5908-99-6

Basic information

• Product Name: Atropine sulfate monohydrate
• Synonyms: Atropsiol;HYOSCYAMINE SULFATE;ATROPINE SULPHATE MONOHYDRATE;ATROPINI SULFAS;ATROPINE SULFATE MONOHYDRATE;ATROPINE SULFATE SALT MONOHYDRATE;ALPHA-(HYDROXYMETHYL)BENZENEACETIC ACID 8-METHYL-8-AZABICYCLO[3.2.1]OCT-3-YL ESTER MONOHYDRATE;TROPINE TROPATE MONOHYDRATE
• CAS NO: 5908-99-6
• Molecular Formula: C₁₇H₂₃NO₃*H₂O₄S
• Molecular Weight: 694.84
• EINECS: 200-235-0
• Product Categories: Heterocyclic Compounds;Tropane Alkaloids;Alkaloids;Biochemistry;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Acetylcholine receptor;Aromatics;Other APIs;Pharma
• Mol File: 5908-99-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 189-192 °C (A)(lit.)
• Boiling Point: 853 °C at 760 mmHg
• Flash Point: 469.7 °C
• Appearance: white/Powder
• Vapor Pressure: 5.76E-31mmHg at 25°C
• Storage Temp.: Poison room
• Solubility: H2O: soluble2.5g/mL (stable for several days at 4°C.)
• Water Solubility: soluble
• Sensitive: Light Sensitive
• Merck: 14,875
• BRN: 6109275
• CAS DataBase Reference: Atropine sulfate monohydrate(CAS DataBase Reference)
• NIST Chemistry Reference: Atropine sulfate monohydrate(5908-99-6)
• EPA Substance Registry System: Atropine sulfate monohydrate(5908-99-6)

Safety Data

• Hazard Codes: T+
• Statements: 26/28-43-36/37/38
• Safety Statements: 23-45-36/37/39-26-1-25
• RIDADR: UN 1544 6.1/PG 2
• WGK Germany: 2
• RTECS: CK2455000
• F: 3-8-10
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 5908-99-6(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline Solid

Uses

Different sources of media describe the Uses of 5908-99-6 differently. You can refer to the following data:
1. Atropine sulfate is mydriatic; antispasmodic; used in preanesthetic medication.
2. Anticholinergic;Muscarinic antagonist
3. mydriatic and anticholinergie agent in ophthalmie preparations and pre-anesthetie medications; antidote to organophosphous insecticides

General Description

Atropine is isolated from Atropa belladonna, Datura stramonium and Mandragora officinarum. It is a tertiary amine, which acts as a cholinergic receptor antagonist.

Biological Activity

atropine is a competitive antagonist of muscarinic acetylcholine receptor with ic50 values of 2.22±0.60nm, 4.32±1.63nm, 4.16±1.04nm, 2.38±1.07nm and 3.39±1.16nm for m1, m2, m3, m4 and m5, respectively [1].atropine is an antimuscarinic agent and has shown the pharmacological effects because of binding to muscarinic acetylcholine receptors. atropine, the orthosteric antagonist, has been reported to compete with [3h]-nms for all muscarinic subtypes with a potency consistent with the high affinities at the machr subtypes. the ki values are 1.27±0.36nm, 3.24±1.16nm, 2.21±0.53nm, 0.77±0.43nm and 2.84±0.84nm, respectively [1, 2, 3].

references

[1] lebois ep1, bridges tm, lewis lm, dawson es, kane as, xiang z, jadhav sb, yin h, kennedy jp, meiler j, niswender cm, jones ck, conn pj, weaver cd, lindsley cw. discovery and characterization of novel subtype-selective allosteric agonists for the investigation of m(1) receptor function in the central nervous system.acs chem neurosci. 2010;1(2):104-121.[2] busch h, allen h, anderson dc.effects of atropine and carbachol on labeling of protein fractions of mouse pancreas in vitro.j pharmacol exp ther. 1959 nov; 127:200-4.[3] feron o1, smith tw, michel t, kelly ra.dynamic targeting of the agonist-stimulated m2 muscarinic acetylcholine receptor to caveolae in cardiac myocytes. j biol chem. 1997 jul 11; 272(28):17744-8.

