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Substance Name: Tacrine [INN:BAN]
RN: 321-64-2
UNII: 4VX7YNB537
InChIKey: YLJREFDVOIBQDA-UHFFFAOYSA-N

Note

  • A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.

Molecular Formula

  • C13-H14-N2

Molecular Weight

  • 198.2676
 

Classification Codes

  • Autonomic Agents
  • Central Nervous System Agents
  • Cholinergic Agents
  • Cholinesterase Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Neurotransmitter Agents
  • Nootropic Agents
  • Parasympathomimetics
  • Peripheral Nervous System Agents

Names and Synonyms

Name of Substance

  • Tacrine
  • Tacrine [INN:BAN]

MeSH Heading

  • Tacrine

Synonyms

  • 1,2,3,4-Tetrahydro-9-acridinamine
  • 5-22-10-00480 (Beilstein Handbook Reference)
  • 5-Amino-6,7,8,9-tetrahydroacridine (European)
  • 9-Amino-1,2,3,4-tetrahydroacridine
  • BRN 0147610
  • CS 12602
  • EINECS 206-291-2
  • Tacrina
  • Tacrina [INN-Spanish]
  • Tacrine
  • Tacrinum
  • Tacrinum [INN-Latin]
  • Tetrahydroaminacrine
  • Tetrahydroaminoacridine
  • Tetrahydroaminocrin
  • Tetrahydroaminocrine
  • UNII-4VX7YNB537

Systematic Names

  • 9-Acridinamine, 1,2,3,4-tetrahydro- (9CI)
  • Acridine, 1,2,3,4-tetrahydro-9-amino-
  • Tacrine

Registry Numbers

CAS Registry Number

  • 321-64-2

FDA UNII

  • 4VX7YNB537

Related Registry Number

  • 1684-40-8 (hydrochloride)

System Generated Number

  • 0000321642

Structure Descriptors

InChI

1S/C13H14N2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1,3,5,7H,2,4,6,8H2,(H2,14,15)

InChIKey

YLJREFDVOIBQDA-UHFFFAOYSA-N

Smiles

c12c(c(c3c(n1)CCCC3)N)cccc2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 unreported 31mg/kg (31mg/kg) BEHAVIORAL: EUPHORIA

BEHAVIORAL: ANTIPSYCHOTIC
Pharmaceutical Chemistry Journal Vol. 8, Pg. 409, 1974.
man TDLo oral 176mg/kg/7W-I (176mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED

GASTROINTESTINAL: NAUSEA OR VOMITING
Australian and New Zealand Journal of Medicine. Vol. 20, Pg. 193, 1990.
mouse LD50 intramuscular 29mg/kg (29mg/kg)   Drugs of the Future. Vol. 15, Pg. 126, 1990.
mouse LD50 intraperitoneal 20mg/kg (20mg/kg)   Indian Journal of Pharmacology. Vol. 19, Pg. 44, 1987.
mouse LD50 oral 39800ug/kg (39.8mg/kg)   Journal of Medicinal Chemistry. Vol. 31, Pg. 1278, 1988.
mouse LD50 subcutaneous 25mg/kg (25mg/kg)   British Journal of Experimental Pathology. Vol. 28, Pg. 1, 1947.
rat LD50 intramuscular 34mg/kg (34mg/kg)   Drugs of the Future. Vol. 15, Pg. 126, 1990.
rat LD50 intraperitoneal 30mg/kg (30mg/kg)   Iugoslavica Physiologica et Pharmacologica Acta. Vol. 3, Pg. 43, 1967.
rat LD50 oral 70mg/kg (70mg/kg)   Journal of Medicinal Chemistry. Vol. 38, Pg. 2802, 1995.
rat LDLo intravenous 20mg/kg (20mg/kg)   United States Patent Document. Vol. #5409948,
women TDLo oral 84mg/kg/6W-I (84mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"
Australian and New Zealand Journal of Medicine. Vol. 20, Pg. 193, 1990.
women TDLo oral 294mg/kg/14W- (294mg/kg) BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED)

LIVER: LIVER FUNCTION TESTS IMPAIRED

LIVER: FATTY LIVER DEGERATION
Lancet. Vol. 1, Pg. 887, 1988.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 183.5 deg C   EXP
pKa Dissociation Constant 9.95 (none) 20 EXP
log P (octanol-water) 2.71 (none)   EXP
Water Solubility 217 mg/L 25 EST
Vapor Pressure 7.50E-06 mm Hg 25 EST
Henry's Law Constant 2.30E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.05E-10 cm3/molecule-sec 25 EST

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