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4-(aminomethyl)-1-phenethylpiperidin-4-ol is an organic compound that is primarily known as an impurity in Fenspiride (F265000), a bronchodilator with anti-inflammatory properties. It is characterized by its ability to inhibit mucus secretion and reduce the release of tachykinins at a prejunctional level through its anti-muscarinic action.

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  • 23808-42-6 Structure
  • Basic information

    1. Product Name: 4-(aminomethyl)-1-phenethylpiperidin-4-ol
    2. 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
    3. CAS NO:23808-42-6
    4. Molecular Formula: C14H22N2O
    5. Molecular Weight: 234.33728
    6. EINECS: 245-896-6
    7. Product Categories: N/A
    8. Mol File: 23808-42-6.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 387.6 °C at 760 mmHg
    3. Flash Point: 188.2 °C
    4. Appearance: /
    5. Density: 1.085±0.06 g/cm3 (20 ºC 760 Torr)
    6. Vapor Pressure: 1.06E-06mmHg at 25°C
    7. Refractive Index: 1.563
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 12.55±0.20(Predicted)
    11. CAS DataBase Reference: 4-(aminomethyl)-1-phenethylpiperidin-4-ol(CAS DataBase Reference)
    12. NIST Chemistry Reference: 4-(aminomethyl)-1-phenethylpiperidin-4-ol(23808-42-6)
    13. EPA Substance Registry System: 4-(aminomethyl)-1-phenethylpiperidin-4-ol(23808-42-6)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 23808-42-6(Hazardous Substances Data)

23808-42-6 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.

Check Digit Verification of cas no

The CAS Registry Mumber 23808-42-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,3,8,0 and 8 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 23808-42:
(7*2)+(6*3)+(5*8)+(4*0)+(3*8)+(2*4)+(1*2)=106
106 % 10 = 6
So 23808-42-6 is a valid CAS Registry Number.
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

23808-42-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(aminomethyl)-1-(2-phenylethyl)piperidin-4-ol

1.2 Other means of identification

Product number -
Other names EINECS 245-896-6

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:23808-42-6 SDS

23808-42-6Downstream Products

23808-42-6Relevant articles and documents

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

Del Vecchio, Antonio,Talbot, Alex,Caillé, Fabien,Chevalier, Arnaud,Sallustrau, Antoine,Loreau, Olivier,Destro, Gianluca,Taran, Frédéric,Audisio, Davide

supporting information, p. 11677 - 11680 (2020/10/19)

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.

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

García, Mónica,Virgili, Marina,Alonso, Mònica,Alegret, Carles,Fernández, Bego?a,Port, Adriana,Pascual, Rosalía,Monroy, Xavier,Vidal-Torres, Alba,Serafini, María-Teresa,Vela, José Miguel,Almansa, Carmen

, p. 2434 - 2454 (2019/12/25)

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

García, Mónica,Virgili, Marina,Alonso, Mònica,Alegret, Carles,Farran, Joan,Fernández, Bego?a,Bordas, Magda,Pascual, Rosalia,Burgue?o, Javier,Vidal-Torres, Alba,Fernández De Henestrosa, Antonio R.,Ayet, Eva,Merlos, Manuel,Vela, Jose Miguel,Plata-Salamán, Carlos R.,Almansa, Carmen

, p. 15508 - 15526 (2020/11/17)

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.

Nitro-Aldol Approach for Commercial Manufacturing of Fenspiride Hydrochloride

Pramanik, Chinmoy,Bapat, Kiran,Patil, Pradip,Kotharkar, Sandeep,More, Yogesh,Gotrane, Dinkar,Chaskar, Sudhir P.,Mahajan, Ulhas,Tripathy, Narendra K.

, p. 1252 - 1256 (2019/06/13)

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

-

Page/Page column 173; 174, (2015/12/30)

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

-

Page/Page column 138, (2015/12/30)

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.

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