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63605

α-Melanocyte stimulating hormone

≥97.0% (HPCE/HPLC)

Synonym(s):

α-MSH, α-Melanotropin

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About This Item

Empirical Formula (Hill Notation):
C77H109N21O19S
CAS Number:
581-05-5
Molecular Weight:
1664.88
PubChem Substance ID:
24882755
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
741840
MDL number:
MFCD00133062
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assay

≥70% peptide basis, ≥97.0% (HPCE/HPLC)

solubility

H2O: 1 mg/mL, clear, colorless

storage temp.

2-8°C

SMILES string

CSCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(C)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](Cc2c[nH]cn2)C(=O)N[C@@H](Cc3ccccc3)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](Cc4c[nH]c5ccccc45)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N6CCC[C@H]6C(=O)N[C@@H](C(C)C)C(N)=O

InChI

1S/C77H109N21O19S/c1-42(2)64(65(79)106)97-75(116)61-20-13-30-98(61)76(117)54(18-10-11-28-78)88-62(103)38-85-66(107)57(34-46-36-84-50-17-9-8-16-49(46)50)94-67(108)51(19-12-29-83-77(80)81)89-70(111)55(32-44-14-6-5-7-15-44)92-72(113)58(35-47-37-82-41-86-47)95-68(109)52(25-26-63(104)105)90-69(110)53(27-31-118-4)91-74(115)60(40-100)96-71(112)56(33-45-21-23-48(102)24-22-45)93-73(114)59(39-99)87-43(3)101/h5-9,14-17,21-24,36-37,41-42,51-61,64,84,99-100,102H,10-13,18-20,25-35,38-40,78H2,1-4H3,(H2,79,106)(H,82,86)(H,85,107)(H,87,101)(H,88,103)(H,89,111)(H,90,110)(H,91,115)(H,92,113)(H,93,114)(H,94,108)(H,95,109)(H,96,112)(H,97,116)(H,104,105)(H4,80,81,83)/t51-,52-,53-,54-,55-,56-,57-,58-,59-,60-,61-,64-/m0/s1

InChI key

WHNFPRLDDSXQCL-UAZQEYIDSA-N

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General description

Ac-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2

Biochem/physiol Actions

Pituitary hormone which causes darkening skin pigmentation from amphibians to humans. In mammals, it can also have behavioral effects on learning, attention, and memory.

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBD2956V
BCBD1273V
BCBD1274V
BCBC1350
BCBC6459

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P C Datta et al.
Neuroscience and biobehavioral reviews, 6(3), 297-310 (1982-01-01)
Melanocyte-stimulating hormone (MSH) has putative adaptive significance in all forms of species where it is present. In mammals the polypeptide chain influences learning, memory and attention. Chemically MSH shares the first 13 (alpha-MSH) or the first 18 or 22 (beta-MSH)
Emma I Kay et al.
Journal of molecular endocrinology, 50(2), 203-215 (2013-01-09)
Human melanocortin 2 receptor accessory protein (hMRAPa) is hypothesised to have functions beyond promoting human melanocortin 2 receptor (hMC2R) functional expression. To understand these potential functions, we exogenously co-expressed hMRAPa-FLAG with each of the five hMCR subtypes in HEK293 cells
Mark E Samuels et al.
The Journal of clinical endocrinology and metabolism, 98(2), 736-742 (2013-01-08)
A 4-year-old girl and a 4-month-old boy presented with hypoglycemia, normal electrolytes, low cortisol, and high ACTH. A diagnosis of primary adrenal insufficiency was made and initial treatment was with glucocorticoids and mineralocorticoids. The genes known to cause ACTH resistance
Paula C Eves et al.
Peptides, 27(2), 444-452 (2005-11-09)
Alpha-melanocyte stimulating hormone (alpha-MSH) arises from the proteolytic cleavage of proopiomelanocortin (POMC) and is the most potent naturally occurring melanotropic peptide. The biological effects of alpha-MSH are mediated via melanocortin receptors (MCRs), which are expressed in virtually every cutaneous cell
Maurício Morais et al.
Journal of medicinal chemistry, 56(5), 1961-1973 (2013-02-19)
Aiming at the design of specific melanocortin-1 receptor (MC1R) targeted imaging probes, we report on the effect of different azolyl-ring substitution patterns (carboxylate at the 4-position and/or methyl groups at the 3,5 positions) of pyrazolyl-diamine bifunctional chelators (Pz(2)-Pz(4)) on the
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