(-)-norephedrine

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Names

[ CAS No. ]:
492-41-1

[ Name ]:
(-)-norephedrine

[Synonym ]:
Benzenemethanol, α-[(1S)-1-aminoethyl]-, (αR)-
(-)-Norephedrin
MFCD00066044
(1S,2R)-H2NCH(Me)CH(OH)Ph
l-Norephedrine
(-)-Phenylpropanolamine
(-)-erythro-2-Amino-2-methyl-1-phenylethanol
(1R,2S)-2-amino-1-phenyl-propan-1-ol
(1R,2S)-(-)-norephedrine
(1R,2S)-2-Amino-1-phenyl-1-propanol
(aR)-a-[(1S)-1-Aminoethyl]benzenemethanol
USAF CS-6
l-Phenylpropanolamine
L-ERYTHRO-(1R,2S)-2-AMINO-1-PHENYLPROPAN-1-OL
Mydriatin
EINECS 207-755-7
(R,S)-(-)-Norephedrine
(-)-norephedrine
(1R,2S)-2-amino-1-phenylpropan-1-ol
[R-(R*,S*)]-a-(1-Aminoethyl)benzenemethanol

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
288.1±20.0 °C at 760 mmHg

[ Melting Point ]:
51-53 °C(lit.)

[ Molecular Formula ]:
C9H13NO

[ Molecular Weight ]:
151.206

[ Flash Point ]:
128.1±21.8 °C

[ Exact Mass ]:
151.099716

[ PSA ]:
46.25000

[ LogP ]:
0.81

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.558

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RC2275000
CHEMICAL NAME :
Norephedrine, (-)-
CAS REGISTRY NUMBER :
492-41-1
LAST UPDATED :
199707
DATA ITEMS CITED :
16
MOLECULAR FORMULA :
C9-H13-N-O
MOLECULAR WEIGHT :
151.23
WISWESSER LINE NOTATION :
ZY1&YQR -L

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
45 mg/kg/30D-I
TOXIC EFFECTS :
Cardiac - cardiomyopathy including infarction Cardiac - EKG changes not diagnostic of specified effects Vascular - BP elevation not characterized in autonomic section
REFERENCE :
AEMED3 Annals of Emergency Medicine. (American College of Emergency Physicians, 1125 Executive Circle, Irving, TX 75038) Volume(issue)/page/year: 28,359,1996
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
1071 ug/kg/1D-I
TOXIC EFFECTS :
Behavioral - wakefulness Behavioral - euphoria Behavioral - toxic psychosis
REFERENCE :
HETOEA Human & Experimental Toxicology. (Macmillan Press Ltd., Brunel Road, Houndmills, Basingstoke, Hampshire, RG21 2XS, UK) V.9- 1990- Volume(issue)/page/year: 11,295,1992
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
2500 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - headache
REFERENCE :
AJDCAI American Journal of Diseases of Children. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1-80(3), 1911-50; V.100- 1960- Volume(issue)/page/year: 138,683,1984
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
8 mg/kg
TOXIC EFFECTS :
Behavioral - sleep Cardiac - pulse rate increase, without fall in BP Lungs, Thorax, or Respiration - chronic pulmonary edema
REFERENCE :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 289,591,1984
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
714 ug/kg
TOXIC EFFECTS :
Vascular - BP elevation not characterized in autonomic section
REFERENCE :
LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 1,60,1980
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
500 ug/kg
TOXIC EFFECTS :
Behavioral - headache
REFERENCE :
NEURAI Neurology. (Modern Medicine Pub., Inc., 1 E. First St., Duluth, MN 55802) V.1- 1951- Volume(issue)/page/year: 36,593,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1538 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 109,132,1970
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
60 mg/kg
TOXIC EFFECTS :
Behavioral - excitement
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 22,138,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1060 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 109,132,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: AD277-689
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
124 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. (Bethesda, MD) V.1-46, 1942-87. Volume(issue)/page/year: 4,139,1945
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
114 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CLDND* Compilation of LD50 Values of New Drugs. (J.R. MacDougal, Dept. of National Health and Welfare, Food and Drug Divisions, 35 John St., Ottawa, Ont., Canada)
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
700 mg/kg
TOXIC EFFECTS :
Autonomic Nervous System - sympathomimetic
REFERENCE :
AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 153,161,1930
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
75 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 36,363,1929 *** REVIEWS *** TOXICOLOGY REVIEW CHREAY Chemical Reviews. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1924- Volume(issue)/page/year: 9,389,1931

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22;R36/37/38

[ Safety Phrases ]:
S26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
RC2275000

[ HS Code ]:
2939440000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • (1R,2S)-1-phenyl-2-[((1R)-phenylethyl)amino]-1-propanol
  • (R)-1-hydroxy-1-phenyl-acetone oxime
  • Nitroethane
  • Benzaldehyde
  • L-erythro-(1R,2S)-2-(N-benzylamino)-1-phenylpropan-1-ol
  • (R)-1-Hydroxy-1-Phenylacetone
  • Benzylamine
  • (S,Z)-N-((1S,4R)-1-((N,N-dicyclohexylsulfamoyl)methyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-ylidene)-1-oxo-1-phenylpropan-2-amine oxide

DownStream

  • 1R,2S-(-)-Norephedrine hydrochloride
  • Cathine
  • (S)-(+)-1-DIMETHYLAMINO-2-PROPANOL
  • (S)-2-AMINO-5-METHOXYTETRALINHYDROCHLORIDE
  • (1R,2S)-2-[N-Benzyl-N-(mesitylenesulfonyl)amino]-1-phenyl-1-propanol
  • 2,6-DIHYDROXYBENZAMIDE
  • (R)-4-PHENYLBUTAN-2-AMINE
  • 2-(4-Methylphenyl)-1-phenylethanamine
  • L-(-)-Ephedrine
  • PROPIONIC ACID (1R,2S)-2-[N-BENZYL-N-(MESITYLENESULFONYL)AMINO]-1-PHENYLPROPYL ESTER

Customs

[ HS Code ]: 2939440000

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Related Compounds

  • 1R,2S-(-)-Norephedrine hydrochloride
  • DL-Norephedrine hydrochloride
  • rac-Norephedrine hydrochloride
  • D-(+)-Norephedrine hydrochloride
  • n-diethyl norephedrine
  • (1S,2R)-(+)-Norephedrine
  • 4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
  • methyl 3-[(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)methyl]benzoate
  • 1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
  • 2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
  • 2-Methoxy-5-(tributylstannyl)pyrazine
  • 1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
  • (4-Methyl-tetrahydro-furan-2-yl)-methanol
  • N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
  • 4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
  • tert-Butyl-DL-alanine