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Substance Name: Tyramine
RN: 51-67-2
UNII: X8ZC7V0OX3
InChIKey: DZGWFCGJZKJUFP-UHFFFAOYSA-N

Note

  • An indirect sympathomimetic that occurs naturally in cheese and other foods. Tyramine does not directly activate adrenergic receptors, but it can serve as a substrate for adrenergic uptake systems and MONOAMINE OXIDASE to prolong the actions of adrenergic transmitters. It also provokes transmitter release from adrenergic terminals and may be a neurotransmitter in some invertebrate nervous systems.

Molecular Formula

  • C8-H11-N-O

Molecular Weight

  • 137.1809
 

Classification Codes

  • Adrenergic Agents
  • Adrenergic Uptake Inhibitors
  • Autonomic Agents
  • Drug / Therapeutic Agent
  • Membrane Transport Modulators
  • Mutation Data
  • Neurotransmitter Agents
  • Neurotransmitter Uptake Inhibitors
  • Peripheral Nervous System Agents
  • Sympathomimetics
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Names and Synonyms

Name of Substance

  • Tyramine

MeSH Heading

  • Tyramine

Synonyms

  • 2-(4-Hydroxyphenyl)ethylamine
  • 2-(p-Hydroxyphenyl)ethylamine
  • 4-(2-Aminoethyl)phenol
  • 4-13-00-01788 (Beilstein Handbook Reference)
  • 4-Hydroxyphenethylamine
  • 4-Hydroxyphenylethylamine
  • alpha-(4-Hydroxyphenyl)-beta-aminoethane
  • Benzeneethanamine, 4-hydroxy-
  • beta-Hydroxyphenylethylamine
  • BRN 1099914
  • EINECS 200-115-8
  • HSDB 2132
  • NSC 249188
  • p-(2-Aminoethyl)phenol
  • p-beta-Aminoethylphenol
  • p-Hydroxyphenethylamine
  • p-Hydroxyphenylethylamine
  • p-Tyramine
  • Phenethylamine, p-hydroxy-
  • Systogene
  • Tenosin-wirkstoff
  • Tocosine
  • Tyramin
  • Tyramine
  • Tyrosamine
  • UNII-X8ZC7V0OX3
  • Uteramine

Systematic Names

  • 4-(2-Aminoethyl)phenol
  • Phenol, 4-(2-aminoethyl)-
  • Phenol, p-(2-aminoethyl)-

Registry Numbers

CAS Registry Number

  • 51-67-2

FDA UNII

  • X8ZC7V0OX3

System Generated Number

  • 0000051672

Structure Descriptors

InChI

1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2

InChIKey

DZGWFCGJZKJUFP-UHFFFAOYSA-N

Smiles

NCCc1ccc(O)cc1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo subcutaneous 30mg/kg (30mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1412, 1935.
mouse LD50 intracervical 30mg/kg (30mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)		 Tohoku Yakka Daigaku Kenkyu Nempo. Annual Report of the Tohoku College of Pharmacy. Vol. 27, Pg. 131, 1980.
mouse LD50 intravenous 229mg/kg (229mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Acta Pharmacologica et Toxicologica. Vol. 38, Pg. 474, 1976.
mouse LDLo intraperitoneal 800mg/kg (800mg/kg)   Journal of Physiology. Vol. 76, Pg. 224, 1932.
mouse LDLo subcutaneous 225mg/kg (225mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. -, 1965.
mouse LDLo unreported 2200mg/kg (2200mg/kg) AUTONOMIC NERVOUS SYSTEM: SYMPATHOMIMETIC Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 153, Pg. 161, 1930.
rabbit LD50 intravenous 300mg/kg (300mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 691, 1986.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 164.5 deg C   EXP
pKa Dissociation Constant 9.77 (none)   EXP
log P (octanol-water) 0.860 (none)   EST
Water Solubility 1.04E+04 mg/L 15 EXP
Vapor Pressure 3.17E-03 mm Hg 25 EST
Henry's Law Constant 8.45E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 7.36E-11 cm3/molecule-sec 25 EST

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