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Scopolamine information


Scopolamine
Clinical data
Trade namesTransdermscop, Kwells, others
Other namesHyoscine[1]
AHFS/Drugs.comMonograph
MedlinePlusa682509
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[2]
  • UK: POM (Prescription only) / P[3][4]
  • US: ℞-only[5]
Pharmacokinetic data
MetabolismLiver
Elimination half-life4.5 hours[6]
ExcretionKidney
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 checkY
PubChem CID
  • 5184
IUPHAR/BPS
  • 330
DrugBank
  • DB00747 checkY
ChemSpider
  • 10194106 checkY
UNII
  • DL48G20X8X
KEGG
  • D00138 checkY
  • as salt: D02071 checkY
ChEBI
  • CHEBI:16794 checkY
ChEMBL
  • ChEMBL569713 ☒N
CompTox Dashboard (EPA)
  • DTXSID6023573 Edit this at Wikidata
ECHA InfoCard100.000.083 Edit this at Wikidata
Chemical and physical data
FormulaC17H21NO4
Molar mass303.358 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 checkY
  • Key:STECJAGHUSJQJN-FWXGHANASA-N checkY
 ☒NcheckY (what is this?)  (verify)

Scopolamine, also known as hyoscine,[7] or Devil's Breath,[8] is a natural or synthetically produced tropane alkaloid and anticholinergic drug that is used as a medication to treat motion sickness[9] and postoperative nausea and vomiting.[10][1] It is also sometimes used before surgery to decrease saliva.[1] When used by injection, effects begin after about 20 minutes and last for up to 8 hours.[1] It may also be used orally and as a transdermal patch since it has been long known to have transdermal bioavailability.[1][11]

Scopolamine is in the antimuscarinic family of drugs and works by blocking some of the effects of acetylcholine within the nervous system.[1] Scopolamine was first written about in 1881 and started to be used for anesthesia around 1900.[12][13] 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.[10] In these contexts, its mind-altering effects have been utilized for recreational and occult purposes.[14][15][16] 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.[17][18] It is on the World Health Organization's List of Essential Medicines.[19]

  1. ^ a b c d e f "Scopolamine". The American Society of Health-System Pharmacists. Archived from the original on 7 October 2016. Retrieved 8 December 2016.
  2. ^ "Poisons Standard October 2020". Federal Register of Legislation. 30 September 2020. Retrieved 23 October 2020.
  3. ^ "Hyoscine Hydrobromide 400 micrograms/ml Solution for Injection - Summary of Product Characteristics (SmPC)". (emc). Archived from the original on 27 October 2020. Retrieved 23 October 2020.
  4. ^ "Kwells 300 microgram tablets - Summary of Product Characteristics (SmPC)". (emc). Archived from the original on 26 October 2020. Retrieved 23 October 2020.
  5. ^ "Transderm Scop- scopolamine patch, extended release". DailyMed. Retrieved 4 February 2022.
  6. ^ Putcha L, Cintrón NM, Tsui J, Vanderploeg JM, Kramer WG (June 1989). "Pharmacokinetics and oral bioavailability of scopolamine in normal subjects". Pharmaceutical Research. 06 (6): 481–485. doi:10.1023/A:1015916423156. PMID 2762223. S2CID 27507555.
  7. ^ Juo PS (2001). Concise Dictionary of Biomedicine and Molecular Biology (2nd ed.). Hoboken: CRC Press. p. 570. ISBN 978-1-4200-4130-9. Archived from the original on 10 September 2017.
  8. ^ Duffy R (23 July 2007). "Colombian Devil's Breath". Vice. Retrieved 3 February 2022.
  9. ^ "About hyoscine hydrobromide". nhs.uk. 24 October 2022. Retrieved 14 March 2023.
  10. ^ a b Osbourn AE, Lanzotti V (2009). Plant-derived Natural Products: Synthesis, Function, and Application. Springer Science & Business Media. p. 5. ISBN 978-0-387-85498-4. Archived from the original on 10 September 2017.
  11. ^ Sollmann T (1957). A Manual of Pharmacology and Its Applications to Therapeutics and Toxicology (8th ed.). Philadelphia and London: W.B. Saunders.
  12. ^ Keys TE (1996). The history of surgical anesthesia (PDF) (Reprint ed.). Park Ridge, Ill.: Wood Library, Museum of Anesthesiology. p. 48ff. ISBN 978-0-9614932-7-1.
  13. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 551. ISBN 978-3-527-60749-5.
  14. ^ Kennedy DO (2014). "The Deliriants - The Nightshade (Solanaceae) Family". Plants and the Human Brain. New York: Oxford University Press. pp. 131–137. ISBN 978-0-19-991401-2. LCCN 2013031617. Archived from the original on 17 September 2021. Retrieved 17 September 2021.
  15. ^ Cite error: The named reference Uribe_et_al_2005 was invoked but never defined (see the help page).
  16. ^ Raetsch C (2005). The encyclopedia of psychoactive plants: ethnopharmacology and its applications. US: Park Street Press. pp. 277–282.
  17. ^ The Chambers Dictionary. Allied Publishers. 1998. pp. 788, 1480. ISBN 978-81-86062-25-8.
  18. ^ Cattell HW (1910). Lippincott's new medical dictionary: a vocabulary of the terms used in medicine, and the allied sciences, with their pronunciation, etymology, and signification, including much collateral information of a descriptive and encyclopedic character. Lippincott. p. 435. Archived from the original on 10 September 2017. Retrieved 25 February 2012.
  19. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

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Scopolamine

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Scopolamine, also known as hyoscine, or Devil's Breath, is a natural or synthetically produced tropane alkaloid and anticholinergic drug that is used...

