28957-72-4

Basic information

• Product Name: N-Benzyltropinone
• Synonyms: 3-BENZYL-3,8-DIAZABICYCLO[3.2.1]OCTANE;3-benzyl-3-azedicyclo(3,2,1)octan-8-one;8-Benzyl-8-azabicyclo[3.2.1]octane-3-one;N-Benzyl-3-nortropinone;N-Benzyltropinone,96%;8-Benzyl-8-azabicyclo[3.2...;8-Benzyl-1αH,5αH-nortropan-3-one;8-Benzyl-3-nortropanone
• CAS NO: 28957-72-4
• Molecular Formula: C₁₄H₁₇NO
• Molecular Weight: 215.29
• EINECS: 249-329-3
• Product Categories: pharmacetical;Heterocycle;Various Intermediates;Intermediates;Miscellaneous Reagents;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Heterocycles series
• Mol File: 28957-72-4.mol
• Article Data: 61

Chemical Properties

• Melting Point: 28-29°C
• Boiling Point: 134-137°C/0.4 mm
• Flash Point: 151 °C
• Appearance: off-white to pale yellow low-melting solid
• Density: 1.14 g/cm³
• Vapor Pressure: 7.27E-05mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Dichloromethane, Methanol
• PKA: 7.98±0.20(Predicted)
• CAS DataBase Reference: N-Benzyltropinone(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzyltropinone(28957-72-4)
• EPA Substance Registry System: N-Benzyltropinone(28957-72-4)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 23-26-36/37/39-45
• RIDADR: UN1760
• Hazardous Substances Data: 28957-72-4(Hazardous Substances Data)

Usage

Description

N-Benzyltropinone is an off-white to pale yellow low-melting solid that serves as an intermediate in the synthesis of various pharmaceutical compounds. It is a crucial component in the preparation of drugs targeting specific receptors in the body, such as β-Cocaine, opioid receptor antagonists, and CCR-5 receptor antagonists.

Uses

Used in Pharmaceutical Industry:
N-Benzyltropinone is used as an intermediate for the synthesis of [β-Cocaine, opioid receptor antagonists, and CCR-5 receptor antagonists] for [their potential applications in treating various medical conditions and addressing specific receptor-related issues].
The specific applications and reasons for using N-Benzyltropinone in the pharmaceutical industry are as follows:
1. As an intermediate for β-Cocaine synthesis:
N-Benzyltropinone is used for the preparation of β-Cocaine, a compound with potential applications in the medical field. Its synthesis involves the use of N-Benzyltropinone as a key component, highlighting its importance in the development of this drug.
2. As an intermediate for opioid receptor antagonists:
N-Benzyltropinone plays a vital role in the synthesis of opioid receptor antagonists, which are drugs that block the effects of opioids in the body. These antagonists are crucial in the treatment of opioid addiction and overdose, as well as in managing chronic pain without the risk of addiction.
3. As an intermediate for CCR-5 receptor antagonists:
N-Benzyltropinone is also used in the preparation of CCR-5 receptor antagonists, which are drugs that inhibit the action of the CCR-5 receptor. These antagonists have potential applications in the treatment of various diseases, including HIV, multiple sclerosis, and certain types of cancer, by modulating the immune system's response.

InChI:InChI=1/C14H17NO/c16-14-8-12-6-7-13(9-14)15(12)10-11-4-2-1-3-5-11/h1-5,12-13H,6-10H2

Upstream product

• 638-37-9 butanedial 
• 3287-99-8 benzylamine hydrochloride 
• 105-50-0 diethyl 1,3-acetonedicarboxylate 
• 6690-08-0 8,8-dimethyl-3-oxo-8-azonia-bicyclo[3.2.1]octane iodide 
• 100-46-9 benzylamine 
• 542-05-2 acetonedicarboxylic acid 
• 133200-67-6 2,5-dihydroxy-tetrahydrofuran 
• 50893-53-3 carbonochloridic acid 1-chloro-ethyl ester 
• 100-39-0 benzyl bromide 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 532-24-1 tropinone 
• 24424-99-5 di-tert-butyl dicarbonate 
• 560-27-0 dihydroxymalonic acid 
• 473-90-5 acetonedicarboxylic acid 

Downstream Products

• 102463-22-9 N,N-diethyl-N'-(8-benzyl-nortropane-3endo-yl)-ethylenediamine 
• 142838-94-6 (1R,3S,5S)-3-Amino-8-benzyl-8-aza-bicyclo[3.2.1]octane-3-carbonitrile 
• 83393-30-0 (1S,3R,5R)-8-Benzyl-3-(3-trifluoromethyl-phenyl)-8-aza-bicyclo[3.2.1]octan-3-ol 
• 473968-94-4 (1S,3R,5R)-8-Benzyl-3-naphthalen-2-yl-8-aza-bicyclo[3.2.1]octan-3-ol 
• 473969-01-6 (1S,3R,5R)-3-Benzo[b]thiophen-3-yl-8-benzyl-8-aza-bicyclo[3.2.1]octan-3-ol 
• 83393-26-4 8-benzyl-3-phenyl-8-aza-bicyclo[3.2.1]octan-3-ol 
• 473969-11-8 8-benzyl-3-(2-methoxy-phenyl)-8-aza-bicyclo[3.2.1]octan-3-ol 
• 185099-67-6 Boc-tropinone 
• 474534-35-5 8-benzyl-3-naphthalen-2-yl-8-aza-bicyclo[3.2.1]octan-3-ol 
• 185985-38-0 8-benzyl-8-azabicyclo[3.2.1]octane-3-carbonitrile 
• 143557-91-9 (1R,3S,5S)-tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate 
• 79521-68-9 methyl 8-benzyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate 
• 1181265-86-0 8-benzyl-3-(4-fluoro-phenyl)-8-aza-bicyclo[3.2.1]octan-3-ol 
• 949902-02-7 trifluoro-methanesulfonic acid 8-benzyl-8-aza-bicyclo[3.2.1]oct-2-en-3-yl ester 

