Tacrine hydrochloride

Names

[ Name ]:
Tacrine hydrochloride

[Synonym ]:
1,2,3,4-Tetrahydroacridin-9-amine hydrochloride (1:1)
1,2,3,4-Tetrahydroacridin-9-aminhydrochlorid
9-Acridinamine, 1,2,3,4-tetrahydro-, hydrochloride, hydrate (1:1:2)
1,2,3,4-tetrahydroacridin-9-amine hydrochloride
Cognex
9-Amino-1,2,3,4-tetrahydroacridine hydrochloride hydrate
1,2,3,4-Tetrahydro-9-acridinamine hydrochloride (1:1)
THA
1,2,3,4-tetrahydroacridin-9-amine,hydrochloride
1,2,3,4-Tetrahydro-9-acridinamine hydrochloride dihydrate
EINECS 216-867-5
MFCD00012657
9-Acridinamine, 1,2,3,4-tetrahydro-, hydrochloride (1:1)
1,2,3,4-tétrahydroacridin-9-amine chlorhydrate
Tacrin hydrochloride

Biological Activity

[Description]:

Tacrine hydrochloride is a potent inhibitor of both AChE and BChE, with IC50s of 31 nM and 25.6 nM, respectively. Tacrine hydrochloride is also a NMDAR inhibitor, with an IC50 of 26 μM. Tacrine hydrochloride can be used for the research of Alzheimer’s disease[1][2].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> iGluR

Research Areas >> Neurological Disease

Signaling Pathways >> Membrane Transporter/Ion Channel >> iGluR

Signaling Pathways >> Neuronal Signaling >> AChE

[Target]

IC50: 31 nM (AChE), 25.6 nM (BChE), 26 μM (NMDAR)[1][2]

[In Vitro]

Tacrine (12.5-37.5 nM) inhibits venom acetylcholinesterase as well as human serum butyrylcholinesterase in a concentration-dependent manner[1]. Tacrine reduces the neurotoxicity induced by the activation of the NMDARs in murine cortical neuronal cultures with an IC50of ~500 μM[2]. Tacrine inhibits the NMDAR responses in a concentration-dependent manner with an IC50 of ~190 μM at -60 mV[2].

[In Vivo]

Tacrine (20-40 μmol/kg; s.c.) disrupts retention of learning in 17- and 30-day old mice in passive avoidance, and while the low dose of tacrine treatment (5 μmol/kg; s.c.) improves retention in 17-day old mice[2]. Tacrine (0.1-0.4 mg/mL; i.p. for 7 d) inhibits the expression of AChE, but does not significantly improve the protection of the retina function and morphology in mice[3].

[References]

[1]. Ahmed M, et, al. Inhibition of two different cholinesterases by tacrine. Chem Biol Interact. 2006 Aug 25; 162(2):165-71.c

[2]. Horak M, et, al. The pharmacology of tacrine at N-methyl-d-aspartate receptors. Prog Neuropsychopharmacol Biol Psychiatry. 2017 Apr 3;75: 54-62.

[3]. The protective role of tacrine and donepezil in the retina of acetylcholinesterase knockout mice. Yi YM, et, al. Int J Ophthalmol. 2015 Oct 18; 8(5): 884-90.

Chemical & Physical Properties

[ Boiling Point ]:
409.4ºC at 760mmHg

[ Melting Point ]:
280-284 °C(lit.)

[ Molecular Formula ]:
C₁₃H₁₅ClN₂

[ Molecular Weight ]:
270.755

[ Flash Point ]:
230.5ºC

[ Exact Mass ]:
270.113495

[ PSA ]:
38.91000

[ LogP ]:
4.07900

[ Vapour Pressure ]:
6.49E-07mmHg at 25°C

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AR9532500

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

CAS REGISTRY NUMBER :: 1684-40-8

LAST UPDATED :: 199506

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C13-H14-N2.Cl-H

MOLECULAR WEIGHT :: 234.75

WISWESSER LINE NOTATION :: T C666 BN&&TJ IZ &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 40 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949- Volume(issue)/page/year: 10,638,1958

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5600 ug/kg

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

REFERENCE :: CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#07602

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H315-H319-H335

[ Precautionary Statements ]:
Missing Phrase - N15.00950417-P305 + P351 + P338

[ Hazard Codes ]:
T: Toxic;Xn: Harmful;

[ Risk Phrases ]:
25-36/37/38-20/22

[ Safety Phrases ]:
S26-S36-S45

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
AR9532500

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

[ 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%