Atropine sulfate

Base Information

• Chemical Name: Atropine sulfate
• CAS No.: 51-55-8
• Molecular Formula: C17H23NO3
• Molecular Weight: 289.375
• Hs Code.: 29399900
• European Community (EC) Number: 202-933-0
• DSSTox Substance ID: DTXSID00858967
• Nikkaji Number: J721.767F,J23.935F
• Wikipedia: Hyoscyamine
• Wikidata: Q27181620
• NCI Thesaurus Code: C2744,C29104,C74575
• RXCUI: 1225,153970,153971
• Pharos Ligand ID: X6TMUUXQUXLF
• Metabolomics Workbench ID: 143569
• ChEMBL ID: CHEMBL9751
• Mol file: 51-55-8.mol

Synonyms:Anaspaz;Atropine Sulfate, 3(S)-endo-Isomer;Atropine, 3(S)-endo-Isomer;Cytospaz;Hyoscyamine;Hyoscyamine Hydrobromide;Hyoscyamine Hydrochloride;Hyoscyamine Sulfate;Hyoscyamine Sulfate Anhydrous

Chemical Property of Atropine sulfate

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 115-118 °C
• Refractive Index: 1.581
• Boiling Point: 429.804 °C at 760 mmHg
• PKA: 9.7(at 21℃)
• Flash Point: 213.738 °C
• PSA: 49.77000
• Density: 1.194 g/cm³
• LogP: 1.86880
• Storage Temp.: ?20°C
• Sensitive.: Light Sensitive
• Solubility.: H2O: 2 mg/mL
• Water Solubility.: 1.6g/L(18 oC)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 289.16779360
• Heavy Atom Count: 21
• Complexity: 353

Purity/Quality:

99% ^*data from raw suppliers

Hyoscyamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,Xn
• Hazard Codes: T+,Xn,F
• Statements: 26/28-36/37/38-20/21/22-36-11
• Safety Statements: 25-45-36-26-36/37-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Gastrointestinal Agents
• Canonical SMILES: CN1C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3
• Recent ClinicalTrials: Low-dose Atropine Eye Drops to Reduce Progression of Myopia in Children in the United Kingdom
• Recent EU Clinical Trials: Investigator led, double-masked, multicenter, randomized clinical trial for the comparison of Atropine 0.5% versus Atropine 0.05% eye drops for the prevention of myopia progression in Dutch children.
• Description: Atropine is a naturally occurring tropane alkaloid extracted from plants of the family Solanaceae including deadly nightshade (A. belladonna). It is a non-selective, competitive antagonist of the muscarinic acetylcholine receptor types M1, M2, M3, M4, and M5 (pKBs range from 8.9-9.8). Atropine increases firing of the sinoatrial node and conduction through the atrioventricular node of the heart, opposes the actions of the vagus nerve, blocks acetylcholine receptor sites, and decreases bronchial secretions. It is classified as an anticholinergic (parasympatholytic) drug and commonly used to dilate the pupils, increase heart rate, reduce salivation and other secretions, and as an antidote against organophosphate poisoning. Atropine is considered to be the most effective antidote for both OP and CB intoxication. By effectively competing with acetylcholine for the same cellular receptors, it prevents overstimulation of the autonomous parasympathetic system. Most importantly, it helps prevent asphixia, the main cause of death. In human subjects, it is customary to constantly infuse atropine in order to maintain optimal concentration throughout recovery from the “cholinergic crisis.” In wildlife rehabilitation, this is impractical and subjects need to be repeatedly injected with atropine.
• Physical properties: Appearance: atropine appears as colourless, odourless crystals or a white crystalline powder. Solubility: very soluble in water and soluble in ethanol. Melting point: melting point of atropine isn’t higher than 189?°C (melting time decomposition) (Chinese Pharmacopoeia), 114–118?°C (United States Pharmacopeia) and 115– 119?°C (British Pharmacopoeia). The chemical structure of atropine is made up of amino alcohol esters. It is easy for atropine to be hydrolysed into tropine and despun tropic acid under alkaline condition. Atropine is stable in faintly acid and neutral aqueous solution, most stable at pH 3.5–4.0.
• Uses: anticholinergic, mydriatic Atropine is used in medicine and is an antidote for cholinesteraseinhibiting compounds, such as organophosphorus insecticides and certain nerve gases. Atropine is commonly offered as the sulfate. Atropine is used in connection with the treatment of disturbances of cardiac rhythm and conductance, notably in the therapy of sinus bradycardia and sick sinus syndrome. Atropine is also used in some cases of heart block. In particularly high doses, atropine may induce ventricular tachycardia in an ischemic myocardium. Atropine is frequently one of several components in brand name prescription drugs. Scopolamine is found in the leaves of Daturametel L., D. meteloides L., and D. fastuosavar. alba (Cordell 1978). It is used as asedative, a preanesthetic agent, and in thetreatment of motion sickness (Merck 1989).
• Indications: This product was recorded in the Pharmacopoeia of the People’s Republic of China (2015), the British Pharmacopoeia (2017), the United States Pharmacopeia (40), the Japanese Pharmacopoeia (17th ed.), the Indian Pharmacopoeia (2010), the European Pharmacopoeia (9.0th ed.), the International Pharmacopoeia (5th ed.) and the Korean Pharmacopoeia (10th ed.). Atropine sulphate is commonly used in clinics. Dosage forms are injection, tablet and eye ointment; atropine sulphate was mainly used to treat toxic shock and organic phosphorus pesticide poisoning, to relieve visceral colic, as preanaesthetic medication and to reduce bronchial mucus secretion. The indications of atropine sulphate eye gel are iridocyclitis, fundus examination and mydriasis.
• Therapeutic Function: Anticholinergic
• Clinical Use: The best known of the muscarinic blocking drugs are the belladonna alkaloids, atropine (Atropine) and scopolamine (Scopolamine).They are tertiary amines that contain an ester linkage. Atropine is a racemic mixture of DL-hyoscyamine, of which only the levorotatory isomer is pharmacologically active.Atropine and scopolamine are parent compounds for several semisynthetic derivatives, and some synthetic compounds with little structural similarity to the belladonna alkaloids are also in use.All of the antimuscarinic compounds are amino alcohol esters with a tertiary amine or quaternary ammonium group.

