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MedKoo Cat#: 319932 | Name: Oxytocin acetate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Oxytocin is a medication and hormone. As a medication, it is used to cause contraction of the uterus, which is used to start labor, increase the speed of labor, and to stop bleeding following delivery. It is used either by injection into a muscle or into a vein. Medical uses can result in excessive contraction of the uterus that can cause distress in an unborn baby. Common side effects in the mother include nausea and a slow heart rate. Oxytocin is normally produced in the hypothalamus and stored in the posterior pituitary gland. It plays a role in social bonding, sexual reproduction in both sexes, and during and after childbirth. It is released due to stretching of the cervix and uterus during labor and with stimulation of the nipples from breastfeeding.

Chemical Structure

Oxytocin acetate
Oxytocin acetate
CAS#6233-83-6 (acetate)

Theoretical Analysis

MedKoo Cat#: 319932

Name: Oxytocin acetate

CAS#: 6233-83-6 (acetate)

Chemical Formula: C45H70N12O14S2

Exact Mass: 0.0000

Molecular Weight: 1067.25

Elemental Analysis: C, 50.64; H, 6.61; N, 15.75; O, 20.99; S, 6.01

Price and Availability

Size Price Availability Quantity
10mg USD 90.00 Ready to ship
25mg USD 150.00 Ready to ship
50mg USD 225.00 Ready to ship
100mg USD 350.00 Ready to ship
200mg USD 550.00 Ready to ship
500mg USD 1,150.00 Ready to ship
1g USD 2,050.00 Ready to ship
2g USD 3,450.00 Ready to ship
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Related CAS #
6233-83-6 (acetate) 50-56-6 (free base)
Synonym
Orasthin; Ossitocina; Ossitocina; Oxetakain; Oxitocina; Oxoject; Oxystin; Partocon; Pitocin; Piton S; Oxt,; Oxytocin.
IUPAC/Chemical Name
(S)-N-((S)-1-((2-amino-2-oxoethyl)amino)-4-methyl-1-oxopentan-2-yl)-1-((4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-((S)-sec-butyl)-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl)pyrrolidine-2-carboxamide acetate
InChi Key
DSZOEVVLZMNAEH-BXUJZNQYSA-N
InChi Code
InChI=1S/C43H66N12O12S2.C2H4O2/c1-5-22(4)35-42(66)49-26(12-13-32(45)57)38(62)51-29(17-33(46)58)39(63)53-30(20-69-68-19-25(44)36(60)50-28(40(64)54-35)16-23-8-10-24(56)11-9-23)43(67)55-14-6-7-31(55)41(65)52-27(15-21(2)3)37(61)48-18-34(47)59;1-2(3)4/h8-11,21-22,25-31,35,56H,5-7,12-20,44H2,1-4H3,(H2,45,57)(H2,46,58)(H2,47,59)(H,48,61)(H,49,66)(H,50,60)(H,51,62)(H,52,65)(H,53,63)(H,54,64);1H3,(H,3,4)/t22-,25-,26-,27-,28-,29-,30-,31-,35-;/m0./s1
SMILES Code
O=C([C@H]1N(C([C@@H](NC([C@H](CC(N)=O)NC([C@H](CCC(N)=O)NC([C@H]([C@@H](C)CC)NC([C@H](CC2=CC=C(O)C=C2)N3)=O)=O)=O)=O)CSSC[C@H](N)C3=O)=O)CCC1)N[C@@H](CC(C)C)C(NCC(N)=O)=O.CC(O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Oxytocin is a nonapeptide hormone released from the neurohypophysis (PITUITARY GLAND, POSTERIOR). It differs from VASOPRESSIN by two amino acids at residues 3 and 8. Oxytocin acts on smooth muscle cells, such as causing UTERINE CONTRACTIONS and MILK EJECTION. Oxytocin was discovered in 1952.[8] It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system. The wholesale cost is between 0.10 and 0.56 USD per dose as of 2014. Oxytocin free base: Chemical Formula: C43H66N12O12S2 Exact Mass: 1006.4365 Molecular Weight: 1007.1930 Elemental Analysis: C, 51.28; H, 6.61; N, 16.69; O, 19.06; S, 6.37
