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Merck

R0875

Sigma-Aldrich

Reserpine

Sinónimos:

(3β, 16β, 17α, 18β, 20α)-11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester

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About This Item

Fórmula empírica (notación de Hill):
C33H40N2O9
Número de CAS:
Peso molecular:
608.68
Beilstein/REAXYS Number:
102014
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

mp

~265 °C (dec.)

SMILES string

CO[C@H]1[C@@H](C[C@@H]2CN3CCc4c([nH]c5cc(OC)ccc45)[C@H]3C[C@@H]2[C@@H]1C(=O)OC)OC(=O)c6cc(OC)c(OC)c(OC)c6

InChI

1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m1/s1

InChI key

QEVHRUUCFGRFIF-MDEJGZGSSA-N

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Application

Reserpine has been used:
  • to study its effect on minimal inhibitory concentration of trovafloxacin and ciprofloxacin
  • inject rats, to study its effect on behavioural parameters such as locomotion and fear/anxiety
  • as a lock spray reference compound in lipid profiling

Biochem/physiol Actions

Reserpine is an alkaloid present in Rauwolfia species. It is useful in treating systemic hypertension, schizophrenia, psychiatric disorders and Raynaud′s syndrome. Reserpine is known to inhibit adrenaline induced-cutaneous blood vessel constriction. It diminishes the effect of hyperthyroidism on cardiovascular and nervous system.
Inhibits vesicular uptake of catecholamines and serotonin.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Biogenic Amine Transporters page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Health hazardExclamation mark

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Repr. 1A - STOT SE 3

target_organs

Central nervous system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


Certificados de análisis (COA)

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Organic letters, 15(3), 706-709 (2013-01-22)
A catalytic, enantioselective synthesis of (+)-reserpine is reported. The route features a highly diastereoselective, chiral catalyst-controlled formal aza-Diels-Alder reaction between a 6-methoxytryptamine-derived dihydro-β-carboline and an enantioenriched α-substituted enone to form a key tetracyclic intermediate. This approach addresses the challenge of

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