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87616-84-0

87616-84-0 Structure

87616-84-0 Structure
IdentificationMore
[Name]

Growth hormone releasing peptide
[CAS]

87616-84-0
[Synonyms]

[D-TRP7, ALA8, D-PHE10]-ALPHA-MELANOCYTE STIMULATING HORMONE (6-11) AMIDE
[D-TRP7,ALA8,D-PHE10]-ALPHA-MELANOCYTE STIMULATING HORMONE FRAGMENT 6-11 AMIDE
(D-TRP7,ALA8,D-PHE10)-ALPHA-MSH (6-11) AMIDE
GHRP-6
GHRP-6 ACETATE
GROWTH HORMONE RELEASING PEPTIDE-6
GROWTH HORMONE RELEASING PROTEIN-6
H-HIS-D-TRP-ALA-TRP-D-PHE-LYS-NH2
[HIS1, LYS6]-GHRP
HIS-D-TRP-ALA-TRP-D-PHE-LYS-NH2
HWAWFK-NH2
sk&f110679
(D-trp7,ala8,D-phe10)-A-melanocyte*stimulating ho
(D-TRP7,ALA8,D-PHE10)-A-MELANOCYTE*STIMU LATING HORM
Growth
[d-trp7, ala8, d-phe10]-α-melanocyte stimulating hormone amide fragment 6-11
D-TRP7,ALA8,D-PHE10]-A-MELANOCYTESTIMULATINGHORMONEAMIDEFRAGMENT6-11
(2S)-6-amino-2-[[2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-amino-3-(3H-imidazol-4-yl)propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-phenyl-propanoyl]amino]hexanamide
Growth hormone releasing peptide
alpha-melanotropin, fragment 6-11, [D-Trp7,Ala8,D-Phe10]
[EINECS(EC#)]

212-729-3
[Molecular Formula]

C46H56N12O6
[MDL Number]

MFCD00872694
[Molecular Weight]

873.01
[MOL File]

87616-84-0.mol
Questions And AnswerBack Directory
[Synthesis]

Peptide synthesis was performed under standard conditions in an automated shaker using Rink resin. Amino acid coupling (3 equivalents) was carried out in DMF with HBTU (3 equivalents) as the coupling agent and DIEA (initially 3 equivalents, then 1 equivalent after 20 minutes of coupling) as the base. Fmoc deprotection was performed by treating the resin with 20% piperidine in DMF for 10 and 20 minutes. After each coupling and deprotection step, the resin was washed with DMF (2x), MeOH (2x), and DCM (2x), respectively. Side chain deprotection and Aza-peptide cleavage were then performed. The resin was then treated with freshly prepared TFA/H2O/TES solution (95:2.5:2.5, v/v/v, 20 mL/g Aza-peptide resin) at room temperature for 2 h. The cleavage mixture was filtered, and the resin was washed with a clean TFA solution. The filtrate was concentrated to approximately 1 ml and treated with Et2O. The obtained azide precipitate was filtered, washed with Et₂O, dissolved in acetonitrile/water (1:1, v/v) solution, and lyophilized to produce light foam or powder, yielding growth hormone-releasing peptide-6.
Chemical PropertiesBack Directory
[Melting point ]

>160o C (Dec.)
[Boiling point ]

1407.0±65.0 °C(Predicted)
[density ]

1.333±0.06 g/cm3(Predicted)
[storage temp. ]

−20°C
[solubility ]

Methanol (Slightly), Water (Slightly)
[form ]

Solid
[pka]

13.42±0.46(Predicted)
[color ]

White to Off-White
[Sequence]

is-D-Trp-Ala-Trp-D-Phe-Lys-NH2|H-His-D-Trp-Ala-Trp-D-Phe-Lys-NH2
[Cosmetics Ingredients Functions]

SKIN CONDITIONING
[InChIKey]

WZHKXNSOCOQYQX-FUAFALNISA-N
[SMILES]

