Structure via PubChem · Public domain (PubChem)
hyoscyamine
Sign in to saveAlso known as Tropine-L-tropate, Daturin, [3(S)-Endo]-alpha-(hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (−)-atropine, (-)-Hyoscyamine, Daturine, L-Hyoscyamine, Duboisine
Hyoscyamine (also known as daturine or duboisine) is a naturally occurring tropane alkaloid and plant toxin. It is a secondary metabolite found in certain plants of the family Solanaceae, including henbane, mandrake, angel's trumpets, jimsonweed, the sorcerers' tree, and Atropa belladonna (deadly nightshade). It is the Levorotatory isomer of atropine.
Key facts
- Drug.Verifiedfields
- changed
- Drug.verifiedrevid
- 461742575
- Drug.image
- Hyoscyamine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200
- Drug.image2
- Hyoscyamine-from-xtal-3D-balls.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Anaspaz, Levbid, Levsin
- Drug.MedlinePlus
- a684010
- Drug.routes_of_administration
- By mouth, Injection
- Drug.ATC_prefix
- A03
- Drug.ATC_suffix
- BA03
- Drug.legal_AU
- S4
- Drug.legal_US
- Rx only
- Drug.bioavailability
- 50% protein binding
- Drug.metabolism
- Liver
- Drug.elimination_half life
- 3–5 hrs.
- Drug.excretion
- Kidney
via Wikipedia infobox
Chemical data
- Formula
- C17H23NO3
- Molecular weight
- 289.4 g/mol
- IUPAC name
- [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2S)-3-hydroxy-2-phenylpropanoate
- SMILES
- CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)[C@H](CO)C3=CC=CC=C3
- InChIKey
- RKUNBYITZUJHSG-VFSICIBPSA-N
- XLogP
- 1.8
- Polar surface area
- 49.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
- Indications
- gastrointestinal disease
via ChEMBL · EBI
Research
638 papers- Hyoscyamine.2012
- The Evolutionary Pattern of Cocaine and Hyoscyamine Biosynthesis Provides Strategies To Produce Tropane Alkaloids.Chembiochem : a European journal of chemical biology · 2023
- Atropine.2006
- Hyoscyamine induces developmental toxicity by disrupting metabolism in zebrafish embryo (Danio rerio).Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association · 2023
- Modeling the functionalized genistein-hyoscyamine derivatives.Scientific reports · 2025
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 289.167793596
- Has use
- medication
Show 8 more facts
- chemical formula
- C₁₇H₂₃NO₃
- found in taxon
- Tura candida
- canonical SMILES
- CN1C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3
- Commons category
- Hyoscyamine
- medical condition treated
- irritable bowel syndrome
- defined daily dose
- 1.2
- isomeric SMILES
- CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)[C@H](CO)C3=CC=CC=C3
- NCI Thesaurus ID
- C29104
via Wikidata · CC0
~8 min read
Encyclopedic overview
9 sectionsContents
- Medical uses
- Adverse effects
- Pharmacology
- Pharmacodynamics
- Biosynthesis in plants
- [[Ethnopharmacology]]
- Society and culture
- Further reading
- References
Hyoscyamine (also known as daturine or duboisine) is a naturally occurring tropane alkaloid and plant toxin. It is a secondary metabolite found in certain plants of the family Solanaceae, including henbane, mandrake, angel's trumpets, jimsonweed, the sorcerers' tree, and Atropa belladonna (deadly nightshade). It is the Levorotatory isomer of atropine.
In 2021, it was the 272nd most commonly prescribed medication in the United States, with more than 900,000 prescriptions.
Excerpted from Wikipedia’s “hyoscyamine” article, available under the CC BY-SA 4.0 licence.