1684-40-8

1684-40-8 structure

Name: Tacrine hydrochloride
Chemical Name: 9-Amino-1,2,3,4-tetrahydroacridine Hydrochloride Dihydrate
CAS Number: 1684-40-8
Molecular Formula: C₁₃H₁₅ClN₂
Molecular Weight: 270.755
Catalog: API Special medicine Antidote
Create Date: 2018-05-10 08:00:00
Modify Date: 2025-08-20 10:58:16
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].

Name	9-Amino-1,2,3,4-tetrahydroacridine Hydrochloride Dihydrate
Synonyms	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

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.

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

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

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

321-64-2

1684-40-8

Literature: European Journal of Medicinal Chemistry, , vol. 77, p. 343 - 350

Precursor 1
321-64-2
DownStream 0

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%

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