(S)-(-)-Propranolol hydrochloride

Product Name(S)-(-)-Propranolol hydrochloride
CAS4199-10-4
MFC16H22ClNO2
MW295.8
EINECS224-096-0
MOL File4199-10-4.mol

Chemical Properties

Melting point	193-195 °C(lit.)
storage temp.	2-8°C
solubility	ethanol: 10 mg/mL
form	powder
color	White to off-white
optical activity	[α]25/D 25.5°, c = 1.0 in ethanol(lit.)
Water Solubility	Soluble to 100 mM in water
BRN	3574966
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
InChIKey	ZMRUPTIKESYGQW-UQKRIMTDSA-N
SMILES	Cl[H].CC(C)NC[C@H](O)COc1cccc2ccccc12
CAS DataBase Reference	4199-10-4(CAS DataBase Reference)

Safety Information

Hazard Codes	Xn
Risk Statements	20/21/22
Safety Statements	36
WGK Germany	3
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Dermal Acute Tox. 4 Inhalation Acute Tox. 4 Oral

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Description

(S)-(-)-Propranolol is the active enantiomer of propranolol, a β-adrenergic receptor antagonist with log K_d values of -8.16, -9.08, and -6.93 for β₁, β₂, and β₃, respectively. It is also a non-specific serotonin receptor antagonist. Propanolol was one of the first β-adrenergic receptor blockers to be widely used in clinical practice for the treatment of hypertension, angina pectoris, and cardiac ischemia.

Chemical Properties

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

Uses

Antihypertensor;Beta-adrenergic blocking agent

Uses

active enantiomer, 5-HT1 receptor antagonist

Uses

The S-enantiomer of Propranolol (P831800). βAdrenergic blocker. Antihypertensive; antianginal; antiarrhythmic (class II).

Biological Activity

More active enantiomer of the β -adrenoceptor antagonist propranolol ((RS)-1-[(1-Methylethyl)amino]-3-(1-naphthalenyloxy)-2-propanol hydrochloride ).

Biochem/physiol Actions

(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.

storage

Store at RT

Purification Methods

The (+)-salt is the active isomer which blocks isoprenaline tachycardia and is a -adrenergic blocker. [Leclerc et al. Trends Pharmacol Sci 2 18 1981, Howe & Shanks Nature 210 1336 1966.]

References

[1] D W COSTAIN A R G. beta-Adrenoceptor antagonists inhibit the behavioural responses of rats to increased brain 5-hydroxytryptamine.[J]. British Journal of Pharmacology, 1978, 64 2: 193-200. DOI: 10.1111/j.1476-5381.1978.tb17289.x

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