Scopolamine
| Names | |
|---|---|
| IUPAC name
(–)-(S)-3-Hydroxy-2-phenylpropionic acid (1R,2R,4S,5S,7α,9S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester
| |
| Other names
6β,7β-epoxy-1αH,5αH-tropan-3α-ol (-)-tropate
9-methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]non-7-yl-3'-hydroxy-2'-phenyl propanoate Atroscine Devil's Breath Hyoscine | |
| Properties | |
| C17H21NO4 | |
| Molar mass | 303.358 g/mol |
| Appearance | Colorless crystalline solid |
| Odor | Odorless |
| Melting point | Anhydrous 82–83 °C (180–181 °F; 355–356 K) Monohydrate 55–57 °C (131–135 °F; 328–330 K) Dihydrate 38–40 °C (100–104 °F; 311–313 K) |
| Slightly soluble | |
| Solubility | Reacts with strong acids and strong bases Soluble in acetone, chloroform, diethyl ether, ethanol, isopropanol Sparingly soluble in benzene, petroleum ether |
| Vapor pressure | ~0 mmHg |
| Acidity (pKa) | 7.55-7.81 |
| Hazards | |
| Related compounds | |
| Related compounds
|
Atropine |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Scopolamine, also known as hyoscine or Devil's Breath, is a tropane alkaloid and anticholinergic drug, with a variety of uses in medicine as well as other unconventional uses.
The racemic form of scopolamine is known as atroscine. It exists as anhydrous and two hydrated (monohydrate and dihydrate) forms.
Contents
Properties
Chemical
Scopolamine reacts with acids to form salts.
Physical
Scopolamine is a colorless crystalline solid, slightly soluble in cold water, but more soluble in organic solvents and hot water.
Availability
Scopolamine is found in many members of the family Solanaceae, such as Scopolia carniolica (from where its name comes from), as well as Datura strammonium, deadly nightshade (Atropa belladonna), Hyoscyamus niger, etc.[1][2] Seeds of such plants can be bought from plant stores, online or sometimes found growing near fences, as the plant is known to be invasive if left to grow unchecked. All these plants contain a mixture of the tropane alkaloids, namely atropine, scopolamine, and hyoscyamine, and thus purification is required to separate scopolamine. A video showing and (attempted) extraction of Datura alkaloids can be found here.
Scopolamine is sold by chemical suppliers, more than often as hydrochloride or hydrobromide salt. Freebase scopolamine is less available than its salt form. It can however be made by treating the salt with a base.
Preparation
Scopolamine can be obtained by reaction of scopine with tropic acid.
As scopine is hard to come by, total synthesis of scopolamine is expensive and difficult, compared to its extraction and purification from natural sources.
Projects
- Anticholinergic drug (for nausea, excessive drooling)
- Make scopine
- Compound collecting
Handling
Safety
Scopolamine is toxic. Ingestion of this compound is known to cause mydriasis (dilated pupils), dry mouth, anhidrosis (reduced ability to sweat), tachycardia (usually occurs at higher doses and is succeeded by bradycardia), while at high doses, scopolamine will cause dizziness, seizures, blurred vision, hallucinations and memory loss, although many other side effects are known.
Physostigmine, usually as physostigmine salicylate, can be used as antidote in case of scopolamine poisoning.
Storage
Should be kept in glass ampoules, away from light.
Disposal
Can be hydrolyzed with a strong acid or base to less harmful compounds. Can also be destroyed using a strong oxidizing solution.
