124936-74-9

Basic information

• Product Name: 2-[3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-methylphenol
• Synonyms: 2-[3-[BIS(1-METHYLETHYL)AMINO]-1-PHENYLPROPYL]-4-METHYLPHENOL MONOHYDROBROMIDE;(R)-2,3-BIS(1-METHYLETHYL)AMINO-1-PHENYLPROPYL-4-METHYLPHENOL;TOLTERODINE HYDROBROMIC ACID SALT;2-[3-BIS(1-METHYLETHYL)AMINO]-1-PHENYLPROPYL]-4-METHYLPHENOL HBR;2-[3-[BIS(1-METHYLETHYL)AMINO]-1-PHENYLPROPY]-4-METHYLPHENYL MONOHYDROBROMIDE;N,N-Diisopropyl-3-(2-Hydroxy-5-Methylphenyl)-3-PhenylPropylAmine(ForTolterodine-L-Tartrate);2-(3-(Bis(1-methylethyl)amino)-1-phenylpropyl)-4-methylphenylmonohydrobromide;2-[3-[bis(1-methylethyl)amino]1-phenylpropyl]-4-methyl phenol monohydrobromide (intermediate of tolterodine tartrate)
• CAS NO: 124936-74-9
• Molecular Formula: C₂₂H₃₁NO
• Molecular Weight: 325.49
• Product Categories: (intermediate of tolterodine tartrate)
• Mol File: 124936-74-9.mol
• Article Data: 23

Chemical Properties

• Melting Point: 72.3-73.5 °C
• Boiling Point: 473°C at 760 mmHg
• Flash Point: 239.9°C
• Appearance: /
• Density: 1.003±0.06 g/cm3(Predicted)
• Vapor Pressure: 1.44E-09mmHg at 25°C
• PKA: 10.13±0.48(Predicted)
• CAS DataBase Reference: 2-[3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-methylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-methylphenol(124936-74-9)
• EPA Substance Registry System: 2-[3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-methylphenol(124936-74-9)

Safety Data

• Hazardous Substances Data: 124936-74-9(Hazardous Substances Data)

Usage

General Description

The chemical compound "2-[3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-methylphenol", also known as Iprindole, is a psychoactive drug that functions as a tricyclic antidepressant. It works by inhibiting the reuptake of serotonin and norepinephrine, two neurotransmitters that play a role in mood regulation. Iprindole has been used in the treatment of depression and has shown efficacy in improving mood and relieving symptoms of depression in some patients. However, it is important to note that Iprindole can also come with side effects such as dry mouth, dizziness, and drowsiness, and should be used with caution and under the supervision of a healthcare professional.

InChI:InChI=1/C22H31NO.BrH/c1-16(2)23(17(3)4)14-13-20(19-9-7-6-8-10-19)21-15-18(5)11-12-22(21)24;/h6-12,15-17,20,24H,13-14H2,1-5H3;1H

Upstream product

• 345948-96-1 6-methyl-2-oxo-2H-chromen-4-yl 4-methylbenzenesulfonate 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 40546-94-9 6-methyl-4-phenyl-3,4-dihydrocoumarin 
• 108-18-9 diisopropylamine 
• 55359-68-7 2-(methoxymethoxy)-5-methylbenzaldehyde 
• 854306-67-5 methyl 3-(2-benzyloxy-5-methylphenyl)-3-phenylpropionate 
• 389068-22-8 N,N-diisopropyl-3-(2-benzyloxy-5-methylphenyl)-3-phenylpropylamine 
• 854306-68-6 3-(2-benzyloxy-5-methylphenyl)-3-phenylpropanol 
• 106-44-5 p-cresol 
• 536-74-3 phenylacetylene 
• 62594-94-9 1-[(2-hydroxy-5-methyl)phenyl]-1-phenylethylene 
• 1161940-88-0 N,N-diisopropyl-3-(2-methoxy-5-methylphenyl)-3-phenylpropan-1-amine hydrochloride 
• 124937-73-1 3-(2-methoxy-5-methylphenyl)-3-phenylpropan-1-ol 
• 4850-49-1 1-phenyl-1,3-propanediol 

Downstream Products

• 873551-03-2 (S)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine L-hydrogen tartrate 
• 124937-52-6 tolterodine tartrate 
• 848768-06-9 (R)-3-[2-(benzyloxy)-5-methylphenyl]-N,N-diisopropyl-3-phenylpropan-1-amine 
• 214601-54-4 (R)-[4-benzyloxy-3-(3-diisopropylamino-1-phenyl-propyl)-phenyl]-methanal 
• 156755-37-2 {4-(benzyloxy)-3-[(1R)-3-(dipropan-2-ylamino)-1-phenylpropyl]phenyl}methanol 
• 948844-07-3 (R)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine L-hydrogen tartrate 
• 1043911-42-7 N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propylamine L-tartrate 
• 944241-58-1 racemic tolterodine hydrogen sulfate 
• 209747-05-7 (+)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine L-hydrogen tartrate 

Relevant articles and documents

An efficient synthesis of racemic tolterodine

The efficient and cost effective of the synthesis of (±)-tolterodine (1), a precursor of (+)-(R)-tolterodine was efficiently performed from 6-methyl-4-chroman-2-one (2) via 4 steps in high yield. This process is suitable for large-scale commercial production by avoiding hazardous reagents and high pressure of hydrogen gas.

The lactol route to fesoterodine: An amine-promoted Friedel-Crafts alkylation on commercial scale

We report the discovery and optimization of an amine-promoted Friedel-Crafts alkylation of cinnamaldehyde with 4-hydroxymethyl phenol. This reaction has been used successfully on commercial scale (200 kg) in the context of the manufacture of fesoterodine, a muscarinic antagonist used for the treatment of overactive bladder. Reductive aminations of diisopropylamine and lactol 4 are also discussed, as well as the resolution of the racemic amine rac-2 into its enantiomerically pure form.

Ligand-Phospholipid Conjugation: A Versatile Strategy for Developing Long-Acting Ligands That Bind to Membrane Proteins by Restricting the Subcellular Localization of the Ligand

We hypothesized that if drug localization can be restricted to a particular subcellular domain where their target proteins reside, the drugs could bind to their target proteins without being metabolized and/or excreted, which would significantly extend the half-life of the corresponding drug-target complex. Thus, we designed ligand-phospholipid conjugates in which the ligand is conjugated with a phospholipid through a polyethylene glycol linker to restrict the subcellular localization of the ligand in the vicinity of the lipid bilayer. Here, we present the design, synthesis, pharmacological activity, and binding mode analysis of ligand-phospholipid conjugates with muscarinic acetylcholine receptors as the target proteins. These results demonstrate that ligand-phospholipid conjugation can be a versatile strategy for developing long-acting ligands that bind to membrane proteins in drug discovery.

Rearrangement of ethers: A new route to tolterodine

The rearrangement of benzyl phenolic ether in the presence of an acid or AlCl3 is utilized to produce biphenyl methane compounds in very good yields. The synthesis of muscarine receptor antagonist tolterodine is described.