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Substance Name: Octopamine [INN]
RN: 104-14-3
UNII: 14O50WS8JD
InChIKey: QHGUCRYDKWKLMG-UHFFFAOYSA-N

Note

  • An alpha-adrenergic sympathomimetic amine, biosynthesized from tyramine in the CNS and platelets and also in invertebrate nervous systems. It is used to treat hypotension and as a cardiotonic. The natural D(-) form is more potent than the L(+) form in producing cardiovascular adrenergic responses. It is also a neurotransmitter in some invertebrates.

Molecular Formula

  • C8-H11-N-O2

Molecular Weight

  • 153.1799
 

Classification Codes

  • Adrenergic Agents
  • Adrenergic Agonists
  • Adrenergic alpha-Agonists
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Neurotransmitter Agents
  • Vasoconstrictor Agents
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Names and Synonyms

Name of Substance

  • Octopamine
  • Octopamine [INN]

MeSH Heading

  • Octopamine

Synonyms

  • 1-(p-Hydroxyphenyl)-2-aminoethanol
  • 4-13-00-02656 (Beilstein Handbook Reference)
  • alpha-(Aminoethyl)-4-hydroxybenzenemethanol
  • alpha-(Aminoethyl)-p-hydroxybenzyl alcohol
  • alpha-(Aminomethyl)-p-hydroxybenzyl alcohol
  • alpha-Aminoethyl-4-hydroxybenzylalkohol
  • Analet
  • Benzenemethanol, alpha-(aminomethyl)-4-hydroxy-
  • BRN 1211019
  • EINECS 203-179-5
  • ND 50
  • Norden
  • Norfen
  • Norphen
  • Norsympathol
  • Norsympatol
  • Norsynephrine
  • Octapamine
  • Octopamina
  • Octopamina [INN-Spanish]
  • Octopamina [Spanish]
  • Octopamine
  • Octopaminum
  • Octopaminum [INN-Latin]
  • Octopaminum [Latin]
  • p-Hydroxyphenylethanolamine
  • p-Norsynephrin
  • Paraoxyphenyl aminoethanol
  • UNII-14O50WS8JD
  • WIN 5512
  • WV 569

Systematic Names

  • alpha-(Aminomethyl)-p-hydroxybenzyl alcohol
  • Benzenemethanol, alpha-(aminomethyl)-4-hydroxy-
  • Benzyl alcohol, alpha-(aminomethyl)-p-hydroxy-
  • Octopamine

Registry Numbers

CAS Registry Number

  • 104-14-3

FDA UNII

  • 14O50WS8JD

System Generated Number

  • 0000104143

Structure Descriptors

InChI

1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2

InChIKey

QHGUCRYDKWKLMG-UHFFFAOYSA-N

Smiles

c1(ccc(O)cc1)[C@@H](CN)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LDLo intravenous 200mg/kg (200mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 101, Pg. 81, 1955.
mouse LD50 intracrebral 2100mg/kg (2100mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64(4), Pg. 140S, 1968.
mouse LD50 intraperitoneal 600mg/kg (600mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 106, Pg. 341, 1952.
mouse LD50 intravenous 75mg/kg (75mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 106, Pg. 341, 1952.
mouse LD50 oral 4200mg/kg (4200mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64(4), Pg. 140S, 1968.
mouse LD50 subcutaneous 2070mg/kg (2070mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64(4), Pg. 140S, 1968.
rat LD50 intraperitoneal 1350mg/kg (1350mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64(4), Pg. 140S, 1968.
rat LD50 oral 1240mg/kg (1240mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64(4), Pg. 140S, 1968.
rat LD50 subcutaneous 350mg/kg (350mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64(4), Pg. 140S, 1968.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 8.81 (none)   EXP
log P (octanol-water) -0.9 (none)   EXP
Water Solubility 1.00E+06 mg/L 25 EST
Vapor Pressure 2.50E-05 mm Hg 25 EST
Henry's Law Constant 3.09E-15 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 8.04E-11 cm3/molecule-sec 25 EST

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