An MC1R agonist
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BMS 470539 (hydrochloride)

Item No. 22231

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-[1-(3-methyl-L-histidyl-O-methyl-D-tyrosyl)-4-phenyl-4-piperidinyl]-1-butanone, dihydrochloride
CAS Number
2341796-82-3
Molecular Formula
C32H41N5O4 • 2HCl
Formula Weight
632.6
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 10 mg/mlEthanol: 20 mg/mlPBS (pH 7.2): 5 mg/ml
λmax
273 nm
SMILES
O=C([C@@H](CC1=CC=C(OC)C=C1)NC([C@@H](N)CC2=CN=CN2C)=O)N3CCC(C4=CC=CC=C4)(C(CCC)=O)CC3.Cl.Cl
InChi Code
InChI=1S/C32H41N5O4.2ClH/c1-4-8-29(38)32(24-9-6-5-7-10-24)15-17-37(18-16-32)31(40)28(19-23-11-13-26(41-3)14-12-23)35-30(39)27(33)20-25-21-34-22-36(25)2;;/h5-7,9-14,21-22,27-28H,4,8,15-20,33H2,1-3H3,(H,35,39);2*1H/t27-,28+;;/m0../s1
InChi Key
DUAOBJHRUKFKIH-YDVFRNEYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    BMS 470539 is an agonist of melanocortin receptor 1 (MC1R).1 It induces cAMP accumulation in B16/F10 murine melanoma cells and in CHO cells overexpressing human MC1R (EC50s = 11.6 and 16.8 nM, respectively). It inhibits TNF-α-induced NF-κB activation in vitro in a concentration-dependent manner. In vivo, BMS 470539 inhibits LPS-induced TNF-α production in mice (ED50 = 10 μmol/kg, s.c.). It reduces LPS-induced leukocyte infiltration and paw swelling in mouse models of lung inflammation and delayed-type hypersensitivity, respectively. BMS 470539 decreases retinal damage in a mouse model of streptozotocin-induced diabetic retinopathy.2 It also increases striatal dopamine levels and decreases the number of striatal α-synuclein aggregates in a mouse model of Parkinson’s disease when administered at a dose of 20 mg/kg.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kang, L., McIntyre, K.W., Gillooly, K.M., et al. A selective small molecule agonist of the melanocortin-1 receptor inhibits lipopolysaccharide-induced cytokine accumulation and leukocyte infiltration in mice. J. Leukoc. Biol. 80(4), 897-904 (2006).

    2. Rossi, S., Maisto, R., Gesualdo, C., et al. Activation of melanocortin receptors MC1 and MC5 attenuates retinal damage in experimental diabetic retinopathy. Mediators Inflamm. 7368389 (2016).

    3. Cai, W., Srivastava, P., Feng, D., et al. Melanocortin 1 receptor activation protects against alpha-synuclein pathologies in models of Parkinson’s disease. Mol. Neurodegener. 17(1), 16 (2022).