Dextromethorphan
(9S,13S,14S)-3-methoxy-17-methylmorphinan
Overview
Dextromethorphan belongs to Dissociatives.
Effects
- At antitussive doses DXM simply suppresses coughing, with little or no psychoactive effect.
- Recreationally the effects rise through four dose-dependent 'plateaus': the first (~1.5–2.5 mg/kg) feels like mild stimulation, a 'drunk' euphoria and enhanced music. The second (~2.5–7.5 mg/kg) adds stronger euphoria, sedation, spatial disorientation and mild hallucinations.
- Higher plateaus are intensely dissociative: the third (~7.5–15 mg/kg) brings memory suppression, ego-loss, hallucinations and profound disconnection, and the fourth (~15+ mg/kg) a near-anaesthetic, fully dissociated state with a high risk of injury, vomiting, blackouts and overdose. Throughout, common bodily effects include ataxia (the characteristic 'robo-walk'), nausea, sweating, itching and a raised heart rate.
Dosing & duration
Oral (syrup, gel-caps, extended-release suspension). The recreational figures below are the commonly cited dissociative 'plateaus', not safe or recommended doses (the antitussive dose is only ~10–30 mg). The single most important harm-reduction point: use ONLY single-ingredient dextromethorphan. Most cough products also contain paracetamol/acetaminophen, chlorphenamine, pseudoephedrine or guaifenesin, and a plateau dose of those co-formulated drugs can cause liver failure, anticholinergic delirium, seizures or cardiac harm well before the DXM. Because response depends on CYP2D6 genetics it is unpredictable. Onset is slow, so redosing early risks a much heavier trip than intended.
Dose ranges
10–30 mg per dose
~1.5–2.5 mg/kg (≈100–200 mg)
~2.5–7.5 mg/kg (≈200–400 mg)
~7.5–15 mg/kg (≈300–600 mg)
~15–20 mg/kg (≈600 mg +): near-anaesthetic, dangerous
Duration
30–120 minutes
3–6 hours
8–12 hours
4–24 hours
Chemical & Physical Properties
| Formula | C18H25NO |
| Molar mass | 271.4 g/mol |
| State | Solid |
| Melting point | 109–111 °C |
| Boiling point | Not reported |
| Density | Not reported |
| Vapor pressure | Not reported |
| pKa | Not reported |
| LogP | 3.4 (predicted, XLogP3) |
| Solubility | 1.5 g/100 mL, Practically insoluble in water, Freely soluble in chloroform |
| Refractive index | Not reported |
Identifiers & Synonyms
| CAS | 125-71-3 |
| CAS (enantiomer) | |
| PubChem CID | 5360696 |
| InChIKey | MKXZASYAUGDDCJ-NJAFHUGGSA-N |
| InChI | 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 |
| SMILES | CN1[C@H]2CC3=CC=C(OC)C=C3[C@@]4(CC1)C2CCCC4 |
Synonyms
- DXM
- Robitussin (component)
- Dextromethorphan
- Delsym
- Robo
Pharmacodynamics & Biochemistry
Dextromethorphan (DXM) is the dextrorotatory morphinan cough suppressant found in many over-the-counter cold and cough products. Unusually for a morphinan it has essentially no classical opioid (μ-receptor) activity at normal doses, so it produces neither opioid analgesia nor a typical opioid high. DXM itself acts mainly as a sigma-1 receptor agonist and a serotonin–noradrenaline reuptake inhibitor, with only weak NMDA activity. Its antitussive effect comes from a central action that raises the cough threshold. The dissociative, 'robotripping' effects come mostly from its metabolite: the liver enzyme CYP2D6 O-demethylates DXM to dextrorphan, a considerably more potent non-competitive NMDA-receptor antagonist (the same channel-blocking mechanism as ketamine and PCP). Because dextrorphan formation depends on CYP2D6, a highly variable enzyme, the experience is unpredictable: extensive metabolizers convert quickly and reach dissociation, while poor metabolizers (or people taking CYP2D6 inhibitors such as quinidine, fluoxetine, paroxetine or bupropion, or drinking grapefruit juice) accumulate the parent drug, prolonging its effects and raising the serotonin-related risk.
