124257-62-1

Basic information

• Product Name: (1-Benzylpiperidin-3-yl)methanamine
• Synonyms: (1-Benzylpiperidin-3-yl)methanamine;1-(Phenylmethyl)-3-piperidinemethanamine;3-(Aminomethyl)-1-benzylpiperidine;1-(1-benzylpiperidin-3-yl)methanamine(SALTDATA: FREE)
• CAS NO: 124257-62-1
• Molecular Formula: C₁₃H₂₀N₂
• Molecular Weight: 204.31
• Mol File: 124257-62-1.mol

Chemical Properties

• Boiling Point: 303 °C
• Flash Point: 126 °C
• Appearance: /
• Density: 1.018
• Vapor Pressure: 0.00095mmHg at 25°C
• Refractive Index: 1.551
• CAS DataBase Reference: (1-Benzylpiperidin-3-yl)methanamine(CAS DataBase Reference)
• NIST Chemistry Reference: (1-Benzylpiperidin-3-yl)methanamine(124257-62-1)
• EPA Substance Registry System: (1-Benzylpiperidin-3-yl)methanamine(124257-62-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 124257-62-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1-Benzylpiperidin-3-yl)methanamine is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of drugs with potential therapeutic applications. Its structural properties allow for the creation of molecules that can interact with specific biological targets, making it valuable in medicinal chemistry.
Used in Research and Development:
In the realm of scientific research, (1-Benzylpiperidin-3-yl)methanamine serves as a subject of study for understanding its psychoactive effects. It is used as a model compound to investigate the mechanisms of action related to stimulant and anxiolytic activities, contributing to the advancement of knowledge in neurochemistry and psychopharmacology.
Used in Regulatory and Forensic Chemistry:
Due to its association with the production of designer drugs, (1-Benzylpiperidin-3-yl)methanamine is utilized in regulatory and forensic chemistry to monitor and control its distribution and use. Analytical methods are developed to detect and quantify this compound in samples, ensuring compliance with legal restrictions and preventing its misuse in illicit drug manufacturing.

InChI:InChI=1/C13H20N2/c14-9-13-7-4-8-15(11-13)10-12-5-2-1-3-6-12/h1-3,5-6,13H,4,7-11,14H2

Upstream product

• 170701-83-4 N-(1-benzylpiperidin-3-yl)methylacetamide 
• 100-44-7 benzyl chloride 
• 22977-34-0 N-(pyridin-3-ylmethyl)acetamide 
• 124257-64-3 3-<(acetylamino)methyl>-1-benzyltetrahydropyridin-3-ene 
• 4138-26-5 nipecotamide 
• 98-88-4 benzoyl chloride 
• 1378312-69-6 (±)-1-benzoylpiperidine-3-carboxamide 
• 23099-21-0 3-Aminomethylpiperidine 
• 100-52-7 benzaldehyde 
• 100-39-0 benzyl bromide 

Downstream Products

• 220031-61-8 tert-butyl (1-benzylpiperidin-3-yl)methylcarbamate 
• 142643-29-6 tert-butyl (piperidin-3-ylmethyl)carbamate 

Relevant articles and documents

Design, synthesis, and in vitro evaluation of hydroxybenzimidazole-donepezil analogues as multitarget-directed ligands for the treatment of Alzheimer's disease

A series of multi-target-directed ligands (MTDLs), obtained by attachment of a hydroxyphenylbenzimidazole (BIM) unit to donepezil (DNP) active mimetic moiety (benzylpiperidine /-piperazine) was designed, synthesized, and evaluated as potential anti-Alzheimer's disease (AD) drugs in terms of biological activity (inhibition of acetylcholinesterase (AChE) and β-amyloid (Aβ) aggregation), metal chelation, and neuroprotection capacity. Among the DNP-BIM hybrids studied herein, the structural isomerization did not significantly improve the biological properties, while some substitutions, namely fluorine atom in each moiety or the methoxy group in the benzyl ring, evidenced higher cholinergic AChE activity. All the compounds are able to chelate Cu and Zn metal ions through their bidentate BIM moieties, but compound 5, containing a three-dentate chelating unit, is the strongest Cu(II) chelator. Concerning the viability on neuroblastoma cells, compounds 9 and 10 displayed the highest reduction of Aβ-induced cell toxicity. In silico calculations of some pharmacokinetic descriptors indicate that all the compounds but the nitro derivatives have good potential oral-bioavailability. Overall, it can be concluded that most of the studied DNP-BIM conjugates showed quite good anti-AD properties, therefore deserving to be considered in further studies with the aim of understanding and treating AD.

