| Identification | More | [Name]
Dextromethorphan hydrobromide monohydrate | [CAS]
6700-34-1 | [Synonyms]
D-3-METHOXY-N-METHYLMORPHINAN HYDROBROMIDE
DEXTROMETHORPHAN HYDROBROMIDE
DEXTROMETHORPHAN HYDROBROMIDE MONOHYDRATE
dextromethorphansigmareference*standard
DMHM
DEXTROMETHORPHAN HYDROBROMIDE, PH EUR
DEXTROMETHORPHAN HYDROBROMIDE*MONOHYDRAT E USP
D-Methorphan hydrobromide monohydrate
Morphinan, 3-methoxy-17-methyl-, hydrobromide, monohydrate, (9.alpha.,13.alpha.,14.alpha.)-
Dextromethorphan monohydrate hydrobromide, (9S,13S,14S)-3-Methoxy-17-methylmorphinan hydrobromide
Dextromethorphan hydrobromicum, (9S,13S,14S)-3-Methoxy-17-methylmorphinan hydrobromide
Dextromethorphan monohydrate hydrobromide | [EINECS(EC#)]
629-741-3 | [Molecular Formula]
C18H28BrNO2 | [MDL Number]
MFCD02173901 | [Molecular Weight]
370.32 | [MOL File]
6700-34-1.mol |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [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 | [Usage]
An antitussive drug | [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) |
| Hazard Information | Back Directory | [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.1 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).1,2,3 DXM has been used in multimodal analgesic therapies for acute and neuropathic pain.1,4 | [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 OROS
Tablets (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 |
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