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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

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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)

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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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD6347V
WXBD5256V
WXBD4843V
WXBD1985V
WXBD0706V

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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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