Latrepirdine

Base Information

• Chemical Name: Latrepirdine
• CAS No.: 3613-73-8
• Deprecated CAS: 12687-54-6,20684-30-4
• Molecular Formula: C21H25N3
• Molecular Weight: 319.45
• European Community (EC) Number: 638-815-4
• UNII: OD9237K1Z6
• DSSTox Substance ID: DTXSID20189705
• Nikkaji Number: J14.525D
• Wikipedia: Latrepirdine
• Wikidata: Q408580
• NCI Thesaurus Code: C78757
• Pharos Ligand ID: DQ23Q75WQ524
• Metabolomics Workbench ID: 152835
• ChEMBL ID: CHEMBL589390
• Mol file: 3613-73-8.mol

Synonyms:dimebolin;dimebon;dimebone;latrepirdine;PF 01913539;PF 1913539;PF-01913539;PF-1913539;PF01913539;PF1913539

Chemical Property of Latrepirdine

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 2.37E-10mmHg at 25°C
• Melting Point: 115-116 °C
• Refractive Index: 1.628
• Boiling Point: 505.7 °C at 760 mmHg
• PKA: 9.05±0.20(Predicted)
• Flash Point: 259.7 °C
• PSA: 21.06000
• Density: 1.13 g/cm³
• LogP: 3.82160
• Solubility.: ≤30mg/ml in ethanol;1mg/ml in DMSO;3mg/ml in dimethyl formamide
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 319.204847810
• Heavy Atom Count: 24
• Complexity: 425

Purity/Quality:

99%, ^*data from raw suppliers

Dimebon dihydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)N(C3=C2CN(CC3)C)CCC4=CN=C(C=C4)C
• Recent ClinicalTrials: A Phase 3 Study To Evaluate The Safety And Tolerability Of Dimebon Patients With Mild To Moderate Alzheimer's Disease
• Recent EU Clinical Trials: CONCERT PLUS: An Open-Label Extension of the CONCERT Protocol (DIM18) Evaluating Dimebon (Latrepirdine) in Patients with Alzheimer's Disease
• Uses: Non-steroidal anti-inflammatory with analgesic and antipyretic effects

Technology Process of Latrepirdine

There total 30 articles about Latrepirdine 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: 80.0%

2-methyl-5-vinylpyridine (140-76-1,25038-86-2) + 2.8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (19686-05-6) → dimebon (3613-73-8)

Guidance literature:

With potassium phosphate; In ISOPROPYLAMIDE; at 100 ℃; for 24h; Inert atmosphere;

Reference yield: 70.0%

tert-butyl 8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (1227258-81-2) → dimebon (3613-73-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h; Reflux;

Reference yield:

N'-(1-methyl-piperidin-4-ylidene)-N-[2-(6-methyl-pyridin-3-yl)-ethyl]-N-p-tolyl-hydrazine (1229621-60-6) → dimebon (3613-73-8)

Guidance literature:

With hydrogenchloride; In ethanol; water; at 100 ℃; for 0.5h;

upstream raw materials:

2-methyl-5-vinylpyridine

2.8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

tert-butyl 8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

1-Methyl-4-piperidone

Refernces

• 1、 -. "Sustained-release composition containing tetrahydropyrido[4,3-b]indole derivatives and preparation of the derivatives". Page/Page column 6. . Retrieved 2012/05/21.
• 2、 Dong, Huijun,Latka, Regina T.,Driver, Tom G.. "Ruthenium-catalyzed γ-carbolinium ion formation from aryl azides; Synthesis of dimebolin". . p. 2726 - 2729. Retrieved 2011/06/28.