CAS 125-71-3PubChem CID 5360696
Dextromethorphan
Dextromethorphan is a 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene in which the sterocenters at positions 4a, 10 and 10a have S-configuration. It is a prodrug of dextrorphan and used as an antitussive drug for suppressing cough. It has a role as a oneirogen, a xenobiotic, a prodrug, a neurotoxin, an antitussive, a NMDA receptor antagonist and an environmental contaminant. It is functionally related to a dextrorphan. It is an enantiomer of a levomethorphan. — ChEBI
- IUPAC name
- (1S,9S,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene
- Molecular formula
- C18H25NO
- Molecular weight
- 271.4 g/mol
- Exact mass
- 271.193614421 Da
- XLogP3
- 3.4
- Topological polar surface area
- 12.5 Ų
- Hydrogen-bond donors
- 0
- Hydrogen-bond acceptors
- 2
- Covalent units
- 1
- Defined stereocentres
- 3
Also known as
d-Methorphandelta-MethorphanDextromorphanDextromethorfanDextrometorfanoDextromethorphaneAlbutussinDestrometerfano
16 more reported names
DextromethorphanumBA 2666Balminil DM(+)-Dextromethorphan3-Methoxy-17-methyl-9alpha,13alpha,14alpha-morphinanMorphinan, 3-methoxy-17-methyl-, (9alpha,13alpha,14alpha)-DXM [Antitussive]BA-26667355X3ROTSCHEBI:4470(+)-3-Methoxy-N-methylmorphinonNSC-751452DXM (Antitussive)(+)-cis-1,3,4,9,10,10a-Hexahydro-6-methoxy-11-methyl-2H-10,4alpha-iminoethanophenanthren(+)-3-methoxy-17-methyl-9alpha,13alpha,14alpha-morphinanRoboTablets
External database identifiers
- ChEBI:CHEBI:4470
- ChEBI:CHEBI:92579
- ChEMBL:CHEMBL52440
- EPA DTXSID:DTXSID3022908
- PubMed:22608604
- PubMed:22073096
- PubMed:22066053
- PubMed:22044595
- PubMed:21973086
- PubMed:21867562
- PubMed:21614312
- PubMed:21445282
- PubMed:21436715
- PubMed:21266064
- PubMed:21244712
- PubMed:21175434
Evidence from additional scientific databases
NIH PubChem PUG-View
Exact identifier match5360696
Attributed physical-property, hazard, environmental and use annotations.
- Color/Form: White to slightly yellow crystalline powder Source: Hazardous Substances Data Bank (HSDB)
- Melting Point: 122-124 Source: DrugBank
- Melting Point: 109-111 °C Source: Hazardous Substances Data Bank (HSDB)
- Odor: Odorless Source: Hazardous Substances Data Bank (HSDB)
- Solubility: 1.5 g/100 mL Source: DrugBank
- Solubility: Practically insoluble in water Source: Hazardous Substances Data Bank (HSDB)
- Solubility: Freely soluble in chloroform Source: Hazardous Substances Data Bank (HSDB)
- Carcinogen Classification: No indication of carcinogenicity to humans (not listed by IARC). Source: Toxin and Toxin Target Database (T3DB)
- Exposure Routes: Oral, rapidly absorbed from the gastrointestinal tract. Source: Toxin and Toxin Target Database (T3DB)
- Note: This chemical does not meet GHS hazard criteria for 46.8% (36 of 77) of reports. Source: European Chemicals Agency (ECHA)
- Signal: Danger Source: European Chemicals Agency (ECHA)
- GHS Hazard Statements: H301 (51.9%): Toxic if swallowed [Danger Acute toxicity, oral] Source: European Chemicals Agency (ECHA)
- Precautionary Statement Codes: P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement) Source: European Chemicals Agency (ECHA)
- ECHA C&L Notifications Summary: Aggregated GHS information provided per 77 reports by companies from 4 notifications to the ECHA C&L Inventory.; Reported as not meeting GHS hazard criteria per 36 of 77 reports by companies.; There are 3 notifications provided by 41 of 77 reports by companies with hazard statement code(s).; Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. Source: European Chemicals Agency (ECHA)
- Health Effects: Hypertension, shallow respiration. Dextromethorphan can cause other gastrointestinal disturbances. [Wikipedia] Source: Toxin and Toxin Target Database (T3DB)
- Toxicity Summary: IDENTIFICATION AND USE: Dextromethorphan is a white odorless solid crystal or powder. It is an opium alkaloid derivative, which is found in cough and cold preparations. HUMAN STUDIES: Dextromethorphan is a drug of abuse. The main risks associated with dextromethorphan are ataxia, central nervous system (CNS) stimulation, dizziness, lethargy and psychotic behavior. Less frequently with large doses seizures and respiratory depression can occur. Nausea, vomiting, constipation and tachycardia may also occur. CNS effects include ataxia, drowsiness, vertigo and rarely coma. CNS stimulation may be observed. Restlessness, increased muscle tone with body rigidity have been reported. With extremely large ingestions respiratory depression can occur. Gastrointestinal effects include nausea, vomiting, constipation and dry mouth. Urinary retention may be seen. Dextromethorphan abuse has been described and produces euphoria, CNS stimulation, visual and/or auditory hallucinations. Dextromethorphan hydrobromide is the drug form, thus the possibility of bromide poisoning should be considered in the long term abuser. Dextromethorphan enhances serotonin activity by inhibiting the reuptake of serotonin Source: Hazardous Substances Data Bank (HSDB)
- Toxicity Summary: Signs and Symptoms of Overdose; One significant concern regarding dextromethorphan toxicity is its OTC misuse, which has steadily increased since the early 2000s. This misuse is referred to by slang terms such as "going pharming," "robotripping," and "dexing." In 2006, three specific OTC product formulations accounted for 66% of reported dextromethorphan misuse cases in the United States, with Coricidin HBP Cough & Cold Tablets and Robitussin products being prominent. A life-threatening toxicity associated with dextromethorphan abuse is serotonin syndrome, resulting from its serotonin reuptake inhibition properties. When combined with SSRIs or MAOIs, the risk of serotonin syndrome increases significantly. Symptoms include agitation, confusion, dilated pupils, headache, tachycardia, hypotension, high fever, seizures, irregular heartbeat, and may progress to unconsciousness.; Despite the rise in misuse, public health efforts and legislative actions restricting the sale of dextromethorphan-containing products to minors have helped stabilize or reduce abuse rates in recent years. However, continued vigilance is essential to prevent misuse and associated toxicities, given dextromethorph Source: StatPearls
