An MC3R agonist
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[D-Trp8]-γ-MSH (trifluoroacetate salt)

Item No. 14037

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
L-tyrosyl-L-valyl-L-methionylglycyl-L-histidyl-L-phenylalanyl-L-arginyl-D-tryptophyl-L-α-aspartyl-L-arginyl-L-phenylalanyl-glycine, trifluoroacetate salt
Molecular Formula
C74H99N21O16S • XCF3COOH
Formula Weight
1570.8
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
Water: soluble
SMILES
O=C(N[C@@H](CC(O)=O)C(N[C@@H](CCCNC(N)=N)C(N[C@H](C(NCC(O)=O)=O)CC1=CC=CC=C1)=O)=O)[C@H](NC([C@H](CCCNC(N)=N)NC([C@@H](NC([C@@H](NC(CNC([C@H](CCSC)NC([C@H](C(C)C)NC([C@@H](N)CC2=CC=C(O)C=C2)=O)=O)=O)=O)CC3=CN=CN3)=O)CC4=CC=CC=C4)=O)=O)CC5=CNC6=CC=CC=C56.OC(C(F)(F)F)=O
InChi Code
InChI=1S/C74H99N21O16S.C2HF3O2/c1-41(2)62(95-63(102)49(75)30-44-22-24-47(96)25-23-44)72(111)90-53(26-29-112-3)64(103)84-38-59(97)87-57(34-46-37-80-40-86-46)70(109)92-55(32-43-16-8-5-9-17-43)68(107)88-52(21-13-28-82-74(78)79)67(106)93-56(33-45-36-83-50-19-11-10-18-48(45)50)69(108)94-58(35-60(98)99)71(110)89-51(20-12-27-81-73(76)77)66(105)91-54(65(104)85-39-61(100)101)31-42-14-6-4-7-15-42;3-2(4,5)1(6)7/h4-11,14-19,22-25,36-37,40-41,49,51-58,62,83,96H,12-13,20-21,26-35,38-39,75H2,1-3H3,(H,80,86)(H,84,103)(H,85,104)(H,87,97)(H,88,107)(H,89,110)(H,90,111)(H,91,105)(H,92,109)(H,93,106)(H,94,108)(H,95,102)(H,98,99)(H,100,101)(H4,76,77,81)(H4,78,79,82);(H,6,7)/t49-,51-,52-,53-,54-,55-,56+,57-,58-,62-;/m0./s1
InChi Key
DREXBIMZEHERHW-JDYKNHKYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    [D-Trp8]-γ-MSH is a melanocortin receptor 3 (MC3R) agonist and an analog of γ-melanocyte-stimulating hormone (γ-MSH).1 It selectively induces cAMP accumulation in cells expressing MC3R over cells expressing MC4R or MC5R (EC50s = 0.33, 100, and 82 nM, respectively, for the human receptors). In vivo, [D-Trp8]-γ-MSH (162 nmol/kg, i.v.) reduces the incidence of ventricular tachycardia, ventricular fibrillation, and death in a rat model of myocardial ischemia-reperfusion injury.2 It also inhibits urate-induced chemokine (C-X-C) motif ligand 1 (CXCL1) release and peritoneal polymorphonuclear leukocyte accumulation in recessive yellow (e/e) mice with a non-functional MC1R.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Grieco, P., Balse, P.M., Weinberg, D., et al. D-Amino acid scan of γ-melanocyte-stimulating hormone: Importance of Trp8 on human MC3 receptor selectivity. J. Med. Chem. 43(26), 4998-5002 (2000).

    2. Mioni, C., Giuliani, D., Cainazzo, M.M., et al. Further evidence that melanocortins prevent myocardial reperfusion injury by activating melanocortin MC3 receptors. Eur. J. Pharmacol. 477(3), 227-234 (2003).

    3. Getting, S.J., Lam, C.W., Leoni, G., et al. [D-Trp8]-γ-melanocyte-stimulating hormone exhibits anti-inflammatory efficacy in mice bearing a nonfunctional MC1R (recessive yellow e/e mouse). Mol. Pharmacol. 70(6), 1850-1855 (2006).