Dextromethorphan hydrobromide monohydrate CAS 6700-34-1

Introduction：Basic information about Dextromethorphan hydrobromide monohydrate CAS 6700-34-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Dextromethorphan hydrobromide monohydrate Basic information

• Product Name: Dextromethorphan hydrobromide monohydrate
• Synonyms: Dextromethorphan Hydrobromide dextrorotation;dextromethorphansigmareference*standard;DMHM;(9α,13α,14α)-3-Methoxy-17-MethylMorphinan HydrobroMide Hydrate;3-Methoxy-17-Methyl-9α,13α,14α-Morphinan HydrobroMide Hydrate;d-3-Methoxy-N-MethylMorphinan HydrobroMide Monohydrate;DextroMethorphan hydrobroMide:Monohydrat;DextroMethorphan hydrobroMide hydrate
• CAS: 6700-34-1
• MF: C18H28BrNO2
• MW: 370.33
• EINECS: 629-741-3
• Product Categories: Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Other APIs
• Mol File: 6700-34-1.mol

Dextromethorphan hydrobromide monohydrate Chemical Properties

• Melting point: 116-119°C
• alpha: [α]D25 +26～+30° (c=1.85, H2O)
• Fp: 11 °C
• storage temp.: Store at RT
• solubility: Sparingly soluble in water, freely soluble in ethanol (96 per cent).
• form: solid
• color: White to Off-White
• PH: pH (10g/l, 25℃) : 5.2～6.5
• BRN: 6453793
• InChI: InChI=1/C18H25NO.BrH.H2O/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;1H2/t15-,17+,18+;;/s3
• InChIKey: QYPSYPPSHXDFLV-UHFFFAOYSA-N
• SMILES: O(C1C=CC2C[C@]3([H])N(C)CC[C@]4(CCCC[C@@]43[H])C=2C=1)C.Br.O |&1:6,12,17,r|
• LogP: 1.351 (est)
• CAS DataBase Reference: 6700-34-1(CAS DataBase Reference)

Safety Information

• Hazard Codes: F,T
• Risk Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45
• WGK Germany: 3
• HS Code: 3822000002
• Storage Class: 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
• Hazard Classifications: Acute Tox. 3 Oral Aquatic Chronic 2

Dextromethorphan hydrobromide monohydrate Usage And Synthesis

Description

Dextromethorphan (DXM) is a dextratrorotatory morphinan with structural similarity to levorphanol, codeine, and morphine. Because of its strong antitussive effects, dextromethorphan is widely used as a cough suppressant. However, it does not provoke opioid activity as is characteristic of several other morphine derivatives. DXM binds to and inhibits NMDA (IC₅₀ = 0.55 μM) and nicotinic receptors (IC₅₀s = 0.7-3.9 μM) and blocks receptor-gated and voltage-gated calcium channels (IC₅₀ = 60 μM) and voltage-gated sodium channels (IC₅₀ = 78 μM). DXM has been used in multimodal analgesic therapies for acute and neuropathic pain.

Chemical Properties

White Solid

Uses

An antitussive drug. Orally active synthetic morphine analog. Analgesic (narcotic). Racemethorphan and levomethorpham are controlled substances (opiates).

Uses

Antitussive;Opioid ligand

Definition

ChEBI: Dextromethorphan hydrobromide is the hydrobromide and monohydrate of the antitussive drug dextromethorphan. It is a hydrate and a hydrobromide. It contains a dextromethorphan.

Brand name

Benylin DM(Parke-Davis); Dextromethorphan Hydrobromide OROSTablets (Ciba-Geigy); Drixoral Cough (Schering-Plough HealthCare); PediaCare 1 (McNeil Consumer); Romilar(Hoffmann-LaRoche-International); St. Joseph Cough Syrup(Schering-Plough HealthCare).

Biological Activity

Non-competitive, low affinity NMDA receptor antagonist. Antitussive, anticonvulsive and neuroprotective agent.

Toxics Screening Level

The Initial Threshold Screening Level (ITSL) is 0.4 μg/m3 annual average.

References

[1] DONALD C. BOLSER. Antitussive effects of GABAB agonists in the cat and guinea-pig[J]. British Journal of Pharmacology, 1993, 110 1: 491-495. DOI: 10.1111/j.1476-5381.1993.tb13837.x
[2] HASSAN JAMALI  Azhdar H. Effect of dextromethorphan/quinidine on pentylenetetrazole- induced clonic and tonic seizure thresholds in mice[J]. Neuroscience Letters, 2020, 729: Article 134988. DOI: 10.1016/j.neulet.2020.134988
[3] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[4] CHULATHIDA CHOMCHAI  Boonying M. Stimulant methamphetamine and dextromethorphan use among Thai adolescents: implications for health of women and children.[J]. Journal of Medical Toxicology, 2012: 291-294. DOI: 10.1007/s13181-012-0228-0