Name: Scopolamine hydrobromide
SKU: 114-49-8

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Basic Information

Molecular Structure:
CAS No.:	114-49-8
Name:	Scopolamine hydrobromide

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

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
at 120℃; for 7h;	88%

: 114-49-8
hyoscine hydrobromide

: 498-45-3
scopine

Conditions

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20℃; Cooling with ice;	87%

: 114-49-8
hyoscine hydrobromide

: 24676-80-0
(-)-Norscopolamin-hydrochlorid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With hydrogen; Nickel Raney W1	A 41.7% B 33.9% C 19.7%

...Expand

: 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

Conditions	Yield
at 120℃; for 7h;	10%

: 114-49-8
hyoscine hydrobromide

: 4684-28-0
Norscopolamine

Conditions

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;

: 114-49-8
hyoscine hydrobromide

: 25650-58-2
(-)-Formylnorscopollamin

Conditions

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

Downstream Products

24676-80-0

101-31-5

55869-99-3

30286-75-0

Total:165 Page 1 of 5 1 2 3 4 5 Next>>

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Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

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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Consensus Reports

Specification