192989-99-4

Basic information

• Product Name: Piperidine, 1-(3-butynyl)-4-(phenylmethyl)-
• CAS NO: 192989-99-4
• Molecular Formula: C16H21N
• Molecular Weight: 227.349
• Mol File: 192989-99-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Piperidine, 1-(3-butynyl)-4-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Piperidine, 1-(3-butynyl)-4-(phenylmethyl)-(192989-99-4)
• EPA Substance Registry System: Piperidine, 1-(3-butynyl)-4-(phenylmethyl)-(192989-99-4)

Safety Data

• Hazardous Substances Data: 192989-99-4(Hazardous Substances Data)

Upstream product

• 31252-42-3 4-benzylpyperidine 
• 72486-09-0 methanesulfonic acid but-3-ynyl ester 
• 192989-95-0 1-methanesulfonyl-3-butyn 
• 584-08-7 potassium carbonate 
• 23418-85-1 3-butyn-1-yl p-toluenesulfonate 

Downstream Products

• 192989-87-0 4-[4-(4-benzyl-piperidin-1-yl)-but-1-ynyl]-benzene-1,2-diamine 
• 192989-91-6 5-[4-(4-Benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole-2,3-dione 
• 192989-86-9 4-<4-(4-benzylpiperidin-1-yl)but-1-ynyl>-2-nitrobenzeneamine 
• 302800-03-9 5-[4-(4-benzylpiperidin-1-yl)but-1-ynyl]-2-nitrophenol 
• 302800-05-1 5-[4-(4-benzylpiperidin-1-yl)but-1-ynyl]-2-nitrophenyl ethyl carbonate 
• 302800-07-3 5-[4-(4-benzylpiperidin-1-yl)but-1-ynyl]-2-aminophenyl ethyl carbonate 

Relevant articles and documents

Subtype-selective NMDA receptor ligands and the use thereof

The invention relates to subtype-selective NMDA receptor ligands and the use thereof for treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neuro-degenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the overstimulation of the excitatory amino acids, treating anxiety, psychosis, convulsions, aminoglycoside antibiotics-induced hearing loss, migraine headache, chronic pain, Parkinson's disease, glaucoma, CMV retinitis, urinary incontinence, opioid tolerance or withdrawal, and inducing anesthesia, as well as for enhancing cognition.

Subtype-selective N-methyl-D-aspartate receptor antagonists: Synthesis and biological evaluation of 1-(arylalkynyl)-4-benzylpiperidines

A search of our compound library for compounds with structural similarity to ifenprodil (5) and haloperidol (7) followed by in vitro screening revealed that 4-benzyl-1-(4-phenyl-3-butynyl)piperidine (8) was a moderately potent and selective antagonist of the NR1A/2B subtype of NMDA receptors. Substitution on the benzyl group of 8 did not significantly affect NR1A/2B potency, while addition of hydrogen bond donors in the para position of the phenyl group enhanced NR1A/2B potency. Addition of a hydroxyl moiety to the 4-position of the piperidine group slightly reduced NR1A/2B potency while reducing α-1 adrenergic and dopamine D2 receptor binding affinities substantially, resulting in improved overall selectivity for NR1A/2B receptors. Finally, the butynyl linker was replaced with propynyl or pentynyl. When the phenyl was para substituted with amine or acetamide groups, the NR1A/2B potency order was butynyl > pentynyl >> propynyl. For the para methanesulfonamide or hydroxyl groups, the order was butynyl ? propynyl > pentynyl. The hydroxyl propyne (48) and butyne (23) were among the most potent NR1A/2B antagonists from this study. They both potentiated the effects of L-DOPA in the 6-hydroxydopamine-lesioned rat, a model of Parkinson's disease, dosed at 10 mg/kg ip, but 48 was not active at 30 mg/kg po.