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4199-10-4 molecular structure
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[(2S)-2-hydroxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)amine hydrochloride

ChemBase ID: 133757
Molecular Formular: C16H22ClNO2
Molecular Mass: 295.80438
Monoisotopic Mass: 295.13390663
SMILES and InChIs

SMILES:
CC(C)NC[C@@H](COc1cccc2c1cccc2)O.Cl
Canonical SMILES:
O[C@H](COc1cccc2c1cccc2)CNC(C)C.Cl
InChI:
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

Cite this record

CBID:133757 http://www.chembase.cn/molecule-133757.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
[(2S)-2-hydroxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)amine hydrochloride
IUPAC Traditional name
[(2S)-2-hydroxy-3-(naphthalen-1-yloxy)propyl](isopropyl)amine hydrochloride
Synonyms
(S)-1-Isopropylamino-3-(1-naphthyloxy)-2-propanol hydrochloride
(S)-(-)-Propranolol hydrochloride
(2S)-1-[(1-Methylethyl)amino]-3-(1-naphthalenyloxy)-2-propanol Hydrochloride
S-(-)-1-Isopropylamino-3-(1-naphthoxy)-2-propanol Hydrochloride
(-)-Propranolol Hydrochloride
(S)-(-)-Propranolol Hydrochloride
L-(-)-Propranolol Hydrochloride
l-Propranolol Chlorhydrate
l-Propranolol Hydrochloride
(S)-Propranolol Hydrochloride
(S)-1-异丙基氨基-3-(1-萘氧基)-2-丙醇 盐酸盐
(S)-(-)-普奈洛尔 盐酸盐
CAS Number
4199-10-4
EC Number
224-096-0
MDL Number
MFCD00064547
Beilstein Number
3574966
PubChem SID
24278657
24887925
162228034
PubChem CID
165193

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 165193 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 14.08793  H Acceptors
H Donor LogD (pH = 5.5) -0.6095358 
LogD (pH = 7.4) 0.3584574  Log P 2.583696 
Molar Refractivity 76.8257 cm3 Polarizability 31.766071 Å3
Polar Surface Area 41.49 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble8.0 mg/mL expand Show data source
DMSO: <14.5 mg/mL expand Show data source
ethanol: soluble10 mg/mL expand Show data source
H2O: soluble50 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.) expand Show data source
Apperance
powder expand Show data source
Melting Point
193-195 °C(lit.) expand Show data source
193-197 °C expand Show data source
Optical Rotation
[α]20/D -25±2°, c = 1% in ethanol expand Show data source
[α]20/D -26°, c = 1 in ethanol expand Show data source
[α]25/D -25.5°, c = 1.0 in ethanol(lit.) expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
20/21/22 expand Show data source
Safety Statements
36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H312-H332 expand Show data source
GHS Precautionary statements
P280 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Gene Information
human ... ADRB1(153), ADRB2(154), ADRB3(155), HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355) expand Show data source
Purity
≥98% (TLC) expand Show data source
≥99.0% (AT) expand Show data source
98% expand Show data source
Grade
puriss. expand Show data source
Optical Purity
enantiomeric ratio: ≥99:1 (HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Linear Formula
C10H7OCH2CH(OH)CH2NHCH(CH3)2·HCl expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - P8688 external link
包装
100, 500 mg in glass bottle
Biochem/physiol Actions
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
Sigma Aldrich - 82066 external link
Other Notes
β-adrenergic blocker1
Toronto Research Chemicals - P831795 external link
The S-enantiomer of Propranolol (P831800). β-Adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic (class II).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Bond, et al.: Nature, 213, 721 (1967)
  • • Hansteen, V., et al.: Br. Med. J., 284, 155 (1967)
  • • Diamond, S., et al.: J. Clin. Pharmacol., 28, 193 (1967)
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PATENTS

PATENTS

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INTERNET

INTERNET

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