CAS 125-69-9 Dextromethorphan Hydrobromide (HCID 5464025)

Teilstruktursuche Ähnliche Strukturen suchen

Grundinformationen

CAS: 125-69-9
Standard-SMILES: Br.COc1ccc2c(c1)[C@]13CCCC[C@@H]1[C@H](C2)N(C)CC3
InChIKey: MISZALMBODQYFT-URVXVIKDSA-N
Summenformel: C18H26BrNO
Durchschnittliche Molmasse: 352,3 g/mol
Monoisotopische Masse: 351,11977655

Überblick

Dextromethorphan Hydrobromide is the hydrobromide salt form of dextromethorphan, a synthetic, methylated dextrorotary analogue of levorphanol, a substance related to codeine and a non-opioid derivate of morphine. Dextromethorphan exhibits antitussive activity and is devoid of analgesic or addictive property. This agent crosses the blood-brain-barrier and activates sigma opioid receptors on the cough center in the central nervous system, thereby suppressing the cough reflex.

Namen und Bezeichner

Bevorzugter Name: Dextromethorphan Hydrobromide
IUPAC: (1S,9S,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene;hydrobromide

Namen und Synonyme

Dextromethorphan hydrobromide125-69-9DelsymAntussanDemorphanTusiland-Methorphan hydrobromideRomilarDextromethorphan bromideDextromethorphan HBrDextromethorphan polistirexDextromethorphan hydrobromide anhydrous

Weitere Namen anzeigen

Z0CG3115FGBenylin DMCHEBI:4471DTXSID60872346AzedipaminOrthoxicolTussi-OrganidinEndotussin-NN

Datenbank-Bezeichner

CAS: 125-69-9
PubChem CID: 5464025
DTXSID: DTXSID60872346
ChEMBL: CHEMBL1256818
UNII: Z0CG3115FG
EC Number: 204-750-1

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA): 12,5 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 1
Schwere Atome: 21
Formalladung: 0
Komplexität: 370

Experimentelle und physikochemische Eigenschaften

Human Drugs · 4 Einträge

Breast Feeding; Lactation; Milk, Human; Antitussive Agents

FDA approved drugs -> Active ingredient

Collision Cross Section165.2 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 0.6% (1 of 157) of reports.

Warning

H302 (98.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 157 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory InformationDextromethorphan hydrobromide anhydrous: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationIMAP assessments - Morphinan, 3-methoxy-17-methyl-, hydrobromide, (9.alpha.,13.alpha.,14.alpha.)-: Environment tier I assessment

Hazard Classes and CategoriesAcute Tox. 4 (98.7%)

Toxikologische Informationen

Health EffectsHypertension, shallow respiration. Dextromethorphan can cause other gastrointestinal disturbances. [Wikipedia]

Exposure RoutesOral, rapidly absorbed from the gastrointestinal tract.

Toxicity Summary · 1 Eintrag

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.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/MetabolitesHepatic. 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

FDA Pharmacological Classification · 6 Einträge

DEXTROMETHORPHAN HBR

Sigma-1 Agonist [EPC]; Uncompetitive NMDA Receptor Antagonists [MoA]; Sigma-1 Receptor Agonists [MoA]; Uncompetitive N-methyl-D-aspartate Receptor Antagonist [EPC]

DEXTROMETHORPHAN HBR 15 MG

Sigma-1 Agonist [EPC]; Uncompetitive N-methyl-D-aspartate Receptor Antagonist [EPC]; Uncompetitive NMDA Receptor Antagonists [MoA]; Sigma-1 Receptor Agonists [MoA]

DEXTROMETHORPHAN HYDROBROMIDE

Sigma-1 Agonist [EPC]; Uncompetitive NMDA Receptor Antagonists [MoA]; Sigma-1 Receptor Agonists [MoA]; Uncompetitive N-methyl-D-aspartate Receptor Antagonist [EPC]

MeSH Pharmacological Classification · 2 Einträge

Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.

Drugs that bind to but do not activate excitatory amino acid receptors, thereby blocking the actions of agonists.

Verwendung und Herstellung

Uses · 1 Eintrag

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.