Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

83580

Sigma-Aldrich

Reserpine

crystallized, ≥99.0% (HPLC)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C33H40N2O9
CAS Number:
50-55-5
Molecular Weight:
608.68
Beilstein:
102014
EC Number:
200-047-9
MDL number:
MFCD00005091
UNSPSC Code:
12352200
PubChem Substance ID:
329769078
NACRES:
NA.77

Assay

≥99.0% (HPLC)

form

solid

optical activity

[α]20/D −123±3°, c = 1% in chloroform

quality

crystallized

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

Gene Information

human ... SLC18A2(6571)

Looking for similar products? Visit Product Comparison Guide

General description

Reserpine is an indole alkaloid that irreversibly binds vesicular monoamine transporters VMAT1 and VMAT2. It is a sympatholytic drug useful in treating systemic hypertension.

Application

Reserpine has been used as a test chemical in performance studies.

Biochem/physiol Actions

Reserpine is used to treat hypertensive pregnancy difficulties. This drug is also considered as antipsychotic and antihypertensive, to regulate high blood pressure.
Inhibits vesicular uptake of catecholamines and serotonin.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H336,H351,H360D

Hazard Classifications

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

Target Organs

Central nervous system

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
WXBF4430V
WXBF1136V
WXBD6347V
WXBD5256V
WXBD4843V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Heart and circulatory system drugs and diuretics
Drugs During Pregnancy and Lactation, 193-236 (2007)
What All Should Know about Plant Drugs
Essentials of Biochemistry for Medical Students, 35-61 (2015)
Intra-laboratory validated human cell-based in vitro vasculogenesis/angiogenesis test with serum-free medium
Toimela T, et al.
Reproductive Toxicology, 70, 116-125 (2017)
Julia Zwirchmayr et al.
Scientific reports, 10(1), 12323-12323 (2020-07-25)
In this study a robust, whole organism screening based on Caenorhabditis elegans is presented for the discovery of natural products (NP) with beneficial effects against obesity and age-related diseases. Several parameters of the elaborated workflow were optimized to be adapted
Naomi S Rajapaksa et al.
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service