6-Chloromelatonin

Names

[ Name ]:
6-Chloromelatonin

[Synonym ]:
Tocris-0443
6-CHLOROMELATONIN
6-Cl-melatonin
Lopac-C-0331

Biological Activity

[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 Receptor

Research Areas >> Endocrinology

Signaling 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

[ 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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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%