Tacrine

Base Information

• Chemical Name: Tacrine
• CAS No.: 321-64-2
• Molecular Formula: C13H14 N2
• Molecular Weight: 198.268
• Hs Code.: 2933990090
• European Community (EC) Number: 206-291-2,693-573-7
• UNII: 4VX7YNB537
• DSSTox Substance ID: DTXSID1037272
• Nikkaji Number: J5.670G
• Wikipedia: Tacrine
• Wikidata: Q421076
• NCI Thesaurus Code: C61961
• Pharos Ligand ID: 5L7ZPW8RPXA9
• Metabolomics Workbench ID: 42749
• ChEMBL ID: CHEMBL95
• Mol file: 321-64-2.mol

Synonyms:1,2,3,4-Tetrahydro-9-acridinamine;1,2,3,4-Tetrahydroaminoacridine;9-Amino-1,2,3,4-Tetrahydroacridine;Cognex;Romotal;Tacrine;Tacrine Hydrochloride;Tenakrin;Tetrahydroaminoacridine;THA

Chemical Property of Tacrine

Chemical Property:

• Melting Point: 183.5℃
• Refractive Index: 1.4400 (estimate)
• Boiling Point: 409.4°Cat760mmHg
• PKA: 9?+-.0.20(Predicted)
• Flash Point: 230.5°C
• PSA: 38.91000
• Density: 1.195g/cm³
• LogP: 3.27700
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 198.115698455
• Heavy Atom Count: 15
• Complexity: 229

Purity/Quality:

99%, ^*data from raw suppliers

1,2,3,4-tetrahydro-9-acridinamine AldrichCPR ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T:Toxic
• Statements: R25:Toxic if swallowed.
• Safety Statements: S28A:After contact with skin, wash immediately with plenty of water.; S45:In case of accident of if you feel unwell, seek

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Alzheimer Disease Agents
• Canonical SMILES: C1CCC2=NC3=CC=CC=C3C(=C2C1)N
• Recent ClinicalTrials: Tacrine Effects on Cocaine Self-Administration and Pharmacokinetics
• Description: In the 1950s, tacrine was used experimentally to reverse cholinergic coma in animals. In the 1960s, tacrine was used to reverse the effects of phencyclidine-like drugs. It was also marketed for many years as a respiratory stimulant. In 1993, the US Food and Drug Administration approved tacrine for the treatment of symptoms of mild to moderate Alzheimer’s disease.
• Uses: The current use of tacrine is limited due to its poor oral bioavailability, the necessity for four daily doses, and serious side effects (including nausea, vomiting, dry mouth, indigestion, diarrhea, loss of appetite, urinary incontinence, collapse, convulsions, and hepatotoxicity). Currently, newer cholinesterase inhibitors (such as donepezil, rivastigmine, and galantamine) are preferred over tacrine.

Technology Process of Tacrine

There total 25 articles about Tacrine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + anthranilic acid nitrile (1885-29-6) → tacrin (321-64-2)

Guidance literature:

cyclohexanone; anthranilic acid nitrile; With boron trifluoride diethyl etherate; sodium; In toluene; at 200 ℃; for 24h;

With sodium hydroxide; In water; for 48h; Reflux;

DOI:10.1016/j.bioorg.2021.105479

Reference yield: 93.4%

aq sodium hydroxide + anthranilic acid nitrile (1885-29-6) → tacrin (321-64-2)

Guidance literature:

With p-toluenesulfonic acid monohydrate; potassium carbonate; In dichloromethane; water; cyclohexanone;

Reference yield: 86.0%

9-hydrazino-1,2,3,4-tetrahydroacridine (65197-42-4) → tacrin (321-64-2)

Guidance literature:

With sodium tetrahydroborate; nickel dichloride; In methanol; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2008.01.128

upstream raw materials:

9-chloro-1,2,3,4-tetrahydroacridine

1,2,3,4-tetrahydro-acridine-9-carboxylic acid amide

aminacrine

p-toluidine hydrochloride

Downstream raw materials:

2-chloro-N-(1,2,3,4-tetrahydroacridin-9-yl)acetamide

2-(2-oxopyrrolidin-1-yl)-N-(1,2,3,4-tetrahydroacidin-9-yl)acetamide hydrochloride

Refernces

• 1、 Qin, Qi-Pin,Wang, Shu-Long,Tan, Ming-Xiong,Wang, Zhen-Feng,Luo, Dong-Mei,Zou, Bi-Qun,Liu, Yan-Cheng,Yao, Peng-Fei,Liang, Hong. "Novel tacrine platinum(II) complexes display high anticancer activity via inhibition of telomerase activity, dysfunction of mitochondria, and activation of the p53 signaling pathway". . p. 106 - 122. Retrieved 2018.
• 2、 Ekiz, Makbule,Tutar, Ahmet,?kten, Salih. "Convenient synthesis of disubstituted tacrine derivatives via electrophilic and copper induced reactions". . p. 5323 - 5330. Retrieved 2016.
• 3、 Cirillo, Davide,Dallanoce, Clelia,De Amici, Marco,Holzgrabe, Ulrike,Maspero, Marco,Messerer, Regina,Sotriffer, Christoph,Volpato, Daniela,Yuan Chen, Natalia. "Tacrine-xanomeline and tacrine-iperoxo hybrid ligands: Synthesis and biological evaluation at acetylcholinesterase and M1 muscarinic acetylcholine receptors". . . Retrieved 2020/02/11.
• 4、 Chen, Guoliang,Chen, Yuanguang,Du, Fangyu,Fu, Yang,Wu, Ying,Zhou, Qifan. "Copper(ii)-catalyzed c-n coupling of aryl halides and n-nucleophiles promoted by quebrachitol or diethylene glycol". supporting information. p. 2161 - 2168. Retrieved 2019/11/25.