QuickView for Dextromethorphan (compound)

Summary
General Info

PubChem

PubChem Compound 11957506

Name:	Dextromethorphan
PubChem Compound ID:	11957506
Description:	Methyl analog of DEXTRORPHAN that shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist (RECEPTORS, N-METHYL-D-ASPARTATE) and acts as a non-competitive channel blocker. It is one of the widely used ANTITUSSIVES, and is also used to study the involvement of glutamate receptors in neurotoxicity.
Molecular formula:	C₁₈H₂₆BrNO
Molecular weight:	352.309 g/mol
Synonyms:	EU-0100337

DrugBank

Identification

Name:	Dextromethorphan
Name (isomeric):	DB00514
Drug Type:	small molecule
Description:	Methyl analog of DEXTRORPHAN that shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist (RECEPTORS, N-METHYL-D-ASPARTATE) and acts as a non-competitive channel blocker. It is one of the widely used ANTITUSSIVES, and is also used to study the involvement of glutamate receptors in neurotoxicity.
Synonyms:	Dexyromethorphan; Demorphine; Demorphan; Levometorfano [INN-Spanish]; Destrometerfano [Dcit]; Levomethorphanum [INN-Latin]; Delta-Methorphan; Dextrometorfano [INN-Spanish]; D-Methorphan Hydrobromide; Dextromethorphan Bromide. show more » Dexyromethorphan; Demorphine; Demorphan; Levometorfano [INN-Spanish]; Destrometerfano [Dcit]; Levomethorphanum [INN-Latin]; Delta-Methorphan; Dextrometorfano [INN-Spanish]; D-Methorphan Hydrobromide; Dextromethorphan Bromide; L-Methorphan; Levomethorphan; Levomethorphan [Ban:Dcf:Inn]; Demorphan Hydrobromide; D-Methorphan; Dextromethorphan Bromhydrate; Dextromethorfan [Czech]; Levomethorphane [INN-French]; Dextromorphan; Dextrometorphan show less «
Brand:	Benylin Pediatric Cough Suppressant, Antussan, Koffex DM, Robitussin Pediatric, Calmylin #1, Diabe-Tuss DM Syrup, Pertussin CS Children's Strength, Methorphan, Romilar, Methorate Hydrobromide, Creo-Terpin, Benylin DM 12 Hour, Cosylan, Tusilan, Pertussin DM Extra Strength, Balminil DM, Triaminic DM Long Lasting for Children, Benylin DM, Balminil DM Children, Benylin DM for Children, Hold DM, Sucrets 4 Hour Cough Suppressant, Vicks 44 Cough Relief, Medicon, Robitussin Pediatric Cough Suppressant, Dormetan, Canfodion, Cough-X, Benylin Adult Formula Cough Suppressant, Dormethan, Tussade, Benylin DM for Children 12 Hour, Novahistine DM, Robitussin Maximum Strength Cough Suppressant, Trocal, Delsym, Delsym Cough Formula, Novahistex DM, Metrorat, Hihustan M.
Brand name mixture:	Novahistex Dm Expectorant with Decongestant(Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Koffex Dm + Decongestant + Expectorant(Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Cough Syrup Dm-D-E(Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Cough Syrup... show more » Novahistex Dm Expectorant with Decongestant(Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Koffex Dm + Decongestant + Expectorant(Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Cough Syrup Dm-D-E(Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Cough Syrup Dm Decongestant Expectorant(Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Sudafed Cold and Flu Gel Caps(Acetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Calmylin Cough and Flu Liq(Acetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Extra Strength Daytime Cold Relief-Caplet(Acetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Benylin 4 Flu - Syrup(Acetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Cough Syrup W.Guaifenesin W.Dextromethorphan(Dextromethorphan Hydrobromide + Guaifenesin), Nyquil Liquicaps(Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride), Biohisdex Dm Decongestant(Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride), Dayquil Liquicaps - Cap(Acetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Calmylin #3 Syr(Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Calmylin #2 Syr(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Demdec Syr(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Calmylin Pediatric Syrup(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Cough, Cold & Allergy Relief(Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), Robitussin Honey Cough and Cold(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Dayquil Medicine - Liq(Acetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Dm Expectorant Cough Syrup(Dextromethorphan Hydrobromide + Guaifenesin), Dayquil Liquicaps(Acetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Dm Plus Decongestant Cough Syrup(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Novahistex Dm with Decongestant(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Novahistine Dm Expectorant with Decongestant(Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Pharminicol Dm Syrup(Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate), Hot Lemon Relief Dm Adult(Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylephrine Hydrochloride), Actifed Dm Tablets(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride + Triprolidine Hydrochloride), Biohisdine Dm Decongestant(Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride), Koffex Dm + Decongestant Syrup(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Children's Tylenol Cold Liquid with Dm(Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Citron Chaud Dm Cumberland Pws(Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C), Triaminic Dm Plus Decongestant Syrup(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Regular Strength Cold Medication(Daytime R.) (Acetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Pediatric Cough Syrup(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Cough and Flu Syrup(Acetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Ornade Dm 30 Liq(Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride), Cough Syrup Dm-Expectorant(Dextromethorphan Hydrobromide + Guaifenesin), Cough Syrup Dm Decongestant(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Robitussin Honey Flu(Acetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Promatussin Dm Adult Formula Syr(Dextromethorphan Hydrobromide + Promethazine Hydrochloride + Pseudoephedrine Hydrochloride), Pharmitussin