Oxytocin injection

Base Information

• Chemical Name: Oxytocin injection
• CAS No.: 50-56-6
• Molecular Formula: C43H66N12O12S2
• Molecular Weight: 1007.2
• Hs Code.: 2937190000
• Mol file: 50-56-6.mol

Synonyms:alpha-Hypophamine;oxytocin injection;Gly-Leu-Pro-c;Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2;Disulfide bridge Cys1-Cys6;SCHEMBL21527573;Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH2

Chemical Property of Oxytocin injection

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 192-194 °C
• Refractive Index: 1.6700 (estimate)
• Boiling Point: 1533.3 °C at 760 mmHg
• PKA: pKa ～6.1(free amino group on Cys) (Occasionally);～10(free phenol on Tyr) (Occasionally)
• Flash Point: 881.1 °C
• PSA: 450.13000
• Density: 1.27 g/cm³
• LogP: 1.55630
• Storage Temp.: 2-8°C
• Solubility.: Very soluble in water. It dissolves in dilute solutions of acetic acid and of ethanol (96 per cent).
• Water Solubility.: Soluble in water.
• XLogP3: -2.6
• Hydrogen Bond Donor Count: 12
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 17
• Exact Mass: 1006.43645793
• Heavy Atom Count: 69
• Complexity: 1870

Purity/Quality:

99% ^*data from raw suppliers

Oxytocin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)N1)CC2=CC=C(C=C2)O)N)C(=O)N3CCCC3C(=O)NC(CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N
• Isomeric SMILES: CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N1)CC2=CC=C(C=C2)O)N)C(=O)N3CCCC3C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N
• Physiological Functions: Oxytocin is a neuropeptide primarily known for its peripheral actions, including regulating uterine contraction during parturition (childbirth) and facilitating milk letdown during nursing.; Within the brain, oxytocin coordinates a range of social behaviors, such as maternal nurturing, mother-infant bonding, social recognition, and pair-bonding. It is involved in synchronous firing and pulsatile release during parturition and nursing, acting within brain regions like the paraventricular nucleus (PVN) and supraoptic nucleus (SON).
• Synthesis and Distribution: Oxytocin is a cyclic peptide composed of nine amino acids, synthesized in hypothalamic neurons, particularly in the PVN, SON, and accessory magnocellular hypothalamic nuclei. It is packaged into dense-core vesicles and transported into dendrites and axons for release.; Most oxytocin is secreted into the bloodstream via axonal release from the posterior pituitary, but it also acts somatodendritically within the SON and PVN.
• Role in Social Behavior and Cognition: Oxytocin is of significant interest due to its role in social behavior and cognition.Studies have explored its potential as a therapeutic agent for improving social impairments in psychiatric disorders, although recent research has not consistently supported these effects. While oxytocin was historically associated with terms like the "moral molecule" and the "cuddle chemical," it is now recognized to modulate both prosocial and non-prosocial cognitive processes and behaviors.
• Pleiotropic Effects and Therapeutic Potential: Oxytocin is a pleiotropic peptide hormone with broad implications for general health, adaptation, development, reproduction, and social behavior. It functions as a stress-coping molecule, anti-inflammatory, and antioxidant, exerting protective effects, especially in adversity or trauma.; Oxytocin influences the autonomic nervous system and immune system, making it a possible therapeutic agent in various disorders.
• Synthesis and Distribution in the Brain: Oxytocin is primarily synthesized in the hypothalamus, particularly in the parvocellular neurons of the PVN and magnocellular neurons of both the PVN and SON. It is also produced in smaller quantities in other brain areas outside the hypothalamus, with various pathways facilitating its distribution to different regions of the brain, spinal cord, and peripheral circulation.
• General Description: Oxytocin is a neuropeptide hormone with critical roles in childbirth (stimulating uterine contractions) and social bonding, often referred to by various trade and chemical names such as Pitocin, Syntocinon, and α-hypophamine. Research on its analogs, such as [9-leucine]-oxytocin and oxytocinoyl-glycinamide, reveals that structural modifications at position 9 can influence pharmacological potency, with leucinamide substitution retaining partial activity (8% potency) compared to native oxytocin. Additionally, advancements in peptide synthesis, including acid-labile anchor groups in Fmoc solid-phase synthesis, have enabled efficient production of oxytocin, yielding pure peptides identical to natural forms. These findings underscore the hormone's structural flexibility and the potential for synthetic optimization in therapeutic applications.

