L-scopolamine

Also known as hyoscine, levo-duboisine, (1S,3S,5R,6R,7S)-6,7-epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoate, scopine (-)-tropate, (-)-hyoscine, (-)-scopolamine, 6,7-epoxytropine tropate, epoxytropine tropate

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.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 464387972
Drug.image: L-Scopolamin.svg
Drug.image_class: skin-invert-image
Drug.width: 200
Drug.image2: Scopolamine structure.png
Drug.image_class2: bg-transparent
Drug.tradename: Transderm Scop, others
Drug.MedlinePlus: a682509
Drug.DailyMedID: Scopolamine
Drug.pregnancy_AU: B2
Drug.routes_of_administration: By mouth, transdermal, ophthalmic, subcutaneous, intravenous, sublingual, rectal, buccal, transmucosal, intramuscular
Drug.ATC_prefix: A04
Drug.ATC_suffix: AD01
Drug.ATC_supplemental: ,
Drug.legal_AU: S4
Drug.legal_AU_comment: / S2

via Wikipedia infobox

Chemical data

Formula: C17H21NO4
Molecular weight: 303.35 g/mol
IUPAC name: [(1R,5S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl] (2S)-3-hydroxy-2-phenylpropanoate
SMILES: CN1[C@@H]2CC(C[C@H]1C3C2O3)OC(=O)[C@H](CO)C4=CC=CC=C4
InChIKey: STECJAGHUSJQJN-MKXJHAPZSA-N
XLogP: 0.9
Polar surface area: 62.3 Å²
H-bond donors: 1
H-bond acceptors: 5
Formal charge: 0

via PubChem

Research

11 papers

Pharmacokinetics and pharmacodynamics in clinical use of scopolamine.Therapeutic drug monitoring · 2005
The Induction of Disease Resistance by Scopolamine and the Application of Datura Extract Against Potato (Solanum tuberosum L.) Late Blight.International journal of molecular sciences · 2024
Detection of scopolamine in urine and hair in a drug-facilitated sexual assault.Forensic science international · 2023
Presynaptic effects of scopolamine, oxotremorine, noradrenaline and morphine on [3H]acetylcholine release from the myenteric plexus at different stimulation frequencies and calcium concentrations.Naunyn-Schmiedeberg's archives of pharmacology · 1987
Intra- and inter-laboratory validation of a dipstick immunoassay for the detection of tropane alkaloids hyoscyamine and scopolamine in animal feed.Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment · 2014

via PubMed

~16 min read

Encyclopedic overview

20 sections

Contents

Medical uses
Breastfeeding
Adverse effects
Overdose
Pharmacology
Pharmacodynamics
Pharmacokinetics
Chemistry
Biosynthesis in plants
History
Society and culture
Names
Australian bush medicine
Recreational and religious use
Interrogation
Use in crime
Research
See also
References
External links

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.

Excerpted from Wikipedia’s “L-scopolamine” article, available under the CC BY-SA 4.0 licence.