All Photos(2)

R0875

Sigma-Aldrich

Reserpine

Synonym(s):
(3β, 16β, 17α, 18β, 20α)-11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester
Empirical Formula (Hill Notation):
C33H40N2O9
CAS Number:
Molecular Weight:
608.68
Beilstein:
102014
EC Number:
MDL number:
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

Packaging

1 g in glass bottle

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 featured on the Biogenic Amine Transporters page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
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.

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

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

Certificate of Analysis

Certificate of Origin

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What information do you have on the solubility of Product R0875, Reserpine?

    This product is soluble in chloroform at a concentration of 50 mg/mL.  It is freely soluble in chloroform (approx. 1 g in 6 mL), methylene chloride, glacial acetic acid, benzene, ethyl acetate. It is slightly soluble in acetone, methanol, alcohol (1 g/1800 mL), ether, and in aqueous solutions of acetic and citric acids. It is very sparingly soluble in water.

  4. Can solutions of Product R0875, Reserpine, be autoclaved?

    You can filter sterilize the solution. Autoclaving is not recommended as it discolors the solution.

  5. What is the purity of Product R0875, Reserpine?

    The purity of each lot is given on the Certificate of Analysis; it is typically 98% as determined by Thin Layer Chromatography (TLC).

  6. Is Product R0875, Reserpine, synthetic?

    The initial product is derived from Rauwolfia species; the final product is chemically synthesized.

  7. Is Product R0875, Reserpine, soluble in DMSO?

    Reserpine can be dissolved in DMSO at 50 mg/mL, according to Stevenson, P.A., et al., J. Neurobiol., 43(2), 107-120 (2000).

  8. What is the shelf life/expiration date of Product R0875, Reserpine?

    This product does not have an assigned shelf life or expiration date.  The QC testing date is given on the certificate of analysis for each lot. The standard Sigma-Aldrich guarantee of one year from date of receipt applies.

  9. Where do you store Product R0875, Reserpine?

    Product No. R0875 may be stored at ambient temperature, in a cool dry place.

  10. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  11. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  12. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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)
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)
Current Cardiovascular Drugs, 302-302 (2005)
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)
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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