Benztropine

Base Information

• Chemical Name: Benztropine
• CAS No.: 86-13-5
• Molecular Formula: C₂₁H₂₅NO
• Molecular Weight: 307.436
• UNII: 1NHL2J4X8K
• DSSTox Substance ID: DTXSID9022659
• Nikkaji Number: J4.933F,J232.148C
• Wikipedia: Benzatropine
• Wikidata: Q415026
• NCI Thesaurus Code: C61649
• RXCUI: 1424
• Pharos Ligand ID: 1GT44A3AKFB7
• Metabolomics Workbench ID: 49977
• ChEMBL ID: CHEMBL1201203,CHEMBL438151,CHEMBL1618180
• Mol file: 86-13-5.mol

Synonyms:Apo Benztropine;Apo-Benztropine;Bensylate;Benzatropine;Benzatropine Mesylate;Benzatropine Methanesulfonate;Benzatropine Methanesulfonate, Hydrobromide;Benzatropine Methanesulfonate, Hydrobromide, (endo)-Isomer;Benzatropine Methanesulfonate, Hydrochloride, (endo)-Isomer;Benztropine;Benztropine Mesylate;Cogentin;Cogentinol;Hydrobromide Benzatropine Methanesulfonate;Mesylate, Benzatropine;Mesylate, Benztropine;Methanesulfonate, Benzatropine;Methanesulfonate, Hydrobromide Benzatropine;N Methylbenztropine;N-Methylbenztropine;PMS Benztropine;PMS-Benztropine

Chemical Property of Benztropine

Chemical Property:

• Vapor Pressure: 6.73E-07mmHg at 25°C
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 409°C at 760 mmHg
• PKA: 10.54±0.40(Predicted)
• Flash Point: 120.1°C
• PSA: 12.47000
• Density: 1.11g/cm³
• LogP: 4.35570
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 307.193614421
• Heavy Atom Count: 23
• Complexity: 340

Purity/Quality:

98%Min ^*data from raw suppliers

Benzatropine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiparkinson Agents
• Canonical SMILES: CN1C2CCC1CC(C2)OC(C3=CC=CC=C3)C4=CC=CC=C4
• Isomeric SMILES: CN1[C@@H]2CC[C@H]1CC(C2)OC(C3=CC=CC=C3)C4=CC=CC=C4
• Recent ClinicalTrials: Evaluation of Benztropine for Cocaine Craving - 2
• Recent EU Clinical Trials: Efficacy of patient education and duloxetine, alone and in combination, for patients with multiorgan bodily distress syndrome: a partial-factorial randomized controlled trial (the EDULOX-trial)
• Description: Benztropine, with the chemical formula 3alpha-diphenylmethoxytropane, is a tropane-based dopamine inhibitor used for the symptomatic treatment of Parkinson's disease. It is a combination molecule between a tropane ring, similar to cocaine, and a diphenyl ether from the dialkylpiperazines determined to be a dopamine uptake inhibitor since 1970.
• Uses: Benzatropine is used to reduce?extrapyramidal side effects?of?antipsychotic?treatment. Benzatropine is also a second-line drug for the treatment of Parkinson's disease. It improves?tremor, and may alleviate rigidity and?bradykinesia.Benzatropine is also sometimes used for the treatment of?dystonia, a rare disorder that causes abnormal muscle contraction, resulting in twisting postures of limbs, trunk, or face.

Technology Process of Benztropine

There total 11 articles about Benztropine 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: 93.0%

diphenylchloromethane (90-99-3) + 3-tropanol (120-29-6) → benzatropine (86-13-5,13050-78-7)

Guidance literature:

at 160 ℃; for 1h;

DOI:10.1021/acschembio.8b00454

Reference yield: 83.0%

3α-benzhydryloxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid methyl ester (797763-49-6) → benzatropine (86-13-5,13050-78-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 2h; Heating;

DOI:10.1039/b405768f

Reference yield:

3α-benzhydryloxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (797763-48-5) → benzatropine (86-13-5,13050-78-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / 2,6-lutidine; TMSOTf / CH₂Cl₂ / 0.75 h / 20 °C

2: 83 percent / pyridine / 0.5 h / 20 °C

3: 83 percent / LiAlH₄ / diethyl ether / 2 h / Heating

With pyridine; 2,6-dimethylpyridine; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; In diethyl ether; dichloromethane;

DOI:10.1039/b405768f

upstream raw materials:

Bromodiphenylmethane

3-tropanol

diazodiphenylmethane

3α-benzhydryloxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid methyl ester

Downstream raw materials:

Benztropine N-oxide

3α-benzhydryloxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid methyl ester

Refernces

• 1、 Pedersen, Hanne,Sinning, Steffen,Buelow, Anne,Wiborg, Ove,Falborg, Lise,Bols, Mikael. "Combinatorial synthesis of benztropine libraries and their evaluation as monoamine transporter inhibitors". . p. 2861 - 2869. Retrieved 2007/10/03.