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

This base has been isolated from Rauwolfia serpentina and is an isomer of Ajmalinine (q.v.). Pharmacologically it has between three and four times the effect of the total Rauwolfia alkaloids on isolated rabbit uterus and is very specific. In the cat, the blood pres~ure is lowered by 0.5-2.0 mgm per kilo body weight. The toxicity is low.

Definition

ChEBI: An indole alkaloid that is sarpagan bearing hydroxy groups at positions 10 and 17.

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

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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.