Melatonin | CAS#73-31-4

MedKoo Cat#: 318181 | Name: Melatonin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Melatonin is an indoleamine neurohormone found across plants and animals, produced endogenously from serotonin (5-HT) and secreted in animals as a regulatory signal for synchronization of the circadian rhythm and the sleep-wake cycle. The melatonin receptor system, consisting of the MEL-1A-R, MEL-1B-R, and MT3 subtypes, demonstrates particular plasticity and modularity - antagonists such as Luzindole and 2-Phenylmelatonin show modification of systemic responses to the Melatonin signal without impeding activation of the receptors by Melatonin. Powerful antioxidant activity is associated with Melatonin, and it is known to provide protection to lipids, proteins, and DNA against oxidative damage.

Chemical Structure

Melatonin

CAS#73-31-4

Theoretical Analysis

MedKoo Cat#: 318181

Name: Melatonin

CAS#: 73-31-4

Chemical Formula: C13H16N2O2

Exact Mass: 232.1212

Molecular Weight: 232.28

Elemental Analysis: C, 67.22; H, 6.94; N, 12.06; O, 13.78

Price and Availability

Size	Price	Availability
5g	USD 250.00	2 weeks
10g	USD 350.00	2 weeks
25g	USD 650.00	2 Weeks

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Related CAS #

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Synonym

Melatonin; Melatonine; N-Acetyl-5-methoxytryptamine; Circadin; 5-Methoxy-N-acetyltryptamine; NSC 56423; NSC 113928; Regulin;

IUPAC/Chemical Name

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

InChi Key

DRLFMBDRBRZALE-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

CC(=O)NCCC1=CNC2=C1C=C(C=C2)OC

Appearance

Solid powder

Purity

>97% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Melatonin is a hormone made by the pineal gland that can activates melatonin receptor.

In vitro activity:

Melatonin selectively blocked activating transcription factor 6 (ATF-6) and then inhibited cyclooxygenase-2 (COX-2) expression, leading to enhanced liver cancer cell apoptosis under ER stress condition. Dramatically increased CCAAT-enhancer-binding protein homologous protein level, suppressed COX-2 and decreased Bcl-2/Bax ratio by melatonin or ATF-6 siRNA contributed the enhanced HepG2 cell apoptosis under tunicamycin (an ER stress inducer) stimulation. Reference: World J Gastroenterol. 2017 Feb 14;23(6):986-998. https://pubmed.ncbi.nlm.nih.gov/28246472/

In vivo activity:

This study compared the roles of the NLRP3 inflammasome and/or melatonin treatment in the septic response of wild-type and NLRP3-/- mice. Melatonin treatment reduced the septic response in a comparable manner as did the lack of NLRP3, but unlike the latter, it normalized the clock genes turnover through the induction of RORα and repression of Rev-Erbα and Per2, leading to enhanced Nampt and Sirt1. Reference: J Pineal Res. 2017 Aug;63(1). https://pubmed.ncbi.nlm.nih.gov/28370493/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	129.15
	DMSO	46.9	201.92
	DMSO:PBS (pH 7.2) (1:1)	0.5	2.15
	Ethanol	26.2	112.65
	Water	1.1	4.74

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 232.28 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Bu LJ, Yu HQ, Fan LL, Li XQ, Wang F, Liu JT, Zhong F, Zhang CJ, Wei W, Wang H, Sun GP. Melatonin, a novel selective ATF-6 inhibitor, induces human hepatoma cell apoptosis through COX-2 downregulation. World J Gastroenterol. 2017 Feb 14;23(6):986-998. doi: 10.3748/wjg.v23.i6.986. PMID: 28246472; PMCID: PMC5311108. 2. Chen Z, Lei L, Wen D, Yang L. Melatonin attenuates palmitic acid-induced mouse granulosa cells apoptosis via endoplasmic reticulum stress. J Ovarian Res. 2019 May 10;12(1):43. doi: 10.1186/s13048-019-0519-z. PMID: 31077207; PMCID: PMC6511168. 3. Ma F, Hao H, Gao X, Cai Y, Zhou J, Liang P, Lv J, He Q, Shi C, Hu D, Chen B, Zhu L, Xiao X, Li S. Melatonin ameliorates necrotizing enterocolitis by preventing Th17/Treg imbalance through activation of the AMPK/SIRT1 pathway. Theranostics. 2020 Jun 19;10(17):7730-7746. doi: 10.7150/thno.45862. PMID: 32685016; PMCID: PMC7359097. 4. Rahim I, Djerdjouri B, Sayed RK, Fernández-Ortiz M, Fernández-Gil B, Hidalgo-Gutiérrez A, López LC, Escames G, Reiter RJ, Acuña-Castroviejo D. Melatonin administration to wild-type mice and nontreated NLRP3 mutant mice share similar inhibition of the inflammatory response during sepsis. J Pineal Res. 2017 Aug;63(1). doi: 10.1111/jpi.12410. Epub 2017 Apr 29. PMID: 28370493.