Dm(Dextromethorphan Hydrobromide + Guaifenesin), Calmylin #4 Syr(Ammonium Chloride + Dextromethorphan Hydrobromide + Diphenhydramine Hydrochloride), Triaminic Dm+Decongestant Liqui-Gels Capsules(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Regular Strength Tylenol Cough Suspension with Decongestant(Acetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Dimetapp Children's Cough and Cold Liquid(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Dm Plus Expectorant Syrup(Dextromethorphan Hydrobromide + Guaifenesin), Extra Strength Nighttime Cold Relief-Caplet(Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Triaminic Dm Daytime Syr(Dextromethorphan Hydrobromide + Guaifenesin + Phenylpropanolamine Hydrochloride), Personnelle Dm Syr(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Theraflu Flu Cold and Cough Medicine(Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Chemhisdine Dm Decongestant(Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride), Children's Tussin Cough Medicine Dm Antitussive Decongestant(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Triaminic Dm Expectorant Syr(Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Dm Plus Decongestant Plus Expector.Ex.St.Syr(Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Cough Syrup Dm Expectorant(Dextromethorphan Hydrobromide + Guaifenesin), Cough Syrup Dm-E(Dextromethorphan Hydrobromide + Guaifenesin), Dm-D-Expectorant Cough and Cold Syrup(Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Novahistine Dm with Decongestant - Liq(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Nitetime Cold Medicine(Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride), Triaminicol Dm Syrup(Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Cough Syrup Dm Decongestant for Children(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Bronchodex Fort-Dm Syr(Ammonium Chloride + Dextromethorphan Hydrobromide + Menthol + Pyrilamine Maleate + Sodium Citrate), Nighttime Cold and Flu Relief(Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride), Bronchodex Pediatrique(Dextromethorphan Hydrobromide + Guaifenesin + Pheniramine Maleate + Pseudoephedrine Hydrochloride), Tantacol Dm Syr(Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate), Nighttime Cold and Flu Liquid Capsules(Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride), Neo Citran Daycaps Extra Strength - Caplet(Acetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Regular Strength Tylenol Cold and Flu Powder(Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Reg.Str.Cold Medic.(Night Time Relief)Caplet (Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Cold/Flu Relief(Acetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Dm Syrup(Ammonium Chloride + Dextromethorphan Hydrobromide + Diphenhydramine Hydrochloride), Dimetapp Dm Elixir(Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), Regular Strength Tylenol Cough Suspension(Acetaminophen + Dextromethorphan Hydrobromide), Promatussin Dm Children Formula(Dextromethorphan Hydrobromide + Promethazine Hydrochloride + Pseudoephedrine Hydrochloride), Dm Cough Syr(Ammonium Chloride + Dextromethorphan Hydrobromide + Diphenhydramine Hydrochloride), Sudafed Dm(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Actifed Dm Syrup(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride + Triprolidine Hydrochloride), Dm Plus Cough Syrup(Ammonium Chloride + Dextromethorphan Hydrobromide + Diphenhydramine Hydrochloride), Cold Relief Dm(Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride), Centracol Dm - Syr(Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate), Sudafed Cold and Cough Extra Strength Caplet(Acetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Extra Strength Tylenol Cold and Flu Powder(Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Daytime Cold & Flu Liquid Capsules(Acetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Antitussive Decong Antihistamine Syr(Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate), Pharmacol Dm Syr(Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate), Contac Cough Cold and Flu Caplets(Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride), Ornade Dm 15 Liq(Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride), Extra Strength Cold Medication Daytime Rlf(Acetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Koffex Dm + Expectorant Extra Strength(Dextromethorphan Hydrobromide + Guaifenesin), Dimetapp Cough, Cold & Flu(Acetaminophen + Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride), Centracol Pediatrique - Syr(Dextromethorphan Hydrobromide + Guaifenesin + Pheniramine Maleate + Pseudoephedrine Hydrochloride), Dm Plus Decongestant Plus Expectorant Cough Syrup(Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Ornade Dm 10 Liq(Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride), Koffex Dm + Expectorant(Dextromethorphan Hydrobromide + Guaifenesin), Dimetapp Dm Tab(Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), Regular Strength Tylenol Cold Chest Congestion(Acetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Dm Cough Syrup Expectorant(Dextromethorphan Hydrobromide + Guaifenesin), Daytime Liquid - Liq(Acetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Koffex Dm-D-E - Liq(Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Chemhisdex Dm Decongestant(Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride), Bronchosirum Pour Enfants(Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate), Koffex Dm + Decongestant + Expectorant Extra Strength(Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride), Dimetapp Cough & Cold Liqui-Gels - Cap(Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride), Dm Cough Syrup Decongestant(Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride), Metrate(Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Potassium Iodide + Sodium Citrate), Tussin Cough Medicine Dm Antitussive Expectorant Decongestant(Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride) show less «
Category:	Antitussive Agents, Analgesics, Opioid, Excitatory Amino Acid Antagonists
CAS number:	125-71-3

