10338-69-9

Basic information

• Product Name: 1,2,3,6-Tetrahydro-4-phenyl-pyridine
• Synonyms: 4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE;1,2,3,6-tetrahydro-4-phenyl-pyridine;4-Phenyl-1,2,3,6-tetrahydropyr;Pyridine, 1,2,3,6-tetrahydro-4-phenyl-;1,2,3,6-tetrahydro-4-phenyl-pyridine:4-phenyl-1,2,3,6-tetrahydropyridine
• CAS NO: 10338-69-9
• Molecular Formula: C₁₁H₁₃N
• Molecular Weight: 159.23
• EINECS: 256-071-5
• Product Categories: Pyridines derivates
• Mol File: 10338-69-9.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 267.923 °C at 760 mmHg
• Flash Point: 119.944 °C
• Appearance: /
• Density: 1.008 g/cm³
• Storage Temp.: 2-8°C(protect from light)
• PKA: 9.41±0.10(Predicted)
• CAS DataBase Reference: 1,2,3,6-Tetrahydro-4-phenyl-pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,6-Tetrahydro-4-phenyl-pyridine(10338-69-9)
• EPA Substance Registry System: 1,2,3,6-Tetrahydro-4-phenyl-pyridine(10338-69-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-51
• Safety Statements: 26
• Hazardous Substances Data: 10338-69-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 1702, 1956 DOI: 10.1021/ja01589a060

InChI:InChI=1/C11H13N.ClH/c1-2-4-10(5-3-1)11-6-8-12-9-7-11;/h1-6,12H,7-9H2;1H

Upstream product

• 19798-94-8 6-methyl-6-phenyl-[1,3]oxazinane 
• 137-40-6 sodium proprionate 
• 80866-85-9 4-bromo-4-phenyl-piperidine; hydrobromide 
• 802294-64-0 propionic acid 
• 98-83-9 isopropenylbenzene 
• 50-00-0 formaldehyd 
• 28289-54-5 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine 
• 108-86-1 bromobenzene 
• 939-23-1 p-phenylpyridine 
• 591-51-5 phenyllithium 
• 40807-61-2 4-hydroxy-4-phenylpiperidin 
• 43064-12-6 1,2,3,6-tetrahydro-4-phenylpyridine hydrochloride 
• 98-80-6 phenylboronic acid 
• 172734-33-7 4-hydroxy-4-phenylpiperidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 32273-45-3 1-(cyanomethyl)-4-phenyl-1,2,3,6-tetrahydropyridine 
• 109241-03-4 1-(2'-iodobenzoyl)-4-phenyl-1,2,5,6-tetrahydropyridine 
• 127331-73-1 1-Phenoxy-4-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-butan-2-ol 
• 123333-02-8 N-<(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)methylene>-1,1-dimethylethanamine 
• 4600-95-7 1-ethoxycarbonyl-4-phenyl-1,2,5,6-tetrahydropyridine 
• 105277-32-5 7-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propoxy]-4H-1-benzopyran-4-one 
• 127625-39-2 2-<2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl>-2H-naphth<1,8-cd>isothiazole 1,1-dioxide 
• 127625-30-3 2-<3-(4-phenyl-1,2,3,6-tetrahydropyridyl)propyl>-2H-naphth<1,8-cd>isothiazole 1,1-dioxide 
• 127625-43-8 2-<4-(4-phenyl-1,2,3,6-tetrahydropyridyl)butyl>-2H-naphth<1,8-cd>isothiazole 1,1-dioxide 
• 105915-42-2 1--3-(4-phenylpiperidienyl)propane 
• 107336-04-9 2-[2-(4-Phenyl-3,6-dihydro-2H-pyridin-1-yl)-ethoxy]-benzaldehyde 
• 107336-03-8 2-[3-(4-Phenyl-3,6-dihydro-2H-pyridin-1-yl)-propoxy]-benzaldehyde 
• 98323-99-0 Methyl-3-<4-(1,2,3,6-tetrahydro-4-phenyl-1-pyridyl)butyl>-5-indolcarboxylat 
• 107335-59-1 2-{4-[2-(4-Phenyl-3,6-dihydro-2H-pyridin-1-yl)-ethoxy]-phenyl}-thiazolidine-3-carbothioic acid methylamide 

