23808-42-6

Basic information

• Product Name: 4-(aminomethyl)-1-phenethylpiperidin-4-ol
• Synonyms: 4-(aminomethyl)-1-phenethylpiperidin-4-ol;4-Aminomethyl-1-(2-phenylethyl)piperidin-4-ol;Einecs 245-896-6;4-(Aminomethyl)-1-(2-phenylethyl)-4-piperidinol;4-Piperidinol, 4-(aMinoMethyl)-1-(2-phenylethyl)-;4-(Aminomethyl)-1-phenethyl-4-piperidinol
• CAS NO: 23808-42-6
• Molecular Formula: C₁₄H₂₂N₂O
• Molecular Weight: 234.33728
• EINECS: 245-896-6
• Mol File: 23808-42-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 387.6 °C at 760 mmHg
• Flash Point: 188.2 °C
• Appearance: /
• Density: 1.085±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.06E-06mmHg at 25°C
• Refractive Index: 1.563
• PKA: 12.55±0.20(Predicted)
• CAS DataBase Reference: 4-(aminomethyl)-1-phenethylpiperidin-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(aminomethyl)-1-phenethylpiperidin-4-ol(23808-42-6)
• EPA Substance Registry System: 4-(aminomethyl)-1-phenethylpiperidin-4-ol(23808-42-6)

Safety Data

• Hazardous Substances Data: 23808-42-6(Hazardous Substances Data)

Usage

Uses

4-(Aminomethyl)-1-phenethyl-4-piperidinol is an impurity of Fenspiride (F265000), an bronchodilator with anti-inflammatory properties. Inhibits mucus secretion and reduces the release of tachykinins a t a prejunctional level by its anti-muscarinic action

InChI:InChI=1/C14H22N2O/c15-12-14(17)7-10-16(11-8-14)9-6-13-4-2-1-3-5-13/h1-5,17H,6-12,15H2

Upstream product

• 39742-60-4 1-(2-phenylethyl)-4-piperidinone 
• 5053-08-7 Fenspiride hydrochloride 
• 67685-98-7 6-phenethyl-1-oxa-6-azaspiro[2.5]octane 
• 66670-11-9 methyl 1-(2-phenylethyl)-4-oxo-piperidine-3-carboxylate 
• 38129-46-3 dimethyl β,β'-(2-phenylethylamino)dipropionate 
• 64-04-0 phenethylamine 
• 156215-50-8 1-(2-phenethyl)-4-cyano-4-trimethylsilyloxypiperidine 

Downstream Products

• 5053-06-5 fenspiride 

Relevant articles and documents

Carbon isotope labeling of carbamates by late-stage [11C], [13C] and [14C]carbon dioxide incorporation

A general procedure for the late-stage [11C], [13C] and [14C]carbon isotope labeling of cyclic carbamates is reported. This protocol allows the incorporation of carbon dioxide, the primary source of carbon-14 and carbon-11 radioisotopes, in a direct, cost-effective and sustainable manner. A disconnection/reconnection strategy, involving ring opening/isotopic closure, was also implemented.

Discovery of EST73502, a Dual μ-Opioid Receptor Agonist and σ1Receptor Antagonist Clinical Candidate for the Treatment of Pain

The synthesis and pharmacological activity of a new series of 4-alkyl-1-oxa-4,9-diazaspiro[5.5]undecane derivatives as potent dual ligands for the σ1 receptor (σ1R) and the μ-opioid receptor (MOR) are reported. A lead optimization program over the initial 4-aryl analogues provided 4-alkyl derivatives with the desired functionality and good selectivity and ADME profiles. Compound 14u (EST73502) showed MOR agonism and σ1R antagonism and a potent analgesic activity, comparable to the MOR agonist oxycodone in animal models of acute and chronic pain after single and repeated administration. Contrary to oxycodone, 14u produces analgesic activity with reduced opioid-induced relevant adverse events, like intestinal transit inhibition and naloxone-precipitated behavioral signs of opiate withdrawal. These results provide evidence that dual MOR agonism and σ1R antagonism may be a useful strategy for obtaining potent and safer analgesics and were the basis for the selection of 14u as a clinical candidate for the treatment of pain.

ALKYL AND ARYL DERIVATIVES OF 1-OXA-4,9-DIAZASPIRO UNDECANE COMPOUNDS HAVING MULTIMODAL ACTIVITY AGAINST PAIN

The present invention relates to compounds of general formula (I) having dual pharmacological activity towards both the sigma (σ) receptor, and the μ-opiod receptor and more particularly to diazaspiro undecane compounds having this pharmacological activity, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use in therapy, in particular for the treatment of pain.