Cevimeline hydrochloride

Base Information

• Chemical Name: Cevimeline hydrochloride
• CAS No.: 107220-28-0
• Molecular Formula: C₁₀H₁₇NOS*ClH
• Molecular Weight: 235.778
• European Community (EC) Number: 689-009-4
• DSSTox Substance ID: DTXSID10891421
• NCI Thesaurus Code: C1337
• RXCUI: 260036
• Mol file: 107220-28-0.mol

Synonyms:2-methyspiro(1,3-oxathiolane-5,3)quinuclidine;AF 102B;AF 102B, (cis-(+))-isomer;AF 102B, (trans)-isomer;AF-102B;AF102B;cevimeline;cevimeline hydrochloride;Evoxac;FKS 508;FKS-508;SNI 2011;SNI-2011

Chemical Property of Cevimeline hydrochloride

Chemical Property:

• Melting Point: 195-197?C
• Boiling Point: 308.5°Cat760mmHg
• Flash Point: 140.4°C
• PSA: 37.77000
• Density: g/cm³
• LogP: 2.30010
• Storage Temp.: Store at -20°C
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 235.0797631
• Heavy Atom Count: 14
• Complexity: 215

Purity/Quality:

99%, ^*data from raw suppliers

Cevimeline, Hydrochloride Salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1OC2(CN3CCC2CC3)CS1.Cl
• Isomeric SMILES: C[C@@H]1O[C@]2(CN3CCC2CC3)CS1.Cl
• Recent ClinicalTrials: Cevimeline in Treating Patients With Dry Mouth Caused by Radiation Therapy for Head and Neck Cancer
• Uses: A novel muscarinic M1 and M3 receptor agonist. Sialagogue.

Technology Process of Cevimeline hydrochloride

There total 13 articles about Cevimeline hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

3-hydroxy-3-(mercaptomethyl)quinuclidine (107220-26-8,158568-64-0) + acetaldehyde (75-07-0,9002-91-9) → Cevimeline hydrochloride (173553-37-2,107220-28-0)

Guidance literature:

3-hydroxy-3-(mercaptomethyl)quinuclidine; acetaldehyde; With boron trifluoride diethyl etherate; In dichloromethane;

With hydrogenchloride; In diethyl ether;

DOI:10.1016/j.tetlet.2013.03.090

Reference yield:

2’-methylspiro{1-azabicyclo [2.2.2]octane-3,5'[1,3]oxathiolane} (107220-27-9,107233-08-9) → cevimeline hydrochloride (153504-70-2,107220-28-0)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; diethyl ether; water;

Reference yield:

3-hydroxy-3-(mercaptomethyl)quinuclidine (107220-26-8,158568-64-0) + acetaldehyde (75-07-0,9002-91-9) → trans-cevimeline hydrochloride (107220-28-0) + (+/-)-cis-2-methylspiro[1,3-oxathiolane-5,3'-quinuclidine] monohydrochloride hemihydrate (153504-70-2,107220-28-0)

Guidance literature:

3-hydroxy-3-(mercaptomethyl)quinuclidine; acetaldehyde; With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 25 ℃;

With sodium hydroxide; In dichloromethane; water; pH=12 - 14;

upstream raw materials:

2’-methylspiro{1-azabicyclo [2.2.2]octane-3,5'[1,3]oxathiolane}

3-hydroxy-3-(mercaptomethyl)quinuclidine

acetaldehyde

trans-cevimeline

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