17768-41-1

Basic information

• Product Name: 1-Adamantanemethylamine
• Synonyms: 1-Adamantylmethanamine;Tricyclo[3.3.1.1(3,7)-]decane-1-methanamine;1-ADMA;1-ADAMANTYLMETHYLAMINE;1-AMINOMETHYLADAMANTANE;AKOS BC-0196;AKOS B014406;tricyclo(3.3.1.13,7)dec-1-ylmethylamine
• CAS NO: 17768-41-1
• Molecular Formula: C₁₁H₁₉N
• Molecular Weight: 165.28
• EINECS: 241-752-1
• Product Categories: Adamantane derivatives;Adamantanes
• Mol File: 17768-41-1.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 83-85 °C0.3 mm Hg(lit.)
• Flash Point: 198 °F
• Appearance: Colorless to pale yellow/Liquid
• Density: 0.933 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0697mmHg at 25°C
• Refractive Index: n20/D 1.5137(lit.)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 10.71±0.29(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: 1-Adamantanemethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Adamantanemethylamine(17768-41-1)
• EPA Substance Registry System: 1-Adamantanemethylamine(17768-41-1)

Safety Data

• Hazard Codes: Xi,C
• Statements: 34
• Safety Statements: 24/25-45-36/37/39-27-26
• RIDADR: UN 2735
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 17768-41-1(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless to very slightly yellow liquid

General Description

1-Adamantanemethylamine is a large amine present on the wall of 6,7-diaminoquinoxaline. The thermodynamic complex formation constant of 1-adamantanemethylamine was studied.

Purification Methods

Dissolve the amine in Et2O, dry over KOH and distil it. The N-Tosyl derivative has m 134-135o (from EtOH). [Stetter & Goebel Chem Ber 96 550 1963.]

InChI:InChI=1/C11H19N/c12-7-11-4-8-1-9(5-11)3-10(2-8)6-11/h8-10H,1-7,12H2/p+1

Upstream product

• 4942-47-6 (adamant-1-yl)-acetic acid 
• 170952-87-1 N-hydroxyiminomethyl 1-adamantanecarboxylate 
• 2094-72-6 1-Adamantanecarbonyl chloride 
• 23074-42-2 1-adamantanecarbonitrile 
• 828-51-3 1-Adamantanecarboxylic acid 
• 5511-18-2 adamantane-1-carboxamide 
• 313231-15-1 N-(adamantan-1-ylmethyl)phthalimide 
• 768-95-6 1-adamanthanol 
• 768-90-1 1-Adamantyl bromide 
• 123933-30-2 O-methyl adamantane-1-carbothioate 
• 711-01-3 methyl adamantane-1-carboxylate 

Downstream Products

• 65738-69-4 2-<<(1-adamantyl)methyl>amino>ethanol 
• 97508-78-6 N-(1-adamantylmethyl)cyclohexylideneamine 
• 118202-61-2 N-(1-Adamantylmethyl)-2-phenylisopropylamine 
• 1027664-33-0 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-benzofuran-5-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid diallyl ester 
• 1026292-72-7 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-benzo[b]thiophene-5-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid di-tert-butyl ester 
• 338450-87-6 5-[(S)-2-({5-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-indole-6-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid dibenzyl ester 
• 167992-88-3 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-indole-5-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid dibenzyl ester 
• 1026556-36-4 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-indole-5-carbonyl}-amino)-3-(2-fluoro-phenyl)-propionylamino]-isophthalic acid dibenzyl ester 
• 1027934-40-2 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-benzoimidazole-5-carbonyl}-amino)-3-(4-hydroxy-phenyl)-propionylamino]-isophthalic acid dibenzyl ester 
• 1026318-99-9 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-benzoimidazole-5-carbonyl}-amino)-3-(2-fluoro-phenyl)-propionylamino]-isophthalic acid dibenzyl ester 
• 1026901-39-2 2,2-Dimethyl-propionic acid 5-{3-[(S)-2-({6-[(adamantan-1-ylmethyl)-carbamoyl]-1H-indole-5-carbonyl}-amino)-3-phenyl-propionylamino]-5-[1-(2,2-dimethyl-propionyloxymethyl)-1H-tetrazol-5-yl]-phenyl}-tetrazol-1-ylmethyl ester 
• 167992-94-1 2,2-Dimethyl-propionic acid 5-{3-[(S)-2-({6-[(adamantan-1-ylmethyl)-carbamoyl]-1H-benzoimidazole-5-carbonyl}-amino)-3-phenyl-propionylamino]-5-[1-(2,2-dimethyl-propionyloxymethyl)-1H-tetrazol-5-yl]-phenyl}-tetrazol-1-ylmethyl ester 
• 178896-45-2 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-indole-5-carbonyl}-amino)-3-(4-iodo-phenyl)-propionylamino]-isophthalic acid dibenzyl ester 
• 192133-97-4 5-[[[[3,5-bis(benzyloxycarbonyl)phenyl]amino]carbonyl]-[3-(1,2,3,4-tetrahydroisoquinolino)carbonyl]]-6-[[(1-adamantanemethyl)amino]carbonyl]benzimidasole 

Relevant articles and documents

Design, Synthesis, and in vitro Evaluation of P2X7 Antagonists

The P2X7 receptor is a promising target for the treatment of various diseases due to its significant role in inflammation and immune cell signaling. This work describes the design, synthesis, and in vitro evaluation of a series of novel derivatives bearing diverse scaffolds as potent P2X7 antagonists. Our approach was based on structural modifications of reported (adamantan-1-yl)methylbenzamides able to inhibit the receptor activation. The adamantane moieties and the amide bond were replaced, and the replacements were evaluated by a ligand-based pharmacophore model. The antagonistic potency of the synthesized analogues was assessed by two-electrode voltage clamp experiments, using Xenopus laevis oocytes that express the human P2X7 receptor. SAR studies suggested that the replacement of the adamantane ring by an aryl-cyclohexyl moiety afforded the most potent antagonists against the activation of the P2X7 cation channel, with analogue 2-chloro-N-[1-(3-(nitrooxymethyl)phenyl)cyclohexyl)methyl]benzamide (56) exhibiting the best potency with an IC50 value of 0.39 μΜ.

Continuous-Flow Hydrogenation and Reductive Deuteration of Nitriles: a Simple Access to α,α-Dideutero Amines

A simple and efficient continuous flow methodology has been developed for hydrogenation and reductive deuteration of nitriles to yield primary amines and also valuable α,α-dideutero analogues. Raney nickel proved to be a useful catalyst for the transformation of a wide range of nitriles under reasonably mild conditions with excellent deuterium incorporation (>90 %) and quantitative conversion. Among known model compounds, three new deuterated primary amines were prepared. The large-scale synthesis of deuterated tryptamine was also carried out to deliver 1.1 g product under flow conditions.

The role of polycyclic frameworks in modulating P2X7 receptor function

Herein we describe our recent attempts to target the P2X7 receptor for potential treatment of neurological disorders. This work focusses on different polycycles including carborane, adamantane or cubane, joined by either a cyanoguanidine or an amide linker to phenyl or isoquinoline moieties. We have demonstrated the superiority of the adamantyl moiety over other polycycles in terms of synthetic accessibility and biological (cellular) activity. We have also shown that an amide or cyanoguanidine linker can greatly alter the biological activity of compounds. This SAR study provides important insights into the types of functionality required to target the P2X7 receptor.