InChI:InChI=1/2C17H23NO3.H2O4S.H2O/c2*1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12;1-5(2,3)4;/h2*2-6,13-16,19H,7-11H2,1H3;(H2,1,2,3,4);1H2/t2*13-,14+,15?,16?;;

Upstream product

• 51-55-8 Atropine 
• 101-41-7 benzeneacetic acid methyl ester 
• 103-82-2 phenylacetic acid 
• 103-80-0 phenylacetyl chloride 
• 120-29-6 3-tropanol 
• 5894-79-1 methyl 2-formyl-2-phenylacetate 
• 532-24-1 tropinone 
• 542-05-2 acetonedicarboxylic acid 
• 59216-85-2 α-formyl phenyl acetic acid 
• 55-48-1 L-hyoscyamine sulphate 

Downstream Products

• 100-52-7 benzaldehyde 
• 120-29-6 3-tropanol 
• 55-48-1 L-hyoscyamine sulphate 
• 22226-37-5 α-formyl phenyl acetic acid tropine ester 
• 51-55-8 Atropine 
• 6835-16-1 (S)-atropine sulfate 
• 13269-35-7 (+)-Atropine 
• 101-31-5 Hyoscyamine 
• 529-64-6 Tropic acid 
• 500-55-0 apoatropine 
• 16839-98-8 Noratropine 
• 532-24-1 tropinone 
• 510-25-8 β-Belladonnin 
• 510-25-8 α-Belladonnin 

Relevant articles and documents

Synthesis method of atropine sulfate

The invention belongs to the field of chemical synthesis, and particularly relates to a preparation method of atropine sulfate. The preparation method comprises the following steps: firstly preparing tropine ester, then preparing atropine, salifying to prepare atropine sulfate, and finally refining to obtain the product. In the preparation process of the tropine ester, the reaction temperature is strictly controlled to be 105-111 DEG C, and the crystallization temperature is controlled to be 0-5 DEG C, so that the yield of the tropine ester is improved. In the process of preparing atropine through reduction reaction, palladium-carbon is adopted as a catalyst, and the reaction temperature is strictly controlled to be 10-15 DEG C, so that the product quality is effectively improved. Sulfuric acid is diluted by preparing a sulfuric acid ethanol solution, and the dripping speed of the sulfuric acid ethanol solution is controlled, so that the stable quality of atropine sulfate is ensured.

Preparation method for atropine sulfate

The invention discloses a preparation method for atropine sulfate. The preparation method comprises the following steps: 1) adding dry powder of daturae flower into hydrochloric acid with a concentration of 1 to 4% and a volume 0.5 to 1 time of the volume of the dry powder for wetting and swelling, then adding the swollen daturae flower powder into a percolating barrel, adding the hydrochloric acid with a concentration of 1 to 4%, dipping the powder for 24 h or above and carrying out percolating so as to obtain brown-yellow stiff paste; 2) dissolving brown-yellow stiff paste in acetone, adding active carbon, carrying out decoloring and filtering, adding acid drop by drop until a pH value is less than 7 and carrying out standing at room temperature so as to obtain hyoscyamine sulfate; and 3) spreading hyoscyamine sulfate on a sample disc, putting the sample disc into a baking oven, carrying out heating for racemization, then carrying out cooling to obtain a crude atropine sulfate product, adding ethanol, carrying out dissolving under stirring and then filtering, subjecting a filtrate to crystallization overnight and then successively carrying out pressure-reduced filtering and vacuum drying so as to obtain atropine sulfate. According to the invention, the daturae flower is used as a raw material; acid water is used for percolation and extraction; total alkali is obtained through chloroform extraction; sulfuric acid is added into an acetone solution for salt forming so as to obtain hyoscyamine sulfate, then heating is carried out for racemization, and ethanol recrystallization is carried out to obtain atropine sulfate; and the method is simple in process operation, small in pollution, low in cost and suitable for industrial production.