26652-09-5

Basic information

• Product Name: RITODRINE
• Synonyms: 4-hydroxy-alpha-(1-((2-(4-hydroxyphenyl)ethyl)amino)ethyl)-benzenemethano(;4-hydroxy-alpha-(1-((2-(4-hydroxyphenyl)ethyl)amino)ethyl)benzenemethanol(r*;erythro-p-hydroxy-alpha-(1-((p-hydroxyphenethyl)amino)ethyl)benzylalcohol;p-hydroxy-alpha-(1-((p-hydroxyphenethyl)amino)ethyl)-benzylalcohoerythr;ritodrina;RITODRINE;Benzenemethanol, 4-hydroxy-a-[(1R)-1-[[2-(4-hydroxyphenyl)ethyl]amino]ethyl]-, (aS)-rel- (9CI);Benzenemethanol, 4-hydroxy-a-[1-[[2-(4-hydroxyphenyl)ethyl]amino]ethyl]-, (R*,S*)-
• CAS NO: 26652-09-5
• Molecular Formula: C17H21NO3
• Molecular Weight: 287.35
• EINECS: 247-879-9
• Mol File: 26652-09-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 512.3 °C at 760 mmHg
• Flash Point: 175.6 °C
• Appearance: /
• Density: 1.213 g/cm³
• Vapor Pressure: 2.55E-11mmHg at 25°C
• Refractive Index: 1.618
• PKA: pKa 9.0 (Uncertain)
• CAS DataBase Reference: RITODRINE(CAS DataBase Reference)
• NIST Chemistry Reference: RITODRINE(26652-09-5)
• EPA Substance Registry System: RITODRINE(26652-09-5)

Safety Data

• Hazardous Substances Data: 26652-09-5(Hazardous Substances Data)

Usage

Description

Ritodrine, also known as 4-hydroxy-α-[1-[(4′-hydroxyphenethyl)amino]ethyl]benzylic alcohol, is a selective β2-agonist that was developed specifically for use as a uterine relaxant. It differs slightly from epinephrine and has a unique chemical structure with a methyl group at the α-atom of the phenylethylamine region, making it similar to isoetharine. Ritodrine's uterine inhibitory effects are more sustained than its effects on the cardiovascular system, which are minimal compared to those caused by nonselective β-agonists.

Uses

Used in Medical Industry:
Ritodrine is used as a tocolytic agent for problems associated with premature miscarriages, and only in specialized medical facilities. It acts as a selective β2-adrenoreceptor stimulant, predominantly of the urino-genital system, helping to relax smooth muscle and prevent premature labor.
Additionally, Ritodrine is used as a uterine relaxant in the following applications:
1. As an intravenous infusion to stop premature labor, with the possibility of subsequent oral administration.
2. To cause mild tachycardia and slight diastolic pressure decrease, which are the usually associated cardiovascular effects of its administration.

Clinical Use

Ritodrine is a selective β2-agonist that is used exclusively for relaxing uterine muscle and inhibiting the contractions of premature labor. Terbutaline, in addition to its use as a bronchodilator, also has been used for halting the contractions of premature labor.

Synthesis

Ritodrine is synthesized from 4-benzyloxypropiophenone, which undergoes bromination into 4-benzyloxy-α-bromopropiophenone (11.1.17). This is reacted with 2-(4-benzyloxyphenyl)ethylamine, forming an intermediate product (11.1.18), which undergoes further debenzylation by hydrogen using a palladium catalyst, giving ritodrine (11.1.19) [24,25].

InChI:InChI=1/C17H21NO3/c1-12(17(21)14-4-8-16(20)9-5-14)18-11-10-13-2-6-15(19)7-3-13/h2-9,12,17-21H,10-11H2,1H3/t12-,17-/m0/s1

Upstream product

• 79-24-3 Nitroethane 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 40167-10-0 2-[4-(benzyloxy)phenyl]acetaldehyde 
• 1104584-63-5 (1R,2S)-1-(4-benzyloxyphenyl)-2-[2-(4-benzyloxyphenyl)ethyl]amino-1-propanol 
• 21086-33-9 2-bromo-1-(4-methoxyphenyl)-1-propanone 
• 121-97-1 4-Methoxypropiophenone 

Relevant articles and documents

Preparation method for high purity ritodrine hydrochloride

The invention provides a preparation method for erythro form ritodrine hydrochloride shown as formula I. The method includes: subjecting a compound II and a bromination reagent to alpha bromination reaction to obtain a compound III, then conducting nucleophilic substitution with a compound IV to synthesize a compound V, performing deprotection to generate (1-(4-hydroxyphenyl)-2-[2-(4-hydroxyphenyl)ethylamino]propyl-1-one (VI), and then conducting reduction synthesis of ritodrine, performing splitting, and finally adding hydrochloric acid to form ritodrine hydrochloride. The method provided by the invention can significantly reduce the isomer impurity D, and can achieve efficient preparation of the medicinal purity product.

Catalytic asymmetric synthesis of (-)-ritodrine hydrochloride via silyl enol ether amination using dirhodium(II) tetrakis [tetrafluorophaloyl-(S)-tert-leucinate]

A catalytic asymmetric synthesis of (-)-ritodrine hydrochloride was achieved, incorporating an enantioselective amination of (Z)-silyl enol ether derived from 4-benzyloxypropiophenone with [(2-nitrophenylsulfonyl)imino]phenyliodinane (NsN=IPh) and a chelation-controlled reduction of the ketone carbonyl group with Zn(BH4)2 as the key steps. The use of dirhodium(II) tetrakis[tetrafluorophthaloyl-(S)-tert-leucinate] as a catalyst produced the targeted α-amino ketone in 94% yield with 91% ee.

Synthesis of β phenylethylamine derivatives. X. N (hydroxy and methoxy aralkyl) derivatives

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