Ladostigil

Base Information

• Chemical Name: Ladostigil
• CAS No.: 209394-27-4
• Molecular Formula: C16H20N2O2
• Molecular Weight: 272.347
• UNII: SW3H1USR4Q
• DSSTox Substance ID: DTXSID101045854
• Nikkaji Number: J1.441.441J
• Wikipedia: Ladostigil
• Wikidata: Q374426
• NCI Thesaurus Code: C77584
• ChEMBL ID: CHEMBL255231
• Mol file: 209394-27-4.mol

Synonyms:(N-propargyl-(3R) aminoindan-5-yl)-ethyl methyl carbamate;Ladostigil;TV 3326;TV3326

Chemical Property of Ladostigil

Chemical Property:

• Vapor Pressure: 5.19E-07mmHg at 25°C
• Boiling Point: 412.4°C at 760 mmHg
• Flash Point: 203.2°C
• PSA: 41.57000
• Density: 1.14g/cm³
• LogP: 2.73810
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 272.152477885
• Heavy Atom Count: 20
• Complexity: 387

Purity/Quality:

99% ^*data from raw suppliers

LADOSTIGIL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(C)C(=O)OC1=CC2=C(CCC2NCC#C)C=C1
• Isomeric SMILES: CCN(C)C(=O)OC1=CC2=C(CC[C@H]2NCC#C)C=C1
• Recent EU Clinical Trials: A 36-month, multi-centre, randomized double-blind placebo-controlled study to evaluate the safety and efficacy of low dose Ladostigil in patients with Mild Cognitive Impairment (MCI)
• Uses: Treatment of Alzheimer’s disease (an inhibitor of monoamine oxidase (MAO-A and B), an acetylcholinesterase inhibitor, and a neuroprotectant).

Technology Process of Ladostigil

There total 15 articles about Ladostigil 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:

C14H19NO5S + Propargylamine (2450-71-7) → ladostigil (209394-27-4)

Guidance literature:

In N,N-dimethyl-formamide; at -40 - 20 ℃; for 5h;

DOI:10.1016/j.tetasy.2012.02.022

Reference yield:

C14H19NO5S + Propargylamine (2450-71-7) → ladostigil (209394-27-4) + (S)-6-(N-methyl-N-ethylcarbamyloxy)-N-propargyl-1-aminoindan

Guidance literature:

In dichloromethane; at -35 - 20 ℃;

Reference yield:

propargyl bromide (106-96-7) + Ethyl-methyl-carbamic acid (R)-3-amino-indan-5-yl ester; hydrochloride → ladostigil (209394-27-4)

Guidance literature:

With potassium carbonate; In acetonitrile; at 20 ℃; for 24h;

DOI:10.1021/jm020120c

upstream raw materials:

propargyl bromide

(R)-1-Aminoindane

(R)-3-amino-2,3-dihydro-1H-inden-5-ol

N-trifluoroacetyl-(R)-1-aminoindan

Downstream raw materials:

ladostigil tartrate

ladostigil hemitartrate

Refernces

• 1、 -. "Methods for isolating propargylated aminoindans". Page/Page column 8-9. . Retrieved 2008/06/13.
• 2、 Sterling, Jeffrey,Herzig, Yaacov,Goren, Tamar,Finkelstein, Nina,Lerner, David,Goldenberg, Willy,Miskolczi, Istvan,Molnar, Sandor,Rantal, Ferenc,Tamas, Tivadar,Toth, Gyorgy,Zagyva, Adela,Zekany, Andras,Lavian, Gila,Gross, Aviva,Friedman, Rachel,Razin, Michal,Huang, Wei,Krais, Boris,Chorev, Michael,Youdim, Moussa B.,Weinstock, Marta. "Novel dual inhibitors of AChE and MAO derived from hydroxy aminoindan and phenethylamine as potential treatment for Alzheimer's disease". . p. 5260 - 5279. Retrieved 2007/10/03.