Reserpine

• Catalog No.: Bio-0088
• CAS Number: 50-55-5
• M. F.: C33H40N2O9
• M. W.: 608.6787

SYNONYMS

• IUPAC name: methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0^2,^1^0.0^4,^9.0^1^5,^2^0]henicosa-2(10),4,6,8-tetraene-19-carboxylate
• IUPAC Traditional name: methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0^2,^1^0.0^4,^9.0^1^5,^2^0]henicosa-2(10),4,6,8-tetraene-19-carboxylate
• Synonyms: Carpacil; Sandril; Apoplon; Serpasil; Sermix; Reserpoid

DATABASE IDS

• CAS Number: 50-55-5

PROPERTIES

• Application(s): Antiadrenergic
• Application(s): Anticonvulsant agent
• Application(s): Antineoplastic agent
• Application(s): Possesses sedative tranquilliser props.
• Application(s): Antihypertensive agent acting by depleting stores of noradrenaline in sympathetic neurones
• Biological Source: Alkaloid from Rauwolfia serpentina, Rauwolfia vomitoria, Rauwolfia macrophylla , very many other Rauwolfia spp., Vinca minor, Alstonia constricta and many other spp. in the Apocynaceae, e.g. Tenduzia longifolia, Vallesia dichotoma and Excavatia coccinea
• Mechanism of Action: Disruption of norepinephrine, serotonin, and dopamine presynaptic vesicles by the transporter VMAT

REFERENCES

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1069C, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 615A, (nmr)
• Furlenmeyer, A. et al., Experientia, 1953, 9, 331, (uv, ir)
• Velluz, L. et al., Bull. Soc. Chim. Fr., 1958, 145; 673, (synth)
• Woodward, R.B. et al., Tetrahedron, 1958, 2, 1, (synth)
• Ban, Y. et al., Tetrahedron, 1964, 20, 2877, (config)
• Schlittler, E., Alkaloids (N.Y.), 1965, 8, 287, (rev)
• Levin, R.H. et al., J.O.C., 1973, 38, 1983, (cmr)
• Taylor, W.I. et al., The Vinca Alkaloids, Marcel Dekker, 1973, (rev, props)
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• Bein, H.J., Handb. Exp. Pharmacol., (Part 1), 1980, 55, 43-58, (rev, pharmacol)
• IARC Monog., 1980, 24, 211; Suppl., 6, 485; Suppl., 7, 330, (rev, tox)
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• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 343; 386
• Chu, C.S. et al., Chem. Comm., 1996, 1537, (synth)
• Nicolaou, K.C. et al., Classics in Total Synthesis, Targets, Strategies, Methods, VCH, 1996, 55, (bibl, synth)
• Hanessian, S. et al., J.O.C., 1997, 62, 465, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DIG800; DIH000; RDK000