File:Dextromethorphan-2D-Skeletal-Chemical-Formula.png · Wikimedia Commons · See Wikimedia Commons
dextromethorphan
Sign in to saveAlso known as d-methorphan, DM, D-methorphan, Dex, (+)-dextromethorphan, (9S,13S,14S)-3-methoxy-17-methylmorphinan, dextromethorfan, delta-methorphan
Dextromethorphan is a cough suppressant used in many cough and cold medicines. 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.
OverviewAI-generated
Dextromethorphan is a chemical compound with the formula C₁₈H₂₅NO. Its IUPAC name is (1S,9S,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene. The substance has a mass of 271.193614 and a weight of 271.4. It possesses a defined daily dose of 90.
Chemical properties include an xlogp of 3.4 and a topological polar surface area of 12.5. The molecule contains zero hydrogen bond donors and two hydrogen bond acceptors, with a charge of 0. Dextromethorphan is referenced by 1,873 other encyclopedia articles.
Synthesized by Vinony from 20 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 470624518
- Drug.image
- Dextromethorphan-2D-Skeletal-Chemical-Formula.png
- Drug.image_class
- skin-invert-image
- Drug.width
- 300
- Drug.image2
- Dextromethorphan-3D-Ball-And-Stick-Model.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 234
- Drug.tradename
- Delsym, others
- Drug.MedlinePlus
- a682492
- Drug.DailyMedID
- Dextromethorphan
- Drug.pregnancy_AU
- A
- Drug.addiction_liability
- Low–moderate
- Drug.routes_of_administration
- By mouth
- Drug.class
- Antitussive;Serotonin–norepinephrine reuptake inhibitor; NMDA receptor antagonist; Dissociative hallucinogen
- Drug.ATC_prefix
- R05
- Drug.ATC_suffix
- DA09
via Wikipedia infobox
Chemical data
- Formula
- C18H25NO
- Molecular weight
- 271.4 g/mol
- IUPAC name
- (1S,9S,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene
- SMILES
- CN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC4=C3C=C(C=C4)OC
- InChIKey
- MKXZASYAUGDDCJ-NJAFHUGGSA-N
- XLogP
- 3.4
- Polar surface area
- 12.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1982
- Admin. routes
- oral
- Indications
- Cough, Cognitive impairment, peripheral neuropathy, neuropathic pain
via ChEMBL · EBI
Research
3,486 papers- Dextromethorphan/Bupropion: First Approval.CNS drugs · 2022
- Effect of AXS-05 (Dextromethorphan-Bupropion) in Major Depressive Disorder: A Randomized Double-Blind Controlled Trial.The American journal of psychiatry · 2022
- Dextromethorphan abuse.Pediatric emergency care · 2004
- Classics in Chemical Neuroscience: Dextromethorphan (DXM).ACS chemical neuroscience · 2023
- Dextromethorphan as an Opioid-Sparing Analgesic in Postoperative Pain.Clinical neuropharmacology · 2025
via PubMed
Wikidata facts
- Mass
- 271.193614
- Has use
- medication
Show 13 more facts
- significant drug interaction
- isocarboxazid
- Commons category
- Dextromethorphan
- chemical formula
- C₁₈H₂₅NO
- canonical SMILES
- CN1CCC23CCCCC2C1CC4=C3C=C(C=C4)OC
- NCI Thesaurus ID
- C62022
- medical condition treated
- nasopharyngitis
- isomeric SMILES
- COC1=CC=C2C[C@H]3[C@H]4CCCC[C@@]4(CCN3C)C2=C1
- subject has role
- antitussive
- physically interacts with
- Sigma non-opioid intracellular receptor 1
- stereoisomer of
- levomethorphan
- different from
- dextrorphan
- has characteristic
- bitterness
- defined daily dose
- 90
Sources (6)
via Wikidata · CC0
~19 min read
Encyclopedic overview
25 sectionsContents
- Medical uses
- Cough suppression
- Pseudobulbar affect
- Major depressive disorder
- Adverse effects
- Neurotoxicity
- Dependence and withdrawal
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Metabolism
- Chemistry
- Synthesis
- Racemate separation
- Traditional synthesis
- Grewe's cyclization
- Improved Grewe's cyclization
- History
- Society and culture
- Marketing
- Recreational use
- Research
- References
- External links
Dextromethorphan is a cough suppressant used in many cough and cold medicines. 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.
It is in the morphinan class of medications with 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. In its pure form, dextromethorphan occurs as a white powder.
Excerpted from Wikipedia’s “dextromethorphan” article, available under the CC BY-SA 4.0 licence.