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Grundinformationen
- Standard-SMILES
CC[C@H](C)[C@@H]1NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](N)CSSC[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC1=O- InChIKey
XNOPRXBHLZRZKH-DSZYJQQASA-N- Summenformel
- C43H66N12O12S2
- Durchschnittliche Molmasse
- 1.007,207 g/mol
- Monoisotopische Masse
- 1.006,43645755
Namen und Bezeichner
- Bevorzugter Name
- Oxytocin
- IUPAC
- 1-{(4R,7S,10S,13S,16S,19R)-19-Amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-[(2S)-butan-2-yl]-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl}-L-prolyl-L-leucylglycinamide
- Lokaler Name
- Oxytocin
- Englischer Name
- Oxytocin
- Summenformel
- C43H66N12O12S2
- Molmasse
- 1007.19
Namen und Synonyme
Datenbank-Bezeichner
- CAS
50-56-6- PubChem CID
- 439302
- DTXSID
DTXSID8048361- ChEMBL
CHEMBL395429- ChEBI
CHEBI:7872- EC Number
- 200-048-4
Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 192 · 192-194°C
- Siedepunkt
- 1533.3 · 1533.3±65.0 °C(Predicted)
- Dichte
- 1.1086 · 1.1086 (rough estimate)
- Brechungsindex
- 1.67 · 1.6700 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Very soluble in water. It dissolves in dilute solutions of acetic acid and of ethanol (96 per cent).
- Aggregatzustand
- lyophilized powder
- pka
- 6.1 · pKa ~6.1(free amino group on Cys) (Occasionally);~10(free phenol on Tyr) (Occasionally)
- Farbe
- White
- Biologische Quelle
- synthetic (organic)
- Wasserlöslichkeit
- Soluble in water.
- Merck
- 13 · 13,7049
- BRN
- 3586108 · 3586108
- InChIKey
- DSZOEVVLZMNAEH-BXUJZNQYSA-N
- SMILES
- CCC(C)C1NC(=O)C(Cc2ccc(O)cc2)NC(=O)C(N)CSSCC(NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC1=O)C(=O)N3CCCC3C(=O)NC(CC(C)C)C(=O)NCC(N)=O
- CAS Datenbank
- 50 · 50-56-6(CAS DataBase Reference)
Sicherheit und Regulatorisches
Sicherheitsdaten
- F
- 3-8-10-23
- wgk
- 3
- ridadr
- 3249
- hs_code
- 2937190000
- RTECS-Nr.
- RS7534000
- risk_code
- 36/37/38
- Toxizität
- LD50 oral in rat: > 20520ug/kg
- hazard_code
- Xi
- safety_code
- 26-36
- hazard_class
- 6.1(a)
- packing_group
- II
- Speicherklasse
- 11 - Combustible Solids
- Giftige Stoffe Daten
- 50-56-6(Hazardous Substances Data)
Chemie und Industrie
Anwendungen
BeschreibungOxytocin is a peptide hormone containing nine amino acids secreted and synthesized by the paraventricular and supraoptic nuclei of the hypothalamus and stored and released by the neurohypophysis. It acts in females by inducing uterine contractions during parturition and stimulating milk ejection by the mammary glands. No actions in males are known. Synthetic derivatives of oxytocin are used to induce labor and for therapeutic abortions. In recent years the safety of oxytocin has been greatly enhanced by the use of continuous maternal and fetal monitoring and by the use of controlled intravenous infusion of the drug.
HistoryOxytocin was discovered by Sir Henry Dale in 1909 when he found that an extract from the human posterior pituitary gland contracted the uterus of a pregnant cat. (The hormone is found unchanged in every mammalian species.) Dale named the unknown substance oxytocin, using the Greek words for "quick" and "birth." As early as 1911, physicians began using the pituitary extract to stimulate childbirth contractions. Dale subsequently found that the same extract facilitates the release of mother's milk. In the early 1950s, American biochemist Vincent du Vigneaud found that oxytocin is made up of nine amino acids, and he identified its amino acid sequence. In 1953 du Vigneaud carried out the synthesis of oxytocin, making it the first polypeptide hormone to be synthesized. (Du Vigneaud received the Nobel Prize for Chemistry in 1955 for his breakthrough.)
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Ergänzende Hinweise
DefinitionChEBI: Oxytocin is a cyclic nonapeptide hormone with amino acid sequence CYIQNCPLG that also acts as a neurotransmitter in the brain; the principal uterine-contracting and milk-ejecting hormone of the posterior pituitary. Together with the neuropeptide vasopressin, it is believed to influence social cognition and behaviour. It has a role as an oxytocic and a vasodilator agent. It is a peptide hormone and a heterodetic cyclic peptide.
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