A peptide agonist of MC1R
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Alternative(s)
41548[Nle4,D-Phe7]-α-MSH (acetate)
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[Nle4,D-Phe7]-α-MSH (trifluoroacetate salt)

Item No. 24475

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Molecular Formula
C78H111N21O19 • XCF3COOH
Formula Weight
1646.8
Purity
≥95%
Formulation (Request formulation change)
A lyophilized powder
Solubility(Learn about Variance in Solubility)
Water: 1 mg/ml
SMILES
O=C([C@H](CCCNC(N)=N)NC([C@H](NC([C@@H](NC([C@H](CCC(O)=O)NC([C@H](CCCC)NC([C@H](CO)NC([C@@H](NC([C@H](CO)NC(C)=O)=O)CC1=CC=C(O)C=C1)=O)=O)=O)=O)CC2=CN=CN2)=O)CC3=CC=CC=C3)=O)N[C@H](C(NCC(N[C@H](C(N4CCC[C@H]4C(N[C@@H](C(C)C)C(N)=O)=O)=O)CCCCN)=O)=O)CC5=CNC6=CC=CC=C56.FC(F)(C(O)=O)F
InChi Code
InChI=1S/C78H111N21O19.C2HF3O2/c1-5-6-19-52(91-75(116)61(41-101)97-72(113)57(34-46-24-26-49(103)27-25-46)94-74(115)60(40-100)88-44(4)102)68(109)92-54(28-29-64(105)106)70(111)96-59(36-48-38-83-42-87-48)73(114)93-56(33-45-16-8-7-9-17-45)71(112)90-53(22-14-31-84-78(81)82)69(110)95-58(35-47-37-85-51-20-11-10-18-50(47)51)67(108)86-39-63(104)89-55(21-12-13-30-79)77(118)99-32-15-23-62(99)76(117)98-65(43(2)3)66(80)107;3-2(4,5)1(6)7/h7-11,16-18,20,24-27,37-38,42-43,52-62,65,85,100-101,103H,5-6,12-15,19,21-23,28-36,39-41,79H2,1-4H3,(H2,80,107)(H,83,87)(H,86,108)(H,88,102)(H,89,104)(H,90,112)(H,91,116)(H,92,109)(H,93,114)(H,94,115)(H,95,110)(H,96,111)(H,97,113)(H,98,117)(H,105,106)(H4,81,82,84);(H,6,7)/t52-,53-,54-,55-,56+,57-,58-,59-,60-,61-,62-,65-;/m0./s1
InChi Key
BFGBZOSHJJSHTQ-CRYSLBJVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $183

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    Product Description

    [Nle4,D-Phe7]-a-Melanocyte-stimulating hormone ([Nle4,D-Phe7]-a-MSH) is a peptide agonist of melanocortin receptor I (MC1R).1 It induces cAMP accumulation in mouse L-cells expressing human MC1R (EC50 = 0.5 nM). It also induces tyrosinase activity in mouse melanoma cells.2 In vivo, [Nle4,D-Phe7]-a-MSH (1.8 mg/kg) induces long-term skin darkening in frogs (R. pipiens).3 Formulations containing [Nle4,D-Phe7]-a-MSH have been used in the treatment of erythropoietic protoporphyria and as tanning agents.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Haskell-Luevano, C., Miwa, H., Dickinson, C., et al. Binding and cAMP studies of melanotropin peptides with the cloned human peripheral melanocortin receptor, hMC1R. Biochem. Biophys. Res. Commun. 204(30), 1137-1147 (1994).

    2. Sawyer, T.K., Sanfilippo, P.J., Hruby, V.J., et al. 4-Norleucine, 7-D-phenylalanine-α-melanocyte-stimulating hormone: A highly potent α-melanotropin with ultralong biological activity. Proc. Natl. Acad. Sci. USA 77(10), 5754-5758 (1980).

    3. Hadley, M.E., Anderson, B., Heward, C.B., et al. Calcium-dependent prolonged effects on melanophores of [4-norleucine, 7-D-phenylalanine]-α-melanotropin. Science 213(4511), 1025-1027 (1981).