Biological target:
Oxytocin is a mammalian neurohypophysial hormone, a ligand of oxytocin receptor.
In vitro activity:
Oxytocin provoked 3-, 2.5-, and 4-fold increases in inositol triphosphate, inositol bisphosphate, and inositol monophosphate, respectively. [Ca2+]i, measured with the fluorescent dye fura-2, was stimulated by oxytocin and vasopressin (oxytocin greater than vasopressin) in a dose-dependent manner. The [Ca2+]i transient produced by oxytocin reached a peak in 15 sec, followed by a slow return to baseline over 10 min. Preincubation with phorbol 12-myristate-13 acetate (PMA) markedly blunted the oxytocin-induced transient. No [Ca2+]i transient was seen with leukotrienes, PG, serotonin, angiotensin, or alpha- or beta-adrenergic agents. PGE2 production increased 30- to 50-fold with phospholipase-C and PMA, and 10-fold with the calcium ionophore A23187. Oxytocin and vasopressin produced 10- and 3-fold PGE2 increases, respectively. Increased PGE2 production induced by PMA, oxytocin, and A23187 was first seen after 8 hr of incubation and reached maximal levels at 24 h. Minimal PGE2 stimulation occurred with agents that produced no [Ca2+]i transient. Direct activators of the inositol phospholipid-protein kinase-C system in human amnion induce large increases in PGE2 in human amnion cells. Oxytocin and vasopressin are hormonal activators of this system in these cells, as demonstrated by their effects on inositol phosphate turnover and [Ca2+]i. These hormones also increase PGE2 production and may influence labor by stimulating PGE2 production in amnion through the inositol phospholipid-protein kinase-C system. Reference: Moore JJ, Dubyak GR, Moore RM, Vander Kooy D. Oxytocin activates the inositol-phospholipid-protein kinase-C system and stimulates prostaglandin production in human amnion cells. Endocrinology. 1988 Oct;123(4):1771-7. doi: 10.1210/endo-123-4-1771. PMID: 3138102.
In vivo activity:
Immunohistochemistry reveals that in the caudal VTA oxytocin-containing axons/fibres (originating from the paraventricular nucleus of the hypothalamus) contact cell bodies of mesolimbic dopaminergic (tyrosine hydroxylase-positive) neurons containing both NO synthase and guanylate cyclase. These results suggest that oxytocin injected into the VTA induces penile erection by activating NO synthase in the cell bodies of mesolimbic dopaminergic neurons. NO in turn activates guanylate cyclase present in these neurons, thereby increasing cyclic GMP concentration. Reference: Succu S, Sanna F, Cocco C, Melis T, Boi A, Ferri GL, Argiolas A, Melis MR. Oxytocin induces penile erection when injected into the ventral tegmental area of male rats: role of nitric oxide and cyclic GMP. Eur J Neurosci. 2008 Aug;28(4):813-21. doi: 10.1111/j.1460-9568.2008.06385.x. Epub 2008 Jul 30. PMID: 18671741.
Solvent mg/mL mM
Solubility
DMSO 44.0 41.23
Water 50.0 46.85
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,067.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