C(N)(=O)[C@H](CCCCN)NC(=O)[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1C2=C(C=CC=C2)NC=1)NC(=O)[C@H](C)NC(=O)[C@@H](CC1C2=C(C=CC=C2)NC=1)NC(=O)[C@H](CC1N=CNC=1)N
[CAS DataBase Reference]

87616-84-0(CAS DataBase Reference)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[WGK Germany ]

3
Hazard InformationBack Directory
[Description]

Growth hormone-releasing peptides (GHRPs) are synthetic, non-natural peptides endowed with potent stimulatory effects on somatotrope secretion in animals and humans. They have no structural homology with GHRH and act via specific receptors present either at the pituitary or the hypothalamic level both in animals and in humans. 
[Uses]

Growth hormone releasing peptide-6 can promote the secretion of growth hormone, regulate food intake, increase weight, and promote animal growth.
[Uses]

L-Histidyl-D-tryptophyl-L-alanyl-L-tryptophyl-D-phenylalanyl-L-lysinamide is a growth hormone releasing peptide.
[benefits]

When Growth hormone releasing peptide is administered, a selective pulse is sent to the brain that stimulates the hypothalamus and anterior pituitary to release growth hormones. Once this pulse is sent, the cells go directly to the muscle to support development while staying clear of any possible bone or cartilage growth. When the Peptide is injected it increases cell synthesis, elevates secretion levels of insulin from pancreatic tissue, and increases ghrelin in the stomach—which helps release GH and control hunger. All of these functions work to promote fat loss, shuttling of nutrients, and building clean muscle mass.
[Biological Functions]

Growth hormone releasing peptide (GHRH) is an endocrine hormone produced in the hypothalamus that acts on the receptors (GHRH-R) of the anterior pituitary gland to stimulate the release of growth hormone (GH).  GHRH includes GHRH-2 and GHRH-6, which have slightly different functions.  GHRH-2 is widely used to diagnose patients with growth hormone deficiency (GHD) and is believed to induce not only growth hormone (GH) release, but also adrenocorticotropic hormone (ACTH) release. GHRH-6 is part of a group of synthetic small peptides with potent growth hormone releasing activity, which has cellular and cardioprotective effects and can be used in heart disease treatment research.
[Mechanism of action]

Growth hormone releasing peptide is generally accepted that GHRPs stimulate the release of GH by acting at the level of the pituitary through a receptor different to that for the endogenous GH-releasing hormone (GHRH). In addition, it has been reported that there are specific binding sites for these peptides in the hypothalamus and that systemic administration of GHRPs increases the expression of the immediate early gene c-fos in a subpopulation of hypothalamic neurons. 
[Side effects]

Carpal tunnel syndrome.

Increased insulin resistance.

Type 2 diabetes.

Swelling in the arms and legs (edema)

Joint and muscle pain.

For men, enlargement of breast tissue (gynecomastia).

Increased risk of certain cancers.

[Physiological effects]

Growth hormone releasing peptide (GHRP) is a cyclase inhibitor that blocks the release of endogenous growth hormone.The peptide acts on both igf-i and somatotrophs, with receptor activity in the hypothalamus.GHRP can be used to increase body weight and control obesity.It has been shown to stimulate cell division and inhibit apoptosis in vitro.
[Solubility in water]

It is recommended to reconstitute the lyophilized growth hormone releasing peptide in sterile 18MΩ-cm H2O not less than 100 μg/ml, which can then be further diluted to other aqueous solutions.
[storage]

Lyophilized Growth hormone releasing peptide although stable at room temperature for 3 weeks, should be stored desiccated below -18°C. Upon reconstitution Growth hormone releasing peptide should be stored at 4°C between 2-7 days and for future use below -18°C. For long term storage it is recommended to add a carrier protein (0.1% HSA or BSA). Please prevent freeze-thaw cycles.
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

87616-84-0(sigmaaldrich)
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