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Hyoscine butylbromide

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Hyoscine butylbromide, also known as scopolamine butylbromide and sold under the brandname Buscopan among others, is an anticholinergic medication used...

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Deliriant

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include plants of the genera Datura and Brugmansia (both containing scopolamine) as well as higher than recommended dosages of diphenhydramine (Benadryl)...

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Truth serum

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unable or unwilling to provide it otherwise. These include ethanol, scopolamine, 3-quinuclidinyl benzilate, midazolam, flunitrazepam, sodium thiopental...

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Twilight sleep

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without the loss of consciousness, induced by an injection of morphine and scopolamine, with the purpose of pain management during childbirth. The obstetric...

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Love potion

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European scopolia or autumn mandrake, which contain alkaloids (atropine and scopolamine, which are hallucinogenic in higher doses) characterized by a narrow...

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Motion sickness

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horizon. Three types of medications are useful: antimuscarinics such as scopolamine, H1 antihistamines such as dimenhydrinate, and amphetamines such as dexamphetamine...

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Datura

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in both the New and Old Worlds due to the presence of the alkaloids scopolamine and atropine, which are also produced by plants associated with Old World...

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Datura stramonium

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younger, the ratio of scopolamine to atropine is about 3:1; after flowering, this ratio is reversed, with the amount of scopolamine continuing to decrease...

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Real Raw News

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cause a disease called "monsterism" and that they contain pesticides and scopolamine. In September 2021, it published a false story about 27 U.S. Air Force...

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Tropane alkaloid

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plant family Solanaceae. Certain tropane alkaloids such as cocaine and scopolamine are notorious for their psychoactive effects, related usage and cultural...

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Muscarinic antagonist

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long the effect persists. Scopolamine and atropine have similar effects on the peripheral nervous system. However, scopolamine has greater effects on the...

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Atropa belladonna

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

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Hyoscyamine

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Atropa belladonna-derived drug hyoscine (known in the United States as Scopolamine) has 92 per cent of the antimuscarinic potency of atropine. Hyoscyamine...

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Brugmansia aurea

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the psychoactive scopolamine. It has also been used as a truth serum. Borrachero loosely translates to "get-you-drunk", and scopolamine is also known as...

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C17H21NO4

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to: Cocaine Cocaine reverse ester Fenoterol Hydromorphinol Hyoscine (scopolamine) Oxymorphol This set index page lists chemical structure articles associated...

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Phytochemistry

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

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Death rattle

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palliative care, drugs such as glycopyrronium, hyoscine hydrobromide (scopolamine) or atropine may be used for their anticholinergic effects to reduce...

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Cocaine

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Amanita muscaria PCP Salvinorin A Salvia divinorum Deliriants Atropine and Scopolamine Atropa belladonna Datura Hyoscyamus niger Mandragora officinarum Dimenhydrinate...

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Preanesthetic agent

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Examples of preanesthetic agents are: Acepromazine atropine diazepam Scopolamine Opioid analgesics, such as morphine, pethidine and buprenorphine. These...

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Anticholinergic

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Orphenadrine Oxitropium Oxybutynin Promethazine Propantheline bromide Scopolamine Solifenacin Tolterodine Tiotropium Tricyclic antidepressants Trihexyphenidyl...

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Heart rate variability

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and scopolamine, may produce a paradoxical increase in vagal effects on the heart, as suggested by a decrease in heart rate. In addition, scopolamine and...

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Muscarinic acetylcholine receptor

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system. Many drugs and other substances (for example pilocarpine and scopolamine) manipulate these two distinct receptors by acting as selective agonists...

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Duboisia myoporoides

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poisonous. The leaves contain a number of alkaloids, including hyoscine (scopolamine), used for treating motion sickness, stomach disorders, and the side...

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Meclizine

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effects than the traditional treatment for motion sickness, transdermal scopolamine. A very serious allergic reaction to this drug is unlikely, but immediate...

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Fish

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Oleandrin Persin Protoanemonin Pseudaconitine Retronecine Resiniferatoxin Scopolamine Solamargine Solanidine Solanine Solasodamine Solasodine Solasonine Solauricidine...

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Psychoplastogen

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various stages of development as medications including Ketamine, MDMA, Scopolamine, and the serotonergic psychedelics, including LSD, psilocin (the active...

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