 / 232.28) x 100 = 6.94% ||
 * <span style="color: #800080; display: block; font-family: Verdana,Geneva,sans-serif; text-align: center;">Nitrogen || <span style="color: #008080; font-family: Verdana,Geneva,sans-serif;">2/33 = 6.06% || <span style="color: #808000; font-family: Verdana,Geneva,sans-serif;">(28.0134 / 232.28) x 100 = 12.06% ||
 * <span style="color: #800080; display: block; font-family: Verdana,Geneva,sans-serif; text-align: center;">Oxygen || <span style="color: #008080; font-family: Verdana,Geneva,sans-serif;">2/33 = 6.06% || <span style="color: #808000; font-family: Verdana,Geneva,sans-serif;">(31.9988 / 232.28) x 100 = 13.78% ||

<span style="background-color: #008080; color: #ffffff; font-family: Verdana,Geneva,sans-serif; font-size: 140%;">Chemical Properties/Reaction Tendencies:
<span style="color: #404040; font-family: Verdana,Geneva,sans-serif;">Melatonin is soluble in lipids and other aqueous environments. It is also an indole, which means that it has a bi-cyclic structure, consisting of a six-member benzene ring fused to a five-member nitrogen containing pyrrole ring. There are two main synthesis routes that indoles can undergo: Leimgruber-Batcho indole synthesis and Fischer indole synthesis. In Leimgruber-Batcho synthesis, a series of organic reactions produce indoles from 0-nitrotoluenes. This method of synthesis is mostly used in the pharmaceutical industry. In Fischer indole synthesis, a chemical reaction produces the aromatic hetero cyclic indole from a phenylhydrazine and an aldehyde or ketone under acidic conditions. Melatonin is an aromatic, hetero cyclic organic compound, which proves that is is likely to be synthesized from the Fischer indol synthesis method.

<span style="background-color: #008080; color: #ffffff; display: block; font-family: Verdana,Geneva,sans-serif; font-size: 140%; line-height: 27px; text-align: left;">3-D Model:



*<span style="color: #008080; font-family: Verdana,Geneva,sans-serif; font-size: 110%;">If you are using a mac, please save the file above and open it with iMol!

<span style="background-color: #008080; color: #ffffff; display: block; font-family: Verdana,Geneva,sans-serif; font-size: 140%; text-align: left;">References:


 * 1) <span style="font-family: Verdana,Geneva,sans-serif;"><span class="wiki_link_ext">@http://en.wikipedia.org/wiki/Melatonin
 * 2) <span style="font-family: Verdana,Geneva,sans-serif;"><span class="wiki_link_ext">@http://www.webmd.com/sleep-disorders/tc/melatonin-overview
 * 3) <span style="font-family: Verdana,Geneva,sans-serif;"><span class="wiki_link_ext">@http://www.sleepfoundation.org/article/sleep-topics/melatonin-and-sleep
 * 4) <span style="font-family: Verdana,Geneva,sans-serif;">@http://www.nlm.nih.gov/medlineplus/druginfo/natural/940.html
 * 5) <span style="font-family: Verdana,Geneva,sans-serif;">@http://www.livestrong.com/article/279680-food-containing-melatonin/
 * 6) <span style="font-family: Verdana,Geneva,sans-serif;">http://en.wikipedia.org/wiki/Epidermis_(skin)
 * 7) <span style="font-family: Verdana,Geneva,sans-serif;">@http://www.merriam-webster.com/dictionary/melanophore
 * 8) <span style="font-family: Verdana,Geneva,sans-serif;">@http://en.wikipedia.org/wiki/Seasonal_affective_disorder
 * 9) <span style="font-family: Verdana,Geneva,sans-serif;"><span class="wiki_link_ext">@http://www.chemspider.com/Chemical-Structure.872.html
 * 10) <span style="font-family: Verdana,Geneva,sans-serif;">@http://purebulk.com/media/catalog/product/cache/1/image/293x/9df78eab33525d08d6e5fb8d27136e95/m/e/melatonin.jpg
 * 11) <span style="font-family: Verdana,Geneva,sans-serif;">@http://upload.wikimedia.org/wikipedia/commons/thumb/d/db/Melatonin.png/220px-Melatonin.png
 * 12) <span style="font-family: Verdana,Geneva,sans-serif;">@http://ecx.images-amazon.com/images/I/51FEX4WJ9EL._SL500_SS500_.jpg
 * 13) <span style="font-family: Verdana,Geneva,sans-serif;">@http://www.worldofmolecules.com/emotions/melatonin.jpg
 * 14) <span style="font-family: Verdana,Geneva,sans-serif;">@http://en.wikipedia.org/wiki/Indole
 * 15) <span style="font-family: Verdana,Geneva,sans-serif;">@http://en.wikipedia.org/wiki/Aromatic
 * 16) <span style="font-family: Verdana,Geneva,sans-serif;">@http://en.wikipedia.org/wiki/Heterocyclic_compound
 * 17) <span style="font-family: Verdana,Geneva,sans-serif;">@http://en.wikipedia.org/wiki/Phenylhydrazine
 * 18) <span style="font-family: Verdana,Geneva,sans-serif;">@http://en.wikipedia.org/wiki/Pyrrole
 * 19) <span style="font-family: Verdana,Geneva,sans-serif;">@http://www.lookchem.com/cas-73/73-31-4.html