In vitro protocol:

In vivo protocol:

1. Ma F, Hao H, Gao X, Cai Y, Zhou J, Liang P, Lv J, He Q, Shi C, Hu D, Chen B, Zhu L, Xiao X, Li S. Melatonin ameliorates necrotizing enterocolitis by preventing Th17/Treg imbalance through activation of the AMPK/SIRT1 pathway. Theranostics. 2020 Jun 19;10(17):7730-7746. doi: 10.7150/thno.45862. PMID: 32685016; PMCID: PMC7359097. 2. Rahim I, Djerdjouri B, Sayed RK, Fernández-Ortiz M, Fernández-Gil B, Hidalgo-Gutiérrez A, López LC, Escames G, Reiter RJ, Acuña-Castroviejo D. Melatonin administration to wild-type mice and nontreated NLRP3 mutant mice share similar inhibition of the inflammatory response during sepsis. J Pineal Res. 2017 Aug;63(1). doi: 10.1111/jpi.12410. Epub 2017 Apr 29. PMID: 28370493.

1: Hukic DS, Lavebratt C, Frisén L, Backlund L, Hilding A, Gu HF, Östenson CG, Erlinge D, Ehrenborg E, Schalling M, Ösby U. Melatonin receptor 1B gene associated with hyperglycemia in bipolar disorder. Psychiatr Genet. 2016 Mar 17. [Epub ahead of print] PubMed PMID: 26991397. 2: Ma Q, Zhang T, Zhang P, Wang ZY. Melatonin attenuates postharvest physiological deterioration of cassava storage roots. J Pineal Res. 2016 Mar 17. doi: 10.1111/jpi.12325. [Epub ahead of print] PubMed PMID: 26989849. 3: Danilov A, Kurganova J. Melatonin in Chronic Pain Syndromes. Pain Ther. 2016 Mar 16. [Epub ahead of print] Review. PubMed PMID: 26984272. 4: Breen DP, Nombela C, Vuono R, Jones PS, Fisher K, Burn DJ, Brooks DJ, Reddy AB, Rowe JB, Barker RA. Hypothalamic volume loss is associated with reduced melatonin output in Parkinson's disease. Mov Disord. 2016 Mar 12. doi: 10.1002/mds.26592. [Epub ahead of print] PubMed PMID: 26971528. 5: Gurer-Orhan H, Karaaslan C, Ozcan S, Firuzi O, Tavakkoli M, Saso L, Suzen S. Novel indole-based melatonin analogues: Evaluation of antioxidant activity and protective effect against amyloid β-induced damage. Bioorg Med Chem. 2016 Mar 2. pii: S0968-0896(16)30129-8. doi: 10.1016/j.bmc.2016.02.039. [Epub ahead of print] PubMed PMID: 26970662. 6: Areco V, Rodriguez V, Marchionatti A, Carpentieri A, de Talamoni NT. Melatonin not only restores but also prevents the inhibition of the intestinal Ca(2+) absorption caused by glutathione depleting drugs. Comp Biochem Physiol A Mol Integr Physiol. 2016 Mar 9. pii: S1095-6433(16)30056-3. doi: 10.1016/j.cbpa.2016.03.005. [Epub ahead of print] PubMed PMID: 26970583. 7: Andrianome S, Hugueville L, de Seze R, Hanot-Roy M, Blazy K, Gamez C, Selmaoui B. Disturbed sleep in individuals with Idiopathic environmental intolerance attributed to electromagnetic fields (IEI-EMF): Melatonin assessment as a biological marker. Bioelectromagnetics. 2016 Mar 10. doi: 10.1002/bem.21965. [Epub ahead of print] PubMed PMID: 26969907. 8: Mori F, Ferraiuolo M, Santoro R, Sacconi A, Goeman F, Pallocca M, Pulito C, Korita E, Fanciulli M, Muti P, Blandino G, Strano S. Multitargeting activity of miR-24 inhibits long-term melatonin anticancer effects. Oncotarget. 2016 Mar 8. doi: 10.18632/oncotarget.7978. [Epub ahead of print] PubMed PMID: 26967561. 9: Reinholds I, Pugajeva I, Radenkovs V, Rjabova J, Bartkevics V. Development and Validation of New Ultra-High-Performance Liquid Chromatography-Hybrid Quadrupole-Orbitrap Mass Spectrometry Method for Determination of Melatonin in Fruits. J Chromatogr Sci. 2016 Mar 9. pii: bmw030. [Epub ahead of print] PubMed PMID: 26966272. 