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5396-30-5 Usage

General Description

9-Chloro-1,2,3,4-tetrahydroacridine, also known as "tacrine," is a chemical compound that has been studied for its potential use in the treatment of Alzheimer's disease. It acts as an acetylcholinesterase inhibitor, meaning it prevents the breakdown of the neurotransmitter acetylcholine in the brain. This is important because Alzheimer's disease is characterized by a decrease in acetylcholine levels, leading to cognitive decline. Tacrine has been shown to improve cognitive function in some patients with Alzheimer's disease, although its use has been limited due to potential side effects and the development of newer, more effective drugs. It is still used in research and may hold promise for future treatments of cognitive disorders.

Check Digit Verification of cas no

The CAS Registry Mumber 5396-30-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,3,9 and 6 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 5396-30:
105 % 10 = 5
So 5396-30-5 is a valid CAS Registry Number.



According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017


1.1 GHS Product identifier


1.2 Other means of identification

Product number -
Other names 1,2,3,4-Tetrahydro-9-chloroacridine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5396-30-5 SDS

5396-30-5Relevant articles and documents

Evaluation of short-tether bis-THA AChE inhibitors. A further test of the dual binding site hypothesis

Carlier, Paul R.,Han, Yi Fan,Chow, Ella S.-H.,Li, Crystal P.-L.,Wang, Hong,Xuan Lieu, Thuy,Sum Wong, Hau,Pang, Yuan-Ping

, p. 351 - 357 (1999)

To provide a further test of the dual binding site hypothesis proposed for acetylcholinesterase (AChE) inhibitor heptylene-linked bis-(9-amino-1,2,3,4-tetrahydroacridine) A7A, short-tether (ethylene-hexylene) homologs A2A-A6A were prepared. En route to these compounds, convenient and scaleable syntheses of useful pharmaceutical intermediate 9-chloro-1,2,3,4-tetrahydroacridine 3 and A7A were developed. AChE and butyrylcholinesterase (BChE) inhibition assays of A2A-A10A confirm that a seven methylene tether (A7A) optimizes AChE inhibition potency and AChE/BChE selectivity. Finally, these studies indicate that simultaneous binding of alkylene-linked 9-amino-1,2,3,4-tetrahydroacridine dimers to the catalytic and peripheral sites of AChE is possible with a tether length as short as 5 methylenes. Copyright (C) 1999 Elsevier Science Ltd.

Potent Acetylcholinesterase Selective and Reversible Homodimeric Agent Based on Tacrine for Theranostics

Meena, Virendra Kumar,Chaturvedi, Shubhra,Sharma, Rakesh Kumar,Mishra, Anil Kumar,Hazari, Puja Panwar

, p. 2296 - 2308 (2019)

Acetylcholinesterase (AChE) has been an important biomarker for diagnosing Alzheimer's disease (AD), due to reduction in AChE activity in post-mortem brains of AD patients. A potent, selective, and reversible homodimeric inhibitor of AChE, 5-amino-N1,N3-bis(2-(1,2,3,4-tetrahydroacridin-9-ylamino)ethyl)isophthalamide (compound 4), was synthesized by using 9-alkyl(1,2,3,4-tetrahydroacridine) pharmacophore with appended functionality. In the present work, we report the synthesis of this bivalent inhibitor of AChE. The homodimeric ligand structure was designed and studied with molecular docking tools, which revealed its high affinity and interactions with active site gorge of AChE, which includes both catalytic active site (CAS) and peripheral active site (PAS). The IC50 value of this bivalent inhibitor for AChE and BuChE were 0.54 ± 0.06 and 32.49 ± 1.2 nM, respectively, with a selectivity ratio of 60.16 toward AChE. The designed ligand also showed potent inhibitory properties on PAS activity as well as on AChE-induced amyloid aggregation with low cytotoxicity on rat hippocampal neurons. The AFM images further corroborated the Aβ1-42 aggregation inhibition by compound 4 to an extent similar to bis(7)-tacrine. Moreover, the bivalent ligand was also proven to be of neurogenic potential due to its ability to induce S-phase post-treatment in rat hippocampal neuronal cells. On the basis of initial results, the agent could be further explored for its theranostic value clinically, which gives the possibility of tracing the AChE levels by molecular imaging techniques in correlation with progression of neurocognitive disorders like AD for better therapy response and patient management.

