(1R,2S)-2-(methylamino)-1-phenylpropan-1-ol

• ChemBase ID: 1189
• Molecular Formular: C10H15NO
• Molecular Mass: 165.2322
• Monoisotopic Mass: 165.11536411
• SMILES: O[C@@H]([C@@H](NC)C)c1ccccc1
• Canonical SMILES: CN[C@H]([C@@H](c1ccccc1)O)C
• InChI: InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1
• InChIKey: KWGRBVOPPLSCSI-WPRPVWTQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S)-2-(methylamino)-1-phenylpropan-1-ol
• IUPAC Traditional name: ephedrine
• Synonyms: (1R,2S)-2-Methylamino-1-phenyl-1-propanol; (-)-Ephedrine; (1R,2S)-(-)-Ephedrine Sulfate; (αR)-,α-[(1S)-1-(Methylamino)ethyl]benzenemethanol Hemisulfate; (-)-erythro-1-Hydroxy-2-(methylamino)-1-phenylpropane Sulfate; (-)-Ephedrine Sulfate; (1R,2S)-1-Phenyl-2-methylaminopropanol-1 Sulfate; Ephedrine Sulphate; Isofedrol; l-Ephedrine Sulfate; (-)-erythro-Ephedrine Sulfate; Ephedrine; (-)-Ephedrine; (1R,2S)-(-)-α-(1-Methylaminoethyl)benzyl alcohol; (1R,2S)-(-)-2-Methylamino-1-phenyl-1-propanol; L-α-(1-Methylaminoethyl)benzyl alcohol; (1R,2S)-(-)-Ephedrine; (1R,2S)-2-甲氨基-苯丙烷-1-醇; (-)-麻黄碱; (-)-麻黄碱; (1R,2S)-(-)-α-(1-甲基氨基乙基)苄醇; (1R,2S)-(-)-2-甲氨基-1-苯丙醇; L-盐酸麻黄碱; (1R,2S)-(-)-麻黄碱

Database IDs

• CAS Number: 299-42-3; 134-72-5
• EC Number: 206-080-5
• MDL Number: MFCD00064257
• Beilstein Number: 2208730
• PubChem SID: 46507538; 24848190; 160964651; 24868714
• PubChem CID: 9294; 5032
• CHEBI ID: 15407
• ATC CODE: R01AB05; R03CA02; C01CA26; QG04BX90; R01AA03; S01FB02
• CHEMBL: 211456
• Chemspider ID: 8935
• DrugBank ID: DB01364
• IUPHAR ligand ID: 556
• KEGG ID: D00124
• Unique Ingredient Identifier: GN83C131XS
• Wikipedia Title: Ephedrine

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.889531
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.8580045
• LogD (pH = 7.4): -0.7786886
• Log P: 1.3178347
• Molar Refractivity: 49.6873 cm^3
• Polarizability: 19.85273 Å^3
• Polar Surface Area: 32.26 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.0
• LOG S: -1.3
• Solubility (Water): 8.26e+00 g/l

PROPERTIES

Physical Property

• Solubility: 63.6 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• Melting Point: ~36 °C; 37-39 °C(lit.)
• Boiling Point: 255 °C(lit.)
• Flash Point: 186.8 °F; 86 °C
• Density: 1.124 g/mL at 25 °C(lit.)
• Optical Rotation: [α]20/D -42±1°, c = 4.5% in 2% HCl; [α]21/D -41°, c = 5 in 1 M HCl
• Hydrophobicity(logP): 1.13 [AVDEEF,A (1997)]

Safety Information

• RTECS: KB0700000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22
• Safety Statements: 22-25
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: oral, IV, IM, SC
• Bioavailability: 85%
• Excretion: 22-99% renal
• Half Life: 3–6 hours
• Metabolism: minimal hepatic
• Legal Status: Behind the Counter (BTC) (US); P (UK); S4 (Australia); Schedule VI (Canada)
• Pregnancy Category: A (Australia); A (US)

Product Information

• Purity: ≥98.0% (NT); 98%
• Grade: purum
• Impurities: ≤0.5% water
• Linear Formula: C6H5CH[CH(NHCH3)CH3]OH
• Empirical Formula (Hill Notation): C10H15NO

DETAILS

DrugBank - DB01364

• Drug Groups: approved
• Description: An alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used in the treatment of several disorders including asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists. [PubChem]
• Indication: Ephedrine commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia.
• Pharmacology: Ephedrine is similar in structure to the derivatives amphetamine and methamphetamine. Chemically, it is an alkaloid derived from various plants in the genus Ephedra (family Ephedraceae). It works mainly by increasing the activity of noradrenaline on adrenergic receptors.
• Toxicity: Cardiovascular: tachycardia, cardiac arrhythmias, angina pectoris, vasoconstriction with hypertension
• Absorption: 85%
• Half Life: 3-6 hours
• Elimination: mainly renal
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - 134910

Packaging
5, 25, 100 g in glass bottle
Application
Versatile chiral synthon,1 employed in catalysis2 and in the preparation of optically pure sulfoxides3 and oxazolidines.4

Sigma Aldrich - 45261

Other Notes
Sales restrictions may apply

Toronto Research Chemicals - E575010

(-)-erythro-Ephedrine Sulfate is the sulfate salt of the α- and β-adrenergic agonist Ephedrine. (-)-erythro-Ephedrine is a sympathomimetic amine with stimulant properties. (-)-erythro-Ephedrine Sulfate is a bronchodilator used in the treatment of asthma.

REFERENCES

• Familiar, R.G. et al.: J. Pharmac. Sci, 56, 768 (1967)
• Weinberger, M. et al.: J. Pediat., 84, 421 (1967)
• Vidrio, H. et al.: J. Pharmacol. Exp. Therap., 187, 308 (1967)