3736-36-5

Basic information

• Product Name: Tropine benzilate
• Synonyms: 2-hydroxy-2-[3-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)phenyl]-2-phenyl- acetic acid;glipin;8-Methyl-8-aza-bicyclo[3.2.1]octan-3-yl 2-hydroxy-2,2-diphenylacetate;Tropine benzilate;BETE;BTE;Glykin;Tropine benzylate
• CAS NO: 3736-36-5
• Molecular Formula: C₂₂H₂₅NO₃
• Molecular Weight: 351.44
• EINECS: 1533716-785-6
• Mol File: 3736-36-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 152-153°
• Boiling Point: 444.7°Cat760mmHg
• Flash Point: 222.7°C
• Appearance: /
• Density: 1.23
• Vapor Pressure: 1.7E-11mmHg at 25°C
• Refractive Index: 1.611
• PKA: 11.29±0.29(Predicted)
• CAS DataBase Reference: Tropine benzilate(CAS DataBase Reference)
• NIST Chemistry Reference: Tropine benzilate(3736-36-5)
• EPA Substance Registry System: Tropine benzilate(3736-36-5)

Safety Data

• Hazardous Substances Data: 3736-36-5(Hazardous Substances Data)

Usage

General Description

Tropine benzilate is a chemical compound that falls under the category of anticholinergic drugs. It is a derivative of atropine and has similar pharmacological effects, including the inhibition of acetylcholine receptors in the nervous system. Tropine benzilate is primarily used as a smooth muscle relaxant and anti-neurotic agent, and it can also be used to treat gastrointestinal disorders, motion sickness, and muscle spasms. Additionally, this compound has been studied for its potential as a treatment for Parkinson's disease, due to its ability to modulate dopamine levels in the brain. However, it is important to note that tropine benzilate can have side effects, including dry mouth, blurred vision, and constipation, and should be used with caution under the guidance of a healthcare professional.

InChI:InChI=1/C22H25NO3/c1-23-19-10-11-20(23)14-16(13-19)15-6-5-9-18(12-15)22(26,21(24)25)17-7-3-2-4-8-17/h2-9,12,16,19-20,26H,10-11,13-14H2,1H3,(H,24,25)

Upstream product

• 134-81-6 benzil 
• 76-93-7 Benzilic acid 
• 76-89-1 methyl benzilate 
• 120-29-6 3-tropanol 
• 15441-11-9 Benzilic acid imidazolide 
• 52182-15-7 ethyl benzilate 

Downstream Products

• 21735-94-4 Tropinbenzilat-methiodid 
• 121707-49-1 3endo-benziloyloxy-8anti-heptyloxycarbonylmethyl-8syn-methyl-nortropanium; chloride 
• 123966-45-0 3endo-benziloyloxy-8anti-hexyloxycarbonylmethyl-8syn-methyl-nortropanium; bromide 
• 120855-51-8 3endo-benziloyloxy-8syn-methyl-8anti-octyloxycarbonylmethyl-nortropanium; chloride 
• 120856-60-2 3endo-benziloyloxy-8anti-decyl-8syn-methyl-nortropanium; bromide 
• 121970-57-8 3endo-benziloyloxy-8syn-methyl-8anti-nonyl-nortropanium; bromide 
• 124136-86-3 3endo-benziloyloxy-8syn-methyl-8anti-octyl-nortropanium; bromide 
• 74051-28-8 3endo-benziloyloxy-8anti-heptyl-8syn-methyl-nortropanium; bromide 

Relevant articles and documents

A 2 the hydroxy [...] ― 2,2 the the ― 3 α [...] diphenylgermanium acetic acid [...] (8 the [...] azabicyclo [3, 2, 1]) ― 3 the method for the preparation of octyl [...]

The invention discloses a method for preparing 2-hydroxy-2,2-diphenylacetic acid-3alpha-(8-aza-bicyclo(3,2,1))-3-trioctyl. The method comprises the following steps of: by taking dibenzoyl as a raw material, carrying out rearrangement on the raw material so as to obtain dihydroxy-phenylacetic acid; reacting dihydroxy-phenylacetic acid with dimethyl carbonate under the DBU catalysis and microwave actions so as to obtain methyl benzilate; reacting the methyl benzilate with tropine so as to obtain tropine benzilate; and carrying out N formylation and alcoholysis on the obtained tropine benzilate so as to obtain nor-tropine benzilate. Compared with the prior art, the total reaction time of the method disclosed by the invention is greatly reduced, the total yield is increased greatly, and the reaction condition is more simple, and therefore, the method is suitable for industrial production.

Synthesis, antimuscarinic activity and quantitative structure-activity relationship (QSAR) of tropinyl and piperidinyl esters

A series of tropinyl and piperidinyl esters was synthesized and evaluated for inhibitory activities on the endothelial muscarinic receptors of rat (M3) and rabbit (M2) aorta. Some of the esters (cyclohexylphenylglycolates and cyclohexylphenylpropionates) were found to be better antimuscarinic compounds than standard M2 and M3 inhibitors such as AFDX116 and 4-diphenylacetoxy-N-methylpiperidine (DAMP), with pKEC50 values in the range of 8-9. A few esters were found to be more selective M3 than M2 inhibitors, but these tended to have low activities. The hydrophobic, electronic and steric characteristics of these esters were correlated with antimuscarinic activity by using appropriate parameters representing hydrophobicity (HPLC capacity factor, log k(w), size (molecular volume) and electronic character (Taft's polar substituent constant δ and 13C chemical shift difference Δδ). Finally, 92% of the M2-inhibitory activities of the esters could be accounted for by the size and electronic character σ* of the side chain. In contrast, the M3-inhibitory activities of these esters were mainly attributed to the electronic nature (σ*, Δδ) of the side chain, with good activity being associated with electron-withdrawing groups. Visualization of the comparative molecular field analysis (CoMFA) steric and electrostatic fields provided further confirmation of the structure-activity relationship (SAR) derived from traditional quantitative structure-activity relationship (QSAR) approaches.