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R0875

Sigma-Aldrich

Reserpine

Sinônimo(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

Fórmula empírica (Notação de Hill):
C33H40N2O9
Número CAS:
Peso molecular:
608.68
Beilstein:
102014
Número CE:
Número MDL:
Código UNSPSC:
12352200
ID de substância PubChem:
NACRES:
NA.77

pf

~265 °C (dec.)

cadeia de caracteres SMILES

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

chave InChI

QEVHRUUCFGRFIF-MDEJGZGSSA-N

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Aplicação

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

Ações bioquímicas/fisiológicas

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.

Características e benefícios

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.

Pictogramas

Health hazardExclamation mark

Palavra indicadora

Danger

Frases de perigo

Declarações de precaução

Classificações de perigo

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

Órgãos-alvo

Central nervous system

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

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


Certificados de análise (COA)

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Visite a Biblioteca de Documentos

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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