Biological targets
- NMDA
- Sigma-1
- SERT
Binding & functional measurements
| Target | Measurement | Species |
|---|---|---|
| sigma non-opioid intracellular receptor 1 | pKi 6.3 | Human |
| NMDA receptor | Ki 3,400 ± 800 nM | Pig |
Pharmacokinetics
| Bioavailability | ≈11% (oral, extensive first-pass) |
| Tmax | ≈2–2.5 h |
| Half-life | ≈2–4 h (CYP2D6-dependent, longer in poor metabolizers) |
| Vd | Not reported |
| Protein binding | Not reported |
| Metabolism | Hepatic CYP2D6 to active dextrorphan |
| Excretion | Renal |
Toxicology & Safety
Not reported
At the low doses in cough medicine DXM is safe for most people, but recreational high-dose use ('robotripping') is risky. By far the biggest hazard is combination products: DXM is usually sold mixed with paracetamol/acetaminophen (liver failure), antihistamines such as chlorphenamine (anticholinergic delirium and seizures), pseudoephedrine (dangerous blood-pressure and heart effects) or guaifenesin (heavy vomiting): taking a 'recreational' dose of a multi-ingredient product can be lethal from those other drugs long before the DXM does harm. Only single-ingredient DXM avoids this. DXM is also serotonergic, so combining it with MAOIs, SSRIs, SNRIs, tramadol or MDMA can cause serotonin syndrome. High doses cause marked dissociation, ataxia, a fast heart rate, raised blood pressure, hyperthermia and, occasionally, psychosis or seizures, because effects hinge on CYP2D6 genetics they are hard to predict, and mixing with alcohol or other depressants sharply increases the danger.[2]
Legal Status
US: OTC. UK: Pharmacy/general sale. DE: Pharmacy only
Interactions & Contraindications
Drug interactions
Contraindications
No interactions or contraindications listed.
Usage & Context
- The active ingredient in most non-prescription cough suppressants (Robitussin, Delsym and many combination cold-and-flu products), taken to relieve dry cough.
- In prescription medicine it is combined with quinidine (Nuedexta) for pseudobulbar affect and, since 2022, with bupropion (Auvelity) as a rapid-acting antidepressant: both pairings use a CYP2D6 inhibitor to raise and stabilise DXM levels.
- It is widely misused recreationally, especially by adolescents ('robotripping', 'skittling'), for its dissociative high, which is why several US states restrict over-the-counter sales to adults.
Sources & Evidence
- PubChem: Dextromethorphan (CID 5360696) — identifiers & experimental properties
- Wikipedia: Dextromethorphan (pharmacology, metabolism, medical use, recreational plateaus & safety) CC BY-SA 4.0
- IUPHAR/BPS Guide to PHARMACOLOGY: dextromethorphan (ligand 6953) — sigma-1 & NMDA (GluN2C) data CC BY-SA 4.0
- PsychonautWiki: Dextromethorphan — recreational dosage, plateaus & duration CC BY-SA 4.0
- FDA / DailyMed: Dextromethorphan prescribing information — pharmacokinetics & metabolism
- U.S. FDA: When to give kids medicine for coughs and colds
- Ganapathy ME, Prasad PD, Huang W, et al. (1999). Molecular and ligand-binding characterization of the sigma-receptor in the Jurkat human T lymphocyte cell line. J Pharmacol Exp Ther 289:251-60.
PMID 10087012
- Codd EE, Shank RP, Schupsky JJ, Raffa RB (1995). Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception. J Pharmacol Exp Ther 274:1263-70.
PMID 7562497
- Temme L, Schepmann D, Schreiber JA, et al. (2018). Comparative Pharmacological Study of Common NMDA Receptor Open Channel Blockers Regarding Their Affinity and Functional Activity toward GluN2A and GluN2B NMDA Receptors. ChemMedChem 13:446-452.
PMID 29377520 · doi:10.1002/cmdc.201700810