Dual GSK-3β/AChE Inhibitors as a New Strategy for Multitargeting Anti-Alzheimer's Disease Drug Discovery

Jiang, Xue-Yang,Chen, Ting-Kai,Zhou, Jun-Ting,He, Si-Yu,Yang, Hong-Yu,Chen, Yao,Qu, Wei,Feng, Feng,Sun, Hao-Peng

, p. 171 - 176 (2018)

Designing multitarget-directed ligands (MTDLs) is considered to be a promising approach to address complex and multifactorial maladies such as Alzheimer's disease (AD). The concurrent inhibition of the two crucial AD targets, glycogen synthase kinase-3β (GSK-3β) and human acetylcholinesterase (hAChE), might represent a breakthrough in the quest for clinical efficacy. Thus, a novel family of GSK-3β/AChE dual-target inhibitors was designed and synthesized. Among these hybrids, 2f showed the most promising profile as a nanomolar inhibitor on both hAChE (IC50 = 6.5 nM) and hGSK-3β kinase activity (IC50 = 66 nM). It also showed good inhibitory effect on β-amyloid self-aggregation (inhibitory rate = 46%) at 20 μM. Western blot analysis revealed that compound 2f inhibited hyperphosphorylation of tau protein in mouse neuroblastoma N2a-Tau cells. In vivo studies confirmed that 2f significantly ameliorated the cognitive disorders in scopolamine-treated ICR mice and less hepatotoxicity than tacrine. This study provides new leads for assessment of GSK-3β and AChE pathway dual inhibition as a promising strategy for AD treatment.

Synthesis and biological evaluation of tacrine-thiadiazolidinone hybrids as dual acetylcholinesterase inhibitors

Dorronsoro, Isabel,Alonso, Diana,Castro, Ana,Del Monte, Maria,Garcia-Palomero, Esther,Martinez, Ana

, p. 18 - 23 (2005)

The synthesis of tacrine-thiadiazolidinone hybrids is described. These compounds are designed as dual acetylcholinesterase inhibitors binding simultaneously to the peripheral and catalytic sites of the enzyme. All tested compounds exhibit significant AChE inhibitory activity. Competition assays using propidium as reference of selective ligand for the peripheral anionic site on acetylcholinesterase indicates the influence of the designed compounds over the peripheral site. They can be considered as new leads in the optimization of Alzheimer's disease modifying agents.

NO-donating tacrine hybrid compounds improve scopolamine-induced cognition impairment and show less hepatotoxicity

Fang, Lei,Appenroth, Dorothea,Decker, Michael,Kiehntopf, Michael,Lupp, Amelie,Peng, Sixun,Fleck, Christian,Zhang, Yihua,Lehmann, Jochen

, p. 7666 - 7669 (2008)

A series of tacrine - NO donor hybrid compounds are synthesized and evaluated for cholinesterase inhibitory activity, cognition improving activity, and hepatotoxicity. The pharmacological results indicate that hybrid compounds 1, 2, and 3a potently inhibit cholinesterase in vitro and significantly improve the scopolamine-induced cognition impairment, whereas an analogue (3h) of 2 without the NO donor moiety does not. Compared to tacrine, 1 and 2 show much less hepatotoxicity. Molecular modeling studies suggest that 2 may interact with the catalytic and the peripheral anionic site of acetylcholinesterase.

