Ipamorelin Chemical Properties

Melting point:

144-147°C

Boiling point:

1185.5±65.0 °C(Predicted)

Density 

1.263±0.06 g/cm3(Predicted)

storage temp. 

-20°C Freezer

solubility 

Acetonitrile (Slightly, Heated), Methanol (Very Slightly), Water (Slightly)

pka

13.04±0.46(Predicted)

form 

Solid

color 

White to Off-White

InChI

InChI=1S/C38H49N9O5/c1-38(2,41)37(52)47-32(21-28-22-42-23-43-28)36(51)46-31(20-25-15-16-26-12-6-7-13-27(26)18-25)35(50)45-30(19-24-10-4-3-5-11-24)34(49)44-29(33(40)48)14-8-9-17-39/h3-7,10-13,15-16,18,22-23,29-32H,8-9,14,17,19-21,39,41H2,1-2H3,(H2,40,48)(H,42,43)(H,44,49)(H,45,50)(H,46,51)(H,47,52)/t29-,30+,31+,32-/m0/s1

InChIKey

NEHWBYHLYZGBNO-BVEPWEIPSA-N

SMILES

C(N)(=O)[C@H](CCCCN)NC(=O)[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](CC1=CC=C2C(=C1)C=CC=C2)NC(=O)[C@H](CC1N=CNC=1)NC(=O)[C@](C)(C)N

Ipamorelin Usage And Synthesis

Description

Ipamorelin (INN) (developmental code name NNC 26-0161) is a peptide selective agonist of the ghrelin/growth hormone secretagogue receptor (GHS) and a growth hormone secretagogue.It is a pentapeptide with the amino acid sequence Aib-His-D-2-Nal-D-Phe-Lys-NH2 that was derived from GHRP-1.

Uses

Ipamorelin was originally developed by Novo Nordisk, and was investigated in phase II clinical trials by Helsinn Therapeutics for the treatment of postoperative ileus, but was discontinued due to lack of efficacy.Ipamorelin has been used by athletes as a performance enhancing drug.

Uses

Ipamorelin is a metabolite of growth hormone releasing peptides (GHRPs). Ipamorelin is a pentapeptide with strong growth hormone releasing potency that evokes insulin release from pancrease of normal and diabetic rats.

benefits

Ipamorelin has a wide range of benefits for the human body such as: reduced body fat, increased collagen production, increased lean muscle mass, improved sleep, increased cell repair and regeneration, elevated IGF-1, increased bone mineral content, counteracted glucocorticoid catabolism, decreased appetite stimulation compared to GHRP-6, decreased release of cortisol, prolactin and aldosterone. Decreased release of cortisol, prolactin and aldosterone.

Biochem/physiol Actions

Ipamorelin is a highly selective, potent pentapeptide (Aib-His-D-2-Nal-D-Phe-Lys-NH2) and gastrin mimetic with growth hormone (GH) releasing activity. It mimics gastrin and binds to the gastrin receptor (or growth hormone secretion receptor, GHSR) in the brain, which selectively stimulates the pituitary gland to release growth hormone. This leads to elevated plasma GH levels, which affects many biological processes. In addition to being found in the brain, GHSR is found in the gastrointestinal tract, heart, lungs, liver, kidneys, pancreas, adipose tissue and immune cells. Unlike other growth hormone releasing peptides, ipamorelin stimulates the release of growth hormone only in a manner very similar to that of growth hormone releasing hormone^[1].

Side effects

Ipamorelin is generally considered safe and well tolerated, with common side effects including dizziness, headache, nausea, diarrhoea and flushing. Allergic or serious adverse reactions are rare.

Synthesis

Ipamorelin was prepared from a total of 4.53 g of the peptide resin Boc-Aib-His (Trt)-D-2Nal-DPhe-Lys (Boc)-NH-resin according to the Fmoc strategy on an Applied Biosystems 431A peptide synthesizer in two identical runs (to obtain sufficient material) in 1 mmol scale using the FastMoc UV protocols supplied by the manufacturer, that employ HBTU mediated couplings in NMP and UV monitoring of the deprotection of the Fmoc protection group.

Description

Ipamorelin Synthetic is a single, non-glycosylated polypeptide chain containing 4 amino acids, having a molecular mass of 711.85 Dalton and a Molecular formula of C₃₈H₄₉N₉O₅.

Background

Ipamorelin is a peptide selective agonist of the ghrelin/growth hormone secretagogue receptor and a growth hormone secretagogue. Ipamorelin is a pentapeptide that was derived from GHRP1. Ipamorelin significantly increases plasma growth hormone levels in both animals and humans. Like pralmorelin and GHRP-6, ipamorelin does not affect prolactin, FSH, LH or TSH levels. However, unlike GHRP2 and GHRP6, but as growth hormone-releasing hormone (GHRH), ipamorelin does not stimulate the secretion of adrenocorticotropic hormone (ACTH) or cortisol, and is highly selective for inducing the secretion only of GH.

References

[1] Ipamorelin[J]. Definitions, 2020. DOI:10.32388/22pzq4.

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