2002-44-0

Basic information

• Product Name: H-PRO-LEU-GLY-NH2
• Synonyms: MSH-RELEASE INHIBITING FACTOR;MSH RELEASE INHIBITING FACTOR, AMIDE;MIF-1;MIF, AMIDE;MIF-I;PRO-LEU-GLY AMIDE;PRO-LEU-GLY-NH2;PLG-NH2
• CAS NO: 2002-44-0
• Molecular Formula: C₁₃H₂₄N₄O₃
• Molecular Weight: 284.35
• EINECS: 217-902-7
• Product Categories: Melanocortin receptor;peptide;SignalTransduction
• Mol File: 2002-44-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 122-123 °C(Solv: water (7732-18-5))
• Boiling Point: 626.2 °C at 760 mmHg
• Flash Point: 332.5 °C
• Appearance: /
• Density: 1.147 g/cm³
• Vapor Pressure: 1.34E-15mmHg at 25°C
• Refractive Index: 1.51
• Storage Temp.: -15°C
• Solubility: ≥59.1 mg/mL in DMSO; ≥50 mg/mL in EtOH; ≥50 mg/mL in H2O
• PKA: 14.10±0.20(Predicted)
• Water Solubility: Soluble in water.
• CAS DataBase Reference: H-PRO-LEU-GLY-NH2(CAS DataBase Reference)
• NIST Chemistry Reference: H-PRO-LEU-GLY-NH2(2002-44-0)
• EPA Substance Registry System: H-PRO-LEU-GLY-NH2(2002-44-0)

Safety Data

• Hazardous Substances Data: 2002-44-0(Hazardous Substances Data)

Usage

Description

H-PRO-LEU-GLY-NH2, also known as L-Prolyl-L-leucylglycinamide, is a synthetic tetrapeptide that has been found to exhibit antidepressant properties. It is composed of four amino acids: proline, leucine, glycine, and an amide group. This peptide has gained attention for its potential therapeutic effects in the treatment of depression and its role in the development of novel analogs for targeting dopamine D2 receptors.

Uses

Used in Pharmaceutical Industry:
H-PRO-LEU-GLY-NH2 is used as an antidepressant agent for its greater efficacy and faster onset of action compared to traditional anti-depressants. It has been shown to be effective in treating human depression, providing an alternative treatment option for patients suffering from this condition.
Used in Research and Development:
H-PRO-LEU-GLY-NH2 is also used in the synthesis of novel analogs to be tested for their ability to enhance the binding of [3H]-N-propylnorapomorphine to the short isoform of human dopamine D2 receptors. This research aims to develop new therapeutic agents that can target these receptors, potentially leading to improved treatments for various neurological and psychiatric disorders.

Biological Activity

melanocyte stimulating hormone release inhibiting factor,(c13h24n4o3), a tri-peptide with the sequence h2n-pro-leu-gly-amide, mw= 284.35. melanocyte-inhibiting factor (also known as pro-leu-gly-nh2, melanostatin, msh release-inhibiting hormone or mif-1) is an endogenous peptide fragment derived from cleavage of the hormone oxytocin, but having generally different actions in the body(1). mif-1 produces multiple effects, both blocking the effects of opioid receptor activation(2), while at the same time acting as a positive allosteric modulator of the d2 and d4 dopamine receptor subtypes, as well as inhibiting release of other neuropeptides such as alpha-msh, and potentiating melatonin activity(3). mif-1 is unusually resistant to metabolism in the bloodstream, and crosses the blood–brain barrier easily, though it is poorly active orally and is usually injected.figure1 formula of melanocyte stimulating hormone release inhibiting factor

references

1. Celis ME, Taleisnik S, Walter R (July 1971). "Regulation of formation and proposed structure of the factor inhibiting the release of melanocyte-stimulating hormone". Proceedings of the National Academy of Sciences of the United States of America 68 (7): 1428–33.2. Contreras PC, Takemori AE (June 1984). "Effect of prolyl-leucyl-glycinamide and alpha-melanocyte-stimulating hormone on levorphanol-induced analgesia, tolerance and dependence". Life Sciences 34 (26): 2559–66.3. Sandyk R (May 1990). "MIF-induced augmentation of melatonin functions: possible relevance to mechanisms of action of MIF-1 inmovement disorders". The International Journal of Neuroscience 52 (1-2): 59–65.