Relevant articles and documents

Synthesis and biological investigation of new equatorial (β) stereoisomers of 3-aminotropane arylamides with atypical antipsychotic profile

A series of novel 3β-aminotropane derivatives containing a 2-naphthalene or a 2-quinoline moiety was synthesised and evaluated for their affinity for 5-HT1A, 5-HT2Aand D2receptors. Their affinity for the receptors was in the nanomolar to micromolar range. p-Substitution (6c, 6f, 6i, 6l, 6o), as well as substitution with chlorine atoms (6g, 6h, 6i), led to a significant increase in binding affinity for D2receptors with compounds 6f (Ki?=?0.6?nM), 6c and 6i (Ki?=?0.4?nM), having the highest binding affinities. m-Substituted derivatives were the most promising ligands in terms of 5-HT2Areceptor binding affinity whereas 2-quinoline derivatives (10a, 10b) displayed the highest affinity for 5-HT1AR and were the most selective ligands with Ki?=?62.7?nM and Ki?=?30.5?nM, respectively. Finally, the selected ligands 6b, 6d, 6e, 6g, 6h, 6k, 6n and 6o, with triple binding activity for the D2, 5-HT1Aand 5-HT2Areceptors, were subjected to in vivo tests, such as those for induced hypothermia, climbing behaviour and the head twitch response, in order to determine their pharmacological profile. The tested ligands presented neither agonist nor antagonist properties for the 5-HT1Areceptors in the induced hypothermia and lower lip retraction (LLR) tests. All tested compounds displayed antagonistic activity against 5-HT2A, with 6n and 6o being the most active. Four (6b, 6k, 6n and 6o) out of eight tested compounds could be classified as D2antagonists. Additionally, evaluation of metabolic stability was performed for selected ligands, and introduction of halogen atoms into the benzene ring of 6h, 6k, 6n and 6o improved their metabolic stability. The project resulted in the selection of the lead compounds 6n and 6o, which had antipsychotic profiles, combining dopamine D2-receptor and 5-HT2Aantagonism and metabolic stability.

Synthesis and biological investigations of 3β-aminotropane arylamide derivatives with atypical antipsychotic profile

This work is a continuation of our previous research, concentrating this time on lead structure modification to increase the 5-HT1A receptor affinity and water solubility of designed compounds. Therefore, the compounds synthesised within the present project included structural analogues of 3β-acylamine derivatives of tropane with the introduction of a methyl substituent in the benzyl ring and a 2-quinoline, 3-quinoline, or 6-quinoline moiety. A series of novel 3β-aminotropane derivatives was evaluated for their affinity for 5-HT1A, 5-HT2A, and D2 receptors, which allowed for the identification of compounds 12e, 12i, and 19a as ligands with highest affinity for the tested receptors; they were then subjected to further evaluation in preliminary in vivo studies. Selected compounds 12i and 19a displayed antipsychotic properties in the d-amphetamine-induced and MK-801-induced hyperlocomotor activity test in mice. Moreover, compound 19a showed significant antidepressant-like activity in the forced swim test in mice.

3-aryl azabicyclo derivative as well as preparation and application thereof in nematode killing

The invention relates to preparation of a 3-aryl azabicyclo derivative and application of the derivative in nematode killing. Specifically, the invention discloses application of a compound with a structure as shown in a formula (I) or a composition, an optical isomer, a cis-trans-isomer and an agricultural pharmacologically acceptable salt of the compound in the field of nematode killing.

Structure-Based Design and Development of Chemical Probes Targeting Putative MOR-CCR5 Heterodimers to Inhibit Opioid Exacerbated HIV-1 Infectivity

Crystal structures of ligand-bound G-protein-coupled receptors provide tangible templates for rationally designing molecular probes. Herein, we report the structure-based design, chemical synthesis, and biological investigations of bivalent ligands targeting putative mu opioid receptor C-C motif chemokine ligand 5 (MOR-CCR5) heterodimers. The bivalent ligand VZMC013 possessed nanomolar level binding affinities for both the MOR and CCR5, inhibited CCL5-stimulated calcium mobilization, and remarkably improved anti-HIV-1BaL activity over previously reported bivalent ligands. VZMC013 inhibited viral infection in TZM-bl cells coexpressing CCR5 and MOR to a greater degree than cells expressing CCR5 alone. Furthermore, VZMC013 blocked human immunodeficiency virus (HIV)-1 entry in peripheral blood mononuclear cells (PBMC) cells in a concentration-dependent manner and inhibited opioid-accelerated HIV-1 entry more effectively in phytohemagglutinin-stimulated PBMC cells than in the absence of opioids. A three-dimensional molecular model of VZMC013 binding to the MOR-CCR5 heterodimer complex is constructed to elucidate its mechanism of action. VZMC013 is a potent chemical probe targeting MOR-CCR5 heterodimers and may serve as a pharmacological agent to inhibit opioid-exacerbated HIV-1 entry.