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CAS No.: | 114-49-8 |
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Name: | Scopolamine hydrobromide |
Article Data: | 2 |
Molecular Structure: | |
Formula: | C17H21NO4.HBr |
Molecular Weight: | 384.27 |
Synonyms: | 1aH,5aH-Tropan-3a-ol, 6b,7b-epoxy-, (-)-tropate (ester), hydrobromide (8CI);Benzeneacetic acid, a-(hydroxymethyl)-, (1a,2b,4b,5a,7b)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-ylester, hydrobromide, (aS)- (9CI);Benzeneacetic acid, a-(hydroxymethyl)-, 9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-ylester, hydrobromide, [7(S)-(1a,2b,4b,5a,7b)]-;Scopolamine bromide (6CI);(-)-Hyoscinehydrobromide;(-)-Scopolamine bromide;(-)-Scopolamine hydrobromide;Beldavrin;Euscopol;Hydroscine hydrobromide;Hyocine F hydrobromide;Hyoscine bromide;Hyoscine hydrobromide;Hysco;Isoscopil;Kwells;Scopamin;Scopolaminehydrobromide;Scopolaminium bromide;Scopolammonium bromide;Scopos;Sea Legs;Sereen;Triptone;Wellcome Brand Scopolamine hydrobromide Injection;l-Hyoscinehydrobromide;l-Scopolamine hydrobromide; |
EINECS: | 204-050-6 |
Melting Point: | 195-199 °C (dry matter)(lit.) |
Boiling Point: | 460.3 °C at 760 mmHg |
Flash Point: | 232.2 °C |
Solubility: | water: 50 mg/mL in water |
Appearance: | white crystalline solid powder |
Hazard Symbols: | Xn |
Risk Codes: | 22 |
Safety: | 36 |
Transport Information: | UN 1544 6.1/PG 1 |
PSA: | 62.30000 |
LogP: | 1.81410 |
Conditions | Yield |
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at 120℃; for 7h; | 95% |
acetic anhydride
hyoscine hydrobromide
9-methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]non-7-yl-3'-(acetyloxy)-2'-phenyl propanoate
Conditions | Yield |
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With sodium carbonate 1.) 2 h, 110 deg C - 115 deg C; 2.) water; | 89.8% |
Conditions | Yield |
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at 120℃; for 7h; | 88% |
Conditions | Yield |
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With sodium tetrahydroborate In ethanol at 20℃; Cooling with ice; | 87% |
hyoscine hydrobromide
(-)-Norscopolamin-hydrochlorid
Conditions | Yield |
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With hydrogenchloride; potassium permanganate; sulfuric acid; sodium carbonate 1.) (pH=7), 30 deg C, water, 2 h; 2.) (pH=5-6), T < 20 deg C, CH2Cl2; | 77.3% |
Conditions | Yield |
---|---|
at 120℃; for 7h; | 70% |
hyoscine hydrobromide
A
(3S,6S,2'S)-6β-hydroxyhyoscyamine
B
(3R,6R,2'S)-6β-hydroxyhyoscyamine
C
Hyoscyamine
Conditions | Yield |
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With hydrogen; Nickel Raney W1 | A 41.7% B 33.9% C 19.7% |
Conditions | Yield |
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at 120℃; for 7h; | 10% |
Conditions | Yield |
---|---|
With potassium permanganate; potassium carbonate | |
(i) Ac2O, (ii) aq. Na2CO3, KMnO4, (iii) aq. HCl; Multistep reaction; | |
With potassium permanganate; sulfuric acid; sodium carbonate In water at 30℃; for 2h; (pH=7); Yield given; |
hyoscine hydrobromide
(-)-Formylnorscopollamin
Conditions | Yield |
---|---|
With potassium permanganate; potassium carbonate | |
Multi-step reaction with 4 steps 1: 89.8 percent / 2.) Na2CO3 / 1.) 2 h, 110 deg C - 115 deg C; 2.) water 2: 81.2 percent / toluene / 1.) 5 h, RT; 2.) 4 d, RT 3: H2O / 1 h / 93 °C 4: 1.) 36percent HCl; 2.) NaOH / 1.) H2O, 2 h, RT; 2.) H2O, 10 deg C to 15 deg C View Scheme |
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Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
