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SML2756

Sigma-Aldrich

Bremelanotide acetate

≥98% (HPLC)

Synonym(s):

Ac-Nle-Asp-His-D-Phe-Arg-Trp-Lys (Asp-Lys), acetate salt, Acetyl-[Nle4, Asp5, D-Phe7, Lys10]-cyclo-α-melanocyte, PT 141 acetate, PT-141 acetate, PT141 acetate

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About This Item

Empirical Formula (Hill Notation):
C50H68N14O10 · xC2H4O2
CAS Number:
1607799-13-2
Molecular Weight:
1025.16 (free base basis)
UNSPSC Code:
12352200
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to off-white

shipped in

wet ice

storage temp.

−20°C

SMILES string

[nH]1cncc1C[C@@H]2NC(=O)[C@H](CC(=O)NCCCC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC2=O)Cc5ccccc5)CCCN=C(N)N)Cc3c4c([nH]c3)cccc4)C(=O)O)NC(=O)[C@@H](NC(=O)C)CCCC.OC(=O)C

InChI

1S/C50H68N14O10.C2H4O2/c1-3-4-16-35(58-29(2)65)43(67)64-41-25-42(66)54-20-11-10-18-37(49(73)74)60-46(70)39(23-31-26-56-34-17-9-8-15-33(31)34)62-44(68)36(19-12-21-55-50(51)52)59-45(69)38(22-30-13-6-5-7-14-30)61-47(71)40(63-48(41)72)24-32-27-53-28-57-32;1-2

InChI key

MAYUSRUHXFWITM-GBRHMYBBSA-N

Biochem/physiol Actions

Brain-penetrant alpha-melanocyte-stimulating hormone (α-MSH)-derived melanocortin receptors (MC1R, MC3R, MC4R) agonist with in vivo sexual arousal efficacy.
Bremelanotide (PT-141) is a brain-penetrant, alpha-melanocyte-stimulating hormone (α-MSH)-derived cyclic heptapeptide agonist toward melanocortin receptors, including MC1R, MC3R and MC4R (affinty = 10 nM by competitive binding against 0.2 nM NDP-α-MSH using human MC4R-expressing HEK-293). Bremelanotide induces cAMP accumulation in hMC4R-expressing HEK-293 cells and exhibits in vivo sexual arousal efficacy among both male (50 μg/kg intranasally or 50-500 pg/kg via lateral ventricle injection) and female rats (100-200 μg/kg sc or 800 μg/kg via lateral ventricle injection) by activating neurons in brain regions responsible for sexual function.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000137059

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P B Molinoff et al.
Annals of the New York Academy of Sciences, 994, 96-102 (2003-07-10)
PT-141, a synthetic peptide analogue of alpha-MSH, is an agonist at melanocortin receptors including the MC3R and MC4R, which are expressed primarily in the central nervous system. Administration of PT-141 to rats and nonhuman primates results in penile erections. Systemic
K L Aughton et al.
British journal of pharmacology, 155(2), 236-243 (2008-07-01)
Hypothalamic neuropeptides centrally modulate sexual arousal. However, the role of neuropeptides in peripheral arousal has been ignored. Vascular and non-vascular smooth muscle relaxation in the vagina is important for female sexual arousal. To date, in vitro studies have focused on
James Pfaus et al.
The journal of sexual medicine, 4 Suppl 4, 269-279 (2007-11-21)
Bremelanotide is an analogue of the naturally occurring peptide alpha-melanocyte-stimulating hormone (alpha-MSH). It stimulates erection in men and male rats, and is currently in clinical trials for the treatment of erectile dysfunction. To review the effects of bremelanotide, an analogue

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