482-68-8

Basic information

• Product Name: SARPAGINE
• Synonyms: SARPAGINE;sarpagan-10,17-diol;Raupine;Sarpagane-10,17-diol
• CAS NO: 482-68-8
• Molecular Formula: C₁₉H₂₂N₂O₂
• Molecular Weight: 310.39
• EINECS: 207-583-2
• Product Categories: Alkaloids
• Mol File: 482-68-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 320°C
• Boiling Point: 450.55°C (rough estimate)
• Flash Point: 271.1°C
• Appearance: /
• Density: 1.1396 (rough estimate)
• Refractive Index: 1.5600 (estimate)
• PKA: 10.24±0.40(Predicted)
• CAS DataBase Reference: SARPAGINE(CAS DataBase Reference)
• NIST Chemistry Reference: SARPAGINE(482-68-8)
• EPA Substance Registry System: SARPAGINE(482-68-8)

Safety Data

• RIDADR: 1544
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 482-68-8(Hazardous Substances Data)

Usage

Description

SARPAGINE is an indole alkaloid derived from Rauwolfia serpentina, an isomer of Ajmalinine. It is characterized by hydroxy groups at positions 10 and 17 on the sarpagan molecule. SARPAGINE exhibits potent pharmacological effects, being three to four times more effective than the total Rauwolfia alkaloids on isolated rabbit uterus. It also has a low toxicity and is known to lower blood pressure in cats.

Uses

Used in Pharmaceutical Industry:
SARPAGINE is used as a pharmaceutical compound for its potent effects on the cardiovascular system. Its ability to lower blood pressure makes it a valuable candidate for the development of drugs targeting hypertension.
Used in Research and Development:
SARPAGINE is used as a research compound for studying its pharmacological properties and potential applications in various therapeutic areas. Its specificity and low toxicity make it an attractive molecule for further investigation and development of novel therapeutic agents.
Used in Drug Delivery Systems:
Similar to gallotannin, SARPAGINE could potentially be incorporated into drug delivery systems to enhance its bioavailability, delivery, and therapeutic outcomes. The development of novel drug delivery systems, such as organic and metallic nanoparticles, could improve the efficacy of SARPAGINE in treating specific conditions.

References

Bodendorf, Eder., Naturwis<., 40, 342 (1953)

InChI:InChI=1/C19H22N2O2/c1-2-10-8-21-17-7-14-13-5-11(23)3-4-16(13)20-19(14)18(21)6-12(10)15(17)9-22/h2-5,12,15,17-18,20,22-23H,6-9H2,1H3/b10-2-/t12-,15?,17-,18-/m0/s1

Upstream product

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Relevant articles and documents

Nature-inspired stereospecific total synthesis of P-(+)-dispegatrine and four other monomeric sarpagine indole alkaloids

All five: The first total synthesis of the C2-symmetric indole alkaloid 1 involved a late-stage thallium(III) acetate-mediated intermolecular oxidative coupling to construct the C9-C9' bond with complete regio- and stereocontrol. The formation of a single atropodiastereomer in this critical step arises from internal asymmetric induction. The first total synthesis of four other monomeric sarpagine indole alkaloids is also described. Copyright

Deoxysarpagine hydroxylase--a novel enzyme closing a short side pathway of alkaloid biosynthesis in Rauvolfia.

Microsomal preparations from cell suspension cultures of the Indian plant Rauvolfia serpentina catalyze the hydroxylation of deoxysarpagine under formation of sarpagine. The newly discovered enzyme is dependent on NADPH and oxygen. It can be inhibited by typical cytochrome P450 inhibitors such as cytochrome c, ketoconazole, metyrapone, tetcyclacis and carbon monoxide. The CO-effect is reversible with light (450 nm). The data indicate that deoxysarpagine hydroxylase is a novel cytochrome P450-dependent monooxygenase. A pH optimum of 8.0 and a temperature optimum of 35 degrees C were determined. K(m) values were 25 microM for NADPH and 7.4 microM for deoxysarpagine. Deoxysarpagine hydroxylase activity was stable in presence of 20% sucrose at -25 degrees C for >3 months. The analysis of presence of the hydroxylase in nine cell cultures of seven different families indicates a very limited taxonomic distribution of this enzyme.

VELLOSIMINE REDUCTASE. A SPECIFIC ENZYME INVOLVED IN THE CELLFREE BIOSYNTHESIS OF SARPAGINE TYPE ALKALOIDS.

Vellosimine reductase is a substrate and cofactor specific enzyme which catalyzes the NADPH-dependent reduction of vellosimine (4) forming 10-deoxy-sarpagine type alkaloids.