Melatonin

Catalog Number	ACM73314-2
CAS Number	73-31-4
Structure
Description	Melatonin is an indoleamine that has traditionally been considered only a sleep hormone in humans. Recently it has been found to naturally occur in plants and has shown attributes which could categorize it as an auxin. It has roles in in plant defense, and stress.
Synonyms	N-Acetyl-5-methoxytryptamine
IUPAC Name	N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide
Molecular Weight	232.28 g/mol
Molecular Formula	C13H16N2O2
Canonical SMILES	CC(=O)NCCC1=CNC2=C1C=C(C=C2)OC
InChI	InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)
InChI Key	DRLFMBDRBRZALE-UHFFFAOYSA-N
Boiling Point	512.8ºC at 760 mmHg
Melting Point	116.5-118 °C
Flash Point	264°C
Purity	98%+
Density	1.175 g/cm³
Solubility	Miscible with water
Appearance	White powder
Application	Initially discovered in animals and later found in a majority of plant species, indoleamine neurotransmitter Melatonin is a multifunctional signaling molecule. Some of these functions include roles in plant defense, growth, development, responses to stress, antioxidant activity, and many more Evidence indicates Melatonin and Serotonin have a relationship similar to how the interaction of cytokinin and auxin affect plant growth.
Complexity	270
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	0
EC Number	200-797-7
Exact Mass	232.121177757
Hazard Statements	T
Heavy Atom Count	17
Hydrogen Bond Acceptor Count	2
Hydrogen Bond Donor Count	2
MDL Number	MFCD00005655
Monoisotopic Mass	232.121177757
PhysicalState	Powder
Rotatable Bond Count	4
Topological Polar Surface Area	54.1 Ų

Case Study

Overview of Melatonin's Multifunctional Actions and Mechanisms

Reiter, Russel J., et al. Physiology, 2014, 29, 325-333.

Melatonin has multiple receptor-mediated and receptor-independent effects. Among them, receptor-dependent functions include circadian rhythm regulation, sleep, and cancer suppression. Receptor-independent effects involve direct detoxification of reactive oxygen species (ROS) and reactive nitrogen species (RNS).
Versatility of melatonin
· Melatonin has a variety of functions including mediating circannual variations in metabolism and reproductive competence, influencing circadian processes, and promoting sleep. It is produced locally in cells, particularly in mitochondria, for protection against free radicals and cellular damage.
· Melatonin's receptor-independent actions involve directly quenching free radicals and toxic species, protecting cells from various forms of damage such as radiation, toxins, and inflammation.
· Aging is associated with the accumulation of oxidative debris and increased production of free radicals, leading to cellular dysfunction. Melatonin's ability to neutralize radicals helps delay age-related dysfunction in various organs.
· Additionally, melatonin has been shown to inhibit the proliferation of many cancer cells and limit tumor metastases, acting as a pro-apoptotic agent in cancer cells while having an anti-apoptotic function in normal cells. This differential effect of melatonin on cancer cells and normal cells still needs further study.

Custom Q&A

What is the chemical name of Melatonine?

The chemical name of Melatonine is N-(2-(5-Methoxyindol-3-yl)ethyl)acetamide.

What is the molecular formula of Melatonine?

The molecular formula of Melatonine is C13H16N2O2.

What is the main physiological function of Melatonine in the body?

The main physiological function of Melatonine is to regulate circadian rhythms and the sleep/awake cycle.

How is Melatonine synthesized in the body?

Melatonine is synthesized in the body by pineal cells obtaining tryptophan and converting it into 5-hydroxyltryptamine, which is further modified to form Melatonine.

What is the mechanism of action of Melatonine at its receptors?

Melatonine acts at the MT1 and MT2 receptors to promote sleep and regulate circadian rhythms.

What are the uses of Melatonine?

Melatonine can be used as a medicine, healthcare product, natural "sleeping pill", and in biochemical research.

How does Melatonine affect the brain?

Melatonine affects the brain by promoting the conversion of neurotransmitters and improving brain activity.

What are the safety guidelines for handling Melatonine?

Melatonine is hazardous and its safety guidelines include specific hazard codes, risk statements, and safety statements.

What are the physiological functions affected by Melatonine in the body?

Melatonine affects the brain, hypothalamus, pituitary gland, gonads, thyroid, adrenal cortex, and pancreatic island functions.

How does Melatonine act as a biological antioxidant?

Melatonine acts as a biological antioxidant by neutralizing reactive oxygen species, stimulating antioxidant enzymes, and protecting DNA.

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