Moore JJ, Dubyak GR, Moore RM, Vander Kooy D. Oxytocin activates the inositol-phospholipid-protein kinase-C system and stimulates prostaglandin production in human amnion cells. Endocrinology. 1988 Oct;123(4):1771-7. doi: 10.1210/endo-123-4-1771. PMID: 3138102.
In vitro protocol:
Moore JJ, Dubyak GR, Moore RM, Vander Kooy D. Oxytocin activates the inositol-phospholipid-protein kinase-C system and stimulates prostaglandin production in human amnion cells. Endocrinology. 1988 Oct;123(4):1771-7. doi: 10.1210/endo-123-4-1771. PMID: 3138102.
In vivo protocol:
Succu S, Sanna F, Cocco C, Melis T, Boi A, Ferri GL, Argiolas A, Melis MR. Oxytocin induces penile erection when injected into the ventral tegmental area of male rats: role of nitric oxide and cyclic GMP. Eur J Neurosci. 2008 Aug;28(4):813-21. doi: 10.1111/j.1460-9568.2008.06385.x. Epub 2008 Jul 30. PMID: 18671741.
1: Freeman SM, Young LJ. Comparative perspectives on oxytocin and vasopressin receptor research in rodents and primates: Translational implications. J Neuroendocrinol. 2016 Mar 4. doi: 10.1111/jne.12382. [Epub ahead of print] Review. PubMed PMID: 26940141. 2: Olszewski PK, Klockars A, Levine AS. Oxytocin: a conditional anorexigen whose effects on appetite depend on the physiological, behavioral and social contexts. J Neuroendocrinol. 2016 Feb 26. doi: 10.1111/jne.12376. [Epub ahead of print] Review. PubMed PMID: 26918919. 3: Aspé-Sánchez M, Moreno M, Rivera MI, Rossi A, Ewer J. Oxytocin and Vasopressin Receptor Gene Polymorphisms: Role in Social and Psychiatric Traits. Front Neurosci. 2016 Jan 28;9:510. doi: 10.3389/fnins.2015.00510. eCollection 2015. Review. PubMed PMID: 26858594; PubMed Central PMCID: PMC4729929. 4: Lefevre A, Sirigu A. The two fold role of oxytocin in social developmental disorders: A cause and a remedy? Neurosci Biobehav Rev. 2016 Apr;63:168-76. doi: 10.1016/j.neubiorev.2016.01.011. Epub 2016 Jan 29. Review. PubMed PMID: 26828138. 5: Romano A, Tempesta B, Micioni Di Bonaventura MV, Gaetani S. From Autism to Eating Disorders and More: The Role of Oxytocin in Neuropsychiatric Disorders. Front Neurosci. 2016 Jan 12;9:497. doi: 10.3389/fnins.2015.00497. eCollection 2015. Review. PubMed PMID: 26793046; PubMed Central PMCID: PMC4709851. 6: Massey SH, Backes KA, Schuette SA. PLASMA OXYTOCIN CONCENTRATION AND DEPRESSIVE SYMPTOMS: A REVIEW OF CURRENT EVIDENCE AND DIRECTIONS FOR FUTURE RESEARCH. Depress Anxiety. 2016 Jan 12. doi: 10.1002/da.22467. [Epub ahead of print] Review. PubMed PMID: 26756305. 7: Lee SY, Lee AR, Hwangbo R, Han J, Hong M, Bahn GH. Is Oxytocin Application for Autism Spectrum Disorder Evidence-Based? Exp Neurobiol. 2015 Dec;24(4):312-24. doi: 10.5607/en.2015.24.4.312. Epub 2015 Dec 16. Review. PubMed PMID: 26713079; PubMed Central PMCID: PMC4688331. 8: van IJzendoorn MH, Bakermans-Kranenburg MJ. The role of oxytocin in parenting and as augmentative pharmacotherapy; critical issues and bold conjectures. J Neuroendocrinol. 2015 Dec 28. doi: 10.1111/jne.12355. [Epub ahead of print] Review. PubMed PMID: 26709101. 9: Wang P, Yang HP, Tian S, Wang L, Wang SC, Zhang F, Wang YF. Oxytocin-secreting system: A major part of the neuroendocrine center regulating immunologic activity. J Neuroimmunol. 