22235-81-0

Basic information

• Product Name: endo-(±)-8-aza-8-isopropylbicyclo[3.2.1]oct-3-yl (hydroxymethyl)phenylacetate
• Synonyms: endo-(±)-8-aza-8-isopropylbicyclo[3.2.1]oct-3-yl (hydroxymethyl)phenylacetate;N-Isopropylnoratropine;rac-(R*)-α-(Hydroxymethyl)benzeneacetic acid (1R,5S)-8-isopropyl-8-azabicyclo[3.2.1]octane-3α-yl ester;N-DesMethyl IpratropiuM;α-(HydroxyMethyl)benzeneacetic Acid (3-Endo)-8-(1-Methylethyl)-8-azabicyclo[3.2.1]- oct-3-yl Ester;α-(HydroxyMethyl)benzeneacetic Acid endo-8-(1-Methylethyl)-8- azabicyclo[3.2.1]oct-3-yl Ester;Ipratropium Impurity E
• CAS NO: 22235-81-0
• Molecular Formula: C₁₉H₂₇NO₃
• Molecular Weight: 317.42258
• EINECS: 244-859-1
• Product Categories: Aroamtics;Intermediates & Fine Chemicals;Pharmaceuticals;Aroamtics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 22235-81-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 112-114°C
• Boiling Point: 448.8°C at 760 mmHg
• Flash Point: 225.2°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 7.72E-09mmHg at 25°C
• Refractive Index: 1.567
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.12±0.10(Predicted)
• CAS DataBase Reference: endo-(±)-8-aza-8-isopropylbicyclo[3.2.1]oct-3-yl (hydroxymethyl)phenylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: endo-(±)-8-aza-8-isopropylbicyclo[3.2.1]oct-3-yl (hydroxymethyl)phenylacetate(22235-81-0)
• EPA Substance Registry System: endo-(±)-8-aza-8-isopropylbicyclo[3.2.1]oct-3-yl (hydroxymethyl)phenylacetate(22235-81-0)

Safety Data

• Hazardous Substances Data: 22235-81-0(Hazardous Substances Data)

Usage

Uses

N-Isopropyl Noratropine is a Noratropine derivative, an intermediate in the production of Ipratropium.

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 articles and documents

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.

Synthesis of ipratropium bromide-related compounds

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