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Description

Spegatrine is a monoterpenoid indole alkaloid from plants in the Apocynaceae family, isolated from Rauvolfia verticillata and reported in other Rauwolfia species, including R. bahiensis. The formula C20H25N2O2 given in the card corresponds to the cation: the alkaloid is a quaternary base, and is commercially supplied in the form of a salt. Additional indication of the nature of the compound is provided by the literary definition of “bisquaternary alkaloid,” which refers to its dimeric form, dispegathrin.

Basic Attributes

• CAS No: 47326-53-4
• Chemical formula: C20H25N2O2 (cation)
• Molecular weight: 325.43
• Exact weight: 325.191603044
• English name: spegatrine

The “Substance synonyms” field in the original card is not filled in. The card does not contain other physical and chemical constants - density, melting and boiling points, refractive index, solubility.

Pharmacological characteristics

• α1- and α2-adrenergic receptor antagonist
• suppression of nitric oxide (NO) production
• suppression of the formation of reactive oxygen species (ROS)
• antioxidant properties
• reported inhibitory effect on tumor cells

The spegathrin dimer dispegatrin has a higher affinity for α-adrenergic receptors as an antagonist, making the monomer-dimer pair a convenient model for studying the effect of dimerization on affinity.

Plant source

Rauwolfia is a genus known for reserpine and ajmaline alkaloids. Spegatrine belongs to the monoterpenoid indole alkaloids of the same biosynthetic pathway: the indole moiety of tryptamine condenses with secologanin, then the skeleton is rearranged. New monoterpenoid indole alkaloids with immunosuppressive activity have been isolated from Rauvolfia yunnanensis, which characterizes the direction of research on the genus as a whole.

Scope of application

• analytical standard for the determination of rauwolfia alkaloids in raw materials and extracts
• pharmacological tool in working with α-adrenergic receptors
• object of research on antioxidant action and influence on NO and ROS production
• example of comparison in chemotaxonomic works on the Kutrov family

Storage and handling

Indole alkaloids are oxidized in light and air; quaternary salts are hygroscopic. Keep the bottle tightly closed in a dark place; The cooled container is brought to room temperature before opening. Alkaloids are physiologically active substances, so weighing is carried out without dust, wearing gloves and safety glasses. The original card does not provide hazard phrases, transport codes and instructions on hazard class; The handling mode is determined according to the supplier's safety data sheet.