Morphine

Morphine
Clinical data
Pronunciation/ˈmɔːrfn/
Trade namesStatex, MS Contin, Oramorph, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa682133
License data
Pregnancy
category
Dependence
liability
High
Addiction
liability
High[3]
Routes of
administration
Inhalation (smoking), insufflation (snorting), by mouth, rectal, subcutaneous, intramuscular, intravenous, epidural, intrathecal
Drug classOpioid
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability20–40% (by mouth), 36–71% (rectally),[7] 100% (IV/IM)
Protein binding30–40%
MetabolismLiver: UGT2B7
MetabolitesMorphine-3-glucuronide (90%)
Morphine-6-glucuronide (10%)
Onset of action5 minutes (IV), 15 minutes (IM),[8] 20 minutes (PO)[9]
Elimination half-life2–3 hours
Duration of action3–7 hours[10][11]
ExcretionKidney 90%, bile duct 10%
Identifiers
  • (4R,4aR,7S,7aR,12bS)-3-Methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinoline-7,9-diol
CAS Number
  • 57-27-2 checkY
    64-31-3 (neutral sulfate),
    52-26-6 (hydrochloride)
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.000.291 Edit this at Wikidata
Chemical and physical data
FormulaC17H19NO3
Molar mass285.343 g·mol−1
3D model (JSmol)
Solubility in waterHCl & sulf.: 60
  • CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5
  • InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1 checkY
  • Key:BQJCRHHNABKAKU-KBQPJGBKSA-N checkY
  (verify)

Morphine is a strong opiate that is found naturally in opium, a dark brown resin produced by drying the latex of opium poppies (Papaver somniferum). It is mainly used as an analgesic (pain medication). There are numerous methods used to administer morphine: oral; sublingual; via inhalation; injection into a muscle, injection under the skin, or injection into the spinal cord area; transdermal; or via rectal suppository.[10][12] It acts directly on the central nervous system (CNS) to induce analgesia and alter perception and emotional response to pain. Physical and psychological dependence and tolerance may develop with repeated administration.[10] It can be taken for both acute pain and chronic pain and is frequently used for pain from myocardial infarction, kidney stones, and during labor.[10] Its maximum effect is reached after about 20 minutes when administered intravenously and 60 minutes when administered by mouth, while the duration of its effect is 3–7 hours.[10][11] Long-acting formulations of morphine are available as MS-Contin, Kadian, and other brand names as well as generically.[10]

Potentially serious side effects of morphine include decreased respiratory effort, vomiting, nausea, and low blood pressure.[10] Morphine is addictive and prone to abuse.[10] If one's dose is reduced after long-term use, opioid withdrawal symptoms may occur.[10] Common side effects of morphine include drowsiness, vomiting, and constipation.[10] Caution is advised for use of morphine during pregnancy or breast feeding, as it may affect the health of the baby.[10][2]

Morphine was first isolated between 1803 and 1805 by German pharmacist Friedrich Sertürner.[13] This is believed to be the first isolation of a medicinal alkaloid from a plant.[14] Merck began marketing it commercially in 1827.[13] Morphine was more widely used after the invention of the hypodermic syringe in 1853–1855.[13][15] Sertürner originally named the substance morphium, after the Greek god of dreams, Morpheus, as it has a tendency to cause sleep.[15][16]

The primary source of morphine is isolation from poppy straw of the opium poppy.[17] In 2013, approximately 523 tons of morphine were produced.[18] Approximately 45 tons were used directly for pain, an increase of 400% over the last twenty years.[18] Most use for this purpose was in the developed world.[18] About 70 percent of morphine is used to make other opioids such as hydromorphone, oxymorphone, and heroin.[18][19][20] It is a Schedule II drug in the United States,[19] Class A in the United Kingdom,[21] and Schedule I in Canada.[22] It is on the World Health Organization's List of Essential Medicines.[23] Morphine is sold under many brand names.[1] In 2021, it was the 156th most commonly prescribed medication in the United States, with more than 3 million prescriptions.[24][25] It is available as a generic medication.[26]

