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Scopolamine hydrobromide

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Name

Scopolamine hydrobromide

EINECS 204-050-6
CAS No. 114-49-8 Density N/A
PSA 62.30000 LogP 1.81410
Solubility water: 50 mg/mL in water Melting Point 195-199 °C (dry matter)(lit.)
Formula C17H21NO4.HBr Boiling Point 460.3 °C at 760 mmHg
Molecular Weight 384.27 Flash Point 232.2 °C
Transport Information UN 1544 6.1/PG 1 Appearance white crystalline solid powder
Safety 36 Risk Codes 22
Molecular Structure Molecular Structure of 114-49-8 (Scopolamine hydrobromide) Hazard Symbols HarmfulXn
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;

Article Data 2

Scopolamine hydrobromide Synthetic route

114-49-8

hyoscine hydrobromide

147-85-3

L-proline

pyrrolidine-2-carboxylic acid 2-(9-methyl-3-oxa-9-aza-tricyclo[3.3.1.02,4]non-7-yloxycarbonyl)-2-phenyl-ethyl ester

Conditions
ConditionsYield
at 120℃; for 7h;95%
108-24-7

acetic anhydride

114-49-8

hyoscine hydrobromide

6820-79-7

9-methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]non-7-yl-3'-(acetyloxy)-2'-phenyl propanoate

Conditions
ConditionsYield
With sodium carbonate 1.) 2 h, 110 deg C - 115 deg C; 2.) water;89.8%
110-89-4

piperidine

114-49-8

hyoscine hydrobromide

2-phenyl-3-piperidin-1-yl-propionic acid 9-methyl-3-oxa-9-aza-tricyclo[3.3.1.02,4]non-7-yl ester

Conditions
ConditionsYield
at 120℃; for 7h;88%
114-49-8

hyoscine hydrobromide

498-45-3

scopine

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 20℃; Cooling with ice;87%
114-49-8

hyoscine hydrobromide

24676-80-0

(-)-Norscopolamin-hydrochlorid

Conditions
ConditionsYield
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%
110-91-8

morpholine

114-49-8

hyoscine hydrobromide

3-morpholin-4-yl-2-phenyl-propionic acid 9-methyl-3-oxa-9-aza-tricyclo[3.3.1.02,4]non-7-yl ester

Conditions
ConditionsYield
at 120℃; for 7h;70%
114-49-8

hyoscine hydrobromide

A

55869-99-3

(3S,6S,2'S)-6β-hydroxyhyoscyamine

B

126371-43-5

(3R,6R,2'S)-6β-hydroxyhyoscyamine

C

101-31-5

Hyoscyamine

Conditions
ConditionsYield
With hydrogen; Nickel Raney W1A 41.7%
B 33.9%
C 19.7%
114-49-8

hyoscine hydrobromide

109-89-7

diethylamine

3-diethylamino-2-phenyl-propionic acid 9-methyl-3-oxa-9-aza-tricyclo[3.3.1.02,4]non-7-yl ester

Conditions
ConditionsYield
at 120℃; for 7h;10%
114-49-8

hyoscine hydrobromide

4684-28-0

Norscopolamine

Conditions
ConditionsYield
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;
114-49-8

hyoscine hydrobromide

25650-58-2

(-)-Formylnorscopollamin

Conditions
ConditionsYield
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

Scopolamine hydrobromide Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Scopolamine hydrobromide Specification

 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

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