88915-26-8

Basic information

• Product Name: (1-Benzyl-4-piperidinyl)methylamine
• Synonyms: 4-PIPERIDINEMETHANAMINE, 1-(PHENYLMETHYL)-;4-AMINOMETHYL-1-BENZYLPIPERIDINE;AKOS B029940;1-BENZYL-PIPERIDIN-4-METHYLAMINE;[(1-BENZYLPIPERIDIN-4-YL)METHYL]AMINE;(1-BENZYL-4-PIPERIDINYL)METHYLAMINE;CHEMBRDG-BB 4009650;C-(1-BENZYL-PIPERIDIN-4-YL)-METHYLAMINE
• CAS NO: 88915-26-8
• Molecular Formula: C₁₃H₂₀N₂
• Molecular Weight: 204.31
• Product Categories: pharmacetical
• Mol File: 88915-26-8.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 125 °C
• Flash Point: 126.4°C
• Appearance: /
• Density: 1.018±0.06 g/cm3(Predicted)
• Vapor Pressure: 0.00095mmHg at 25°C
• PKA: 10.13±0.29(Predicted)
• CAS DataBase Reference: (1-Benzyl-4-piperidinyl)methylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (1-Benzyl-4-piperidinyl)methylamine(88915-26-8)
• EPA Substance Registry System: (1-Benzyl-4-piperidinyl)methylamine(88915-26-8)

Safety Data

• Hazard Codes: Xi,C
• Statements: 34-36/37/38-21/22
• Safety Statements: 26-36/37/39-45-23
• RIDADR: 3261
• HazardClass: IRRITANT
• Hazardous Substances Data: 88915-26-8(Hazardous Substances Data)

Usage

General Description

(1-Benzyl-4-piperidinyl)methylamine, also known as N-Benzylpiperidin-4-ylmethylamine, is a chemical compound with the molecular formula C15H22N2. It is a tertiary amine, which means it contains a nitrogen atom bonded to three carbon atoms. (1-Benzyl-4-piperidinyl)methylamine is often used in medicinal chemistry as a building block for the synthesis of various pharmaceuticals and research chemicals. It is also a common precursor in the synthesis of psychoactive substances, including certain designer drugs and controlled substances. The compound's structure contains a benzene ring and a piperidine ring, which contribute to its pharmacological and psychoactive properties. Due to its potential for abuse and diversion into illegal recreational drugs, (1-Benzyl-4-piperidinyl)methylamine is regulated in many countries and closely monitored by law enforcement and regulatory agencies.

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

Upstream product

• 98-88-4 benzoyl chloride 
• 5274-99-7 1-benzoylisonipecotic acid 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 498-94-2 isonipecotic acid 
• 10315-06-7 1-benzylpiperidine-4-carboxylic acid methyl ester 
• 10315-07-8 N-benzylpiperidine-4-carboxylic acid 
• 173340-23-3 tert-butyl ((1-benzylpiperidin-4-yl)methyl)carbamate 
• 135632-53-0 tert-butyl N-(4-piperidinylmethyl)carbamate 
• 7462-86-4 methyl piperidine-4-carboxylate hydrochloride 
• 153747-01-4 4-(phthalimidomethyl)piperidine 
• 62718-31-4 1-benzylpiperidine-4-carbonitrile 
• 39546-32-2 4-carboxamidopiperidine 
• 71207-29-9 N-hexahydro-4-pyridinylmethyl-N-phenylmethylidenamine 

Downstream Products

• 304905-25-7 naphthalene-1-carboxylic acid (1-benzyl-piperidin-4-ylmethyl)-amide 
• 757236-90-1 2-amino-N-(1-benzyl-piperidin-4-ylmethyl)-acetamide 
• 857650-87-4 N-[[1-(benzyl)-4-piperidinyl]methyl]-1,4-benzodioxane-5-carboxamide 
• 152811-86-4 3,4-dihydro-N-[[1-(phenylmethyl)-4-piperidinyl]methyl]-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide 
• 167753-25-5 3-(1-benzylpiperidin-4-yl)methyl-4-phenyl-3,4-dihydro-2(1H)-quinazolinone 
• 1073635-63-8 (1-benzyl-piperidin-4-yl)-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amine 

