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R0875

Sigma-Aldrich

Reserpine

Monoamine transport inhibitor

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/REAXYS Number:
102014
EC Number:
200-047-9
MDL number:
MFCD00005091
UNSPSC Code:
12352200
PubChem Substance ID:
24278208
NACRES:
NA.77

Key Documents

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Product Name

Reserpine,

Quality Level

200

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 ... HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2B(3357), HTR2C(3358), HTR3A(3359), HTR3B(9177), HTR3C(170572), HTR3D(200909), HTR3E(285242), HTR4(3360), HTR5A(3361), HTR5B(645694), HTR6(3362), HTR7(3363), SLC18A2(6571)

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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

Inhibits vesicular uptake of catecholamines and serotonin.
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.

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
GHS08,GHS07

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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBB4812V
SLBN2685V
SLBJ5380V
SLBD8262V
SLBD6372V

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Effects of long-term intake of lactotripeptides on cardiovascular risk factors in hypertensive subjects
Jauhiainen T, et al.
European Journal of Clinical Nutrition, 66(7), 843-843 (2012)
In vitro activities of six quinolones and mechanisms of resistance in Staphylococcus aureus and coagulase-negative staphylococci
Linde H, et al.
Antimicrobial Agents and Chemotherapy, 45(5), 1553-1557 (2001)
Comparative effects of Rauwolfia vomitoria and chlorpromazine on locomotor behaviour and anxiety in mice
Bisong SA, et al.
Journal of Ethnopharmacology, 132(1), 334-339 (2010)
Current Cardiovascular Drugs, 302-302 (2005)
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
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