Technology Process of Atropine sulfate

There total 43 articles about Atropine sulfate 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: 92.0%

α-formyl phenyl acetic acid tropine ester (22226-37-5,1049970-26-4,60251-89-0) → Atropine (51-55-8)

Guidance literature:

With palladium on activated charcoal; acetic acid; In methanol; chloroform; at 12 - 15 ℃; for 8h; Temperature; Large scale;

Reference yield: 90.0%

(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) → Atropine (51-55-8)

Guidance literature:

With sodium hydroxide; In water; at 5 ℃; pH=12 - 13; Reagent/catalyst;

Reference yield: 59.0%

atropine-N-oxide hydrochloride (4574-60-1) → Atropine (51-55-8) + Noratropine (16839-98-8)

Guidance literature:

atropine-N-oxide hydrochloride; With ferrocene; In isopropyl alcohol; at 80 ℃; for 24h;

With sodium hydroxide; In chloroform; water; isopropyl alcohol;

DOI:10.1016/j.bmcl.2010.06.031

upstream raw materials:

Tropic acid

3-tropanol

Noratropine

methyl iodide

Downstream raw materials:

(+/-)-1-phenyl-1,2,3,4-tetrahydro-naphthalene-1r,4t-dicarboxylic acid di-tropane-3endo-yl ester

8syn-methyl-3endo-DL-tropoyloxy-8anti-undecyl-nortropanium; bromide

optically inactive 8,8'-dimethyl-3endo,3'endo-bis-tropoyloxy-8anti,8'anti-p-xylylene-bis-nortropanium; dibromide

N-Methylatropine bromide

Refernces

• 1、 -. "Synthesis method of atropine sulfate". Paragraph 0032; 0036-0039; 0047; 0051-0054; 0056; 0060-0063. . Retrieved 2021/09/01.
• 2、 -. "Method for preparing atropine". Paragraph 0065-0083. . Retrieved 2019/11/19.