Thioperamide

Base Information

• Chemical Name: Thioperamide
• CAS No.: 106243-16-7
• Molecular Formula: C15H24 N4 S
• Molecular Weight: 408.522
• Hs Code.: 2933990090
• UNII: II4319BWUI
• DSSTox Substance ID: DTXSID50147555
• Nikkaji Number: J248.127H
• Wikipedia: Thioperamide
• Wikidata: Q7784686
• Pharos Ligand ID: AA4F5ML2KBWY
• ChEMBL ID: CHEMBL260374
• Mol file: 106243-16-7.mol

Synonyms:MR 12842;MR-12842;N-cyclohexy-4-(imidazol-4-yl)-1-piperidinecarbothioamide;thioperamide

Chemical Property of Thioperamide

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 4.12E-10mmHg at 25°C
• Boiling Point: 499.5 °C at 760 mmHg
• Flash Point: 255.9 °C
• PSA: 150.64000
• Density: 1.2 g/cm³
• LogP: 2.83690
• Storage Temp.: Store at -20°C
• Solubility.: H2O: 10 mg/mL
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 292.17216796
• Heavy Atom Count: 20
• Complexity: 322

Purity/Quality:

97% ^*data from raw suppliers

Thioperamide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)NC(=S)N2CCC(CC2)C3=CN=CN3
• Uses: Thioperamide is a highly potent and selective ligand for histamine H3-receptors.

Technology Process of Thioperamide

There total 8 articles about Thioperamide 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: 87.0%

4-(1H-imidazol-4-yl)-piperidine (106243-23-6) + isothiocyanatocyclohexane (1122-82-3) → thioperamide (106243-16-7)

Guidance literature:

In toluene; for 2h; Heating;

DOI:10.1021/jm00017a018

Reference yield:

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → thioperamide (106243-16-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-BuLi in hexane / 1.) THF, 1.5 h, 10-15 deg C, 2.) THF, room temperature

2: 97 percent / concd. aq. HCl / 40 h / 95 °C

3: 88 percent / hydrogen / PtO₂ / acetic acid; H₂O / 24 h / 2585.7 Torr / Ambient temperature

4: 1.) NaOH / 1.) methanol, 30 min, 2.) acetonitrile, 2 h, 50 deg C; 40 h, room temperature

With hydrogenchloride; sodium hydroxide; n-butyllithium; hydrogen; platinum(IV) oxide; In water; acetic acid;

DOI:10.1016/0040-4020(95)00881-8

Reference yield:

4-<4-(4-hydroxy-1-tert-butoxycarbonyl)piperidyl>-(1H)-imidazole (173469-30-2) → thioperamide (106243-16-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / concd. aq. HCl / 40 h / 95 °C

2: 88 percent / hydrogen / PtO₂ / acetic acid; H₂O / 24 h / 2585.7 Torr / Ambient temperature

3: 1.) NaOH / 1.) methanol, 30 min, 2.) acetonitrile, 2 h, 50 deg C; 40 h, room temperature

With hydrogenchloride; sodium hydroxide; hydrogen; platinum(IV) oxide; In water; acetic acid;

DOI:10.1016/0040-4020(95)00881-8

upstream raw materials:

4-(1H-imidazol-4-yl)-piperidine

isothiocyanatocyclohexane

N-tert-butyloxycarbonylpiperidin-4-one

4-<4-(4-hydroxy-1-tert-butoxycarbonyl)piperidyl>-(1H)-imidazole

Downstream raw materials:

N-cyclohexyl-4-(5'-nitro-4'-imidazolyl)piperidine-1-carbothioamide