Scopolamine

For the medication used to treat abdominal pain, see Hyoscine butylbromide.
"Hyoscine" redirects here. For Other uses, see Hyoscine (disambiguation).
Not to be confused with hyoscyamine.
"Devil's Breath" redirects here. For the novel, see The Devil's Breath.

Scopolamine
Clinical data
Trade namesTransderm Scop, others
Other namesHyoscine,[1] Devil's Breath
AHFS/Drugs.comMonograph
MedlinePlusa682509
License data
Pregnancy
category
Routes of
administration		By mouth, transdermal, ophthalmic, subcutaneous, intravenous, sublingual, rectal, buccal, transmucosal, intramuscular
Drug class
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability20-40%[7]
MetabolismLiver (CYP3A4)[8]
Elimination half-life5 hours[7]
ExcretionKidney
Identifiers
  • (–)-(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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.000.083 Edit this at Wikidata
Chemical and physical data
FormulaC17H21NO4
Molar mass303.358 g·mol−1
3D model (JSmol)
  • OC[C@H](c1ccccc1)C(=O)O[C@@H]2C[C@H]3N(C)[C@@H](C2)[C@@H]4O[C@H]34
  • 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,[9] or Devil's Breath,[10] is a natural or synthetically produced tropane alkaloid and anticholinergic drug that is used as a medication to treat motion sickness[11] and postoperative nausea and vomiting.[12][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][13]

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.[14][15] 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.[12] In these contexts, its mind-altering effects have been utilized for recreational and occult purposes.[16][17][18] 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.[19][20] It is on the World Health Organization's List of Essential Medicines.[21]

  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. ^ "Scopolamine Use During Pregnancy". Drugs.com. 6 September 2023. Archived from the original on 21 December 2016. Retrieved 21 June 2024.
  3. ^ "Poisons Standard October 2020". Federal Register of Legislation. 30 September 2020. Archived from the original on 25 January 2021. Retrieved 23 October 2020.
  4. ^ "Hyoscine 400 micrograms/ml Solution for Injection". (emc). 18 September 2017. Archived from the original on 8 November 2023. Retrieved 21 June 2024.
  5. ^ "Kwells 300 microgram tablets Summary of Product Characteristics (SmPC)". (emc). 2 September 2020. Archived from the original on 2 March 2024. Retrieved 21 June 2024.
  6. ^ "Transderm Scop - scopolamine patch, extended release". DailyMed. 14 March 2024. Archived from the original on 30 November 2023. Retrieved 21 June 2024.
  7. ^ a b 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.
  8. ^ Renner UD, Oertel R, Kirch W (October 2005). "Pharmacokinetics and pharmacodynamics in clinical use of scopolamine". Therapeutic Drug Monitoring. 27 (5): 655–665. doi:10.1097/01.ftd.0000168293.48226.57. PMID 16175141. S2CID 32720769.
  9. ^ 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.
  10. ^ Duffy R (23 July 2007). "Colombian Devil's Breath". Vice. Archived from the original on 18 April 2022. Retrieved 3 February 2022.
  11. ^ "About hyoscine hydrobromide". nhs.uk. 24 October 2022. Archived from the original on 14 March 2023. Retrieved 14 March 2023.
  12. ^ 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.
  13. ^ Sollmann T (1957). A Manual of Pharmacology and Its Applications to Therapeutics and Toxicology (8th ed.). Philadelphia and London: W.B. Saunders.
  14. ^ 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. Archived (PDF) from the original on 19 April 2022. Retrieved 26 July 2022.
  15. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 551. ISBN 978-3-527-60749-5.
  16. ^ 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.
  17. ^ Cite error: The named reference Uribe_et_al_2005 was invoked but never defined (see the help page).
  18. ^ Raetsch C (2005). The encyclopedia of psychoactive plants: ethnopharmacology and its applications. US: Park Street Press. pp. 277–282.
  19. ^ The Chambers Dictionary. Allied Publishers. 1998. pp. 788, 1480. ISBN 978-81-86062-25-8.
  20. ^ 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.
  21. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.