The Magic of Crystal Structure-Based Inhibitor Optimization: Development of a Butyrylcholinesterase Inhibitor with Picomolar Affinity and in Vivo Activity

The enzymatic activity of butyrylcholinesterase (BChE) in the brain increases with the progression of Alzheimer's disease, thus classifying BChE as a promising drug target in advanced Alzheimer's disease. We used structure-based drug discovery approaches to develop potent, selective, and reversible human BChE inhibitors. The most potent, compound 3, had a picomolar inhibition constant versus BChE due to strong cation-π interactions, as revealed by the solved crystal structure of its complex with human BChE. Additionally, compound 3 inhibits BChE ex vivo and is noncytotoxic. In vitro pharmacokinetic experiments show that compound 3 is highly protein bound, highly permeable, and metabolically stable. Finally, compound 3 crosses the blood-brain barrier, and it improves memory, cognitive functions, and learning abilities of mice in a scopolamine model of dementia. Compound 3 is thus a promising advanced lead compound for the development of drugs for alleviating symptoms of cholinergic hypofunction in patients with advanced Alzheimer's disease.

N-Propargylpiperidines with naphthalene-2-carboxamide or naphthalene-2-sulfonamide moieties: Potential multifunctional anti-Alzheimer's agents

In the brains of patients with Alzheimer's disease, the enzymatic activities of butyrylcholinesterase (BChE) and monoamine oxidase B (MAO-B) are increased. While BChE is a viable therapeutic target for alleviation of symptoms caused by cholinergic hypofunction, MAO-B is a potential therapeutic target for prevention of neurodegeneration in Alzheimer's disease. Starting with piperidine-based selective human (h)BChE inhibitors and propargylamine-based MAO inhibitors, we have designed, synthesized and biochemically evaluated a series of N-propargylpiperidines. All of these compounds inhibited hBChE with good selectivity over the related enzyme, acetylcholinesterase, and crossed the blood-brain barrier in a parallel artificial membrane permeation assay. The crystal structure of one of the inhibitors (compound 3) in complex with hBChE revealed its binding mode. Three compounds (4, 5, 6) showed concomitant inhibition of MAO-B. Additionally, the most potent hBChE inhibitor 7 and dual BChE and MAO-B inhibitor 6 were non-cytotoxic and protected neuronal SH-SY5Y cells from toxic amyloid β-peptide species.

DISUBSTITUTED PIPERIDINE DERIVATIVES AS BUTYRYLCHOLINESTERASE INHIBITORS FOR USE IN THE TREATMENT OF ALZHEIMER

This invention relates to new inhibitors of butyrylcholinesterase with general formulas I and II, where substituents are described in patent description. Compounds can be in the form of pure enantiomers or as racemic mixtures, or in the form of pharmaceutically acceptable salts. The present invention relates to the use of these inhibitors for the treatment of Alzheimer's disease and other forms of dementia.

Design, synthesis, and characterization of novel, nonquaternary reactivators of GF-inhibited human acetylcholinesterase

The goal of this research was to identify structurally novel, non-quaternarypyridinium reactivators of GF (cyclosarin)-inhibited hAChE that possess the capacity to mediate in vitro reactivation of GF-inhibited human acetylcholinesterase (hAChE). New compounds were designed, synthesized and assessed in GF-inhibited hAChE assays. Structure activity relationships for AChE binding and reactivation of GF-inhibited hAChE were developed. Lead compounds from two different chemical series, represented by compounds 17 and 38, displayed proficient in vitro reactivation of GF-inhibited hAChE, while also possessing low inhibition of native enzyme.

Straightforward synthesis of orthogonally protected piperidin-3- ylmethanamine and piperidin-4-ylmethanamine derivatives

The 1,3- and 1,4-disubstituted piperidines are important building blocks in medicinal chemistry and drug discovery. We present the synthesis of orthogonally protected piperidin-3-ylmethanamine and piperidin-4-ylmethanamine derivatives from commercially available nipecotamide, isonipecotamide, nipecotic acid and isonipecotic acid. This is a straightforward two-step procedure that gives high overall yields. Purification of the intermediates using this procedure is not necessary, and the final compounds are purified by simple flash column chromatography.

Synthesis and structure-activity relationships of 4-amino-5-chloro-2- ethoxybenzamides with six- and seven-membered heteroalicycles as potential gastroprokinetic agents

A new series of 4-amino-5-chloro-2-ethoxybenzamides 3b-f and 5-8 bearing six- and seven-membered heteroalicycles was prepared and evaluated for gastroprokinetic activity. Compounds 3b-e, derived by replacement of the morpholine oxygen of 4-amino-N-[(4-benzyl-2-morpholinyl)methyl]-5-chloro-2- ethoxybenzamide (3a) with other atoms (sulfur, nitrogen and carbon), generally exhibited a potent gastric emptying activity. N-(4-Benzyl-3- morpholinyl)methylbenzamide (5a) and its analogues 5b-e had weaker activity. However, N-(4-benzyl-3-morpholinyl)ethylbenzamide 8 was as potent as 3a. Benzamides 6a-e, having seven-membered heteroalicycles, showed fairly potent activity. Molecular superimpositions of 5a, 6a and 8 upon 3a using computer graphics suggested that the direction of the N-benzyl group greatly influences the gastric emptying activity, whereas the location of the alicyclic nitrogen is less critical.