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

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

Uses

Used in Scientific Research:
8-Benzyl-3α-amino-1αH,5αH-nortropane is used as a research compound for studying biological systems and chemical interactions. Its unique structure and properties make it a valuable tool in understanding complex biochemical processes and mechanisms.
Used in Pharmaceutical Industry:
8-Benzyl-3α-amino-1αH,5αH-nortropane is utilized as a key intermediate in the synthesis of various pharmaceutical products. Its presence in the tropane class of compounds allows it to be a potential candidate for the development of new drugs, particularly those targeting the central nervous system.
Used in Drug Synthesis:
8-Benzyl-3α-amino-1αH,5αH-nortropane is employed as a building block in the creation of novel drug molecules. Its structural features enable chemists to modify and optimize its properties, leading to the development of more effective and safer medications.

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

• 91595-94-7 2-Amino-4-methoxy-pyrimidine-5-carboxylic acid ((1R,3R,5S)-8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amide 

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.

Development of a bulk enabling route to maraviroc (UK-427,857), a CCR-5 receptor antagonist

A bulk enabling synthesis of the CCR-5 receptor antagonist, Maraviroc (UK-427,857) (1), is presented. Synthesis of the three key fragments, β-amino ester 3,4,4-difluorohexanecarboxylic acid (2), and 1,3,4-triazole-substituted tropane fragment 4 are described. Coupling strategies for these fragments are discussed and described, including synthetic challenges, protection strategies, impurity generation, and final scale-up of the developed route to 1.

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.

Studies on the neuroleptic benzamides. III - Synthesis and antidopaminergic properties of new 3-nortropane derivatives

Various benzamides prepared from 4-alkoxy pyrimidine 5-carboxylic acids and 3-amino nortropane derivatives have been tested for their potential antipsychotic activity. Two compounds exhibited pharamacological activity equivalent to that of haloperidol but had lower toxicity and lower potency to induced catalepsy. Antidopaminergic activity is observed mainly in compounds in which the nortropane ring is substituted in the equatorial position, having a benzyl substituent on the basic nitrogen. The influence of electron attractor or donor substituents carried by the benzyl ring has been evaluated. Some aspects of structure-activity relationships are discussed.