CAS 63762-74-3|6-Chloromelatonin

Introduction：Basic information about CAS 63762-74-3|6-Chloromelatonin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. 6-Chloromelatonin BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Synonyms

Common Name	6-Chloromelatonin
CAS Number	63762-74-3	Molecular Weight	266.72300
Density	1.272g/cm3	Boiling Point	536.7ºC at 760 mmHg
Molecular Formula	C₁₃H₁₅ClN₂O₂	Melting Point	/
MSDS	/	Flash Point	278.4ºC

Names

Name	N-[2-(6-chloro-5-methoxy-1H-indol-3-yl)ethyl]acetamide
Synonym	More Synonyms

6-Chloromelatonin BiologicalActivity

Description	6-Chloromelatonin is a potent melatonin receptor agonist with greater metabolic stability than melatonin. 6-Chloromelatonin compete for [3H]-melatonin and 2-[125I]-iodomelatonin binding to MT1 receptors (pKi=8.9 and 9.1, respectively). 6-Chloromelatonin compete for [3H]-melatonin binding to MT2 receptors (pKi=9.77)[1][2].
Related Catalog	Signaling Pathways >>Neuronal Signaling >>Melatonin ReceptorResearch Areas >>EndocrinologySignaling Pathways >>GPCR/G Protein >>Melatonin Receptor
Target	MT1:8.9 (pKi) MT2:9.1 (pKi)
In Vitro	6-Chloromelatonin competes for [3H]-melatonin binding sites in human platelet (Ki=11.4 nM)[3]. 6-chloromelatonin (10 pM, 1 nM, 100 nM, 10 μM; 72 hours) inhibits, in a dose-dependent manner, forskolin-stimulated hCG-beta secretion in JEG-3 and BeWo cells but had no effect on basal human chorionic gonadotrophin (hCG-beta) levels[4].
In Vivo	Rats injected with the melatonin agonist, 6-chloromelatonin (0.5 mg/kg) on the day after the phase shift has markedly higher excretion rates of 6-sulphatoxymelatonin compared to those of the controls[5].
References	[1]. Browning C, et al. Pharmacological characterization of human recombinant melatonin mt(1) and MT(2) receptors. Br J Pharmacol. 2000;129(5):877-886. [2]. Clemens JA, et al. Inhibition of luteinizing hormone release and ovulation by 6-chloro- and 6-fluoromelatonin. Neuroendocrinology. 1980;30(2):83-87. [3]. Vacas MI, et al. Binding sites for [3H]-melatonin in human platelets. J Pineal Res. 1992;13(2):60-65. [4]. Lanoix D, et al. Expression of melatoninergic receptors in human placental choriocarcinoma cell lines. Hum Reprod. 2006;21(8):1981-1989. [5]. Kennaway DJ, et al. A melatonin agonist and N-acetyl-N2-formyl-5-methoxykynurenamine accelerate the reentrainment of the melatonin rhythm following a phase advance of the light-dark cycle. Brain Res. 1989;495(2):349-354.

Chemical & Physical Properties

Density	1.272g/cm3
Boiling Point	536.7ºC at 760 mmHg
Molecular Formula	C₁₃H₁₅ClN₂O₂
Molecular Weight	266.72300
Flash Point	278.4ºC
Exact Mass	266.08200
PSA	54.12000
LogP	2.89940
Index of Refraction	1.608
InChIKey	LUINDDOUWHRIPW-UHFFFAOYSA-N
SMILES	COc1cc2c(CCNC(C)=O)c[nH]c2cc1Cl
Storage condition	-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AB5750000

CHEMICAL NAME :: Acetamide, N-(2-(6-chloro-5-methoxy-1H-indol-3-yl)ethyl)-

CAS REGISTRY NUMBER :: 63762-74-3

BEILSTEIN REFERENCE NO. :: 0410191

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C13-H15-Cl-N2-O2

MOLECULAR WEIGHT :: 266.75

WISWESSER LINE NOTATION :: T56 BMJ D2MV1 GO1 HG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 4 mg/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 22,63,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 4 mg/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 22,63,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1260 ug/kg

SEX/DURATION :: female 9 week(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina

REFERENCE :: JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 78,381,1986

Safety Information

Hazard Codes	T
Risk Phrases	60-23/24/25-36/37/38
Safety Phrases	53-26-36/37/39-45
HS Code	2933990090

Customs

HS Code	2933990090
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Synonyms

Tocris-0443

6-CHLOROMELATONIN

6-Cl-melatonin

Lopac-C-0331

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