3717-39-3

Usage

Uses

Used in Pharmaceutical Industry:
N-methyladamantan-1-amine is used as a medication for the treatment of Alzheimer's disease and other forms of dementia. It is employed to block the activity of certain receptors in the brain that are involved in learning and memory processes, helping to regulate the excessive activity of these receptors that can lead to the symptoms of dementia.
Used in Neurodegenerative Disorders:
N-methyladamantan-1-amine is used as a therapeutic agent to improve cognitive function and slow the progression of neurodegenerative disorders, such as Alzheimer's disease. Its ability to regulate the activity of NMDA receptors in the brain makes it a valuable option for individuals suffering from these conditions.

InChI:InChI=1/C11H19N.ClH/c1-12-11-5-8-2-9(6-11)4-10(3-8)7-11;/h8-10,12H,2-7H2,1H3;1H

Upstream product

• 3405-48-9 N-(1-adamantyl)formamide 
• 768-94-5 1-Adamantanamine 
• 67-56-1 methanol 
• 24886-73-5 1-Azidoadamantane 

Relevant academic research and scientific papers

Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources

A Ru(ii) complex mediated synthesis of various N,N-dimethyl and N-monomethyl amines from organic azides using methanol as a methylating agent is reported. This methodology was successfully applied for a one-pot reaction of bromide derivatives and sodium azide in methanol. Notably, by controlling the reaction time several N-monomethylated and N,N-dimethylated amines were synthesized selectively. The practical applicability of this tandem process was revealed by preparative scale reactions with different organic azides and synthesis of an anti-vertigo drug betahistine. Several kinetic experiments and DFT studies were carried out to understand the mechanism of this transformation.

Substituted 1-phenyl-2-cyclopropylmethylamines with high affinity and selectivity for sigma sites

A series of 1-phenyl-2-cyclopropylmethylamines structurally related to (+)- and (-)-MPCB were synthesized and their binding affinities for σ1, σ2, opioid and dopamine (D2) receptors were evaluated. Substitution of the cis-N-normetazocine with different aminic moieties provided compounds with high affinity and selectivity for σ binding sites with respect to opioid and dopamine (D2) receptors. The observed increase in σ2 affinity as compared to the parent (+)-MPCB, supports the idea that the particular stereochemistry of (+)-cis-N-normetazocine affects σ1 selectivity but does not affect σ1 affinity. The (±)-cis isomers of methyl 2-[(1-adamantylamino)methyl]-1-phenylcyclopropane-1-carboxylate (18) displayed a higher affinity and selectivity for the σ1 and σ2 receptor subtypes compared to the (±)-trans 19. Interestingly, the enantiomer (-)-cis 18 displayed a preference for σ1 receptor subtype whereas the (+)-cis 18 did for σ2. These results prompt us to synthesize compounds with modification of nitrogen and carboxyl groups. The compounds obtained showed high affinities and selectivity for σ sites. Moreover, modifications of carboxyl groups provided compounds with the highest affinities in the series. In particular, compound 25 with reverse-type ester showed a K(i) of 0.6 and 4.05nM for σ1 and σ2 binding sites, respectively. Copyright (C) 2000 Elsevier Science Ltd.