76272-35-0

Basic information

• Product Name: 8-Benzyl-3α-amino-1αH,5αH-nortropane
• Synonyms: 8-Benzyl-3α-amino-1αH,5αH-nortropane;8-(phenylmethyl)-,endo-,3-AMINO-8-BENZYL-8-AZABICYCLO[3.2.1]OCTANE (3-ENDO)-,8-BENZYL-3A-AMINO-1AH,5AH-NORTROPANE;8-Azabicyclo[3.2.1]octan-3-amine;3-AMINO-8-BENZYL-8-AZABICYCLO[3.2.1]OCTANE (3-ENDO)-;8-Azabicyclo[3.2.1]octan-3-amine, 8-(phenylmethyl)-,endo-;8-Benzyl-3a-amino-1aH,5aH-nortropane;8-Benzyl-8-azabicyclo[3.2.1]octan-3-endo-amine;8-benzyl-8-azabicyclo[3.2.1]octan-3-amine
• CAS NO: 76272-35-0
• Molecular Formula: C₁₄H₂₀N₂
• Molecular Weight: 216.326
• Product Categories: Heterocycles series;API intermediates
• Mol File: 76272-35-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 317.1 °C at 760 mmHg
• Flash Point: 133.4 °C
• Appearance: /
• Density: 1.082 g/cm³
• Vapor Pressure: 0.000393mmHg at 25°C
• Refractive Index: 1.581
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.23±0.20(Predicted)
• CAS DataBase Reference: 8-Benzyl-3α-amino-1αH,5αH-nortropane(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Benzyl-3α-amino-1αH,5αH-nortropane(76272-35-0)
• EPA Substance Registry System: 8-Benzyl-3α-amino-1αH,5αH-nortropane(76272-35-0)

Safety Data

• Hazardous Substances Data: 76272-35-0(Hazardous Substances Data)

Usage

General Description

8-Benzyl-3α-amino-1αH,5αH-nortropane is a chemical compound that belongs to the class of organic compounds known as tropanes. Tropanes are compounds containing the tropane moiety, which is a bicyclic system made up of a seven-membered ring fused to a five membered nitrogen-containing ring. 8-Benzyl-3α-amino-1αH,5αH-nortropane is used in scientific research and is often used in the study of biological systems, chemical interactions, and in the pharmaceutical industry. Its structure includes an array of elements including carbon, hydrogen, and nitrogen.

InChI:InChI=1/C14H20N2/c15-12-8-13-6-7-14(9-12)16(13)10-11-4-2-1-3-5-11/h1-5,12-14H,6-10,15H2

Upstream product

• 5632-84-8 8-azabicyclo[3.2.1]octan-3-one 
• 100-39-0 benzyl bromide 
• 76272-34-9 8-Benzyl-1αH,5αH-nortropan-3-one Oxime 
• 1415560-32-5 N-benzyl-3-α-aminonortropane dihydrochloride 
• 28957-72-4 N-benzylnortropinone 
• 56880-18-3 (1R,3R,5S)-8-Benzyl-3-chloro-8-aza-bicyclo[3.2.1]octane 

Downstream Products

• 123259-13-2 N-(endo-8-phenylmethyl-8-azabicyclo[3.2.1]oct-3-yl)-2,3-dihydro-2-oxo-1H-benzimidazole-1-carboxamide 

Relevant articles and documents

Structure-Based Design of 1-Heteroaryl-1,3-propanediamine Derivatives as a Novel Series of CC-Chemokine Receptor 5 Antagonists

CC-chemokine receptor 5 (CCR5) is an attractive target for preventing the entry of human immunodeficiency virus 1 (HIV-1) into human host cells. Maraviroc is the only CCR5 antagonist, and it was marketed in 2007. To overcome the shortcomings of maraviroc, structure-based drug design was performed to minimize CYP450 inhibition and to enhance anti-HIV potency and bioavailability. Thirty-four novel 1-heteroaryl-1,3-propanediamine derivatives (1-34) were synthesized, displaying CCR5-antagonist activities in the 2.3-296.4 nM range. Among these, compounds 21 and 34 were the most potent CCR5 antagonists, with excellent in vitro anti-HIV-1 activity, low cytotoxicity, and an acceptable pharmacokinetic profile. Furthermore, the X-ray crystal structures of compounds 21 and 34 bound to CCR5 were determined at 2.8 ? resolution. Compound 34 exhibited no CYP450-inhibition activity at 25 μM, which overcomes the potential drug-drug interaction of maraviroc. Compound 34 represents a promising drug candidate for HIV-infection treatment.

METHOD FOR PRODUCING N-SUBSTITUTED 3β-AMINONORTROPANES

The invention relates to a method for producing, on the basis of the corresponding 3-oxonortropane or the corresponding 3α-aminonortropane, N-substituted 3β-aminonortropanes of formula (I), wherein R1 is defined as in the claim. According to the inventive method, the starting compounds are converted to the corresponding imines by means of an arylmethylamine or an arylaldehyde, said imines are tautomerized or isomerized and then hydrolyzed. The invention also relates to the novel compounds of formula (V), wherein R1 and Ar are defined as in the claims.

Isomeric tropane analogues of histamine H2-receptor antagonists

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