Tacrine

Names

[ CAS No. ]:
321-64-2

[ Name ]:
Tacrine

[Synonym ]:
EINECS 206-291-2
MFCD00046923
9-Acridinamine, 1,2,3,4-tetrahydro-
1,2,3,4-TETRAHYDRO-9-ACRIDINAMINE
9-Amino-1,2,3,4-tetrahydroacridine
Tetrahydroaminocrine
Tenakrin
1,2,3,4-tetrahydro-5-aminoacridine
Cognex
4-Amino-2,3-tetramethylenequinoline
Tetrahydroaminocrin
1,2,3,4-tetrahydro-9-amino-acridine
Tetrahydroaminacrine
1,2,3,4-tetrahdyroacridin-9-amine
1,2,3,4-tetrahydroacridin-9-amine
Romotal
Tetrahydroaminoacridine
Tacrine

Biological Activity

[Description]:

Tacrine is a potent acetylcholinesterse (AChE) inhibitor (IC50=109 nM), also acting as a CYP1A2 substrate drug. Tacrine exhibits certain hepatotoxicity in some individuals. Tacrine can be used for researching Alzheimer's disease (AD)[1][2][3].

[Related Catalog]:

Research Areas >> Neurological Disease

Signaling Pathways >> Neuronal Signaling >> AChE

[Target]

IC50: 109 nM (AChE)[3]

[References]

[1]. Patocka J, et al. Possible role of hydroxylated metabolites of tacrine in drug toxicity and therapy of Alzheimer's disease. Curr Drug Metab. 2008;9(4):332-335.

[2]. Bhatt S, et al. Assessment of the CYP1A2 Inhibition-Mediated Drug Interaction Potential for Pinocembrin Using In Silico, In Vitro, and In Vivo Approaches. ACS Omega. 2022;7(23):20321-20331. Published 2022 Jun 2.

[3]. Romero A, et al. Novel tacrine-related drugs as potential candidates for the treatment of Alzheimer's disease. Bioorg Med Chem Lett. 2013;23(7):1916-1922.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
353.8±42.0 °C at 760 mmHg

[ Melting Point ]:
283-284ºC

[ Molecular Formula ]:
C₁₃H₁₄N₂

[ Molecular Weight ]:
198.264

[ Flash Point ]:
167.8±27.9 °C

[ Exact Mass ]:
198.115692

[ PSA ]:
38.91000

[ LogP ]:
1.78

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.682

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AR9532100

CHEMICAL NAME :: Acridine, 1,2,3,4-tetrahydro-9-amino-

CAS REGISTRY NUMBER :: 321-64-2

BEILSTEIN REFERENCE NO. :: 0147610

LAST UPDATED :: 199707

DATA ITEMS CITED :: 17

MOLECULAR FORMULA :: C13-H14-N2

MOLECULAR WEIGHT :: 198.29

WISWESSER LINE NOTATION :: T C666 BNT&&J IZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 294 mg/kg/14W-I

TOXIC EFFECTS :: Liver - fatty liver degeneration Liver - liver function tests impaired Blood - changes in cell count (unspecified)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 84 mg/kg/6W-I

TOXIC EFFECTS :: Liver - hepatitis (hepatocellular necrosis), zonal Liver - liver function tests impaired

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 176 mg/kg/7W-I

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting Liver - liver function tests impaired

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 70 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 30 mg/kg

TOXIC EFFECTS :: Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - true cholinesterase

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 20 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 34 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 39800 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 20 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 25 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 29 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 31 mg/kg

TOXIC EFFECTS :: Behavioral - euphoria Behavioral - antipsychotic

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 620 mg/kg/18W-C

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: Cytogenetic analysis

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

REFERENCE :: ACNSAX Activitas Nervosa Superior. (Avicenum, Malostranske nam. 28, Prague 1, Czechoslovakia) V.1- 1959- Volume(issue)/page/year: 26,84,1984

Safety Information

[ Hazard Codes ]:
T

[ Risk Phrases ]:
R25

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%