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
chemische Verbindung
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
Article · Deutsch
Dextromethorphan (abgek. oft: DXM, auch DMP) ist ein Arzneistoff, der auf das Nervensystem wirkt. Der Wirkstoff wurde als zentral (im Gehirn) wirksames Antitussivum (Hustenblocker) entwickelt. Heute weiß man, dass die Substanz ein potentes Psychotropikum ist, das auf zahlreiche Hirnfunktionen Einfluss nimmt. Seit 2013 ist Dextromethorphan daher in den USA in fixer Kombination mit Chinidin zur Behandlung neurologischer Erkrankungen in Folge von Schädigungen des Gehirns zugelassen.
Abstract from DBpedia / Wikipedia · CC BY-SA