- Toxicity Summary: Dextromethorphan is an opioid-like drug that binds to and acts as antagonist to the NMDA glutamatergic receptor, it is an agonist to the opioid sigma 1 and sigma 2 receptors, it is also an alpha3/beta4 nicotinic receptor antagonist and targets the serotonin reuptake pump. Dextromethorphan is rapidly absorbed from the gastrointestinal tract, where it enters the bloodstream and crosses the blood-brain barrier. The first-pass through the hepatic portal vein results in some of the drug being metabolized into an active metabolite of dextromethorphan, dextrorphan, the 3-hydroxy derivative of dextromethorphan. Source: Toxin and Toxin Target Database (T3DB)
- Environmental Bioconcentration: The estimated pKa of dextromethorphan is 9.8(1), indicating that dextromethorphan will exist almost entirely in the cation form at pH values of 5 to 9 and, therefore, bioconcentration in fish is not expected to be an important fate process(SRC). Source: Hazardous Substances Data Bank (HSDB)
- Environmental Fate: TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 23,000(SRC), determined from a structure estimation method(2), indicates that dextromethorphan is expected to be immobile in soil(SRC). The estimated pKa of dextromethorphan is 9.8(3), indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of the cation from moist soil is not expected because cations do not volatilize(SRC). Dextromethorphan is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.0X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2017). Source: Hazardous Substances Data Bank (HSDB)
- Environmental Fate: AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 23,000(SRC), determined from a structure estimation method(2), indicates that dextromethorphan is expected to adsorb to suspended solids and sediment(SRC). An estimated pKa of 9.8(3) indicates dextromethorphan will exist almost entirely in the cation form at pH values of 5 to 9 and, therefore, volatilization from water surfaces and bioconcentration in aquatic organisms are not expected to be an important fate processes(SRC). Dextromethorphan is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). Biodegradation data in water were not available(SRC, 2017). Source: Hazardous Substances Data Bank (HSDB)
- Environmental Fate: ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dextromethorphan, which has an estimated vapor pressure of 1.0X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dextromethorphan is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3.3 hours(SRC), calculated from its rate constant of 1.2X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase dextromethorphan may be removed from the air by wet or dry deposition(SRC). Dextromethorphan contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, is expected to be susceptible to direct photolysis by sunlight(SRC). Source: Hazardous Substances Data Bank (HSDB)
- Uses: Antitussive Agents; Excitatory Amino Acid Antagonists Source: Hazardous Substances Data Bank (HSDB)
- Uses: Probe to determine cytochrome 450 phenotype Source: Hazardous Substances Data Bank (HSDB)
- Uses: MEDICATION Source: Hazardous Substances Data Bank (HSDB)
- Uses: Dextromethorphan (DXM) is an over-the-counter (OTC) cough suppressant commonly found in cold medications. DXM is often abused in high doses by adolescents to generate euphoria and visual and auditory hallucinations. Illicit use of DXM is referred to on the street as "Robo-tripping" or "skittling." These terms are derived from the most commonly abused products, Robitussin and Coricidin. Source: Hazardous Substances Data Bank (HSDB)
- Uses: Use (kg; approx.) in Germany (2009): >1000; Use (kg) in USA (2002): 38000; Consumption (g per capita; approx.) in Germany (2009): 0.0122; Consumption (g per capita) in the USA (2002): 0.135; Excretion rate: 0.25; Calculated removal (%): 45.3 Source: NORMAN Suspect List Exchange
- Uses: The primary use of dextromethorphan is as a cough suppressant, for the temporary relief of cough caused by minor throat and bronchial irritation (as commonly accompanies the common cold), as well as those resulting from inhaled irritants. In addition, a combination of dextromethorphan and quinidine has been shown to alleviate symptoms of easy laughing and crying (pseudobulbar affect) in patients with amyotrophic lateral sclerosis and multiple sclerosis. Source: Toxin and Toxin Target Database (T3DB)
Mapped by: Existing checksum-valid CAS to unique PubChem CID match. Retrieved: 2026-08-31. Open source record
Scientific classifications and hazard annotations provide context and do not replace the market-specific regulatory decision shown above.
Additional source coverage and match status
| Source | Result | Checked |
|---|---|---|
| NIH PubChem PUG-View | Exact match | 2026-08-31 |
A recorded no-match is useful evidence that the source was checked; it is not a claim that the substance does not exist elsewhere.
Retrieved from NIH PubChem on 2026-08-31 by checksum-valid CAS matching. Chemical properties do not replace the regulatory decision on this page.