InChI:InChI=1/C13H24N4O3/c1-8(2)6-10(12(19)16-7-11(14)18)17-13(20)9-4-3-5-15-9/h8-10,15H,3-7H2,1-2H3,(H2,14,18)(H,16,19)(H,17,20)/t9-,10-/m0/s1

Upstream product

• 1668-10-6 glycinamide hydrochloride 
• 68385-28-4 (2S)-2-{[(2S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carbonyl]amino}-4-methylpentanoic acid 
• 74763-82-9 PChd-L-Pro-L-Leu-Gly-NH₂ 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 2018-66-8 Z-Leu-OH 
• 2867-06-3 Benzyloxycarbonylleucyl-glycine ethyl ester 
• 7784-82-9 N-[N-(N-benzyloxycarbonyl-L-prolyl)-L-leucyl]glycine ethyl ester 
• 74761-41-4 (S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 147-85-3 L-proline 
• 74761-46-9 MOC-Leu-Gly-OMe 
• 74761-47-0 MOC-Leu-Gly-NH₂ 
• 74761-48-1 (S)-N-(methoxycarbonyl)-2-pyrrolidinecarbonylchloride 
• 74761-37-8 (S)-2-(methoxycarbonylamino)-4-methylpentanoic acid 
• 74763-77-2 PChd-L-Leu-OBzl 

Downstream Products

• 16747-86-7 S-benzyl-N-benzyloxycarbonyl-cysteinyl=>prolyl=>leucyl=>-glycin-amide 
• 21688-11-9 N²-benzyloxycarbonyl-glutaminyl=>asparaginyl=>S-benzyl-cysteinyl=>prolyl=>leucyl=>-glycin-amide 
• 100076-31-1 1-N-(2-carbomethoxyphenyl)-carbamoyl-L-prolyl-L-leucylglycinamide 
• 82215-15-4 Cys(PMB)-Pro-Leu-Gly-NH₂ 
• 82230-21-5 Boc-Can-Cys(PMB)-Pro-Leu-Gly-NH₂ 
• 82215-24-5 Boc-Tan-Cys(PMB)-Pro-Leu-Gly-NH₂ 
• 100076-37-7 1-N-(2-carboxy-phenyl)-carbamoyl-L-prolyl-L-leucyl-glycinamide 
• 90826-25-8 <1-Penicillamine, 2-O-methyltyrosine>deamino-6-carba-oxytocin 
• 90819-45-7 <1-Penicillamine>deamino-6-carba-oxytocin 
• 94991-29-4 o-Nitrobenzenesulphenylisoleucyl-glutaminyl-asparaginyl-S-(2-(2-methyl-1-methoxycarbonylpropyl))homocysteinyl-prolyl-leucyl-glycine Amide 
• 94991-28-3 o-Nitrobenzenesulphenylglutaminyl-asparaginyl-S-(2-(2-methyl-1-methoxycarbonylpropyl))homocysteinyl-prolyl-leucyl-glycine Amide 
• 94991-27-2 o-Nitrobenzenesulphenylasparaginyl-S-(2-(2-methyl-1-methoxycarbonylpropyl))homocysteinyl-prolyl-leucyl-glycine Amide 
• 78221-66-6 C₄₁H₆₆N₁₀O₉S*ClH 
• 78221-65-5 o-nitrobenzenesulfenyl-L-isoleucyl-L-glutaminyl-L-asparaginyl-S-(2,4,6-trimethylbenzyl)-L-cysteinyl-L-prolyl-L-leucyl-glycine amide 

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