16839-98-8

Basic information

• Product Name: Noratropine
• Synonyms: Noratropine;Benzeneacetic acid, alpha-(hydroxymethyl)-, (3-endo)-8-azabicyclo(3.2.1)oct-3-yl ester;Benzeneacetic acid, alpha-(hydroxymethyl)-, 8-azabicyclo(3.2.1)oct-3-yl ester, endo-(+-)-;1αH,5αH-Nortropan-3α-ol, (+/-)-Tropate Ester;N-DeMethylatropine;α-(HydroxyMethyl)benzeneacetic Acid (3-endo)-8-Azabicyclo[3.2.1]oct-3-yl Ester
• CAS NO: 16839-98-8
• Molecular Formula: C₁₆H₂₁NO₃
• Molecular Weight: 275.34284
• Product Categories: Aroamtics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 16839-98-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 113-114 °C
• Boiling Point: 440.2°Cat760mmHg
• Flash Point: 220°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 1.97E-09mmHg at 25°C
• Refractive Index: 1.583
• PKA: 14.12±0.10(Predicted)
• CAS DataBase Reference: Noratropine(CAS DataBase Reference)
• NIST Chemistry Reference: Noratropine(16839-98-8)
• EPA Substance Registry System: Noratropine(16839-98-8)

Safety Data

• Hazardous Substances Data: 16839-98-8(Hazardous Substances Data)

Usage

Uses

A metabolite of Atropine (A794625). Two metabolites of Atropine (apoatropine and noratropine) were found in rat urine.

InChI:InChI=1/C16H21NO3/c18-9-15(16(19)20)11-3-1-2-10(6-11)12-7-13-4-5-14(8-12)17-13/h1-3,6,12-15,17-18H,4-5,7-9H2,(H,19,20)

Upstream product

• 64-17-5 ethanol 
• 537-29-1 norhyoscyamine 
• 5908-99-6 atropine sulfate 
• 4574-60-1 atropine-N-oxide hydrochloride 
• 529-64-6 Tropic acid 
• 149423-39-2 tropoyl chloride 
• 14383-51-8 (endo)-8-Azabicyclo[3.2.1]octan-3-ol Hydrochloride 
• 51-55-8 Atropine 

Downstream Products

• 51-55-8 atropine 
• 51-55-8 Atropine 
• 119293-48-0 N-formyl-noratropine 
• 22235-81-0 (1R,3R,5S)-3'-hydroxy-2'-phenylpropionic acid 8-isopropyl-8-azabicyclo[3.2.1]oct-3-yl ester 

Relevant articles and documents

Preparation of noratropine by oxidative n-demethylation of atropine

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MEANS AND METHODS FOR THE N-DEALKYLATION OF AMINES

The invention relates to improved means and methods for N- dealkylation of alkylated amines. Provided is a method for the catalytic N- dealkylation of an N-alkylated amine substrate, comprising incubating said amine substrate in a suitable solvent in the

Studies on the oxidative N-demethylation of atropine, thebaine and oxycodone using a FeIII-TAML catalyst

The reaction pathway and selectivity of the oxidative N-demethylation of the alkaloid atropine with H2O2 using a Fe III-TAML catalyst has been investigated. The conversion of atropine in ethanol with aqueous H2O

Further investigation of the N-demethylation of tertiary amine alkaloids using the non-classical Polonovski reaction

The iron salt-mediated Polonovski reaction efficiently N-demethylates certain opiate alkaloids. In this process, the use of the hydrochloride salt of the tertiary N-methyl amine oxide was reported to give better yields of the desired N-demethylated product. Herein, we report further investigation into the use of N-oxide salts in the iron salt-mediated Polonovski reaction. An efficient approach for the removal of iron salts that greatly facilitates isolation and purification of the N-nor product is also described.