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Pseudoephedrine

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Name

Pseudoephedrine

EINECS 202-018-6
CAS No. 90-82-4 Density 1.015 g/cm3
PSA N/A LogP N/A
Solubility <0.5g/L(er) Melting Point 118-120 °C
Formula C10H15NO Boiling Point 255 °C at 760 mmHg
Molecular Weight 165.235 Flash Point 85.6 °C
Transport Information N/A Appearance white crystals
Safety 26-37/39 Risk Codes 20/21/22-36/37/38
Molecular Structure Molecular Structure of 90-82-4 (Pseudoephedrine) Hazard Symbols HarmfulXn
Synonyms

Benzenemethanol, α-[(1S)-1-(methylamino)ethyl]-, (αS)-;Pseudoephedrine, (+)- (8CI);(+)-(1S,2S)-Pseudoephedrine;(+)-Pseudoephedrine;(1S,2S)-(+)-Pseudoephedrine;(1S,2S)-Pseudoephedrine;L-(+)-Pseudoephedrine;Lopac E 3250;trans-Ephedrine;y-Ephedrine, (+)-;

Article Data 75

Pseudoephedrine Consensus Reports

Reported in EPA TSCA Inventory.

Pseudoephedrine Specification

The Pseudoephedrine, with the CAS registry number 90-82-4, is also known as Benzenemethanol, α-[(1S)-1-(methylamino)ethyl]-, (αS)-. It belongs to the product categories of Aromatics; Heterocycles; Intermediates & Fine Chemicals; Isotope Labelled Compounds; Pharmaceuticals; Sulfur & Selenium Compounds. Its EINECS number is 202-018-6. This chemical's molecular formula is C10H15NO and molecular weight is 165.23. What's more, its systematic name is (1S,2S)-2-(methylamino)-1-phenylpropan-1-ol. Its classification codes are: (1)Anti-Asthmatic Agents; (2)Autonomic Agents; (3)Bronchodilator Agents; (4)Cardiovascular Agents; (5)Drug / Therapeutic Agent; (6)Human Data; (7)Nasal Decongestants; (8)Peripheral Nervous System Agents; (9)Respiratory System Agents; (10)Vasoconstrictor Agents. It is stable at common pressure and temperature, and it should be sealed and stored in a cool and dry place. Moreover, it should be protected from light. It is a phenethylamine that is an isomer of ephedrine which has less central nervous system effects and usage is mainly for respiratory tract decongestion. It is also used in biochemical research.

Physical properties of Pseudoephedrine are: (1)ACD/LogP: 1.05; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.99; (4)ACD/LogD (pH 7.4): -0.96; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 12.47 Å2; (13)Index of Refraction: 1.528; (14)Molar Refractivity: 50.15 cm3; (15)Molar Volume: 162.7 cm3; (16)Polarizability: 19.88×10-24cm3; (17)Surface Tension: 38 dyne/cm; (18)Density: 1.015 g/cm3; (19)Flash Point: 85.6 °C; (20)Enthalpy of Vaporization: 52.03 kJ/mol; (21)Boiling Point: 255 °C at 760 mmHg; (22)Vapour Pressure: 0.00865 mmHg at 25°C.

Preparation: this chemical can be prepared by  (1S,2S)-N,N-Dimethyl-N'-[(2-hydroxy-2-phenyl)-1-methylethyl]-harnstoff at the temperature of 55 °C. This reaction will need reagent LiAlH4 and solvent diethyl ether with the reaction time of 2 hours. The yield is about 90%.

Pseudoephedrine can be prepared by  (1S,2S)-N,N-Dimethyl-N'-[(2-hydroxy-2-phenyl)-1-methylethyl]-harnstoff at the temperature of 55 °C

Uses of Pseudoephedrine: it can be used to produce 2-(3,4-dimethyl-5-phenyl-oxazolidin-2-yl)-phenol at the temperature of 50 °C. It will need reagent MgSO4 and solvent methanol with the reaction time of 1 hour. The yield is about 82%.

Pseudoephedrine can be used to produce 2-(3,4-dimethyl-5-phenyl-oxazolidin-2-yl)-phenol at the temperature of 50 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing and gloves.

You can still convert the following datas into molecular structure:
(1)SMILES: O[C@@H](c1ccccc1)[C@@H](NC)C
(2)Std. 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
(3)Std. InChIKey: KWGRBVOPPLSCSI-WCBMZHEXSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 20mg/kg/12H-I (20mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" American Journal of Emergency Medicine. Vol. 15, Pg. 521, 1997.
dog LDLo intravenous 125mg/kg (125mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 225, 1973.
man TDLo oral 12mg/kg (12mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER
American Journal of Emergency Medicine. Vol. 4, Pg. 141, 1986.
man TDLo oral 64mg/kg (64mg/kg) BEHAVIORAL: TREMOR

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION
Journal of Toxicology, Clinical Toxicology. Vol. 30, Pg. 109, 1992.
mouse LD50 intravenous 88mg/kg (88mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Pharmacology and Experimental Therapeutics. Vol. 148, Pg. 158, 1965.
mouse LD50 oral 500mg/kg (500mg/kg)   Journal of Pharmaceutical Sciences. Vol. 60, Pg. 1523, 1971.
rabbit LDLo intravenous 85mg/kg (85mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 225, 1973.
rabbit LDLo subcutaneous 400mg/kg (400mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 225, 1973.
rat LD50 oral 660mg/kg (660mg/kg)   Journal of Pharmaceutical Sciences. Vol. 60, Pg. 1523, 1971.
rat LDLo subcutaneous 650mg/kg (650mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 225, 1973.