Scopolamine

Scopolamine, also known as hyoscine, or Devil's Breath, is a natural or synthetically produced tropane alkaloid and anticholinergic drug that is used as a medication to treat motion sickness and postoperative nausea and vomiting. It is also sometimes used before surgery to decrease saliva. When used by injection, effects begin after about 20 minutes and last for up to 8 hours. It may also be used orally and as a transdermal patch since it has been long known to have transdermal bioavailability.

"Hyoscine" redirects here. For Other uses, see Hyoscine (disambiguation).
"Devil's Breath" redirects here. For the novel, see The Devil's Breath.

Scopolamine
Clinical data
Trade namesTransdermscop, Kwells, others
Other namesHyoscine
AHFS/Drugs.comMonograph
MedlinePlusa682509
License data
Pregnancy
category
  • AU: B2
Routes of
administration		By mouth, transdermal, ophthalmic, subcutaneous, intravenous, sublingual, rectal, buccal, transmucosal, intramuscular
Drug class
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only) / S2
  • UK: POM (Prescription only) / P
  • US: ℞-only
Pharmacokinetic data
MetabolismLiver
Elimination half-life4.5 hours
ExcretionKidney
Identifiers
  • (–)-(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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.083
Chemical and physical data
FormulaC17H21NO4
Molar mass303.358 g·mol−1
3D model (JSmol)
  • OC[C@H](c1ccccc1)C(=O)O[C@@H]2C[C@H]3N(C)[C@@H](C2)[C@@H]4O[C@H]34
  • InChI=1S/C17H21NO4/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/t11-,12-,13-,14+,15-,16+/m1/s1 Y
  • Key:STECJAGHUSJQJN-FWXGHANASA-N Y
 NY (what is this?)  (verify)

Scopolamine is in the antimuscarinic family of drugs and works by blocking some of the effects of acetylcholine within the nervous system. Scopolamine was first written about in 1881 and started to be used for anesthesia around 1900. Scopolamine is also the main active component produced by certain plants of the nightshade family, which historically have been used as psychoactive drugs (known as deliriants) due to their antimuscarinic-induced hallucinogenic effects in higher doses. In these contexts, its mind-altering effects have been utilized for recreational and occult purposes. The name "scopolamine" is derived from one type of nightshade known as Scopolia, while the name "hyoscine" is derived from another type known as Hyoscyamus niger, or black henbane. It is on the World Health Organization's List of Essential Medicines.

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