MELATONIN

First marketed in 1921

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H16N2O2
Molecular Weight	232.2783
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(NC=C2CCNC(C)=O)C=C1

InChI

InChIKey=DRLFMBDRBRZALE-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26731279 | https://www.ncbi.nlm.nih.gov/pubmed/19966183 |

Melatonin (5-methoxy N-acetyltryptamine) is a hormone synthesized and released from the pineal gland at night, which acts on specific high affinity G-protein coupled receptors to regulate various aspects of physiology and behaviour, including circadian and seasonal responses, and some retinal, cardiovascular and immunological functions. Melatonin is also made synthetically and available without a prescription as an over-the-counter (OTC) dietary supplement in the U.S. Melatonin supplementation has many uses, however, it has been widely studied for treatment of jet lag and sleep disorders. Parents may consider using melatonin to help their child who has a trouble falling asleep. A medical professional should always evaluate insomnia or other sleeping disorders in children. Additionally, melatonin has been shown to protect against oxidative stress in various, highly divergent experimental systems. There are many reasons for its remarkable protective potential. In mammals, melatonin binds to a number of receptor subtypes including high-affinity (MT1 and MT2) and low-affinity (MT3, nuclear orphan receptors) binding sites, which are distributed throughout the central nervous system and periphery.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Melatonin receptor type 1A 3 Target ID: P48039 Gene ID: 4543.0 Gene Symbol: MTNR1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19966183	Agonist 2637
Melatonin receptor type 1B 4 Target ID: P49286 Gene ID: 4544.0 Gene Symbol: MTNR1B Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19449447	Agonist 2637

Conditions

Condition	Modality	Targets	Highest Phase	Product
Jet lag syndrome 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26731279	Primary		Not Provided 505	Unknown Approved Use Unknown
Insomnia 108 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28364493	Primary		Phase III 651	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Melatonin administration prevents the nephrotoxicity induced by gentamicin.	2000 Apr	10759677
Melatonin suppresses iron-induced neurodegeneration in rat brain.	2000 Mar 15	10802221
Cardiovascular effects of melatonin in hypertensive patients well controlled by nifedipine: a 24-hour study.	2000 May	10792199
Characterization of the protective effects of melatonin and related indoles against alpha-naphthylisothiocyanate-induced liver injury in rats.	2001	11169730
Melatonin as a sedation substitute for diagnostic procedures: MRI and EEG.	2001 Feb	11221904
Effect of exogenous melatonin on vascular reactivity and nitric oxide in postmenopausal women: role of hormone replacement therapy.	2001 Feb	11207642
Coexistence of zinc and iron augmented oxidative injuries in the nigrostriatal dopaminergic system of SD rats.	2001 Feb 1	11165868
An hPer2 phosphorylation site mutation in familial advanced sleep phase syndrome.	2001 Feb 9	11232563
Human melatonin regulation is not mediated by the three cone photopic visual system.	2001 Jan	11232036
Transition from dim to bright light in the morning induces an immediate elevation of cortisol levels.	2001 Jan	11231993
Superior cervical ganglionectomy leads to dampening of amplitude of temperature rhythm in rats.	2001 Jan	11211561
A test of the coincidence and duration models of melatonin action in Siberian hamsters. II. The effects of 4- and 8-hr melatonin infusions on testicular development of pinealectomized juvenile Siberian hamsters (Phodopus sungorus).	2001 Jan	11168908
Melatonin reduces dinitrobenzene sulfonic acid-induced colitis.	2001 Jan	11168901
Comparative analysis of reproductive cycles in female Persian gazelle (Gazella subgutturosa subgutturosa) (Central Asia) and sand gazelle (Gazella subgutturosa marica) (Arabian Peninsula).	2001 Jan	11161770
Circadian time of morning light administration and therapeutic response in winter depression.	2001 Jan	11146760
Melatonin in psychiatric disorders: a review on the melatonin involvement in psychiatry.	2001 Jan	11141317
Melatonin potentiates contractile responses to serotonin in isolated porcine coronary arteries.	2001 Jan	11123220
A single nocturnal exposure to 2-7 millitesla static magnetic fields does not inhibit the excretion of 6-sulfatoxymelatonin in healthy young men.	2001 Jan	11122488
Effects of melatonin, morphine and diazepam on formalin-induced nociception in mice.	2001 Jan 12	11213364
Disruption of the nocturnal testosterone rhythm by sleep fragmentation in normal men.	2001 Mar	11238497
Multiple binding sites for melatonin on Kv1.3.	2001 Mar	11222291
Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms.	2001 Mar	11181495
Dual effects of melatonin on barbiturate-induced narcosis in rats.	2001 Mar 16	11226639
Melatonin inhibits the expression of steroidogenic acute regulatory protein and steroidogenesis in MA-10 cells.	2001 Mar-Apr	11229798

