6-Chloromelatonin CAS: 63762-74-3
MF: C13H15ClN2O2
MW: 266.73
A potent agonist of the melatonin receptors.

6-Chloromelatonin (CAS 63762-74-3)

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Application: 6-Chloromelatonin is a potent agonist of the melatonin receptors
CAS Number: 63762-74-3
Purity: ≥99%
Molecular Weight: 266.73
Molecular Formula: C13H15ClN2O2
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data (including water content).
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6-Chloromelatonin is a Melatonin (sc-207848) derivative and a potent agonist of the MEL-1 (melatonin receptors) with affinity comparable to Melatonin. Along with the Melatonin analogs 2-Iodomelatonin (sc-203463) and 2-Phenylmelatonin (sc-203466), 6-Chloromelatonin is used as part of a panel of agonists and antagonists in binding studies to probe the behavior of melatonin receptors. During characterization studies of a rabbit retinal melatonin receptor, Melatonin and 6-Chloromelatonin demonstrated similar agonist potency at inhibiting calcium-dependent dopamine release from the retina (IC50 = 40 pM for both compounds). Melatonin (at 0.1-2.0 mM) and 6-Chloromelatonin (at 0.1-0.5 mM) both depressed evoked hippocampal potentials similarly, and this action was perturbed by the MEL-1B-R partial antagonist Luzindole (sc-202700), elucidating the mechanism for Melatonin- and 6-Chloromelatonin-induced modulation of neuron potentials. 6-Chloromelatonin is an activator of MEL-1A-R and MEL-1B-R.


References

1. Dubocovich, M.L. 1985. J. Pharmacol. Exp. Ther. 234: 395-401. PMID: 2991499
2. Dubocovich, M.L., et al. 1987. Proc. Natl. Acad. Sci. U.S.A. 84: 3916-3920. PMID: 3035559
3. Vacas, M.I., et al. 1992. J. Pineal Res. 13: 60-65. PMID: 1333527
4. Iuvone, P.M. and Gan, J. 1994. J. Neurochem. 63: 118-124. PMID: 7515941
5. Matuszak, Z., et al. 1997. Free Radic. Biol. Med. 23: 367-372. PMID: 9214572
6. Dubocovich, M.L., et al. 1997. Naunyn Schmiedebergs Arch. Pharmacol. 355: 365-375. PMID: 9089668
7. Nonno, R., et al. 1999. Br. J. Pharmacol. 127: 1288-1294. PMID: 10455277
8. Hogan, M.V., et al. 2001. J. Pineal Res. 30: 87-96. PMID: 11270484

Physical State :
Solid
Solubility :
Soluble in water (partly), and DMSO (100 mM).
Storage :
Store at 4° C
Melting Point :
191.24° C (Predicted)
Boiling Point :
536.69° C at 760 mmHg (Predicted)
Density :
1.27 g/cm3 (Predicted)
Refractive Index :
n20D 1.61 (Predicted)
IC50 :
MEL-1: IC50 = 0.04 nM (human)
Ki Data :
MEL-1: Ki= 0.99 nM (human)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
RTECS :
AB5750000
PubChem CID :
MDL Number :
MFCD00209923
Beilstein Registry :
0410191
SMILES :
CC(=O)NCCC1=CNC2=CC(=C(C=C21)OC)Cl

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Certificate of Analysis

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6-Chloromelatonin (CAS 63762-74-3)  Product Citations

See how others have used 6-Chloromelatonin (CAS 63762-74-3). Click on the entry to view the PubMed entry .

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PMID: # 21809392  León, J. et al. 2012. Mol. Carcinog. 51: 608-18.

Citations 1 to 1 of 1 total
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