10: Jung SJ, Choi YJ, Kim NN, Choi JY, Kim BS, Choi CY. Effects of melatonin injection or green-wavelength LED light on the antioxidant system in goldfish (Carassius auratus) during thermal stress. Fish Shellfish Immunol. 2016 Mar 7. pii: S1050-4648(16)30081-X. doi: 10.1016/j.fsi.2016.03.002. [Epub ahead of print] PubMed PMID: 26965749. 11: Pacini N, Borziani F. Oncostatic-Cytoprotective Effect of Melatonin and Other Bioactive Molecules: A Common Target in Mitochondrial Respiration. Int J Mol Sci. 2016 Mar 7;17(3). pii: E341. doi: 10.3390/ijms17030341. Review. PubMed PMID: 26959015. 12: Kahya MC, Nazıroğlu M, Övey İS. Modulation of Diabetes-Induced Oxidative Stress, Apoptosis, and Ca(2+) Entry Through TRPM2 and TRPV1 Channels in Dorsal Root Ganglion and Hippocampus of Diabetic Rats by Melatonin and Selenium. Mol Neurobiol. 2016 Mar 9. [Epub ahead of print] PubMed PMID: 26957303. 13: Flo A, Calpena AC, Halbaut L, Araya EI, Fernández F, Clares B. Melatonin Delivery: Transdermal and Transbuccal Evaluation in Different Vehicles. Pharm Res. 2016 Mar 8. [Epub ahead of print] PubMed PMID: 26956459. 14: Fernandes PA, Tamura EK, D Argenio-Garcia L, Muxel SM, da Silveira Cruz-Machado S, Marçola M, Carvalho-Sousa CE, Cecon E, Ferreira ZS, Markus RP. Dual Effect of Catecholamines and Corticosterone Crosstalk on Pineal Gland Melatonin Synthesis. Neuroendocrinology. 2016 Mar 9. [Epub ahead of print] PubMed PMID: 26954684. 15: Bougea A, Spantideas N, Lyras V, Avramidis T, Thomaidis T. Melatonin 4 mg as prophylactic therapy for primary headaches: a pilot study. Funct Neurol. 2016 Mar 8:1-5. [Epub ahead of print] PubMed PMID: 26954506. 16: Wang C, Yin LY, Shi XY, Xiao H, Kang K, Liu XY, Zhan JC, Huang WD. Effect of Cultivar, Temperature, and Environmental Conditions on the Dynamic Change of Melatonin in Mulberry Fruit Development and Wine Fermentation. J Food Sci. 2016 Mar 8. doi: 10.1111/1750-3841.13263. [Epub ahead of print] PubMed PMID: 26953927. 17: Burattini S, Battistelli M, Codenotti S, Falcieri E, Fanzani A, Salucci S. Melatonin action in tumor skeletal muscle cells: an ultrastructural study. Acta Histochem. 2016 Mar 4. pii: S0065-1281(16)30028-9. doi: 10.1016/j.acthis.2016.02.004. [Epub ahead of print] PubMed PMID: 26953151. 18: Rath MF, Coon SL, Amaral FG, Weller JL, Møller M, Klein DC. Melatonin synthesis: Acetylserotonin O-methyltransferase (ASMT) is strongly expressed in a subpopulation of pinealocytes in the male rat pineal gland. Endocrinology. 2016 Mar 7:en20151888. [Epub ahead of print] PubMed PMID: 26950199. 19: Zhang L, Cao J, Wang Z, Dong Y, Chen Y. Melatonin modulates monochromatic light-induced GHRH expression in the hypothalamus and GH secretion in chicks. Acta Histochem. 2016 Mar 3. pii: S0065-1281(16)30029-0. doi: 10.1016/j.acthis.2016.02.005. [Epub ahead of print] PubMed PMID: 26948666. 20: Chang SW, Gong Y, McDonough CW, Langaee TY, Nasiri Kenari N, Beitelshees AL, Gums JG, Chapman AB, Turner ST, Johnson JA, Cooper-DeHoff RM. Melatonin Pathway and Atenolol-Related Glucose Dysregulation: Is There a Correlation? Clin Transl Sci. 2016 Mar 7. doi: 10.1111/cts.12389. [Epub ahead of print] PubMed PMID: 26946962.