41100-45-2

Usage

Uses

Used in Pharmaceutical Industry:
3-Ethyladamantan-1-amine is used as an intermediate compound for the synthesis of various pharmaceuticals. Its adamantane-based structure and amine functionality make it a valuable building block for the development of new drugs with potential applications in treating neurological disorders, such as Parkinson's disease and Alzheimer's disease.
Used in Chemical Synthesis:
3-Ethyladamantan-1-amine can be used as a versatile starting material in the synthesis of a wide range of organic compounds. Its unique structure and functional groups can be further modified or reacted with other molecules to create new compounds with specific properties and applications in various industries, such as materials science, agrochemicals, and specialty chemicals.
Used in Research and Development:
Due to its unique structural features, 3-ethyladamantan-1-amine may be employed as a research tool in the study of molecular interactions, conformational analysis, and the development of new synthetic methodologies. It can also be used to investigate the effects of structural modifications on the properties and reactivity of adamantane-based compounds.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 25, p. 51, 1982 DOI: 10.1021/jm00343a010

InChI:InChI=1/C12H21N/c1-2-11-4-9-3-10(5-11)7-12(13,6-9)8-11/h9-10H,2-8,13H2,1H3

Upstream product

• 60931-65-9 N-acetyl-3-ethyl-1-aminoadamantane 
• 15598-87-5 3-ethyladamantane-1-ol 
• 26831-48-1 2-(adamantan-1-yl)ethyl-4-methylbenzenesulfonate 
• 878-61-5 1-Bromo-3-ethyladamantane 
• 770-69-4 1-ethyladamantane 
• 6240-11-5 2-(adamant-1-yl)ethanol 

Downstream Products

• 80121-67-1 3-ethyl-1-aminoadamantane hydrochloride 

Relevant academic research and scientific papers

PROCESS FOR PRODUCING 3-ETHYL-1-ADAMANTYLAMINE

PROBLEM TO BE SOLVED: To provide an industrially economical and efficient synthetic method of 3-ethyl-1-adamantylamine, which does not include a synthetic process of 1-bromo-3-ethyladamantane which uses harmful halogen and which, in a synthetic reaction of 1-amide-3-ethyladamantane, suppresses by-products and improves a yield by reducing amounts of use of an amide or an acid and a nitrile relative to adamantanes, and also remarkably reduces wastes derived from the amide or the acid and the nitrile. SOLUTION: A method for producing 3-ethyl-1-adamantylamine comprises the following steps (i) to (iii): (i) a step of obtaining a reaction mixture by reacting 3-ethyl-1-adamantanol with an acid and a nitrile in an organic solvent; (ii) a step of obtaining 1-amide-3-ethyladamantane by adding water to the reaction mixture obtained in the step (i); and (iii) a step of hydrolyzing 1-amide-3-ethyladamantane obtained in the step (ii) in the presence of an alcohol-containing solvent and an inorganic base. COPYRIGHT: (C)2015,JPO&INPIT

Novel treatment for alzheimer's disease

The present invention concerns a new pharmaceutical composition comprising an antagonist and a co-agonist of the N-methyl-D-aspartate-type glutamate receptor (NMDAR). The inventors found that the co-administration of these two compounds effectively inhibits production of amyloide-β peptide. In patient's suffering from Alzheimer's disease, these peptides are deposited in the extracellular matrix forming neuritic "plaques". Therefore, the present inventors identified a new possibility for prophylaxis and/or treatment of Alzheimer's disease by stopping the continued formation of neuropathological extracellular deposits.

METHODS OF TREATING CNS DISORDERS

The present invention relates to methods of treating various CNS disorders, e.g., mania, bipolar disorder and schizophrenia, by administering NMDA receptor antagonists, alone or in combination with dopamine receptor antagonists.

