[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2R)-3-hydroxy-2-phenylpropanoate;sulfuric acid;hydrate

Base Information

• Chemical Name: [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2R)-3-hydroxy-2-phenylpropanoate;sulfuric acid;hydrate
• CAS No.: 55-48-1
• Molecular Formula: C₁₇H₂₃NO₃*H₂O₄S
• Molecular Weight: 387.454
• Hs Code.: 2933990090
• European Community (EC) Number: 200-235-0
• ChEMBL ID: CHEMBL1363694
• Mol file: 55-48-1.mol

Synonyms:Anhydrous, Atropine Sulfate;AtroPen;Atropin Augen?l;Atropine;Atropine Sulfate;Atropine Sulfate Anhydrous;Atropinol;Augen?l, Atropin;Sulfate Anhydrous, Atropine;Sulfate, Atropine

Chemical Property of [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2R)-3-hydroxy-2-phenylpropanoate;sulfuric acid;hydrate

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 9.1E-28mmHg at 25°C
• Melting Point: 189-192 °C (A)(lit.)
• Refractive Index: 1.6900 (estimate)
• Boiling Point: 806.7 °C at 760 mmHg
• Flash Point: 441.7 °C
• PSA: 182.52000
• Density: 1.1172 (rough estimate)
• LogP: 4.16560
• Storage Temp.: 0-6°C
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 10
• Exact Mass: 694.31353159
• Heavy Atom Count: 48
• Complexity: 434

Purity/Quality:

99%, ^*data from raw suppliers

Atropine sulfate United States Pharmacopeia (USP) Reference Standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 26/28
• Safety Statements: 23-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3.CN1C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3.O.OS(=O)(=O)O
• Isomeric SMILES: CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)[C@@H](CO)C3=CC=CC=C3.CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)[C@@H](CO)C3=CC=CC=C3.O.OS(=O)(=O)O
• Recent ClinicalTrials: Sublingual vs IV Atropine Bioavailability Study
• Recent EU Clinical Trials: A randomized, controlled, parallel-group, double-blind trial of sugammadex or usual care (neostigmine or spontaneous recovery) for reversal of rocuronium- or vecuronium-induced neuromuscular blockade in patients receiving thromboprophylaxis and undergoing hip fracture surgery or joint (hip/knee) replacement. (Protocol No. P07038)
• Uses: anticholinergic agent cholinergic receptor antagonist
• Clinical Use: Atropine may be used to treat some types of arrhythmias. Itincreases the heart rate by blocking the effects of ACh on thevagus. In this context, it is used to treat certain reversible bradyarrhythmiasthat may accompany acute myocardial infarction.It is also used as an adjunct to anesthesia to protect againstbradycardia, hypotension, and even cardiac arrest induced bythe skeletal muscle relaxant succinylcholine chloride.Another use for atropine sulfate emerged following thedevelopment of the organophosphates, which are potent inhibitorsof AChE. Atropine is a specific antidote to preventthe muscarinic effects of ACh accumulation, such as vomiting,abdominal cramps, diarrhea, salivation, sweating, bronchoconstriction,and excessive bronchial secretions. It isused intravenously but does not protect against respiratoryfailure caused by depression of the respiratory center andthe muscles of respiration.

Technology Process of [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2R)-3-hydroxy-2-phenylpropanoate;sulfuric acid;hydrate

There total 12 articles about [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2R)-3-hydroxy-2-phenylpropanoate;sulfuric acid;hydrate 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: 90.0%

Atropine (51-55-8) → (1R,3r,5S)-3-tropoyloxytropanium sulfate (55-48-1,300-40-3,620-61-1,1867-24-9,2472-17-5,2623-69-0,14844-27-0,5908-99-6)

Guidance literature:

With sulfuric acid; In acetone;

Reference yield:

Atropine (51-55-8) → atropine sulfate (5908-99-6,55-48-1,300-40-3,620-61-1,1867-24-9,2472-17-5,2623-69-0,14844-27-0)

Guidance literature:

With sulfuric acid; In dichloromethane; water; acetone; at 29 - 42 ℃; for 3.5h;

Reference yield:

α-formyl phenyl acetic acid (59216-85-2) → atropine sulfate (5908-99-6,55-48-1,300-40-3,620-61-1,1867-24-9,2472-17-5,2623-69-0,14844-27-0)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium methylate / toluene / 5 h / 109 - 115 °C

2: sodium tetrahydroborate; methanol / dichloromethane / 4 h / 0 - 20 °C

3: sulfuric acid / water; dichloromethane; acetone / 3.5 h / 29 - 42 °C

With methanol; sodium tetrahydroborate; sulfuric acid; sodium methylate; In dichloromethane; water; acetone; toluene;

upstream raw materials:

α-formyl phenyl acetic acid

Atropine

acetonedicarboxylic acid

tropinone

Downstream raw materials:

(S)-atropine sulfate

(1R,3r,5S)-3-tropoyloxytropanium sulfate

L-hyoscyamine sulphate

3-tropanol

Refernces

• 1、 -. "An anti-choline medicine preparation method of atropine sulfate". Paragraph 0039; 0040. . Retrieved 2017/03/08.
• 2、 -. "CRYSTALLINE ATROPINE SULFATE". . . Retrieved 2014/07/21.