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P8688

Sigma-Aldrich

(S)-(−)-Propranolol hydrochloride

≥98% (TLC), powder

Sinônimo(s):

(S)-1-Isopropylamino-3-(1-naphthyloxy)-2-propanol hydrochloride

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About This Item

Fórmula linear:
C10H7OCH2CH(OH)CH2NHCH(CH3)2·HCl
Número CAS:
4199-10-4
Peso molecular:
295.80
Beilstein:
3574966
Número CE:
224-096-0
Número MDL:
MFCD00064547
Código UNSPSC:
12352200
ID de substância PubChem:
24278657
NACRES:
NA.77

Nível de qualidade

200

Ensaio

≥98% (TLC)

Formulário

powder

atividade óptica

[α]25/D −25.5°, c = 1.0 in ethanol(lit.)

pf

193-195 °C (lit.)

solubilidade

ethanol: 10 mg/mL
DMSO: <14.5 mg/mL
H2O: 50 mg/mL
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 8.0 mg/mL

originador

AstraZeneca

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

Cl[H].CC(C)NC[C@H](O)COc1cccc2ccccc12

InChI

1S/C16H21NO2.ClH/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16;/h3-9,12,14,17-18H,10-11H2,1-2H3;1H/t14-;/m0./s1

chave InChI

ZMRUPTIKESYGQW-UQKRIMTDSA-N

Informações sobre genes

human ... ADRB1(153) , ADRB2(154) , ADRB3(155) , HTR1A(3350) , HTR1B(3351) , HTR1D(3352) , HTR1E(3354) , HTR1F(3355)

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Descrição geral

With heat. Aqueous solutions are most stable at pH 3.0 and decompose rapidly at basic pH. Decomposition is accompanied by discoloration of the solution.

Aplicação

(S)-(−)-Propranolol hydrochloride has been used:
  • as a non-selective β-blocker propranolol to inhibit the actions of epinephrine in mice
  • as a β1- and β2-aadrenergic receptor blocker in rat
  • as a medium supplement to investigate its effect on adipogenesis in hemangioma-derived stem cells (HemSC)

Ações bioquímicas/fisiológicas

(S)-(−)-Propranolol hydrochloride is biologically active enantiomer. It acts as β1 receptor antagonist in thalamocortical neurons. (S)-(−)-Propranolol hydrochloride elicits its inhibitory function on the β1 adrenoceptor in trigeminovascular pain pathway and serves as a preventive medicine in migraine.
Active β-adrenoceptor blocking enantiomer, as measured by inhibition of isoprenaline-induced tachycardia; Propranolol is also non-specific 5-HT1A, 5-HT1B and 5-HT1C serotonin receptor antagonist. The stereoselective association of mianserin and propranolol with the 5HT1A, 5HT1B and 5HT1C sites may prove useful in the characterization of these sites

Características e benefícios

This compound is featured on the β-Adrenoceptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H302 + H312 + H332

Classificações de perigo

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Código de classe de armazenamento

11 - Combustible Solids

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, Gloves

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Certificados de análise (COA)

Lot/Batch Number
029M4082V
059M4184V
13190131
087M4043V
13170126

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Rizaldy C Zapata et al.
The Journal of nutritional biochemistry, 65, 115-127 (2019-01-28)
Moderate dietary protein restriction promotes hyperphagia and thermogenesis; however, little is known of whether these responses are due to restriction of the essential amino acids tryptophan and histidine. Here, we determined whether restriction of tryptophan and histidine alone recapitulate the
Insulin-like growth factor 2 promotes the adipogenesis of hemangioma-derived stem cells
Zhang K, et al.
Experimental and Therapeutic Medicine, 17(3), 1663-1669 (2019)
Yee Yin Ho et al.
Food & function, 8(6), 2110-2114 (2017-05-18)
We found that intraduodenal administration of l-ornithine (l-Orn) stimulates growth hormone (GH) secretion in Wistar rats, and then investigated its mechanism. GH-releasing activity after intraduodenal administration of l-Orn was blocked by [d-Lys
Dietary Tryptophan Restriction Dose-Dependently Modulates Energy Balance, Gut Hormones, and Microbiota in Obesity-Prone Rats
Zapata RC, et al.
Obesity (Silver Spring, Md.), 26(4), 730-739 (2018)
Matthew J Shepard et al.
Journal of neurosurgery, 1-9 (2018-12-01)
OBJECTIVEVon Hippel-Lindau disease (VHL) is a tumor predisposition syndrome characterized by CNS hemangioblastomas (HBs) and clear cell renal cell carcinomas (RCCs) due to hypoxia-inducible factor activation (pseudohypoxia). Because of the lack of effective medical therapies for VHL, HBs and RCCs
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