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Substance Name: Ephedrine [USAN:BAN]
RN: 299-42-3
UNII: GN83C131XS
InChIKey: KWGRBVOPPLSCSI-WPRPVWTQSA-N

Note

  • A phenethylamine found in EPHEDRA SINICA. PSEUDOEPHEDRINE is an isomer. It is an alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used for 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.

Molecular Formula

  • C10-H15-N-O

Molecular Weight

  • 165.2345
 

Classification Codes

  • Adrenergic Agents
  • Autonomic Agents
  • Bronchodilator
  • Cardiovascular Agents
  • Central Nervous System Agents
  • Central Nervous System Stimulants
  • Drug / Therapeutic Agent
  • Human Data
  • Natural Product
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sympathomimetics
  • Vasoconstrictor Agents

Names and Synonyms

Name of Substance

  • (L)-Ephedrine
  • Ephedrine
  • Ephedrine l-form
  • Ephedrine [USAN:BAN]

MeSH Heading

  • Ephedrine

Synonyms

  • (-)-alpha-(1-Methylaminoethyl)benzyl alcohol
  • (-)-Ephedrine
  • 1-2-Methylamino-1-phenylpropanol
  • 1-alpha-(1-Methylaminoethyl)benzyl alcohol
  • 1-Hydroxy-2-methylamino-1-phenylpropane
  • 1-Phenyl-1-hydroxy-2-methylaminopropane
  • 1-Phenyl-2-methylaminopropanol
  • 1-Sedrin
  • 2-Methylamino-1-phenyl-1-propanol
  • AI3-02761
  • alpha-(1-(Methylamino)ethyl)benzenemethanol
  • alpha-Hydroxy-beta-methyl amine propylbenzene
  • alpha-Hydroxy-beta-methylaminopropylbenzene
  • Benzenemethanol, alpha-(1-(methylamino)ethyl)-, (R-(R*,S*))-
  • Biophedrin
  • EC 206-080-5
  • Eciphin
  • Efedrin
  • EINECS 206-080-5
  • Ephedral
  • Ephedremal
  • Ephedrin
  • Ephedrine
  • Ephedrital
  • Ephedrol
  • Ephedrosan
  • Ephedrotal
  • Ephedsol
  • Ephendronal
  • Ephoxamin
  • Fedrin
  • HSDB 3072
  • i-Sedrin
  • Kratedyn
  • L(-)-Ephedrine
  • l-2-Methylamino-1-phenylpropanol
  • l-alpha-(1-Methylaminoethyl)benzyl alcohol
  • l-Ephedrine
  • Lexofedrin
  • Manadrin
  • Mandrin
  • Nasol
  • NCI-C55652
  • Norephedrine, N-methyl-
  • NSC 170951
  • NSC 8971
  • Sal-Phedrine
  • Sanedrine
  • UNII-GN83C131XS
  • Vencipon
  • Zephrol

Systematic Names

  • Benzenemethanol, alpha-((1S)-1-(methylamino)ethyl)-, (alphaR)-
  • Benzenemethanol, alpha-(1-(methylamino)ethyl)-, (-)-
  • Benzenemethanol, alpha-(1-(methylamino)ethyl)-, (R-(R*,S*))-
  • Ephedrine
  • Ephedrine, L-(-)-

Registry Numbers

CAS Registry Number

  • 299-42-3

FDA UNII

  • GN83C131XS

Other Registry Numbers

  • 321-96-0
  • 6912-63-6

System Generated Number

  • 0000299423

Structure Descriptors

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

Smiles

CN[C@@H](C)[C@H](O)c1ccccc1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 562mg/kg (562mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
cat LDLo intravenous 60mg/kg (60mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 120, Pg. 189, 1927.
dog LDLo intravenous 70mg/kg (70mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 120, Pg. 189, 1927.
frog LDLo parenteral 530mg/kg (530mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 120, Pg. 189, 1927.
guinea pig LD50 subcutaneous 420mg/kg (420mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 169, Pg. 114, 1933.
man LDLo unreported 9mg/kg (9mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LD50 intraperitoneal 350mg/kg (350mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Pharmaceutical Chemistry Journal Vol. 3, Pg. 203, 1969.
mouse LD50 intravenous 74mg/kg (74mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Acta Pharmacologica et Toxicologica. Vol. 38, Pg. 474, 1976.
mouse LD50 oral 689mg/kg (689mg/kg)   Japanese Journal of Toxicology. Vol. 4, Pg. 143, 1991.
mouse LD50 parenteral 170mg/kg (170mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 195, Pg. 647, 1940.
mouse LD50 subcutaneous 132mg/kg (132mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 3, Pg. 328, 1953.
mouse LDLo unreported 600mg/kg (600mg/kg) AUTONOMIC NERVOUS SYSTEM: SYMPATHOMIMETIC Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 153, Pg. 161, 1930.
rabbit LDLo intramuscular 340mg/kg (340mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

CARDIAC: OTHER CHANGES		 Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 120, Pg. 189, 1927.
rabbit LDLo intraperitoneal 310mg/kg (310mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 120, Pg. 189, 1927.
rabbit LDLo intravenous 50mg/kg (50mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

CARDIAC: OTHER CHANGES		 Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 120, Pg. 189, 1927.
rabbit LDLo oral 590mg/kg (590mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

CARDIAC: OTHER CHANGES		 Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 120, Pg. 189, 1927.
rabbit LDLo subcutaneous 320mg/kg (320mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 120, Pg. 189, 1927.
rat LD50 oral 600mg/kg (600mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 341, 1972.
rat LD50 subcutaneous 300mg/kg (300mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 68, Pg. 339, 1942.
rat LDLo intraperitoneal 150mg/kg (150mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 195, Pg. 647, 1940.
rat LDLo intravenous 130mg/kg (130mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 120, Pg. 189, 1927.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 34 deg C   EXP
Boiling Point 255 deg C   EXP
pKa Dissociation Constant 10.252 (none) 0 EXP
log P (octanol-water) 1.13 (none)   EXP
Water Solubility 6.36E+04 mg/L 30 EXP
Vapor Pressure 8.30E-04 mm Hg 25 EST
Henry's Law Constant 8.65E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 9.97E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.