Design and synthesis of tacrine-phenothiazine hybrids as multitarget drugs for Alzheimer's disease

Hui, Ai-Ling,Chen, Yan,Zhu, Shi-Jing,Gan, Chang-Sheng,Pan, Jian,Zhou, An

, p. 3546 - 3557 (2014)

Tacrine is well-known drug for Alzheimer's disease as an acetylcholinesterase inhibitor. Rember is a bright and promising AD drugs targeting tau protein, and it is currently in Phase III clinical trials. Phenothiazine, the key pharmacophore of Rember, can prevent tau filament formation. In this work, several tacrine-phenothiazine hybrids (T1-T26) were designed for inhibiting acetylcholinesterase and tau protein involved in Alzheimer's disease. After initial screening with the help of computational chemistry software and Molegro Virtual Docker, three molecules (T5, T18, and T22) were selected for further synthesis and biological evaluation. Next, T5, T18, and T22 were synthesized and evaluated for their acetylcholinesterase and tau hyperphosphorylation inhibition. All the tested compounds had better acetylcholinesterase inhibitory activity compared with tacrine. Among them, compound T5 was found to be the most potent compound with IC50 89 nM. Meanwhile, T5 markedly prevented tau hyperphosphorylation induced by okadaic acid in N2α cell. Its P-tau level was decreased with 39.5 % inhibition when tested at 10-5 M, lower than that Rember (55.7 %). Besides acetylcholinesterase and tau hyperphosphorylation inhibition, T5 can also interact with fibrill beta amyloid using surface plasmon resonance, the data of KD were 5.51 × 10-8 M. All the above results indicated that tacrine-phenothiazine hybrids are potential multitarget directed ligands targeting acetylcholinesterase, tau protein, and beta amyloid.

Synthesis and in-vitro anticancer evaluation of bis-tacrine congeners


, p. 83 - 88 (2001)

In the search for potential new anticancer drugs, an efficient synthesis of bis-tetrahydro-aminoacridine (bis-tacrine) and its congeners was accomplished by bis-amination of 9-chloro-tetrahydroacridine and its congeners under heated conditions. The critical chlorides were efficiently prepared from o-aminoaromatic acids and cycloketones in-situ in the presence of phosphorus oxychloride. In-vitro cytotoxic evaluation of the compounds was carried out against a panel of 60 human cancer cell lines. Among them, butyl-linked bis-tacrine (5b) exhibited the strongest cytotoxic profile with G150 (concentration causing 50% growth inhibition) values of approximately 0.04-0.08 μm against breast, colon, melanoma and non-small lung cancer cells. Congeners bearing a longer alkyl chain were on average 30- to 100-fold less cytotoxic against these cancer cells. Shorter connecting alkyl chains of bis-tacrine or its congeners dramatically decreased the cytotoxic effects. Compound 5b has been selected for further biological evaluation of its anticancer profile.

Synthesis and bioevaluation of new tacrine-cinnamic acid hybrids as cholinesterase inhibitors against Alzheimer’s disease

Chen, Yao,Zhu, Jie,Mo, Jun,Yang, Hongyu,Jiang, Xueyang,Lin, Hongzhi,Gu, Kai,Pei, Yuqiong,Wu, Liang,Tan, Renxiang,Hou, Jing,Chen, Jingyi,Lv, Yang,Bian, Yaoyao,Sun, Haopeng

, p. 290 - 302 (2018)

Small molecule cholinesterases inhibitor (ChEI) provides an effective therapeutic strategy to treat Alzheimer’s disease (AD). Currently, the discovery of new ChEI with multi-target effect is still of great importance. Herein, we report the synthesis, structure–activity relationship study and biological evaluation of a series of tacrine-cinnamic acid hybrids as new ChEIs. All target compounds are evaluated for their in vitro cholinesterase inhibitory activities. The representatives which show potent activity on cholinesterase, are evaluated for the amyloid β-protein self-aggregation inhibition and in vivo assays. The optimal compound 19, 27, and 30 (human AChE IC50 = 10.2 ± 1.2, 16.5 ± 1.7, and 15.3 ± 1.8 nM, respectively) show good performance in ameliorating the scopolamine-induced cognition impairment and preliminary safety in hepatotoxicity evaluation. These compounds deserve further evaluation for the development of new therapeutic agents against AD.

