| Identification | More | [Name]
Scopolamine hydrobromide | [CAS]
114-49-8 | [Synonyms]
(A,S)-ALPHA-(HYDROXYMETHYL)BENZENEACETIC ACID (1A,2B,4B,5A,7B)-9-METHYL-3-OXA-9-AZATRICYCLO[3.3.1.02,4]NON-7-YL ESTER HYDROBROMIDE
ATROSCINE HYDROBROMIDE
HYOSCINE
HYOSCINE HBR
HYOSCINE HYDROBROMIDE
SCOPINE TROPATE HYDROBROMIDE
SCOPOLAMINE HBR
(-)-SCOPOLAMINE HYDROBROMIDE
SCOPOLAMINE HYDROBROMIDE
SCOPOLOAMINE HYDROBROMIDE
(-)-scopolaminebromide
),hydrobromide
.alpha.-(hydroxymethyl)-,9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-ylester,hydrobromide,[7(Benzeneaceticacid
02,4]non-7-ylester,hydrobromide,[7(s)-(1alpha,2beta,4beta,5alpha,7beta)
5-alpha-h-tropan-3-alpha-ol,6-beta,7-beta-epoxy-1-alpha-(-)-tropate(ester
alpha-(hydroxymethyl)-benzeneaceticaci9-methyl-3-oxa-9-azatricyclo[3.3.1.
beldavrin
euscopol
hydroscinehydrobromide
hyocinefhydrobromide | [EINECS(EC#)]
204-050-6 | [Molecular Formula]
C17H22BrNO4 | [MDL Number]
MFCD00012647 | [Molecular Weight]
384.26 | [MOL File]
114-49-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [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
| [Usage]
An acetylcholine antagonist. Used in treatment of motion sickness; antiemetic; antispasmodic; mydriatic; preanesthetic medicant | [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]
114-49-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S36:Wear suitable protective clothing . | [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) |
| Hazard Information | Back Directory | [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. | [Reactivity Profile]
SCOPOLAMINE HYDROBROMIDE(114-49-8) is incompatible with acids, bases and oxidizing agents. . | [Air & Water Reactions]
Sensitive to air, light and moisture. Water soluble. | [Fire Hazard]
Flash point data for this chemical are not available; however, SCOPOLAMINE HYDROBROMIDE is probably combustible. | [Description]
Scopolamine is a tropane alkaloid that can be found in many plants of the Solanaceae (nightshade) family.1 It is a muscarinic receptor antagonist that can be used to induce memory impairment in animals.2,3,4 Scopolamine prevents motion sickness, nausea, and vomiting in animals.3,5 | [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). | [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. | [Drug interactions]
Potentially hazardous interactions with other drugs
None known | [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.] |
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