Relevant articles and documents

Donepezil-butylated hydroxytoluene (BHT) hybrids as Anti-Alzheimer's disease agents with cholinergic, antioxidant, and neuroprotective properties

The multifactorial nature of Alzheimer's disease (AD) calls for the development of multitarget agents addressing key pathogenic processes. A novel family of donepezil-butylated hydroxytoluene (BHT) hybrids were designed, synthesized and evaluated as multifunctional ligands against AD. The optimal compound 7d displayed a balanced multifunctional profile covering an intriguing acetylcholinesterase (AChE) inhibition (IC50, 0.075 μM for eeAChE and 0.75 μM for hAChE) and Monoamine oxidase B (MAO-B) inhibition (IC50, 7.4 μM for hMAO-B), excellent antioxidant activity (71.7 μM of IC50 by DPPH method, 0.82 and 1.62 trolox equivalent by ABTS method and ORAC method respectively), and inhibitory effects on self-induced, hAChE-induced Aβ aggregation. Moreover, 7d possessed neuroprotective potency against H2O2-induced oxidative damage on PC12 cells and Lipopolysaccharides (LPS)-stimulated inflammation on BV2 cells. Compound 7d was capable of penetrating BBB and presented good liver microsomal metabolic stability. Importantly, compound 7d could dose-dependently reverse scopolamine-induced memory deficit in mice without acute toxicity. Taken together, those outstanding results highlight the donepezil-BHT hybrid 7d as a promising prototype in the research of innovative compound for AD.

Discovery and Biological Evaluation of N-Methyl-pyrrolo[2,3- b]pyridine-5-carboxamide Derivatives as JAK1-Selective Inhibitors

Janus kinase 1 (JAK1) plays a key role in most cytokine-mediated inflammatory and autoimmune responses through JAK/STAT signaling; thus, JAK1 inhibition is a promising therapeutic strategy for several diseases. Analysis of the binding modes of current JAK inhibitors to JAK isoforms allowed the design of N-alkyl-substituted 1-H-pyrrolo[2,3-b] pyridine carboxamide as a JAK1-selective scaffold, and the synthesis of various methyl amide derivatives provided 4-((cis-1-(4-chlorobenzyl)-2-methylpiperidin-4-yl)amino)-N-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (31g) as a potent JAK1-selective inhibitor. In particular, the (S,S)-enantiomer of 31g (38a) exhibited excellent potency for JAK1 and selectivity over JAK2, JAK3, and TYK2. On investigating the effect of 31g on hepatic fibrosis, it was found that it reduces the proliferation and fibrogenic gene expression of TGF-β-induced hepatic stellate cells (HSCs). Specifically, 31g significantly inhibited TGF-β-induced migration of HSCs at 0.25 μM in wound-healing assays.

Novel donepezil?arylsulfonamide hybrids as multitarget-directed ligands for potential treatment of Alzheimer?s disease

Alzheimer’s disease (AD) is one of the most devastating neurodegenerative disorders, characterized by multiple pathological features. Therefore, multi-target drug discovery has been one of the most active fields searching for new effective anti-AD therapies. Herein, a series of hybrid compounds are reported which were designed and developed by combining an aryl-sulfonamide function with a benzyl-piperidine moiety, the pharmacophore of donepezil (a current anti-AD acetylcholinesterase AChE inhibitor drug) or its benzyl-piperazine analogue. The in vitro results indicate that some of these hybrids achieve optimized activity towards two main AD targets, by displaying excellent AChE inhibitory potencies, as well as the capability to prevent amyloid-β (Aβ) aggregation. Some of these hybrids also prevented Aβ-induced cell toxicity. Significantly, drug-like properties were predicted, including for blood-brain permeability. Compound 9 emerged as a promising multi-target lead compound (AChE inhibition (IC50 1.6 μM); Aβ aggregation inhibition 60.7%). Overall, this family of hybrids is worthy of further exploration, due to the wide biological activity of sulfonamides.