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

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

Used in Pharmaceutical Industry:
4-(aminomethyl)-1-phenethylpiperidin-4-ol is used as an impurity in the production of Fenspiride (F265000) for its bronchodilator and anti-inflammatory effects. It contributes to the inhibition of mucus secretion and the reduction of tachykinins release, which can be beneficial in treating respiratory conditions.
Additionally, due to its anti-muscarinic action, it may have potential applications in the development of medications targeting muscarinic receptors, which are involved in various physiological processes and disorders. However, further research and development would be required to explore these potential applications.

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

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

Downstream Products

• 5053-06-5 fenspiride 

Relevant articles and documents

4-Aryl-1-oxa-4,9-diazaspiro[5.5]undecane Derivatives as Dual μ-Opioid Receptor Agonists and σ1 Receptor Antagonists for the Treatment of Pain

The synthesis and pharmacological activity of a new series of 1-oxa-4,9-diazaspiro[5.5]undecane derivatives as potent dual ligands for the sigma-1 receptor (σ1R) and the μ-opioid receptor (MOR) are reported. The different positions of the central scaffold, designed using a merging strategy of both target pharmacophores, were explored using a versatile synthetic approach. Phenethyl derivatives in position 9, substituted pyridyl moieties in position 4 and small alkyl groups in position 2 provided the best profiles. One of the best compounds, 15au, showed a balanced dual profile (i.e., MOR agonism and sigma antagonism) and a potent analgesic activity, comparable to the MOR agonist oxycodone in the paw pressure test in mice. Contrary to oxycodone, as expected from the addition of σ1R antagonism, 15au showed local, peripheral activity in this test, which was reversed by the σ1R agonist PRE-084. At equianalgesic doses, 15au showed less constipation than oxycodone, providing evidence that dual MOR agonism and σ1R antagonism may be a useful strategy for obtaining potent and safer analgesics.

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.

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.

Nitro-Aldol Approach for Commercial Manufacturing of Fenspiride Hydrochloride

An efficient, short manufacturing process for fenspiride hydrochloride is reported. Nitro-aldol condensation is the key reaction in the developed process. Improved routes to key building blocks are demonstrated by expedient multikilogram production. Hazardous reactions are avoided. API produced following this new route meets the quality requirement NLT 99.70% purity by HPLC with any individual impurity NMT 0.10% with very good yield.

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.

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

The present invention relates to compounds having dual pharmacological activity towards both the sigma (σ) receptor, and the μ-opioid 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. (formula 1) wherein Y is (formula 2) or (formula 3) ? n is 1 or 2; ? q is 1, 2, 3, 4, 5 or 6; ? X is a bond, -C(O)O-, -C(0)NR 8-, -C(O)-, -0- or -C(R 4R 4.)-; ? R 1is C(0)R 5or S(O) 2R 5.