26482-53-1

Basic information

• Product Name: 1-C-ethylaminoadamantane
• Synonyms: 1-C-ethylaminoadamantane;2-(1-adamantyl)ethanamine;2-(1-adamantyl)ethanamine(SALTDATA: FREE);1-Adamantaneethylamine;Mrz 2/174;Tricyclo[3.3.1.1(3,7)]decane-1-ethanamine;2-(adamantan-1-yl)ethanamine;1-adamantaneethanamine
• CAS NO: 26482-53-1
• Molecular Formula: C₁₂H₂₁N
• Molecular Weight: 179.3
• Mol File: 26482-53-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 97-98℃ (2 Torr)
• Flash Point: 99.4±13.3℃
• Appearance: /
• Density: 1.021±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.0249mmHg at 25°C
• PKA: 10.94±0.10(Predicted)
• CAS DataBase Reference: 1-C-ethylaminoadamantane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-C-ethylaminoadamantane(26482-53-1)
• EPA Substance Registry System: 1-C-ethylaminoadamantane(26482-53-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 26482-53-1(Hazardous Substances Data)

Usage

General Description

1-C-Ethylaminoadamantane, also known as Amantadine, is a synthetic, tricyclic, antiviral agent primarily used for the prevention and treatment of certain strains of influenza. It is also utilized in the management of Parkinson's disease and other movement disorders. 1-C-ethylaminoadamantane is a derivative of adamantane and works by blocking the viral protein M2, preventing the virus from unpacking its genetic material once it's inside the host cell. Additionally, it has been proven to affect the production of dopamine, thus helping in the management of Parkinson's symptoms. While initially hailed for its efficacy, the chemical has seen reduced effectiveness due to increased resistance among some strains of influenza. Side effects include insomnia, dizziness, constipation, and in some cases, hallucinations and psychosis.

InChI:InChI=1/C12H21N/c13-2-1-12-6-9-3-10(7-12)5-11(4-9)8-12/h9-11H,1-8,13H2/p+1

Upstream product

• 16269-13-9 1-Carboxymethyladamantane nitrile 
• 26831-49-2 2-(adamantane-1-yl)ethyl azide 
• 36949-72-1 1-<2-(mesyloxy)ethyl>adamantane 
• 6240-11-5 2-(adamant-1-yl)ethanol 
• 773-37-5 1-(2-bromo-ethyl)-adamantane 
• 4942-47-6 (adamant-1-yl)-acetic acid 
• 19026-73-4 2-(1-adamantyl)acetamide 
• 19835-38-2 1-adamantylacetyl chloride 

Downstream Products

• 137795-78-9 (S)-4-(2-Adamantan-1-yl-ethylcarbamoyl)-4-benzyloxycarbonylamino-butyric acid benzyl ester 
• 137795-78-9 (R)-4-(2-Adamantan-1-yl-ethylcarbamoyl)-4-benzyloxycarbonylamino-butyric acid benzyl ester 
• 1192412-57-9 2-{[2-(1-adamantyl)ethyl]amino}-6-benzyl-5-methylpyrimidin-4(3H)-one 
• 312749-17-0 2-(adamantan-1-yl)-N-benzylethan-1-amine 
• 1557278-03-1 1-[2-(1-adamantyl)ethylamino]cyclohexanecarbonitrile 
• 1118763-20-4 3-(2-adamantan-1-ylethyl)-2-(3,4,5-trimethoxyphenyl)thiazolidin-4-one 
• 1118763-22-6 3-(2-adamantan-1-ylethyl)-2-(2,6-dichlorophenyl)thiazolidin-4-one 
• 1118763-27-1 3-(2-adamantan-1-ylethyl)-2-(2,6-difluorophenyl)thiazolidin-4-one 
• 137795-55-2 (R)-4-(2-Adamantan-1-yl-ethylcarbamoyl)-4-(3-chloro-benzoylamino)-butyric acid 
• 137795-63-2 (S)-4-(2-Adamantan-1-yl-ethylcarbamoyl)-4-(3-chloro-benzoylamino)-butyric acid 

Relevant articles and documents

Multiple Halogenation of Aliphatic C?H Bonds within the Hofmann–L?ffler Manifold

An innovative approach to position-selective polyhalogenation of aliphatic hydrocarbon bonds is presented. The reaction proceeded within the Hofmann-L?ffler manifold with amidyl radicals as the sole mediators to induce selective 1,5- and 1,6-hydrogen-atom transfer followed by halogenation. Multiple halogenation events of up to four innate C?H bond functionalizations were accomplished. The broad applicability of this new entry into polyhalogenation and the resulting synthetic possibilities were demonstrated for a total of 27 different examples including mixed halogenations.

Synthesis and anti-HIV studies of 2- and 3-adamantyl-substituted thiazolidin-4-ones

A series of novel thiazolidin-4-ones bearing a lipophilic adamantyl substituent at position 2 or 3 were synthesized. A majority of them showed a modest anti-HIV-1 activity, whereas 2-adamantan-1-yl-3-(4,6-dimethylpyrimidin-2-yl)-thiazolidin-4-one (8) was endowed with a remarkable antiviral potency (EC50 = 0.67 μM). The new series of compounds (22-29) with an adamantyl moiety at the 3-position of the thiazolidinone ring showed good to modest anti-HIV-1 activity (EC50 = 1.0-11 μM) but also pronounced cytostatic activity. For example 24, 26 and 29 showed an EC50 of 1.0-2.0 μM, while the 50% effective concentrations for 23 and 28 were 7.8 and 11.0 μM, respectively. X-ray studies and quantum chemical calculations revealed that the anti-HIV activity of the compounds strongly depends on their dipole moments and conformation of the thiazolidinones.

Tnf-alpha production inhibitors

A purpose of the present invention is to provide TNF-α production inhibitors being useful as therapeutic agents for autoimmune diseases such as rheumatoid arthritis. Novel compounds having the structure represented by the general formula [1] or salts ther