Technology Process of Oxytocin injection

There total 44 articles about Oxytocin injection which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.5%

1,Cys(SH)6>-oxytocin (151937-33-6) → oxytocin (50-56-6)

Guidance literature:

1,Cys(SH)⁶>-oxytocin; With iodine; In acetic acid; at 20 ℃;

With isoascorbic acid; In acetic acid;

Reference yield: 98.0%

H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2 (17912-60-6) → oxytocin (50-56-6)

Guidance literature:

With [Pt(en)2Cl₂]⁽²⁺⁾; ethylenediaminetetraacetic acid; sodium chloride; In phosphate buffer; pH=4 - 7;

DOI:10.1021/ja0008618

Reference yield: 86.0%

Boc-Cys(Acm)(O)-Tyr-Ile-Gln-Asn-Cys(MBzl)-Pro-Leu-Gly-NH2 → oxytocin (50-56-6)

Guidance literature:

With dimethylsulfide; In trifluoroacetic acid; 1.) ice bath, 60 min; 2.) 25 deg C, 60 min;

DOI:10.1016/S0040-4020(01)86118-4

upstream raw materials:

Fmoc-Leu-OH

(R)-3-tert-Butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid

{4-[[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyrylamino]-(4-methoxy-phenyl)-methyl]-2-methyl-phenoxy}-acetic acid

Fmoc-Pro-OH

Downstream raw materials:

L-cystine

H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH₂

Oxidized glutathione

Captopril disulfide

Refernces

Analogs of oxytocin containing leucinamide and glycylglycinamide in place of glycinamide.

10.1246/bcsj.41.2772

The research aimed to synthesize and test two analogs of oxytocin, a hormone known for its role in childbirth and social bonding. The analogs, [9-leucine]-oxytocin and oxytocinoyl-glycinamide, were created by replacing the glycinamide residue at position 9 in oxytocin with leucinamide and glycylglycinamide, respectively. The study's purpose was to explore the structure-activity relationships in oxytocin and to understand the impact of these modifications on the hormone's pharmacological properties. The researchers used a variety of chemicals in their synthesis process, including benzyloxycarbonyl-tripeptide azide, hexa- or heptapeptide amide, and various protecting groups such as benzyloxycarbonyl and benzyl groups, which were later removed using sodium in liquid ammonia or anhydrous hydrogen fluoride. The synthesized analogs were then oxidized and tested for their oxytocic potency, with [9-leucine]-oxytocin showing approximately 8% potency and oxytocinoyl-glycinamide showing 0.5% potency compared to the natural oxytocin. The findings suggest that the replacement of glycine with bulkier leucine did not significantly reduce the biological activity, which is significant for understanding the structure-function relationship of the oxytocin molecule.

PREPARATION AND APPLICATION OF NEW ACID LABILE ANCHOR GROUPS FOR THE SYNTHESIS OF PEPTIDE AMIDES BY FMOC SOLID PHASE SYNTHESIS

10.1016/S0040-4039(00)96804-7

The research aims to develop new linkage agents for the preparation of peptide amides using a modified Fmoc (9-fluorenylmethyloxycarbonyl) strategy. The researchers introduce a new anchor group that can be coupled to the resin and releases the peptide amide upon treatment with trifluoroacetic acid (TFA). The new linkers were successfully applied in the solid-phase synthesis of oxytocin and LHRH, yielding pure peptides in 33% and 43% yields, respectively, identical to authentic samples. Oxytocin is synthesized using the newly developed acid-labile anchor group to demonstrate the effectiveness of the new linkage agents in solid-phase peptide synthesis. The synthesis process involves coupling the anchor group to a resin with valine as an anchor, followed by sequential addition of Fmoc-protected amino acids. After the synthesis is complete, the peptide amide is cleaved from the resin using trifluoroacetic acid (TFA) with thioanisole and ethanedithiol. The crude peptide is then purified, and the cysteine residue is deprotected and oxidized to form the disulfide bond. The final product, oxytocin, is obtained in a 33% yield and is identical to an authentic sample, confirming the successful application of the new anchor group in the synthesis of this peptide. The study concludes that the new anchor group provides a practical and efficient alternative for the synthesis of peptide amides, simplifying the cleavage process and improving the overall synthesis efficiency.