22235-81-0

Usage

Uses

Used in Pharmaceutical Industry:
endo-(±)-8-aza-8-isopropylbicyclo[3.2.1]oct-3-yl (hydroxymethyl)phenylacetate is used as an intermediate in the synthesis of various pharmaceutical compounds, including Ipratropium, a muscarinic antagonist used for treating conditions such as chronic obstructive pulmonary disease (COPD) and asthma. Its unique structure and functional groups contribute to the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
endo-(±)-8-aza-8-isopropylbicyclo[3.2.1]oct-3-yl (hydroxymethyl)phenylacetate is also utilized in chemical research for studying the synthesis and properties of complex organic molecules. Its unique structure and reactivity can provide insights into the development of new synthetic methods and the exploration of novel chemical reactions.

Biological Activity

n-isopropylnoratropine is a noratropine derivative and an intermediate in the production of ipratropium, an atropine-like bronchodilator drug via an anticholinergic pathway. n-isopropylnoratropine is used to examine the stability of ipratropium [1].muscarinic acetylcholine receptors are acetylcholine receptors that form g protein-receptor complexes in the cell membranes of certain neurons and other cells.n-isopropylnoratropine is an intermediate in the production of ipratropium and used to examine the stability of ipratropium. ipratropium exhibits broncholytic action by reducing the influence of cholinergic on the bronchial musculature. ipratropium blocks muscarinic acetylcholine receptors and therefore promotes the degradation of cgmp. ipratropium bromide (ib) is an anticholinergic bronchodilatory agent to treat chronic obstructive pulmonary disease. in anesthetized dogs, ipratropium with 0.01 and 0.1 mg/ml constricted the airways to 22 +/- 2% and 20 +/- 3% of control, respectively, whereas larger concentrations caused bronchodilation [2]. in moderate asthmatic patients, ipratropium bromide (ib) induced a significant shift of dose-response curve to inhalation of substance p (sp), suggesting that bronchoconstriction induced by sp could be attributed to a weak cholinergic activation [3].

references

[1]. kasawar gb, farooqui m. development and validation of a stability indicating rp-hplc method for the simultaneous determination of related substances of albuterol sulfate and ipratropium bromide in nasal solution. j pharm biomed anal. 2010 may 1;52(1):19-29.[2]. groeben h, brown rh. ipratropium decreases airway size in dogs by preferential m2 muscarinic receptor blockade in vivo. anesthesiology. 1996 oct;85(4):867-73.[3]. crimi n, palermo f, oliveri r, et al. influence of antihistamine (astemizole) and anticholinergic drugs (ipratropium bromide) on bronchoconstriction induced by substance p. ann allergy. 1990 aug;65(2):115-20.

InChI:InChI=1/C19H27NO3/c1-13(2)20-15-8-9-16(20)11-17(10-15)23-19(22)18(12-21)14-6-4-3-5-7-14/h3-7,13,15-18,21H,8-12H2,1-2H3

Upstream product

• 101-97-3 Ethyl 2-phenylethanoate 
• 3423-25-4 endo-8-(1-methylethyl)-8-azabicyclo<3.2.1>octan-3-ol 
• 14510-37-3 3-acetoxy-2-phenyl-propionyl chloride 
• 51-55-8 Atropine 
• 67-64-1 acetone 
• 16839-98-8 Noratropine 

Relevant academic research and scientific papers

Preparation method for ipratropium bromide

The invention relates to the technical fields of chemical engineering and pharmacy, in particular to a preparation method for ipratropium bromide. The preparation method comprises the following stepsof using N-isopropylnortropine or N-isopropyl tropine as the raw material, and respectively performing methylation reaction with iodomethane, so as to obtain an iodine-containing compound; performingdeiodination reaction on the iodine-containing compound by special metal oxide, metal salt or bromine, and performing follow-up treating, so as to obtain the ipratropium bromide. The preparation method has the advantages that the storage and use condition of the methylation reagent raw material is greatly reduced, so that the transportation and storage cost of the raw material is reduced; comparedwith the bromomethane, the iodomethane has stronger reaction activity, and the reaction conditions are milder, so that the usage amount of the methylation reagent in the methylation reaction is reduced; the safety, operability and reaction effect of the original technology are enhanced by the preparation method, and the requirement on equipment is reduced.

Preparation method of ipratropium bromide

The invention relates to a preparation method of an M-choline receptor blocking agent of ipratropium bromide 1. The preparation method comprises the following steps of using ethyl phenylacetate as starting raw materials; performing reaction with isopropyl tropanol; generating phenylacetate isopropyl tropeine; then, performing substitution, reduction and addition reaction to obtain the ipratropium bromide. The method has the advantages that the operation is simple; safety and controllability are realized; the work protection is low; the preparation method is suitable for industrial production. The formula is shown as the accompanying drawing, and the molecular weight is 412.36.

Synthesis of ipratropium bromide-related compounds

Synthesis of ipratropium bromide metabolites is described. Copyright Taylor & Francis Group, LLC.

Synthesis and radiolabelling of ipratropium and tiotropium for use as PET ligands in the study of inhaled drug deposition

Ipratropium bromide [(1R,3r,5S,8r,2′RS)-3-(3′-hydroxy-2′- phenylpropionyloxy)-8-isopropyl-8-methyl-8-aza-bicyclo[3.2.1]octan-8-ium bromide] and tiotropium bromide [(1R,2R,4S,5S,7s)-7-[2′-hydroxy-2′, 2′-di(thiophen2″-yl)acetoxy]-9,9-dimethyl-9-aza-3-oxatricyclo[3.3.1. 02,4]nonan-9-ium bromide] are inhaled drugs used in the treatment of chronic obstructive pulmonary disease (COPD) and asthma. Tertiary amine precursors have been synthesized and radiolabelled with carbon-11 by N-alkylation with [11C]CH3I. The [11C] ipratropium and [11C]tiotropium positron emission tomography (PET) ligands are obtained with high radiochemical purity, in 0.3 and 0.5% non-decay corrected yields based on [11C]CO2 at end-of-synthesis and specific activities of 11 and 18 GBq μ mol-1, respectively, calculated at end-of-synthesis. These PET radioligands can be used in the study of inhaled drug deposition. CSIRO 2006.