Rivastigmine

Base Information

• Chemical Name: Rivastigmine
• CAS No.: 123441-03-2
• Molecular Formula: C14H22N2O2
• Molecular Weight: 400.429
• Hs Code.: 2924296000
• European Community (EC) Number: 602-936-0
• UNII: PKI06M3IW0
• DSSTox Substance ID: DTXSID7023564
• Nikkaji Number: J982.502I
• Wikipedia: Rivastigmine
• Wikidata: Q411887
• NCI Thesaurus Code: C66519
• RXCUI: 183379
• Pharos Ligand ID: WQ3RHUYHGTKM
• Metabolomics Workbench ID: 43238
• ChEMBL ID: CHEMBL636
• Mol file: 123441-03-2.mol

Synonyms:(S)-N-ethyl-3-((1-dimethyl-amino)ethyl)-N-methylphenylcarbamate;713, ENA;713, SDZ ENA;ENA 713;ENA 713, SDZ;ENA-713;ENA713;Exelon;Hydrogen Tartrate, Rivastigmine;rivastigmine;Rivastigmine Hydrogen Tartrate;RivastigmineTartrate;SDZ ENA 713;Tartrate, Rivastigmine Hydrogen

Chemical Property of Rivastigmine

Chemical Property:

• Vapor Pressure: 0.000416mmHg at 25°C
• Refractive Index: 1.518
• Boiling Point: 316.2 °C at 760 mmHg
• PKA: pKa 8.99 (Uncertain)
• Flash Point: 145 °C
• PSA: 147.84000
• Density: 1.038 g/cm³
• LogP: 0.63710
• Storage Temp.: -20°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 250.168127949
• Heavy Atom Count: 18
• Complexity: 269

Purity/Quality:

99% ^*data from raw suppliers

(S)-Rivastigmine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Alzheimer Disease Agents
• Canonical SMILES: CCN(C)C(=O)OC1=CC=CC(=C1)C(C)N(C)C
• Isomeric SMILES: CCN(C)C(=O)OC1=CC=CC(=C1)[C@H](C)N(C)C
• Recent ClinicalTrials: Efficacy of RIVAstigmine on Motor, Cognitive and Behavioural Impairment in Progressive Supranuclear Palsy
• Recent EU Clinical Trials: Comparison of therapeutic strategies with Cholinesterase Inhibitors: stop or still (SOS) trial
• Recent NIPH Clinical Trials: A Phase 3 Study of TW-4752N in Patients with mild and moderate Alzheimer's disease
• Uses: Antidepressant
• Clinical Use: Mild-moderate dementia in Alzheimer’s disease Idiopathic Parkinson’s disease
• Drug interactions: Potentially hazardous interactions with other drugs Muscle relaxants: enhances effect of suxamethonium; antagonises effect of non-depolarising muscle relaxants.

Technology Process of Rivastigmine

There total 90 articles about Rivastigmine 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: 99.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (S)-3-(1-aminoethyl)phenyl ethyl(methyl)carbamate (1176026-49-5) → rivastigmin (123441-03-2,415973-05-6)

Guidance literature:

With sodium tris(acetoxy)borohydride; In dichloromethane; water; at 20 ℃; for 16.5h;

DOI:10.1016/j.tet.2012.06.031

Reference yield: 98.0%

N-ethyl-N-methylcarbamoyl chloride (42252-34-6) + (S)-3-(1-dimethylaminoethyl)phenol (139306-10-8) → rivastigmin (123441-03-2,415973-05-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 5h; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201504052

Reference yield: 97.6%

N-ethyl-N-methylcarbamoyl chloride (42252-34-6) + (+/-)-3-<1-(Dimethylamino)ethyl>phenol (105601-04-5) → rivastigmin (123441-03-2,415973-05-6)

Guidance literature:

With sodium carbonate; In acetone; for 8h; Solvent;

upstream raw materials:

C₁₇H₁₈N₂O₅

N-Ethylmethylamine

N-ethyl-N-methylcarbamoyl chloride

rivastigmine hydrochloride

Downstream raw materials:

(S)-3-(1-dimethylaminoethyl)phenol

3-(1-methoxyethyl)phenyl N-ethyl-N-methylcarbamate

1-(N-ethyl-N-methylaminocarbonyloxy)-3-acetylbenzene

rac-1-(N-ethyl-N-methylaminocarbonyloxy)-3-(1-hydroxyethyl)benzene

Refernces

• 1、 Andalib, Sina,Azadi, Amir,Hamidi, Mehrdad,Mohamadpour, Hamed,Rostamizadeh, Kobra,Saghatchi Zanjani, Mohammad Reza. "Preparation, Optimization, and Evaluation of Methoxy Poly(ethylene glycol)- co-Poly(?-caprolactone) Nanoparticles Loaded by Rivastigmine for Brain Delivery". . . Retrieved 2020.
• 2、 Cheng, Jiang-Tao,Dong, Xiao-Yang,Gu, Qiang-Shuai,Li, Zhong-Liang,Liu, Juan,Liu, Xin-Yuan,Luan, Cheng,Wang, Fu-Li,Wang, Li-Lei,Yang, Ning-Yuan,Zhang, Yu-Feng. "Enantioconvergent Cu-Catalyzed Radical C-N Coupling of Racemic Secondary Alkyl Halides to Access α-Chiral Primary Amines". supporting information. p. 15413 - 15419. Retrieved 2021/09/30.
• 3、 -. "SYNTHESIS OF NOVEL INTERMEDIATE(S) FOR PREPARING RIVASTIGMINE". Paragraph 0075. . Retrieved 2020/04/10.