Scopolamine

Scopolamine
Clinical data
Trade names	Transderm Scop, others
Other names	Hyoscine, Devil's Breath
AHFS/Drugs.com	Monograph
MedlinePlus	a682509
License data	US DailyMed: Scopolamine;
Pregnancy; category	AU: B2;
Routes of; administration	By mouth, transdermal, ophthalmic, subcutaneous, intravenous, sublingual, rectal, buccal, transmucosal, intramuscular
Drug class	Antimuscarinic; Deliriant; Antiemetic; Amnestic;
ATC code	A04AD01 (WHO) N05CM05 (WHO), S01FA02 (WHO);
Legal status
Legal status	AU: S4 (Prescription only) / S2; UK: POM (Prescription only) / P; US: ℞-only;
Pharmacokinetic data
Bioavailability	20-40%
Metabolism	Liver (CYP3A4)
Elimination half-life	5 hours
Excretion	Kidney
Identifiers
	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;
CAS Number	51-34-3 ;
PubChem CID	3000322;
IUPHAR/BPS	330;
DrugBank	DB00747 ;
ChemSpider	10194106 ;
UNII	DL48G20X8X; as salt: 451IFR0GXB;
KEGG	D00138 ; as salt: D02071 ;
ChEBI	CHEBI:16794 ;
ChEMBL	ChEMBL569713 ;
PDB ligand	OW0 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID6023573 ;
ECHA InfoCard	100.000.083
Chemical and physical data
Formula	C17H21NO4
Molar mass	303.358 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES OC[C@H](c1ccccc1)C(=O)O[C@@H]2C[C@H]3N(C)[C@@H](C2)[C@@H]4O[C@H]34;
	InChI 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 ; Key:STECJAGHUSJQJN-FWXGHANASA-N ;
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Scopolamine, also known as hyoscine, or Devil's Breath, is a medication used 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.

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.