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Dextromethorphan

From Wikipedia
dextromethorphan
type of chemical entity
Subclass ofLSM-1535 Edit
Part ofresponse to dextromethorphan, cellular response to dextromethorphan Edit
Get useMedication Edit
Stereoisomer of(9S,13S,14R)-3-methoxy-17-methylmorphinan, levomethorphan Edit
Chemical formulaC₁₈H₂₅NO Edit
Canonical SMILESCN1CCC23CCCCC2C1CC4=C3C=C(C=C4)OC Edit
Isomeric SMILESCOC1=CC=C2C[C@H]3[C@H]4CCCC[C@@]4(CCN3C)C2=C1 Edit
Medical condition treatedcough, nasopharyngitis Edit
Significant drug interactionisocarboxazid, phenelzine, procarbazine, (±)-deprenyl, tranylcypromine Edit
Physically dey interact plusGlutamate ionotropic receptor NMDA type subunit 2C, Sigma non-opioid intracellular receptor 1 Edit
Pregnancy categoryAustralian pregnancy category A, US pregnancy category C Edit
Get characteristicbitterness Edit
Subject has roleselective serotonin reuptake inhibitor, excitatory amino acid antagonist, antitussive Edit
NCI Thesaurus IDC62022 Edit

Dextromethorphan, dem sell am under de brand name Robitussin among odas, be a cough suppressant dem use insyd chaw cough den cold medicines.[1] Insyd 2022, na de US Food and Drug Administration (FDA) approve de combination dextromethorphan/bupropion to serve as a rapid-acting antidepressant insyd people plus major depressive disorder.[2]

E dey insyd de morphinan class of medications plus dissociative den stimulant properties (at lower doses). Dextromethorphan no get a significant affinity for de mu-opioid receptor activity typical of morphinan compounds den exert ein therapeutic effects thru chaw oda receptors.[3] Insyd ein pure form, dextromethorphan dey occur as a white powder.[4]

When exceeding dosages dem approve, dextromethorphan dey act as a dissociative hallucinogen. E get multiple mechanisms of action, wey dey include actions as a nonselective Serotonin–norepinephrine reuptake inhibitor[5] den a sigma-1 receptor agonist.[6][7] Dextromethorphan den ein major metabolite dextrorphan sanso block de NMDA receptor at high doses, wey dey produce effects similar to those of oda dissociative anesthetics such as ketamine, nitrous oxide, den phencyclidine.

Na dem patent am insyd 1949 wey na dem approve am for medical use insyd 1953.[8] Insyd 2023, na de combination plus promethazine be de 252nd most commonly prescribed medication insyd de United States, plus more dan 1 million prescriptions;[9][10] wey na de combination plus brompheniramine den pseudoephedrine be de 281st most commonly prescribed medication insyd de United States, plus more dan 700,000 prescriptions.[9][11]

References

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  1. ↑ Dicpinigaitis, P (12 September 2022). "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 (in English). 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
  2. ↑ Majeed A, Xiong J, Teopiz KM, Ng J, Ho R, Rosenblat JD, Phan L, Cao B, McIntyre RS (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.
  3. ↑ Taylor CP, Traynelis SF, Siffert J, Pope LE, Matsumoto RR (August 2016). "Pharmacology of dextromethorphan: Relevance to dextromethorphan/quinidine (Nuedexta) clinical use". Pharmacology & Therapeutics. 164: 170–182. doi:10.1016/j.pharmthera.2016.04.010. PMID 27139517.
  4. ↑ "Reference Tables: Description and Solubility - D". U.S Pharmacopeia. 2 May 2006. Archived from the original on 4 July 2017. Retrieved 6 May 2011.
  5. ↑ 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.
  6. ↑ Shin EJ, Nah SY, Chae JS, Bing G, Shin SW, Yen TP, Baek IH, Kim WK, Maurice T, Nabeshima T, Kim HC (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.
  7. ↑ Shin EJ, Nah SY, Kim WK, Ko KH, Jhoo WK, Lim YK, Cha JY, Chen CF, Kim HC (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.
  8. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 527. ISBN 978-3-527-60749-5.
  9. 1 2 "The Top 300 of 2023". ClinCalc. Archived from the original on 17 August 2025. Retrieved 17 August 2025.
  10. ↑ "Dextromethorphan; Promethazine Drug Usage Statistics, United States, 2014 - 2023". ClinCalc. Retrieved 17 August 2025.
  11. ↑ "Brompheniramine; Dextromethorphan; Pseudoephedrine Drug Usage Statistics, United States, 2014 - 2023". ClinCalc. Retrieved 17 August 2025.
[edit | edit source]
  • "DXM". Drug Enforcement Administration (DEA).
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