  1. ^ a b Cite error: The named reference drugs.com-page was invoked but never defined (see the help page).
  2. ^ a b "Morphine Use During Pregnancy". Drugs.com. 14 October 2019. Retrieved 21 August 2020.
  3. ^ Bonewit-West K, Hunt SA, Applegate E (2012). Today's Medical Assistant: Clinical and Administrative Procedures. Elsevier Health Sciences. p. 571. ISBN 978-1-4557-0150-6.
  4. ^ "Sevredol Summary of Product Characteristics (SmPC)". (emc). 13 February 2024. Retrieved 20 February 2024.
  5. ^ "MS Contin- morphine sulfate tablet". DailyMed. 27 December 2023. Retrieved 20 February 2024.
  6. ^ "Modified-released oral opioids". European Medicines Agency. 18 November 2010. Retrieved 20 February 2024.
  7. ^ Jonsson T, Christensen CB, Jordening H, Frølund C (April 1988). "The bioavailability of rectally administered morphine". Pharmacology & Toxicology. 62 (4): 203–5. doi:10.1111/j.1600-0773.1988.tb01872.x. PMID 3387374.
  8. ^ Whimster F (1997). Cambridge textbook of accident and emergency medicine. Cambridge: Cambridge University Press. p. 191. ISBN 978-0-521-43379-2. Archived from the original on 8 September 2017.
  9. ^ Liben S (2012). Oxford textbook of palliative care for children (2 ed.). Oxford: Oxford University Press. p. 240. ISBN 978-0-19-959510-5. Archived from the original on 8 September 2017.
  10. ^ a b c d e f g h i j k "Morphine sulfate". The American Society of Health-System Pharmacists. Archived from the original on 2 May 2015. Retrieved 1 June 2015.
  11. ^ a b Rockwood CA (2009). Rockwood and Wilkins' fractures in children (7th ed.). Philadelphia, Pa.: Lippincott Williams & Wilkins. p. 54. ISBN 978-1-58255-784-7. Archived from the original on 8 September 2017.
  12. ^ Stefano GB, Ptáček R, Kuželová H, Kream RM (2012). "Endogenous morphine: up-to-date review 2011" (PDF). Folia Biologica. 58 (2): 49–56. PMID 22578954. Archived from the original (PDF) on 24 August 2016. Retrieved 10 October 2016. Positive evolutionary pressure has apparently preserved the ability to synthesize chemically authentic morphine, albeit in homeopathic concentrations, throughout animal phyla.
  13. ^ a b c Courtwright DT (2009). Forces of habit drugs and the making of the modern world (1 ed.). Cambridge, Mass.: Harvard University Press. pp. 36–37. ISBN 978-0-674-02990-3. Archived from the original on 8 September 2017.
  14. ^ Luch A, ed. (2009). Molecular, clinical and environmental toxicology. Springer. p. 20. ISBN 978-3-7643-8335-0.
  15. ^ a b Mosher CJ (2013). Drugs and Drug Policy: The Control of Consciousness Alteration. SAGE Publications. p. 123. ISBN 978-1-4833-2188-2. Archived from the original on 8 September 2017.
  16. ^ Fisher GL (2009). Encyclopedia of substance abuse prevention, treatment, & recovery. Los Angeles: SAGE. p. 564. ISBN 978-1-4522-6601-5. Archived from the original on 8 September 2017.
  17. ^ Narcotic Drugs Estimated World Requirements for 2008, Statistics for 2006. New York: United Nations Pubns. 2008. p. 77. ISBN 978-92-1-048119-9. Archived from the original on 8 September 2017.
  18. ^ a b c d Narcotic Drugs 2014 (PDF). INTERNATIONAL NARCOTICS CONTROL BOARD. 2015. pp. 21, 30. ISBN 978-92-1-048157-1. Archived (PDF) from the original on 2 June 2015.
  19. ^ a b Triggle DJ (2006). Morphine. New York: Chelsea House Publishers. pp. 20–21. ISBN 978-1-4381-0211-5.
  20. ^ Karch SB (2006). Drug abuse handbook (2nd ed.). Boca Raton: CRC/Taylor & Francis. pp. 7–8. ISBN 978-1-4200-0346-8.
  21. ^ Macpherson G, ed. (2002). Black's Medical Dictionary. Vol. 87 (40th ed.). p. 162. Bibcode:1911Natur..87R.313.. doi:10.1038/087313b0. ISBN 978-0-7136-5442-4. S2CID 3979058. Archived from the original on 8 September 2017. {{cite book}}: |journal= ignored (help)
  22. ^ Davis's Canadian Drug Guide for Nurses. F.A. Davis. 2014. p. 1409. ISBN 978-0-8036-4086-3.
  23. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  24. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  25. ^ "Morphine - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  26. ^ "First Generic Drug Approvals 2023". U.S. Food and Drug Administration (FDA). 30 May 2023. Archived from the original on 30 June 2023. Retrieved 30 June 2023.