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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H25NO.BrH
Molecular Weight 352.309
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXTROMETHORPHAN HYDROBROMIDE ANHYDROUS

SMILES

Br.[H][C@]12CCCC[C@]13CCN(C)[C@H]2CC4=CC=C(OC)C=C34

InChI

InChIKey=MISZALMBODQYFT-URVXVIKDSA-N
InChI=1S/C18H25NO.BrH/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;1H/t15-,17+,18+;/m1./s1

HIDE SMILES / InChI

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C18H25NO
Molecular Weight 271.3972
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Dextromethorphan is a non-narcotic morphine derivative widely used as an antitussive for almost 40 years. It has attracted attention due to its anticonvulsant and neuroprotective properties. It is a cough suppressant in many over-the-counter cold and cough medicines. In 2010, the FDA approved the combination product dextromethorphan/quinidine for the treatment of pseudobulbar affect. 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 used to study the involvement of glutamate receptors in neurotoxicity. Dextromethorphan (DM) is a sigma-1 receptor agonist and an uncompetitive NMDA receptor antagonist. The mechanism by which dextromethorphan exerts therapeutic effects in patients with pseudobulbar affect is unknown. Dextromethorphan should not be taken with monoamine oxidase inhibitors due to the potential for serotonin syndrome. Dextromethorphan is extensively metabolized by CYP2D6 to dextrorphan, which is rapidly glucuronidated and unable to cross the blood-brain barrier.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
205.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MUCINEX DM
Primary
NUEDEXTA

Cmax

ValueDoseCo-administeredAnalytePopulation
4.2 ng/mL
45 mg 2 times / day steady-state, oral
DEXTROMETHORPHAN plasma
Homo sapiens
7.7 ng/mL
60 mg 2 times / day steady-state, oral
DEXTROMETHORPHAN plasma
Homo sapiens
95.5 ng/mL
30 mg 2 times / day steady-state, oral
DEXTROMETHORPHAN plasma
Homo sapiens
15.9 ng/mL
30 mg single, oral
DEXTROMETHORPHAN plasma
Homo sapiens
2.9 ng/mL
30 mg 2 times / day steady-state, oral
DEXTROMETHORPHAN plasma
Homo sapiens
123.5 ng/mL
30 mg 2 times / day steady-state, oral
DEXTRORPHAN plasma
Homo sapiens
124.9 ng/mL
30 mg single, oral
DEXTRORPHAN plasma
Homo sapiens
599 ng/mL
45 mg 2 times / day steady-state, oral
DEXTRORPHAN plasma
Homo sapiens
709 ng/mL
60 mg 2 times / day steady-state, oral
DEXTRORPHAN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
32 ng × h/mL
45 mg 2 times / day steady-state, oral
DEXTROMETHORPHAN plasma
Homo sapiens
52 ng × h/mL
60 mg 2 times / day steady-state, oral
DEXTROMETHORPHAN plasma
Homo sapiens
1049 ng × h/mL
30 mg 2 times / day steady-state, oral
DEXTROMETHORPHAN plasma
Homo sapiens
133.3 ng × h/mL
30 mg single, oral
DEXTROMETHORPHAN plasma
Homo sapiens
17.8 ng × h/mL
30 mg 2 times / day steady-state, oral
DEXTROMETHORPHAN plasma
Homo sapiens
1000.5 ng × h/mL
30 mg 2 times / day steady-state, oral
DEXTRORPHAN plasma
Homo sapiens
933.8 ng × h/mL
30 mg single, oral
DEXTRORPHAN plasma
Homo sapiens
2898 ng × h/mL
45 mg 2 times / day steady-state, oral
DEXTRORPHAN plasma
Homo sapiens
3608 ng × h/mL
60 mg 2 times / day steady-state, oral
DEXTRORPHAN plasma
Homo sapiens
68 nM*h
30 mg single, oral
DEXTROMETHORPHAN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
13.1 h
30 mg 2 times / day steady-state, oral
DEXTROMETHORPHAN plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
15-30 mg 3 to 4 times per day (cough) 20-30 mg twice daily (pseudobulbar affect)
Route of Administration: Oral
In Vitro Use Guide
In vitro studies pre- and immature oligodendroglial (OLN-93) cells were subjected to hyperoxic conditions for 48 h after pre-treatment with increasing doses of dextromethorphan.
Substance Class Chemical
Record UNII
Z0CG3115FG
Record Status Validated (UNII)
Record Version