Patents

Sample Use Guides

In Vivo Use Guide

Fast Release Melatonin (FR MLT): 3mg capsules of melatonin will be used. The dose of FR MLT will be 3 mg for children less than or equal to 20 kg, and 6 mg for children greater than 20 kg. The study medication will be given one hour before bedtime, once daily. Drug: Timed Release Melatonin (TR MLT): 3 mg capsules will be used. The dose of TR MLT will be will be 3 mg for children less than or equal to 20 kg, and 6 mg for children greater than 20 kg. The study medication will be given one hour before bedtime, once daily.

Route of Administration: Oral

In Vitro Use Guide

It was observed that 10-7 M melatonin was considered an optimum concentration and significantly promoted the in vitro development of murine microinjected pronuclear embryos, as indicated by the increased blastocyst rate, hatching blastocyst rate and blastocyst cell number. When these blastocysts were implanted into recipient mice, the pregnancy rate and birth rate were significantly higher than those of the microinjected control, respectively. Mechanistic studies revealed that melatonin treatment reduced reactive oxygen species (ROS) production and cellular apoptosis during in vitro embryo development and improved the quality of the blastocysts. The implantation of quality-improved blastocysts led to elevated pregnancy and birth rates. In conclusion, the results revealed that the anti-oxidative and anti-apoptotic activities of melatonin improved the quality of microinjected pronuclear embryos and subsequently increased both the efficiency of embryo implantation and the birth rate of the pups. Therefore, the melatonin supplementation may provide a novel alternative method for generating large numbers of transgenic mice and this method can probably be used in human-assisted reproduction and genome editing.

Name

Type

Language

MELATONIN

Official Name

English

MELATONIN [JAN]

Common Name

English

MELATONIN [EMA EPAR]

Common Name

English

ACETAMIDE, N-(2-(5-METHOXYINDOL-3-YL)ETHYL)-

Systematic Name

English

REGULIN

Brand Name

English

MELATONIN [USP-RS]

Common Name

English

MELATONIN [INCI]

Common Name

English

MELATONINE

Common Name

English

NSC-113928

Code

English

MELATONIN [HSDB]

Common Name

English

MELATONIN [DSC]

Common Name

English

BCI-049

Code

English

Melatonin [WHO-DD]

Common Name

English

MELATONIN [MI]

Common Name

English

MELATONIN [GREEN BOOK]

Common Name

English

J5.258B

Code

English

ACETAMIDE, N-(2-(5-METHOXY-1H-INDOL-3-YL)ETHYL)-

Systematic Name

English

MELATOL

Brand Name

English

MELOVINE

Brand Name

English

NSC-56423

Code

English

CIRCADIN

Brand Name

English

5-METHOXY N-ACETYL-TRYPTAMINE

Common Name

English

MELATONIN [MART.]

Common Name

English

MELATONIN [VANDF]

Common Name

English

Classification Tree Code System Code

EU-Orphan Drug

melatonin