2015 Dec 15;289:152-61. doi: 10.1016/j.jneuroim.2015.11.001. Epub 2015 Nov 3. Review. PubMed PMID: 26616885. 10: Ma Y, Shamay-Tsoory S, Han S, Zink CF. Oxytocin and Social Adaptation: Insights from Neuroimaging Studies of Healthy and Clinical Populations. Trends Cogn Sci. 2016 Feb;20(2):133-45. doi: 10.1016/j.tics.2015.10.009. Epub 2015 Nov 23. Review. PubMed PMID: 26616296. 11: Acevedo-Rodriguez A, Mani SK, Handa RJ. Oxytocin and Estrogen Receptor β in the Brain: An Overview. Front Endocrinol (Lausanne). 2015 Oct 15;6:160. doi: 10.3389/fendo.2015.00160. eCollection 2015. Review. PubMed PMID: 26528239; PubMed Central PMCID: PMC4606117. 12: Baribeau DA, Anagnostou E. Oxytocin and vasopressin: linking pituitary neuropeptides and their receptors to social neurocircuits. Front Neurosci. 2015 Sep 24;9:335. doi: 10.3389/fnins.2015.00335. eCollection 2015. Review. PubMed PMID: 26441508; PubMed Central PMCID: PMC4585313. 13: Yamasue H. Promising evidence and remaining issues regarding the clinical application of oxytocin in autism spectrum disorders. Psychiatry Clin Neurosci. 2016 Feb;70(2):89-99. doi: 10.1111/pcn.12364. Epub 2015 Oct 16. Review. PubMed PMID: 26394796. 14: Feldman R, Monakhov M, Pratt M, Ebstein RP. Oxytocin Pathway Genes: Evolutionary Ancient System Impacting on Human Affiliation, Sociality, and Psychopathology. Biol Psychiatry. 2016 Feb 1;79(3):174-84. doi: 10.1016/j.biopsych.2015.08.008. Epub 2015 Aug 18. Review. PubMed PMID: 26392129. 15: Herpertz SC, Bertsch K. A New Perspective on the Pathophysiology of Borderline Personality Disorder: A Model of the Role of Oxytocin. Am J Psychiatry. 2015 Sep 1;172(9):840-51. doi: 10.1176/appi.ajp.2015.15020216. Review. PubMed PMID: 26324303. 16: Elabd S, Sabry I. Two Birds with One Stone: Possible Dual-Role of Oxytocin in the Treatment of Diabetes and Osteoporosis. Front Endocrinol (Lausanne). 2015 Aug 10;6:121. doi: 10.3389/fendo.2015.00121. eCollection 2015. Review. PubMed PMID: 26322016; PubMed Central PMCID: PMC4530313. 17: Shamay-Tsoory SG, Abu-Akel A. The Social Salience Hypothesis of Oxytocin. Biol Psychiatry. 2016 Feb 1;79(3):194-202. doi: 10.1016/j.biopsych.2015.07.020. Epub 2015 Aug 5. Review. PubMed PMID: 26321019. 18: Altirriba J, Poher AL, Rohner-Jeanrenaud F. Chronic Oxytocin Administration as a Treatment Against Impaired Leptin Signaling or Leptin Resistance in Obesity. Front Endocrinol (Lausanne). 2015 Aug 5;6:119. doi: 10.3389/fendo.2015.00119. eCollection 2015. Review. PubMed PMID: 26300847; PubMed Central PMCID: PMC4525065. 19: Maroun M, Wagner S. Oxytocin and Memory of Emotional Stimuli: Some Dance to Remember, Some Dance to Forget. Biol Psychiatry. 2016 Feb 1;79(3):203-12. doi: 10.1016/j.biopsych.2015.07.016. Epub 2015 Jul 31. Review. PubMed PMID: 26300273. 20: Carbonari A, Burgio M, Frattina L, Ceci E, Sciannamblo M, Ricci P, Cicirelli V, Rizzo A. Oxytocin, prostaglandin F2α, and scopolamine for uterine involution of dairy cows. Front Vet Sci. 2024 May 2;11:1405746. doi: 10.3389/fvets.2024.1405746. PMID: 38756512; PMCID: PMC11096567.

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