Pharmaceutical compositions comprising aminoadamantane derivatives

The present invention relates to pharmaceutical compositions comprising 1-aminoadamantane derivatives and a cyclodextrin, which compositions exhibit advantageous safety, convenience, and dosing characteristics. The compositions of the instant invention find particular application in the treatment of various diseases and conditions of the CNS, including those involving the impairment of cognitive function or dementia, such as Alzheimer's disease.

Combination therapy using 1-aminocyclohexane derivatives and acetylcholinesterase inhibitors

The invention relates to a novel drug combination therapy useful in the treatment of dementia comprising administering an 1-aminocyclohexane derivative such as memantine or neramexane and an acetylcholinesterase inhibitor (AChEI) such as galantamine, tacrine, donepezil, or rivastigmine.

NMDA receptor antagonists and their use in inhibiting abnormal hyperphosphorylation of microtubule associated protein tau

Aminocyclohexane and aminoalkylcyclohexane compounds, which are systemic-ally-active as NMDA receptor antagonists, are effective in inhibiting abnormal hyperphosphorylation of microtubule associated protein tau, method of treating disorders resulting from or associated with abnormal hyperphosphorylation of microtubule associated protein tau, and pharmaceutical compositions comprising the same.

Use of aminoadamantane compounds as immunoregulators

wherein R1, R2, R3 and R4 are selected independently from each other from —NR5R6, —NR5R6R7+, hydrogen, aryl or heteroaryl with up to 7 ring members, C1-C20-alkyl, C1-C20-alkenyl and C1-C20-alkinyl, wherein the alkyl, alkenyl and alkinyl residues can be branched, unbranched or cyclized and optionally substituted with halogen, aryl or heteroaryl with up to 7 ring members, with the proviso that at least one of the residues R1, R2, R3 and R4 are represented by —NR5R6 or —NR5R6R7; andR5, R6 and R7 are selected independently from each other from hydrogen, aryl or heteroaryl with up to 7 ring members, C1-C20-alkyl, C1-C20-alkenyl, C1-C20-alkinyl, wherein the alkyl, alkenyl and alkinyl residues can be branched, unbranched or cyclized and optionally substituted with halogen, aryl or heteroaryl with up to 7 ring members, or R5 and R6, together with the nitrogen atom, form a heterocyclic group with up to 7 ring members;for the regulation of the activity of already activated neutrophils.

Adamantane derivatives in the prevention and treatment of cerebral ischemia

A method for the prevention and treatment of cerebral ischemia using an adamantane derivative of the formula STR1 wherein R1 and R2 are identical or different, representing hydrogen or a straight or branched alkyl group of 1 to 6 C atoms or, in conjunction with N, a heterocyclic group with 5 or 6 ring C atoms; wherein R3 and R4 are identical or different, being selected from hydrogen, a straight or branched alkyl group of 1 to 6 C atoms, a cycloalkyl group with 5 or 6 C atoms, and phenyl; wherein R5 is hydrogen or a straight or branched C1 -C6 alkyl group, or a pharmaceutically-acceptable salt thereof, is disclosed.

Structure-Anti-Parkinson Activity Relationships in the Aminoadamantanes. Influence of Bridgehead Substitution

A limited series of bridgehead alkyl-, dialkyl- and trialkyl-substituted amantadines was synthesized and tested for potential anti-Parkinson activity as dopamine (DA) agonists.The compounds were evaluated using a battery of three murine bioassays, including stimulation of locomotor activity, induction of circling in animals with unilateral striatal lesions, and reversal of reserpine/α-methyltyrosine induced akinesia.Apparent mechanistic differences were seen between the methyl-substituted series and the ethyl-substituted series.While activities in both series increase with increasing liphophilicity, the methyl series (1b-d), as well as amantadine itself (1a) exhibits only indirect DA agonist activity, as evidenced by ipsilateral rotation in the circling model and no significant difference from control in reversal of akinesia.The ethyl series (1e,f) exhibits weak but reprodicible direct DA agonist activity, as shown by contralateral rotation in the circling assay for 1e and reversal of akinesia by 1e and 1f.The 3-n-propyl derivative (1g) was devoid of any DA agonist activity.