The Hyoscine hydrobromide with the cas number 114-49-8, is also called (1)Scopolamine hydrobromide; (2) (-)-Hyoscine hydrobromide ; (3) (-)-Scopolamine bromide ; (4) (-)-Scopolamine hydrobromide ; (5) 1alphaH,5alphaH-Tropan-3-alpha-ol, 5beta,7beta-epoxy-, (-)-; (6)tropate (ester), hydrobromide ; (7) Beldavrin ; (8) Euscopol ; (9) Hyoscine bromide ; (10) Hyoscine hydrobromide ; (11) Hyosol ; (12) Hysco ; (13) Isoscopil ; (14) Kwells ; (15) NSC 61806 ; (16) Scopamin ; (17) Scopolamine bromide ; (18) Scopolamine hydrobromide ; (19) Scopolaminium bromide ; (20) Scopolammonium bromide ; (21) Scopos ; (22) Sereen ; (23) Tranaxine ; (24) l-Hyoscine hydrobromide ; (25) l-Scopolamine-hydrobromide
Uses of Hyoscine hydrobromide: Hyoscine hydrobromide, which is a type of medicine called an antimuscarinic (or anticholinergic), is alkaloid and has a strongest pharmacological effect, can be used to block the parasympathetic nerve, but also can be used as preparation for the central nervous system. Role of Hyoscine hydrobromide is similar to belladonna alkaloids. Though it has stronger curative effect, maintain relatively short time. Hyoscine hydrobromide can be used for anesthesia and analgesia, cough, motion sickness, also can be used for stiff and tremor symptom of parkinson's disease. Hyoscine hydrobromide is thought to prevent motion sickness by stopping the messages sent from the vestibular system from reaching an area of the brain called the vomiting centre. This area of the brain co-ordinates the vomiting reflex. Hyoscine blocks receptors called muscarinic (or cholinergic) receptors that are found in the vomiting centre. This prevents the vomiting centre from sending nerve messages to the stomach that would normally cause vomiting.
Preparation of The Hyoscine hydrobromide: The Hyoscine hydrobromide are the extraction of Hindu Datura Flower as raw materials. The Chinese traditional medicine flosdaturae preparations, which is anesthetic agents, derive from HuaTuo well-known mafeisan 2nd century A.D. The effective components extraction is scopolamine. Mixed Hindu Datura Flower powder with 50 ° c ethanol for percolation to obtain percolate without alkaloids. Percolate with reduced pressure distillation, recycle ethanol. Extractum is extracted with sulphuric acid. Add sodium carbonate to extract to pH9-10, then extracted by chloroform. Extraction, distillation and recycling to get tal alkaloid. And separation to get Hyoscine hydrobromide salt. Total yield is 0.15%.
You can still convert the following datas into molecular structure :
1. SMILES: Br.OC[C@H](c1ccccc1)C(=O)O[C@@H]2C[C@H]3N(C)[C@@H](C2)[C@@H]4O[C@H]34
2. 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+;/m1./s1
Hyoscine hydrobromide toxic data can be showed in the following sheet.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LDLo | intravenous | 80mg/kg (80mg/kg) | CARDIAC: OTHER CHANGES VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 120, Pg. 189, 1927. |
guinea pig | LD50 | subcutaneous | 850mg/kg (850mg/kg) | AUTONOMIC NERVOUS SYSTEM: PARASYMPATHOLYTIC | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 137, Pg. 375, 1962. |
mouse | LD50 | intraperitoneal | 650mg/kg (650mg/kg) | Compilation of LD50 Values of New Drugs. | |
mouse | LD50 | intravenous | 203mg/kg (203mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 79, Pg. 127, 1943. | |
mouse | LD50 | oral | 1880mg/kg (1880mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 1132, 1968. | |
mouse | LD50 | subcutaneous | 1650mg/kg (1650mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 1132, 1968. | |
rabbit | LDLo | intravenous | 100mg/kg (100mg/kg) | BEHAVIORAL: GENERAL ANESTHETIC BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 120, Pg. 189, 1927. |
rat | LD50 | intraduodenal | 670mg/kg (670mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 180, Pg. 155, 1969. | |
rat | LD50 | oral | 1270mg/kg (1270mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 180, Pg. 155, 1969. | |
rat | LD50 | subcutaneous | 296mg/kg (296mg/kg) | United States Patent Document. Vol. #3380887 |