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L-(-)-Ephedrine

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Name

L-(-)-Ephedrine

EINECS 207-755-7
CAS No. 492-41-1 Density 1.071 g/cm3
PSA 46.25000 LogP 1.76750
Solubility N/A Melting Point 51-53 °C(lit.)
Formula C9H13NO Boiling Point 288.1 °C at 760 mmHg
Molecular Weight 151.208 Flash Point 128.1 °C
Transport Information N/A Appearance white powder
Safety 26 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 492-41-1 (L-(-)-Ephedrine) Hazard Symbols HarmfulXn
Synonyms

Benzenemethanol,a-(1-aminoethyl)-, [R-(R*,S*)]-;(-)-Norephedrin;(-)-Norephedrine;(-)-Phenylpropanolamine;(-)-erythro-2-Amino-2-methyl-1-phenylethanol;(1R,2S)-(-)-Norephedrine;(1R,2S)-2-Amino-1-phenyl-1-propanol;(1R,2S)-Norephedrine;(1S,2R)-2-Hydroxy-2-phenyl-1-methyl-1-aminoethane;(R,S)-(-)-Norephedrine;L-Norephedrine;NSC 17704;Norephedrine, (-)-;erythro-(1R,2S)-Norephedrine;

Article Data 44

L-(-)-Ephedrine Consensus Reports

Reported in EPA TSCA Inventory.

L-(-)-Ephedrine Specification

The L-(-)-Ephedrine is an organic compound with the formula C9H13NO. The IUPAC name of this chemical is (1R,2S)-2-amino-1-phenylpropan-1-ol. With the CAS registry number 492-41-1, it is also named as (-)-erythro-2-Amino-2-methyl-1-phenylethanol. The product's classification codes are Drug / Therapeutic Agent; Human Data. Besides, it is a white powder, which should be stored in dry and well-ventilated place at temperature of 2 - 8 °C.

Physical properties about L-(-)-Ephedrine are: (1)ACD/LogP: 0.81; (2)ACD/LogD (pH 5.5): -2.21; (3)ACD/LogD (pH 7.4): -1.07; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 2; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 12.47 Å2; (12)Index of Refraction: 1.557; (13)Molar Refractivity: 45.46 cm3; (14)Molar Volume: 141 cm3; (15)Polarizability: 18.02×10-24cm3; (16)Surface Tension: 45 dyne/cm; (17)Density: 1.071 g/cm3; (18)Flash Point: 128.1 °C; (19)Enthalpy of Vaporization: 55.7 kJ/mol; (20)Boiling Point: 288.1 °C at 760 mmHg; (21)Vapour Pressure: 0.0011 mmHg at 25°C.

Uses of L-(-)-Ephedrine: it can be used to produce (4R,5S)-(+)-4-methyl-5-phenyloxazolidin-2-one by heating. It will need reagent potassium carbonate and solvent toluene with reaction temperature of 130 °C. The yield is about 80%.

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: O[C@H](c1ccccc1)[C@@H](N)C
(2)InChI: InChI=1/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s1
(3)InChIKey: DLNKOYKMWOXYQA-CBAPKCEABA
(4)Std. InChI: InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s1
(5)Std. InChIKey: DLNKOYKMWOXYQA-CBAPKCEASA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 2500ug/kg (2.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: HEADACHE
American Journal of Diseases of Children. Vol. 138, Pg. 683, 1984.
human TDLo oral 714ug/kg (0.714mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION Lancet. Vol. 1, Pg. 60, 1980.
man TDLo oral 1071ug/kg/1D- (1.071mg/kg) BEHAVIORAL: WAKEFULNESS

BEHAVIORAL: EUPHORIA

BEHAVIORAL: TOXIC PSYCHOSIS
Human & Experimental Toxicology. Vol. 11, Pg. 295, 1992.
mouse LD50 intraperitoneal 200mg/kg (200mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 oral 1060mg/kg (1060mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Bollettino Chimico Farmaceutico. Vol. 109, Pg. 132, 1970.
mouse LD50 subcutaneous 124mg/kg (124mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 4, Pg. 139, 1945.
mouse LDLo intravenous 114mg/kg (114mg/kg)   Compilation of LD50 Values of New Drugs.
mouse LDLo unreported 700mg/kg (700mg/kg) AUTONOMIC NERVOUS SYSTEM: SYMPATHOMIMETIC Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 153, Pg. 161, 1930.
rabbit LDLo intravenous 75mg/kg (75mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 36, Pg. 363, 1929.
rat LD50 oral 1538mg/kg (1538mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Bollettino Chimico Farmaceutico. Vol. 109, Pg. 132, 1970.
rat LDLo intraperitoneal 60mg/kg (60mg/kg) BEHAVIORAL: EXCITEMENT Toxicology and Applied Pharmacology. Vol. 22, Pg. 138, 1972.
women LDLo oral 8mg/kg (8mg/kg) BEHAVIORAL: SLEEP

LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
British Medical Journal. Vol. 289, Pg. 591, 1984.
women TDLo oral 500ug/kg (0.5mg/kg) BEHAVIORAL: HEADACHE Neurology. Vol. 36, Pg. 593, 1986.
women TDLo oral 45mg/kg/30D-I (45mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION
Annals of Emergency Medicine. Vol. 28, Pg. 359, 1996.

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