Ritodrine

Base Information

• Chemical Name: Ritodrine
• CAS No.: 26652-09-5
• Molecular Formula: C₁₇H₂₁NO₃
• Molecular Weight: 287.359
• European Community (EC) Number: 247-879-9
• DSSTox Substance ID: DTXSID7048534
• Nikkaji Number: J239.135J
• Wikipedia: Ritodrine
• Wikidata: Q5577596
• NCI Thesaurus Code: C61929
• Pharos Ligand ID: AVRXD3GMWW12
• Metabolomics Workbench ID: 43143
• ChEMBL ID: CHEMBL785
• Mol file: 26652-09-5.mol

Synonyms:DU 21220;DU-21220;DU21220;Hydrochloride, Ritodrine;Pre Par;Pre-Par;PrePar;Ritodrine;Ritodrine Hydrochloride;Yutopar

Chemical Property of Ritodrine

Chemical Property:

• Vapor Pressure: 2.55E-11mmHg at 25°C
• Refractive Index: 1.618
• Boiling Point: 512.3 °C at 760 mmHg
• PKA: pKa 9.0 (Uncertain)
• Flash Point: 175.6 °C
• PSA: 72.72000
• Density: 1.213 g/cm³
• LogP: 2.74290
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 287.15214353
• Heavy Atom Count: 21
• Complexity: 284

Purity/Quality:

98% ^*data from raw suppliers

Ritodrine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C1=CC=C(C=C1)O)O)NCCC2=CC=C(C=C2)O
• Isomeric SMILES: C[C@@H]([C@@H](C1=CC=C(C=C1)O)O)NCCC2=CC=C(C=C2)O
• Recent ClinicalTrials: Comparative Study Between Nifedipine and Ritodrine as Maintenance Tocolytic Therapy in Preterm Labor
• Description: Ritodrine, 4-hydroxy-α-[1-[(4′-hydroxyphenethyl)amino]ethyl]benzylic alcohol (11.1.19), differs slightly from epinephrine, and in the given example only one hydroxyl group has been added to the aromatic ring of the phenylethylamino region of classic sympathomimetics. The second major difference between the examined series is the replacement of the traditionally terminal iso-propyl or tert-butylamine region with a p-hydroxyphenylethylamine. Finally, the third difference is the presence of a methyl group at the α-atom of the phenylethylamine region of sympathomimetics, which makes it similar to isoetharine.
• Uses: Relaxant (smooth muscle). Ritodrine is a selective β2-adrenoreceptor stimulant, predominantly of the urino-genital system. It is used as a tocolytic agent for problems associated with premature miscarriages, and only in specialized medical facilities.
• 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.

Technology Process of Ritodrine

There total 14 articles about Ritodrine 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: 96.0%

(1R,2S)-1-(4-benzyloxyphenyl)-2-[2-(4-benzyloxyphenyl)ethyl]amino-1-propanol (1104584-63-5) → DU-21220 (26652-09-5)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethanol; at 20 ℃; for 3h; under 760.051 Torr;

DOI:10.3987/COM-08-S(N)121

Reference yield:

Nitroethane (79-24-3) + p-benzyloxybenzaldehyde (4397-53-9) + 2-[4-(benzyloxy)phenyl]acetaldehyde (40167-10-0) → [14C]-(+/-)-Ritodrine (154459-59-3,26652-09-5) + DU-21220 (26652-09-5)

Guidance literature:

Nitroethane; p-benzyloxybenzaldehyde; In tetrahydrofuran; xylene; at -30 ℃; for 85h;

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 12h; under 760.051 Torr;

2-[4-(benzyloxy)phenyl]acetaldehyde; With hydrogen; palladium on activated charcoal; In ethyl acetate; at 60 ℃; for 24h; under 760.051 Torr; Further stages. Title compound not separated from byproducts.;

DOI:10.1002/anie.200705617

Reference yield:

Nitroethane (79-24-3) + p-benzyloxybenzaldehyde (4397-53-9) + 2-[4-(benzyloxy)phenyl]acetaldehyde (40167-10-0) → [14C]-(+/-)-Ritodrine (154459-59-3,26652-09-5) + DU-21220 (26652-09-5)

Guidance literature:

Nitroethane; p-benzyloxybenzaldehyde; In tetrahydrofuran; xylene; at -30 ℃; for 85h;

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 12h; under 760.051 Torr;

2-[4-(benzyloxy)phenyl]acetaldehyde; With hydrogen; palladium on activated charcoal; In ethyl acetate; at 60 ℃; for 24h; under 760.051 Torr; Further stages. Title compound not separated from byproducts.;

DOI:10.1002/anie.200705617

upstream raw materials:

Nitroethane

p-benzyloxybenzaldehyde

2-[4-(benzyloxy)phenyl]acetaldehyde

(1R,2S)-1-(4-benzyloxyphenyl)-2-[2-(4-benzyloxyphenyl)ethyl]amino-1-propanol

Refernces

• 1、 Handa, Shinya,Nagawa, Keita,Sohtome, Yoshihiro,Matsunaga, Shigeki,Shibasaki, Masakatsu. "A heterobimetallic Pd/La/Schiff base complex for anti-selective catalytic asymmetric nitroaldol reactions and applications to short syntheses of β-adrenoceptor agonists". . p. 3230 - 3233. Retrieved 2008/12/23.
• 2、 -. "Method for the preparation of erythro vicinal amino-alcohols". . . Retrieved 2008/06/13.