Design, synthesis and biological evaluation of multifunctional tacrine-curcumin hybrids as new cholinesterase inhibitors with metal ions-chelating and neuroprotective property

Liu, Zhikun,Fang, Lei,Zhang, Huan,Gou, Shaohua,Chen, Li

, p. 2387 - 2398 (2017)

Total sixteen tacrine-curcumin hybrid compounds were designed and synthesized for the purpose of searching for multifunctional anti-Alzheimer agents. In vitro studies showed that these hybrid compounds showed good cholinesterase inhibitory activity. Particularly, the potency of K3-2 is even beyond tacrine. Some of the compounds exhibited different selectivity on acetylcholinesterase or butyrylcholinesterase due to the structural difference. Thus, the structure and activity relationship is summarized and further discussed based on molecular modeling studies. The ORAC and MTT assays indicated that the hybrid compounds possessed pronounced antioxidant activity and could effectively protect PC12 cells from the H2O2/Aβ42-induced toxicity. Moreover, the hybrid compounds also showed positive metal ions-chelating ability in vitro, suggesting a potential to halt ion-induced Aβ aggregation. All the obtained results demonstrated that the tacrine-curcumin hybrid compounds, in particular compound K3-2, can be considered as potential therapeutic agents for Alzheimer's disease.

Design and synthesis of novel tacrine-dipicolylamine dimers that are multiple-target-directed ligands with potential to treat Alzheimer's disease

Benjamin Naman, C.,Cui, Wei,Dong, Jiahui,He, Shan,Huang, Xinghan,Jin, Haixiao,Lin, Dongdong,Liu, Fufeng,Liu, Hao,Liu, Zhiwen,Mao, Yuechun,Mou, Chenye,Wang, Ning,Wang, Ze,Wei, Jiaxin,Xie, Yanfei,Yang, Mengxiang,Zhang, Bin,Zhang, Panpan,Zhou, Fei,Zou, Jiamei

supporting information, (2021/10/12)

Alzheimer's disease (AD) is a prevalent neurodegenerative disorder that has multiple causes. Therefore, multiple-target-directed ligands (MTDLs), which act on multiple targets, have been developed as a novel strategy for AD therapy. In this study, novel drug candidates were designed and synthesized by the covalent linkings of tacrine, a previously used anti-AD acetylcholinesterase (AChE) inhibitor, and dipicolylamine, an β-amyloid (Aβ) aggregation inhibitor. Most tacrine-dipicolylamine dimers potently inhibited AChE and Aβ1-42 aggregation in vitro, and 13a exhibited nanomolar level inhibition. Molecular docking analysis suggested that 13a could interact with the catalytic active sites and the peripheral anion site of AChE, and bind to Aβ1-42 pentamers. Moreover, 13a effectively attenuated Aβ1-42 oligomers-induced cognitive dysfunction in mice by activating the cAMP-response element binding protein/brain-derived neurotrophic factor signaling pathway, decreasing tau phosphorylation, preventing synaptic toxicity, and inhibiting neuroinflammation. The safety profile of 13a in mice was demonstrated by acute toxicity experiments. All these results suggested that novel tacrine-dipicolylamine dimers, especially 13a, have multi-target neuroprotective and cognitive-enhancing potentials, and therefore might be developed as MTDLs to combat AD.



Paragraph 0026; 0035, (2021/02/04)

The invention concerns a compound according to formula wherein R6 is H or an alkyl and one of R5 and R7 comprises or consists of linker-coupled tacrine residue wherein the linker is coupled to the amino residue of the tacrine residue and couples the tacrine residue to the rest of the molecule, wherein the other one of R5 and R7 is H or an alkyl.

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