2-Phenylmelatonin 2-Phenylmelatonin is a melatonin receptor binder with mixed agonist/antagonist activity.

2-Phenylmelatonin (CAS 151889-03-1)

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Application: 2-Phenylmelatonin is a melatonin receptor binder with mixed agonist/antagonist activity
CAS Number: 151889-03-1
Purity: ≥96%
Molecular Weight: 308.38
Molecular Formula: C19H20N2O2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
Available in US only.
* Refer to Certificate of Analysis for lot specific data (including water content).
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2-Phenylmelatonin is an antagonist of the MEL-1A-R, MEL-1B-R, MT3, observed to demonstrate mixed antagonist/agonist activity in systems with differential expression of the receptor subtypes. In rabbit parietal cortex tissue characterized by the presence of MEL-1A-R/MEL-1B-R receptors, 2-Phenylmelatonin antagonized melatonin-induced inhibition of neuronal firing in only 80% of the neurons tested, prompting the investigators to suggest a mixed activity. In guinea pig colon cells expressing solely MT3 receptors, 2-phenylmelatonin demonstrates antagonism of melatonin-induced contractions at low (subnanomolar) concentrations, and shows partial agonist induction of contractility at higher (nanomolar/micromolar) concentrations. Comparable antagonism (at 0.01nM) to the MT3-specific antagonist Prazocin (sc-204858) in this system further supports direct interaction of 2-Phenylmelatonin at the MT3 receptor. In a mouse fibroblast NIH3T3 system expressing transfected human MEL1A-R (melatonin receptor), 2-Phenylmelatonin demonstrated full agonism comparable to the action of melatonin (sc-207848) itself. This differential mixed antagonist/agonist activity makes 2-Phenylmelatonin a particularly useful tool in studying melatonin receptor characteristics.


References

1. Spadoni, G. et al. 1993. J. Med. Chem. 36(25): 4069-4074. PMID: 8258829

2. Chen, J.J. et al. 1998. Appl Radiat Isot. 49(12): 1573-1579. PMID: 9745693

3. Nonno, R. et al. 1998. Br. J. Pharmacol. 124(3): 485-492. PMID: 9647472

4. Nonno, R. et al. 1999. Br. J. Pharmacol. 127(5): 1288-1294. PMID: 10455277

5. Santagostino-Barbone, M.G. et al. 2000. Pharmacol. Toxicol. 87(4): 156-160. PMID: 11097268

Physical State :
Solid
Solubility :
Soluble in ethanol (100 mM), and DMSO (100 mM).
Storage :
Store at 4° C
Melting Point :
228.40° C (Predicted)
Boiling Point :
612.4° C at 760 mmHg (Predicted)
Density :
1.17 g/cm3 (Predicted)
Refractive Index :
n20D 1.62 (Predicted)
IC50 :
MEL-1: IC50 = 0.06 nM (human)
Ki Data :
MEL-1: Ki= 0.02 nM (human)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
Available in US only.
PubChem CID :
MDL Number :
MFCD00673896
SMILES :
CC(=O)NCCC1=C(NC2=C1C=C(C=C2)OC)C3=CC=CC=C3

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Certificate of Analysis

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