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Dextromethorphan

Not to be confused with Dextrorphan, Dexamethasone, or Dextroamphetamine.

Dextromethorphan
Clinical data
Pronunciation/ˌdɛk.stroʊ.məˈθɔːrˌfæn/
DEK-stroh-məth-OR-fan
Trade namesRobitussin, Delsym, others
Other namesDXM, 3-methoxy-N-methylmorphinan
AHFS/Drugs.comMonograph
MedlinePlusa682492
License data
Pregnancy
category
  • AU: A
Addiction
liability		Low–moderate
Routes of
administration		By mouth
Drug classAntitussive;[1][2]
Serotonin–norepinephrine reuptake inhibitor;[3] NMDA receptor antagonist; Dissociative hallucinogen
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability11%[4]
MetabolismLiver enzymes: major CYP2D6, minor CYP3A4, and minor CYP3A5
Metabolites
Elimination half-life2–4 hours (extensive metabolizers); 24 hours (poor metabolizers)[5]
Duration of action3–8 hours
ExcretionKidney
Identifiers
  • (4bS,8aR,9S)-3-Methoxy-11-methyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.321 Edit this at Wikidata
Chemical and physical data
FormulaC18H25NO
Molar mass271.404 g·mol−1
3D model (JSmol)
ChiralityDextrorotatory enantiomer
Melting point111 °C (232 °F)
  • CN1CC[C@@]23CCCC[C@@H]2[C@@H]1Cc4c3cc(cc4)OC
  • InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18+/m1/s1 checkY
  • Key:MKXZASYAUGDDCJ-NJAFHUGGSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Dextromethorphan, sold under the brand name Robitussin among others, is a cough suppressant used in many cough and cold medicines.[6] In 2022, the US Food and Drug Administration (FDA) approved the combination dextromethorphan/bupropion to serve as a rapid-acting antidepressant in people with major depressive disorder.[7]

It is in the morphinan class of medications with sedative, dissociative, and stimulant properties (at lower doses). Dextromethorphan does not have a significant affinity for the mu-opioid receptor activity typical of morphinan compounds and exerts its therapeutic effects through several other receptors.[8] In its pure form, dextromethorphan occurs as a white powder.[9]

When exceeding approved dosages, dextromethorphan acts as a dissociative hallucinogen. It has multiple mechanisms of action, including actions as a nonselective serotonin reuptake inhibitor[10] and a sigma-1 receptor agonist.[11][12] Dextromethorphan and its major metabolite, dextrorphan, also block the NMDA receptor at high doses, which produces effects similar to other dissociative anesthetics such as ketamine, nitrous oxide, and phencyclidine.

It was patented in 1949 and approved for medical use in 1953.[13] In 2022, the combination with promethazine was the 260th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[14][15] In 2022, the combination with brompheniramine and pseudoephedrine was the 265th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[14][16]

  1. ^ "Dextromethorphan Monograph for Professionals". Drugs.com.
  2. ^ Windhab LG, Gastberger S, Hulka LM, Baumgartner MR, Soyka M, Müller TJ, et al. (2020). "Dextromethorphan Abuse Among Opioid-Dependent Patients". Clinical Neuropharmacology. 43 (5): 127–133. doi:10.1097/WNF.0000000000000403. PMID 32947422. S2CID 221798401.
  3. ^ McCarthy B (2023-11-30). "Dextromethorphan-bupropion (Auvelity) for the Treatment of Major Depressive Disorder". Clinical Psychopharmacology and Neuroscience. 21 (4): 609–616. doi:10.9758/cpn.23.1081. PMC 10591164. PMID 37859435.
  4. ^ Kukanich B, Papich MG (October 2004). "Plasma profile and pharmacokinetics of dextromethorphan after intravenous and oral administration in healthy dogs". Journal of Veterinary Pharmacology and Therapeutics. 27 (5): 337–341. doi:10.1111/j.1365-2885.2004.00608.x. PMID 15500572.
  5. ^ "Balminil DM, Benylin DM (dextromethorphan) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Retrieved 15 April 2014.
  6. ^ Dicpinigaitis P (2022-09-12). "The Current and Emerging Treatment Landscape for Chronic Cough". The American Journal of Managed Care. Uncovering the Economic Burden of Chronic Cough and the Promising Role of Emerging Targeted Therapies. 28 (9): S159–S165. doi:10.37765/ajmc.2022.89244. PMID 36198074. S2CID 252736111. By sales, dextromethorphan is the most widely used OTC antitussive drug in the United States, and approximately 85% to 90% of OTC cough medicines contain dextromethorphan
  7. ^ Majeed A, Xiong J, Teopiz KM, Ng J, Ho R, Rosenblat JD, et al. (March 2021). "Efficacy of dextromethorphan for the treatment of depression: a systematic review of preclinical and clinical trials". Expert Opinion on Emerging Drugs. 26 (1): 63–74. doi:10.1080/14728214.2021.1898588. PMID 33682569. S2CID 232141396.
  8. ^ Cite error: The named reference pmid27139517 was invoked but never defined (see the help page).
  9. ^ "Reference Tables: Description and Solubility – D". Archived from the original on 2017-07-04. Retrieved 2011-05-06.
  10. ^ Schwartz AR, Pizon AF, Brooks DE (September 2008). "Dextromethorphan-induced serotonin syndrome". Clinical Toxicology. 46 (8): 771–773. doi:10.1080/15563650701668625. PMID 19238739. S2CID 37817922.
  11. ^ Shin EJ, Nah SY, Chae JS, Bing G, Shin SW, Yen TP, et al. (May 2007). "Dextromethorphan attenuates trimethyltin-induced neurotoxicity via sigma1 receptor activation in rats". Neurochemistry International. 50 (6): 791–799. doi:10.1016/j.neuint.2007.01.008. PMID 17386960. S2CID 43230896.
  12. ^ Shin EJ, Nah SY, Kim WK, Ko KH, Jhoo WK, Lim YK, et al. (April 2005). "The dextromethorphan analog dimemorfan attenuates kainate-induced seizures via sigma1 receptor activation: comparison with the effects of dextromethorphan". British Journal of Pharmacology. 144 (7): 908–918. doi:10.1038/sj.bjp.0705998. PMC 1576070. PMID 15723099.
  13. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 527. ISBN 9783527607495.
  14. ^ a b "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  15. ^ "Dextromethorphan; Promethazine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  16. ^ "Brompheniramine; Dextromethorphan; Pseudoephedrine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.

Dextromethorphan

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