P8688
Sigma

(S)-(−)-Propranolol hydrochloride

≥98% (TLC), powder

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Synonym

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

Molecular Formula

C₁₀H₇OCH₂CH(OH)CH₂NHCH(CH₃)₂�HCl

Molecular Weight

295.80

CAS Number

4199-10-4

Beilstein Registry Number

3574966

MDL number

MFCD00064547

PubChem Substance ID

24278657

EG/EC Number

224-096-0

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Descriptions

Biochem/physiol Actions

Active β-adrenoceptor blocking enantiomer, as measured by inhibition of isoprenaline-induced tachycardia; Propranolol is also non-specific 5-HT_1A,5-HT_1Band 5-HT_1C serotonin receptor antagonist. The stereoselective association of mianserin and propranolol with the 5HT_1A, 5HT_1Band 5HT_1C sites may prove useful in the characterization of these sites

Properties

assay

≥98% (TLC)

form

powder

optical activity

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

193-195 °C(lit.)

solubility

ethanol: 10 mg/mL

DMSO: <14.5 mg/mL

H₂O: 50 mg/mL 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.

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 8.0 mg/mL

Gene Information

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

storage temp.

2-8°C

References

Reference

Lee, Y.H. and Ku, Y.S., Effects of cyclosporin on the pharmacokinetics of propranolol after intravenous and oral administration to control rats and to rats with uranyl nitrate-induced acute renal failure. J. Pharm. Pharmacol. 51, 1149-1154, (1999) abstract

Stoschitzky, K., et al., Stereoselective vascular effects of the (R)- and (S)-enantiomers of propranolol and atenolol. J. Cardiovasc. Pharmacol. 25, 268-272, (1995) abstract

Whitehurst, V.E., et al., Reversal of propranolol blockade of adrenergic receptors and related toxicity with drugs that increase cyclic AMP. Proc. Soc. Exp. Biol. Med. 221, 382-385, (1999) abstract

Chi, O.Z., et al., The effects of propranolol on heterogeneity of rat cerebral small vein oxygen saturation. Anesth. Analg. 89, 690-695, (1999) abstract

Goodwin, G.M., and Green, A.R., A behavioural and biochemical study in mice and rats of putative selective agonists and antagonists for 5-HT1 and 5-HT2 receptors. Br. J. Pharmacol. 84, 743-753, (1985) abstract

Alexander, B.S., and Wood, M.D., Stereoselective blockade of central [3H]5-hydroxytryptamine binding to multiple sites (5-HT1A, 5-HT1B and 5-HT1C) by mianserin and propranolol. J. Pharm. Pharmacol. 39, 664-666, (1987) abstract

reference

FT-IR 2 (2), 2203:D / FT-NMR 1 (2), 634:A / RegBook 1 (1), 1503:J / Structure Index 1, 235:B:6

Safety

Hazard Codes

Risk Statements

20/21/22

Safety Statements

WGK Germany