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:

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.

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

Refernces

• 1、 Tamamura, Hirokazu,Otaka, Akira,Nakamura, Junko,Okubo, Kaori,Koide, Takaki,Ikeda, Kyoko,Fujii, Nobutaka. "Disulfide bond formation in S-Acetamidomethyl cysteine-containing peptides by the combination of silver trifluoromethanesulfonate and dimethylsulfoxide / aqueous HCI". . p. 4931 - 4934. Retrieved 1993.
• 2、 Ruiz-Gayo, Mariano,Albericio, Fernando,Pedroso, Enrique,Giralt, Ernest. "(S)-9-Fluorenylmethyl-L-cysteine, a Useful HF-stable Derivative for Peptide Synthesis". . p. 1501 - 1502. Retrieved 1986.
• 3、 Konno, Hiroyuki,Yasumiishi, Haruto,Aoki, Reika,Nitanai, Ikumi,Yano, Shigekazu. "Detection of Thiol Functionality and Disulfide Bond Formation by Polyoxometalate". supporting information. p. 745 - 749. Retrieved 2020/11/10.
• 4、 -. "Selective disulfidation reagent using nitrogen-containing compound and method for producing disulfide-containing compound". Page/Page column 26-28; 34-35; 39. . Retrieved 2020/12/02.