Pharmacology

Indication:	For treatment and relief of dry cough.
Pharmacology:	Dextromethorphan suppresses the cough reflex by a direct action on the cough center in the medulla of the brain. Dextromethorphan shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist and acts as a non-competitive channel blocker. It is one of the widely used ... show more » Dextromethorphan suppresses the cough reflex by a direct action on the cough center in the medulla of the brain. Dextromethorphan shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist and acts as a non-competitive channel blocker. It is one of the widely used antitussives, and is also used to study the involvement of glutamate receptors in neurotoxicity. show less «
Mechanism of Action:	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 i... show more » 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. show less «
Absorption:	Rapidly absorbed from the gastrointestinal tract.
Biotransformation:	Hepatic. Rapidly and extensively metabolized to dextrorphan (active metabolite). One well known metabolic catalyst involved is a specific cytochrome P450 enzyme known as 2D6, or CYP2D6.
Half Life:	3-6 hours
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Take without regard to meals.

Drug interaction:

Sibutramine	Combination associated with possible serotoninergic syndrome
Terbinafine	Terbinafine may reduce the metabolism and clearance of Dextromethorphan. Consider alternate therapy or monitor for therapeutic/adverse effects of Dextromethorphan if Terbinafine is initiated, discontinued or dose changed.
Zolmitriptan	Use of two serotonin modulators, such as zolmitriptan and dextromethorphan, increases the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
Tramadol	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Trimipramine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.

Sibutramine	Combination associated with possible serotoninergic syndrome
Terbinafine	Terbinafine may reduce the metabolism and clearance of Dextromethorphan. Consider alternate therapy or monitor for therapeutic/adverse effects of Dextromethorphan if Terbinafine is initiated, discontinued or dose changed.
Zolmitriptan	Use of two serotonin modulators, such as zolmitriptan and dextromethorphan, increases the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
Tramadol	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Trimipramine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Tranylcypromine	Increased risk of serotonin syndrome. Concomitant use should be avoided.
Quinidine	Quinidine increases the toxicity of dextromethorphan
Moclobemide	Increased CNS toxicity
Dihydroquinidine barbiturate	Quinidine increases the toxicity of dextromethorphan
Selegiline	Combination associated with possible serotoninergic syndrome
Fluoxetine	Combination associated with possible serotoninergic syndrome
Phenelzine	Possible severe adverse reaction
Venlafaxine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Isocarboxazid	Possible severe adverse reaction
Paroxetine	Combination associated with possible serotoninergic syndrome
Rasagiline	Possible severe adverse reaction
Vilazodone	Consideration should be given to avoiding the concomitant use of dextromethorphan and selective serotonin reuptake inhibitors (SSRI). Monitor for toxic effects of dextromethorphan (eg, CNS, Cardiovascular) if an SSRI is initiated or the dose is increased. SSRIs, other than fluoxetine and paroxetine, may be safer alternatives due to lesser CYP2D6 inhibition; however, the mechanism for the interaction is not fully understood, and caution is still advised.
Trazodone	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Quinidine barbiturate	Quinidine increases the toxicity of dextromethorphan
Desvenlafaxine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.

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Targets

Sigma 1-type opioid receptor

Opioid receptor, sigma 1

Glutamate [NMDA] receptor subunit 3A

Neuronal acetylcholine receptor subunit alpha-2

Sodium-dependent serotonin transporter

Enzymes

Transporters

Multidrug resistance protein 1