6-Chloromelatonin

Modify Date: 2024-01-02 19:44:19

6-Chloromelatonin Structure
6-Chloromelatonin structure
 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 N/A
MSDS N/A Flash Point 278.4ºC

 Use of 6-Chloromelatonin


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].

 Names

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

 6-Chloromelatonin 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
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

2-Chloro-5-methylphenol structure

2-Chloro-5-meth...

CAS#:615-74-7

~%

6-Chloromelatonin Structure

6-Chloromelatonin

CAS#:63762-74-3
Literature: Huegel, Helmut M. Synthesis, 1983 , # 11 p. 935 - 936
2-CHLORO-5-METHYL-4-NITROPHENOL structure

2-CHLORO-5-METH...

CAS#:40130-97-0

~%

6-Chloromelatonin Structure

6-Chloromelatonin

CAS#:63762-74-3
Literature: Huegel, Helmut M. Synthesis, 1983 , # 11 p. 935 - 936
1-Chloro-2-methoxy-4-methyl-5-nitrobenzene structure

1-Chloro-2-meth...

CAS#:62492-45-9

~%

6-Chloromelatonin Structure

6-Chloromelatonin

CAS#:63762-74-3
Literature: Huegel, Helmut M. Synthesis, 1983 , # 11 p. 935 - 936
2-chloro-5-[(β-dimethylamino)-vinyl]-4-nitroanisole structure

2-chloro-5-[(β-...

CAS#:63762-71-0

~%

6-Chloromelatonin Structure

6-Chloromelatonin

CAS#:63762-74-3
Literature: Huegel, Helmut M. Synthesis, 1983 , # 11 p. 935 - 936
6-Chloro-5-methoxy-1H-indole structure

6-Chloro-5-meth...

CAS#:63762-72-1

~%

6-Chloromelatonin Structure

6-Chloromelatonin

CAS#:63762-74-3
Literature: Huegel, Helmut M. Synthesis, 1983 , # 11 p. 935 - 936
6-chloro-5-methoxyindol-3-ylglyoxylamide structure

6-chloro-5-meth...

CAS#:88817-22-5

~%

6-Chloromelatonin Structure

6-Chloromelatonin

CAS#:63762-74-3
Literature: Huegel, Helmut M. Synthesis, 1983 , # 11 p. 935 - 936

 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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