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Hyoscyamine information


Hyoscyamine
Clinical data
Trade namesAnaspaz, Levbid, Levsin
AHFS/Drugs.comMonograph
MedlinePlusa684010
Routes of
administration
By mouth, Injection
ATC code
  • A03BA03 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Bioavailability50% protein binding
MetabolismLiver
Elimination half-life3–5 hrs.
ExcretionKidney
Identifiers
IUPAC name
  • (S)-(1R,3r,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
CAS Number
  • 101-31-5 checkY
PubChem CID
  • 154417
DrugBank
  • DB00424 checkY
ChemSpider
  • 10246417 checkY
UNII
  • PX44XO846X
KEGG
  • D00147
ChEBI
  • CHEBI:17486 checkY
ChEMBL
  • ChEMBL1697729 ☒N
CompTox Dashboard (EPA)
  • DTXSID80889335 Edit this at Wikidata
ECHA InfoCard100.002.667 Edit this at Wikidata
Chemical and physical data
FormulaC17H23NO3
Molar mass289.375 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • CN3[C@H]1CC[C@@H]3C[C@@H](C1)OC(=O)[C@H](CO)c2ccccc2
InChI
  • InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1 checkY
  • Key:RKUNBYITZUJHSG-FXUDXRNXSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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 levorotary isomer of atropine (third of the three major nightshade alkaloids) and thus sometimes known as levo-atropine.[1]

In 2021, it was the 272nd most commonly prescribed medication in the United States, with more than 900,000 prescriptions.[2][3]

  1. ^ Ushimaru R, Ruszczycky MW, Liu HW (January 2019). "Changes in Regioselectivity of H Atom Abstraction during the Hydroxylation and Cyclization Reactions Catalyzed by Hyoscyamine 6β-Hydroxylase". Journal of the American Chemical Society. 141 (2): 1062–1066. doi:10.1021/jacs.8b11585. PMC 6488026. PMID 30545219.
  2. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  3. ^ "Hyoscyamine - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

and 26 Related for: Hyoscyamine information

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Hyoscyamine

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Hyoscyamine (also known as daturine or duboisine) is a naturally occurring tropane alkaloid and plant toxin. It is a secondary metabolite found in certain...

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Atropine

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an enantiomeric mixture of d-hyoscyamine and l-hyoscyamine, with most of its physiological effects due to l-hyoscyamine. Its pharmacological effects are...

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Tropane alkaloid

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drugs and deliriants: Atropine, racemic hyoscyamine, from the deadly nightshade (Atropa belladonna) Hyoscyamine, the levo-isomer of atropine, from henbane...

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Phytochemistry

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pharmaceutical. Medicines of different classes include atropine, scopolamine, and hyoscyamine (all from nightshade), the traditional medicine berberine (from plants...

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Scopolia japonica

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technique has also been used to produce the alkaloids scopolamine and hyoscyamine. Plant in flower. Single flower (interior). Scopoliae Rhizoma (root of...

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Atropa belladonna

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containing tropane alkaloids. These toxins include atropine, scopolamine, and hyoscyamine, which cause delirium and hallucinations, and are also used as pharmaceutical...

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Solanaceae

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and the genes that produce them. Hyoscyamine 6-β-hydroxylase, for example, catalyses the hydroxylation of hyoscyamine that leads to the production of scopolamine...

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Mandragora officinarum

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deliriant hallucinogenic tropane alkaloids (atropine, scopolamine, and hyoscyamine) which cause delirium and hallucinations, and the shape of their roots...

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Scopolamine

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as Cyp80F1 oxidizes and rearranges littorine to hyoscyamine aldehyde. In the final step, hyoscyamine undergoes epoxidation catalyzed by 6beta-hydroxyhyoscyamine...

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Anticholinergic

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Dimenhydrinate Diphenhydramine Doxepin Doxylamine Flavoxate Glycopyrronium/-late Hyoscyamine Ipratropium Orphenadrine Oxitropium Oxybutynin Promethazine Propantheline...

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Tropic acid

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a laboratory reagent used in the chemical synthesis of atropine and hyoscyamine. Tropic acid is a chiral substance, existing as either a racemic mixture...

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Ketamine

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Imidafenacin Ipratropium bromide (+salbutamol) Isopropamide J-104,129 Hyoscyamine Mamba toxin 3 Mamba toxin 7 Mazaticol Mebeverine Meladrazine Mepenzolate...

Word Count : 11331

Asthmador

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and the smoke inhaled. The primary alkaloid present in the mixture was hyoscyamine, and when the powder was ingested rather than burned, could be used to...

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MDMA

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Diphenhydramine Ditran Doxylamine EA-3167 EA-3443 EA-3580 EA-3834 Flavoxate Hyoscyamine JB-318 JB-336 Meclozine Mepyramine Orphenadrine Oxybutynin Pheniramine...

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Antisialagogue

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procedures. Classic antisialagogues include: atropine, opioids, alkalis, hyoscyamine, scopolamine, tobacco in excess, most cannabinoids, all nauseous or insipid...

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Mydriasis

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and mephedrone. Anticholinergics such as diphenhydramine, atropine, hyoscyamine, and scopolamine antagonize the muscarinic acetylcholine receptors in...

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Solandra

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native traditions. The alkaloids present include atropine, noratropine, hyoscyamine, and tropine with about 0.15% overall content in the leaves. In all ten...

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LSD

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Diphenhydramine Ditran Doxylamine EA-3167 EA-3443 EA-3580 EA-3834 Flavoxate Hyoscyamine JB-318 JB-336 Meclozine Mepyramine Orphenadrine Oxybutynin Pheniramine...

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Muscarinic antagonist

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to vasodilation. Important muscarinic antagonists include atropine, hyoscyamine, hyoscine butylbromide and hydrobromide, ipratropium, tropicamide, cyclopentolate...

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Ipratropium bromide

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tolterodine, certain medications for stomach problems, such as dicyclomine and hyoscyamine, and certain medications for travel sickness, such as scopolamine. Chemically...

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Littorine

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belladonna. It is closely related in chemical structure to atropine, hyoscyamine, and scopolamine, which all share a common biosynthetic pathway. Catuabine...

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Antispasmodic

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spasms of the stomach, intestine or urinary bladder. Both dicyclomine and hyoscyamine are antispasmodic due to their anticholinergic action.[medical citation...

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Oneirogen

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involve flying. [citation needed] Atropa belladonna (contains atropine, hyoscyamine, and scopolamine) Atropine (via blockade of acetylcholine receptors)...

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Donnatal

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mL elixir. Active ingredients are listed as: phenobarbital (16.2 mg), hyoscyamine sulfate (0.1037 mg), atropine sulfate (0.0194 mg), and scopolamine hydrobromide...

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Duboisia myoporoides

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the same substance could be used in the production of scopolamine and hyoscyamine, which are used in eye surgery, and a multi-million dollar industry was...

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Dimenhydrinate

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Imidafenacin Ipratropium bromide (+salbutamol) Isopropamide J-104,129 Hyoscyamine Mamba toxin 3 Mamba toxin 7 Mazaticol Mebeverine Meladrazine Mepenzolate...

Word Count : 1350

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