11018-89-6

Basic information

• Product Name: OUABAIN OCTAHYDRATE
• Synonyms: STROPHANTHIN G;STROPHANTHIN G, OCTAHYDRATE;OUABAIN 8H20;OUABAIN 8H2O;OUABAIN HYDRATE;(-)-OUABAIN OCTAHYDRATE;OUABAIN OCTAHYDRATE;OUBAIN OCTAHYDRATE
• CAS NO: 11018-89-6
• Molecular Formula: C29H60O20
• Molecular Weight: 728.77
• EINECS: 211-139-3
• Product Categories: Carbohydrates & Derivatives;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 11018-89-6.mol
• Article Data: 0

Chemical Properties

• Melting Point: 260 °C
• Boiling Point: 838.2 °C at 760 mmHg
• Flash Point: 272.9 °C
• Appearance: white/powder
• Density: 1.51 g/cm3
• Refractive Index: 1.655
• Storage Temp.: +2C to +8C
• Solubility: H2O: 10 mg/mL cold
• Water Solubility: Soluble in water.
• Sensitive: Light Sensitive
• Stability: Stable for 2 years from date of purchase as supplied. Protect from exposure to moisture. Solutions in DMSO or distilled water may be stored at -20°C for up to 3 months.
• BRN: 101712
• CAS DataBase Reference: OUABAIN OCTAHYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: OUABAIN OCTAHYDRATE(11018-89-6)
• EPA Substance Registry System: OUABAIN OCTAHYDRATE(11018-89-6)

Safety Data

• Hazard Codes: T
• Statements: 23/25-33
• Safety Statements: 45
• RIDADR: UN 1544 6.1/PG 1
• WGK Germany: 3
• RTECS: RN3850000
• F: 8
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 11018-89-6(Hazardous Substances Data)

Usage

Description

OUABAIN OCTAHYDRATE, also known as Ouabain, is a selective inhibitor of Na+ K+-ATPase isolated from Strophanthus gratus. It is a white crystalline solid with chemical properties that make it a valuable compound in various applications. Endogenous ouabain is found in human circulation and displays cardiotonic and diuretic activity. It is used in pharmaceutical secondary standards for quality control in pharmaceutical laboratories and manufacturers, providing a convenient and cost-effective alternative to the preparation of in-house working standards.

Uses

Used in Pharmaceutical Industry:
OUABAIN OCTAHYDRATE is used as a secondary standard for quality control in the pharmaceutical industry. It helps ensure the accuracy and consistency of drug formulations and serves as a reference for the preparation of in-house working standards.
Used in Cardiology:
OUABAIN OCTAHYDRATE is used as an antiarrhythmic, cardiotonic, and hypertensive agent. It inhibits Na(+)/K(+) ATPase, which helps regulate the heart's rhythm and contractility.
Used in Neurology:
OUABAIN OCTAHYDRATE is used as a 5HT2 receptor antagonist, which can be beneficial in the treatment of certain neurological disorders.
Used in Toxicology Research:
OUABAIN OCTAHYDRATE is used as a tool to induce in vivo excitotoxicity, which can help researchers study the effects of various toxins on the nervous system.
Used in Cell Biology:
OUABAIN OCTAHYDRATE is used to regulate the transcription of MDR (increase, Pgp) and MRP (increase MRP1 and decrease CFTR, cystic fibrosis transport receptor or cAMP-activated Clchannel) genes. It also alters the localization of MRP1, which can be useful in studying the mechanisms of multidrug resistance in cancer cells.
Used in Ophthalmology:
OUABAIN OCTAHYDRATE, as well as other endogenous digitalis-like compounds, can down-regulate the expression of 14-3-3 proteins in rat lens. This application can be useful in understanding the effects of ouabain on the eye and potentially developing treatments for ocular disorders.

Biochem/physiol Actions

Ouabain has its specific binding site on integral proteins of the plasma membrane. Heart disease is treated using ouabain derivatives. Increased ouabain production is observed during exercise in humans. Abnormally high levels of ouabain are indicated in congestive heart failure and hypertension. Ouabain signalling affects intracellular calcium levels, which is known to activate nuclear factor κB (NFκB).

Potential Exposure

Ouabain, similar to digitoxin, is used to produce rapid digitalization in acute congestive heart failure. Also recommended in treatment of atrial or nodal paroxysmal tachycardia and atrial flutter; enzyme inhibitor.

Shipping

UN1544 Alkaloids, solid, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

It crystallises from water as the octahydrate. Dry it at 130o. It decomposes at 190o when dry. Store it in the dark as it is light sensitive, but it is stable in air. Its solubility (g/100mL) in H2O is 1.3 (~25o), 20 (~100o), and in EtOH it is 1.0 (~25o) and 12.5 (~78o). It is highly TOXIC as it is an inhibitor of cation transport and of Na+ and K+ ATPase. [Beilstein 18/5 V 625.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.).

References

1) Silva et al. (2012), New insights into the regulation of Na+,K(+)-ATPase by ouabain; Int. Rev. Cell. Mol. Biol., 294 99 2) Dvela et al. (2012), Endogenous ouabain regulates cell viability; Am. J. Physiol. Cell, Physiol., 302 C442

InChI:InChI=1/C29H44O12/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3/t13-,15-,16+,17+,18+,19+,21?,22-,23+,24+,25-,26+,27-,28+,29-/m0/s1