Prenylamine

Base Information

• Chemical Name: Prenylamine
• CAS No.: 390-64-7
• Molecular Formula: C24H27 N
• Molecular Weight: 329.485
• Hs Code.: 2921499090
• European Community (EC) Number: 206-869-4
• UNII: K2OH82Z000
• DSSTox Substance ID: DTXSID0048555
• Nikkaji Number: J5.718E
• Wikipedia: Prenylamine
• Wikidata: Q7240579
• NCI Thesaurus Code: C170345
• Pharos Ligand ID: BK1VCG1S7UY6
• Metabolomics Workbench ID: 149256
• ChEMBL ID: CHEMBL24072
• Mol file: 390-64-7.mol

Synonyms:Corontin;Difril;Prenylamine;Segontin

Chemical Property of Prenylamine

Chemical Property:

• Vapor Pressure: 3.14E-09mmHg at 25°C
• Melting Point: 36.5-37.5°
• Refractive Index: 1.577
• Boiling Point: 476.1°Cat760mmHg
• PKA: pKa 8.74±0.02(40% EtOH,t =25) (Uncertain)
• Flash Point: 219.4°C
• PSA: 12.03000
• Density: 1.023g/cm³
• LogP: 5.82030
• Storage Temp.: Refrigerator
• Water Solubility.: 50mg/L(37 oC)
• XLogP3: 6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 8
• Exact Mass: 329.214349865
• Heavy Atom Count: 25
• Complexity: 316

Purity/Quality:

95-99% ^*data from raw suppliers

Prenylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CC=CC=C1)NCCC(C2=CC=CC=C2)C3=CC=CC=C3
• Description: Prenylamine is a calcium channel inhibitor. It inhibits the plasma membrane Ca2+ ATPase (PMCA) in isolated and purified pig cardiac sarcolemma. It binds to a hydrophobic site on calcium-bound calmodulin (CaM) with a Kd value of 0.5 μM and inhibits CaM-activated cAMP phosphodiesterase (PDE) activity when used at concentrations ranging from 10 to 50 μM, an effect that is negatively associated with the concentration of calmodulin. Prenylamine (30 μM) shortens action potential duration and decreases the amplitude of peak calcium currents in single guinea pig ventricular myocytes in the absence and presence of propranolol and phentolamine . Prenylamine (50 mg/kg) decreases epinephrine, serotonin, and dopamine levels in rat brain. It also decreases epinephrine levels in rat heart. It protects anesthetized rats from coronary artery occlusion-induced arrhythmia when administered at a dose of 0.5 mg/kg but increases mortality due to atrioventricular block leading to asystole when administered at a dose of 5 mg/kg.
• Uses: Vasodilator (coronary).

Technology Process of Prenylamine

There total 5 articles about Prenylamine 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: 80.0%

1-phenylpropadiene (2327-99-3) + 3-diphenylpropyl amine (5586-73-2) → prenylamine (390-64-7,85610-72-6,47445-84-1)

Guidance literature:

1-phenylpropadiene; 3-diphenylpropyl amine; With tris(dimethylamido)(trityl(6-(tritylamino)pyridin-2-yl)amido)-titanium; In toluene; at 80 ℃; for 24h; Schlenk technique; Inert atmosphere;

With sodium cyanoborohydride; zinc(II) chloride; In methanol; at 25 ℃; for 20h; regioselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1002/zaac.201500542

Reference yield:

3,3-diphenyl-propionitrile (2286-54-6) + 2-amino-1-phenylpropane (60-15-1,156-34-3,51-64-9,300-62-9,17108-96-2,96332-84-2) → prenylamine (390-64-7,85610-72-6,47445-84-1)

Guidance literature:

3,3-diphenyl-propionitrile; With diisobutylaluminium hydride; In dichloromethane; at 20 ℃;

2-amino-1-phenylpropane; In dichloromethane; cooling;

With sodium tetrahydroborate; In ethanol; dichloromethane; at 20 ℃;

DOI:10.1071/CH06163

Reference yield:

1-chloro-3,3-diphenylpropane (29648-95-1) + 2-amino-1-phenylpropane (60-15-1,156-34-3,51-64-9,300-62-9,17108-96-2,96332-84-2) → prenylamine (390-64-7,85610-72-6,47445-84-1)

Guidance literature:

With sodium bromide; In N,N-dimethyl-formamide; at 150 ℃; for 1h; Product distribution; different molar ratio of PAP:DPCP, other: temperatures, heating time, reagents,;

DOI:10.1007/BF00765609

upstream raw materials:

1-chloro-3,3-diphenylpropane

2-amino-1-phenylpropane

3,3-diphenyl-propionitrile

1-phenylpropadiene

Downstream raw materials:

N-(3-methylbut-2-enylcarbamothioyl)benzamide

2-Diethylamino-N-(3,3-diphenyl-propyl)-N-(1-methyl-2-phenyl-ethyl)-acetamide

N-(1-methyl-2-phenylethyl)-3,3-diphenylpropan-1-amine hydrochloride

Refernces

• 1、 -. "THERAPY FOR COMPLICATIONS OF DIABETES". . . Retrieved 2009/07/02.
• 2、 -. "Method for treating resistant hypertension". . . Retrieved 2008/06/13.