Difference between revisions of "Scopolamine"

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(Created page with "{{Chembox | Name = Scopolamine | Reference = | IUPACName = (–)-(''S'')-3-Hydroxy-2-phenylpropionic acid (1''R'',2''R'',4''S'',5''S'',7''α'',9''S'')-9-methyl-3-oxa-9-azatric...")
 
 
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| PIN =
 
| PIN =
 
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| SystematicName =
| OtherNames = 6β,7β-epoxy-1αH,5αH-tropan-3α-ol (-)-tropate<br>9-methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]non-7-yl-3'-hydroxy-2'-phenyl propanoateDevil's Breath<br>Hyoscine
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| OtherNames = 6β,7β-epoxy-1αH,5αH-tropan-3α-ol (-)-tropate<br>9-methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]non-7-yl-3'-hydroxy-2'-phenyl propanoate<br>Atroscine<br>Devil's Breath<br>Hyoscine
 
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| MolarMass = 303.358 g/mol
 
| MolarMass = 303.358 g/mol
 
| MeltingPt =  
 
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| MeltingPtC = 59
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| MeltingPt_notes = ''Anhydrous''<br>82–83 °C (180–181 °F; 355–356 K)<br>''Monohydrate''<br>55–57 °C (131–135 °F; 328–330 K)<br>''Dihydrate''<br>38–40 °C (100–104 °F; 311–313 K)
 
| Odor = Odorless
 
| Odor = Odorless
 
| pKa = 7.55-7.81
 
| pKa = 7.55-7.81
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'''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.
 
'''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.
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The racemic form of scopolamine is known as '''atroscine'''. It exists as anhydrous and two hydrated (monohydrate and dihydrate) forms.
  
 
==Properties==
 
==Properties==
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Scopolamine can be obtained by reaction of scopine with tropic acid.
 
Scopolamine can be obtained by reaction of scopine with tropic acid.
  
As tropine is hard to come by, total synthesis of scopolamine is expensive compared to its extraction and purification from natural sources.
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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==
 
==Projects==

Latest revision as of 21:41, 17 September 2023

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.

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.

References

  1. A. Ladenburg, Ann. 206, 274 (1881)
  2. E. Schmidt, Arch. Pharm. 230, 207 (1892)

Relevant Sciencemadness threads