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

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)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36

RIDADR 

UN 1544 6.1/PG 1

WGK Germany 

3

RTECS 

YM4550000

F 

3-8

HS Code 

2939800000

Toxicity

LD50 in rats (mg/kg): 3800 s.c. (Stockhaus, Wick)

MSDS

• Language:English Provider:Scopolamine hydrobromide
• Language:English Provider:SigmaAldrich

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.]

Scopolamine hydrobromide(114-49-8)Related Product Information

• SCOPOLAMINE N-OXIDE HYDROBROMIDE
• Scopolamine Hydrobromide Trihydrate
• Scopolamine
• Pyridine hydrobromide
• Scopolamine butylbromide
• (-)-SCOPOLAMINE
• HYOSCINE HYDROCHLORIDE
• Scopine
• DL-(SCOPOLAMINE HYDROBROMIDE)
• Cimetropium bromide
• DEXTROMETHORPHAN HYDROBROMIDE
• HYOSCINE N BUTYL BROMIDE BP
• Methscopolamine bromide
• Tropic acid
• Scopoletin
• Hydrogen bromide
• DL-TROPIC ACID
• SCOPOLAMINE-D3 HBR 3H2O (N-METHYL-D3)
• Hyoscine Hydrobromide