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| | Scopolamine hydrobromide Basic information |
| Product Name: | Scopolamine hydrobromide | | Synonyms: | Benzeneacetic acid, a-(hydroxyMethyl)-, (1a,2b,4b,5a,7b)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-ylester, hydrobroMide (1:1), (aS)-;ScopolaMine HBr Trihydrate;ScopolaMine-d3 HBr 3H2O;Hyosol;Tranaxine;Benzeneacetic acid, α-(hydroxymethyl)-, (1α,2β,4β,5α,7β)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester, hydrobromide (1:1), (αS)-;Hyoscine HydrobroMide Trihydrate, (1α,2β,4β,5α,7β)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl Ester HydrobroMide Trihydrate;SCOPOLAMINE HBR | | CAS: | 114-49-8 | | MF: | C17H21NO4.BrH | | MW: | 384.26 | | EINECS: | 204-050-6 | | Product Categories: | chemical reagent;pharmaceutical intermediate;API;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Alkaloids;Isotope Labeled Compounds;Acetylcholine receptor | | Mol File: | 114-49-8.mol |  |
| | Scopolamine hydrobromide Chemical Properties |
| Melting point | 195-199 °C (dry matter)(lit.) | | alpha | D25 -24 to -26° (c = 5, calculated on anhydrous basis) | | storage temp. | Store at RT | | solubility | H2O: 50 mg/mL | | form | powder | | color | white to off-white | | Water Solubility | H2O: 100mM | | Major Application | forensics and toxicology | | InChI | InChI=1/C17H21NO4.BrH/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10;/h2-6,11-16,19H,7-9H2,1H3;1H/t11-,12-,13-,14+,15-,16+;/s3 | | InChIKey | WTGQALLALWYDJH-MLRWSLNSNA-N | | SMILES | [C@]12([H])O[C@@]1([H])[C@@]1([H])N(C)[C@]2([H])C[C@@H](OC(=O)[C@H](CO)C2C=CC=CC=2)C1.Br |&1:0,3,5,9,12,16,r| | | CAS DataBase Reference | 114-49-8(CAS DataBase Reference) | | EPA Substance Registry System | Scopolamine hydrobromide (114-49-8) |
| Hazard Codes | Xn | | Risk Statements | 22 | | Safety Statements | 36 | | RIDADR | UN 1544 6.1/PG 1 | | WGK Germany | 3 | | RTECS | YM4550000 | | F | 3-8 | | TSCA | TSCA listed | | HS Code | 2939800000 | | Storage Class | 3 - Flammable liquids | | Hazard Classifications | Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Eye Irrit. 2
Flam. Liq. 2 | | Toxicity | LD50 in rats (mg/kg): 3800 s.c. (Stockhaus, Wick) |
| | Scopolamine hydrobromide Usage And Synthesis |
| Description | Scopolamine is a tropane alkaloid that can be found in many plants of the Solanaceae (nightshade) family. It is a muscarinic receptor antagonist that can be used to induce memory impairment in animals. Scopolamine prevents motion sickness, nausea, and vomiting in animals. | | Chemical Properties | Off-White Solid | | Uses | An acetylcholine antagonist. Used in treatment of motion sickness; antiemetic; antispasmodic; mydriatic; preanesthetic medicant | | Definition | ChEBI: A hydrobromide that is obtained by reaction of scopolamine with hydrogen bromide. | | Brand name | Isopto Hyoscine (Alcon); Transderm-Scop (Ciba-Geigy). | | General Description | Scopolamine hydrobromide(hyoscine hydrobromide) occurs as white orcolorless crystals or as a white, granular powder. It is odorlessand tends to effloresce in dry air. It is freely soluble inwater (1:1.5), soluble in alcohol (1:20), only slightly solublein chloroform, and insoluble in ether.
Scopolamine is a competitive blocking agent of theparasympathetic nervous system as is atropine, but it differsmarkedly from atropine in its action on the higher nervecenters. Both drugs readily cross the blood-brain barrierand, even at therapeutic doses, cause confusion, particularlyin the elderly. | | General Description | Colorless crystals or white powder or solid. Has no odor. pH (of 5% solution): 4-5.5. Slightly efflorescent in dry air. Bitter, acrid taste. | | Air & Water Reactions | Sensitive to air, light and moisture. Water soluble. | | Reactivity Profile | Scopolamine hydrobromide is incompatible with acids, bases and oxidizing agents. . | | Fire Hazard | Flash point data for Scopolamine hydrobromide are not available; however, Scopolamine hydrobromide is probably combustible. | | Biological Activity | Non-selective muscarinic antagonist. Widely used clinically to treat motion sickness. | | Clinical Use | A sufficiently large dose of scopolamine will cause an individualto sink into a restful, dreamless sleep for about8 hours, followed by a period of approximately the samelength in which the patient is in a semiconscious state.During this time, the patient does not remember events thattake place. When scopolamine is administered with morphine,this temporary amnesia is termed twilight sleep. | | Metabolism | Hyoscine hydrobromide is almost entirely metabolised,
probably in the liver; only a small proportion of an oral
dose is excreted unchanged in the urine. In one study in
man, 3.4% of a single dose, administered by subcutaneous
injection was excreted unchanged in urine within 72
hours. | | storage | Store at RT | | Purification Methods | The hydrobromide is recrystallised from Me2CO, H2O or EtOH/Et2O and dried. It is soluble in H2O (60%) and EtOH (5%) but insoluble in Et2O and slightly in CHCl3. The hydrochloride has m 300o (from Me2CO). The free base is a viscous liquid which forms a crystalline hydrate with m 59o and [] D 20 -28o (c 2.7, H2O). It hydrolyses in dilute acid or base. [Meinwald J Chem Soc 712 1953, Fodor Tetrahedron 1 86 1957, Beilstein 6 III 4185.] | | References | [1] JRG ZIEGLER Peter J F. Alkaloid biosynthesis: metabolism and trafficking.[J]. Annual review of plant biology, 2008, 59: 735-769. DOI: 10.1146/annurev.arplant.59.032607.092730
[2] S WOODS. 5-HT6 receptor agonists and antagonists enhance learning and memory in a conditioned emotion response paradigm by modulation of cholinergic and glutamatergic mechanisms[J]. British Journal of Pharmacology, 2012, 167 2: 436-449. DOI: 10.1111/j.1476-5381.2012.02022.x
[3] ENRIQUE SOTO Rosario V. Neuropharmacology of vestibular system disorders.[J]. Current Neuropharmacology, 2010, 8 1: 26-40. DOI: 10.2174/157015910790909511
[4] H E SHANNON. Muscarinic receptor agonists, like dopamine receptor antagonist antipsychotics, inhibit conditioned avoidance response in rats.[J]. Journal of Pharmacology and Experimental Therapeutics, 1999, 290 2: 901-907.
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| | Scopolamine hydrobromide Preparation Products And Raw materials |
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