Relevant articles and documents

Cytochrome P4502D and -2C enzymes catalyze the oxidative N-demethylation of the Parkinsonism-inducing substance 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in rat liver microsomes

We have examined the oxidative N-demethylation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), a Parkinsonism-inducing neurotoxin, in liver microsomes from adult Wistar and Dark Agouti (DA) rats. The oxidation of MPTP to 4-phenyl-1,2,3,6-tetrahydropyridine (PTP) in these preparations required NADPH as a cofactor and was significantly inhibited by SKF 525-A (2 mM). MPTP N-demethylation exhibited biphasic kinetics, consistent with two enzymes, a low Km system (Km1, 10.0 ± 2.2 μM; Vmax1, 0.048 ± 0.009 nmol/(min·mg of protein)) and a high Km system (Km2, 1180 ± 91 μM; Vmax2, 4.80 ± 0.75 nmol/(min·mg of protein)). We thus employed two substrate concentrations, 5 μM and 5 mM, for the low and high Km system, respectively, to assay enzyme activity in subsequent experiments. The oxidation activity was significantly decreased by pretreatment of rats with phenobarbital and β-naphthoflavone. Furthermore, marked strain (Wistar > DA) and sex (male > female) differences were observed at low (5 μM) and high (5 mM) substrate concentrations, respectively. Reconstitution experiments with cytochrome P450BTL, which belongs to the P4502D subfamily, and P450ml (P4502C11) demonstrated that MPTP N-demethylase occurs at concentrations of 5 μM and 5 mM. At 5 mM the male-specific P450ml showed a remarkably high activity, over 400-fold that of P450BTL. Polyclonal antibodies against P450BTL and P450ml effectively suppressed the activity at the low (5 μM) and the high (5 mM) substrate concentrations, respectively. These results suggest that, in the microsomal preparations used, MPTP N-demethylation is mainly mediated by P4502D enzyme(s) at lower substrate concentrations and by P4502C11 at higher substrate concentrations.

B(C6F5)3-Catalyzed Cascade Reduction of Pyridines

B(C6F5)3 has been found to be an effective catalyst for reduction of pyridines and other electron-deficient N-heteroarenes with hydrosilanes (or hydroboranes) and amines as the reducing reagents. The success of this development hinges upon the realization of a cascade process of dearomative hydrosilylation (or hydroboration) and transfer hydrogenation. The broad functional-group tolerance (e.g. ketone, ester, unactivated olefins, nitro, nitrile, heterocycles, etc.) implies high practical utility.

Synthesis and biological evaluation of 1-(isoxazol-5-ylmethylaminoethyl)-4- phenyl tetrahydropyridine and piperidine derivatives as potent T-type calcium channel blockers with antinociceptive effect in a neuropathic pain model

New tetrahydropyridinyl and piperidinyl ethylamine derivatives were designed with hypothetical mapping on pharmacophore model generated from ligand-based virtual screening. The designed compounds were synthesized, and their inhibitory activities on T-type calcium channel were assayed using FDSS and patch-clamp assay. Among them, compounds 7b and 10b showed potent T-type calcium current blocking activity against Cav3.1 (α 1G) and Cav3.2 (α1H) channel simultaneously. With hERG and pharmacokinetics studies, compounds 7b and 10b were evaluated for the antinociceptive effect on rat model of neuropathic pain. They were significantly effective in decreasing the pain responses to mechanical and cold allodynia induced by spinal nerve ligation. These results suggest that modulation of α1G and α1H subtype T-type calcium channels may provide a promising approach for the treatment of neuropathic pain.

Design, synthesis, and evaluation of novel aryl-tetrahydropyridine PPARα/γ dual agonists

Aryl-tetrahydropyridine derivatives were prepared and their PPARα/γ dual agonistic activities were evaluated. Among them, compound (S)-5b was identified as a potent PPARα/γ dual agonist with an EC50 of 1.73 and 0.64 μM in hPPARα and γ, respectively. In diabetic (db/db) mice, compound (S)-5b showed good glucose lowering efficacy and favorable pharmacokinetic properties.