Dextromethorphan hydrobromide monohydrate Chemical Properties

Melting point:

116-119°C

alpha 

[α]D25 +26～+30° (c=1.85, H2O)

Flash point:

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

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

Antitussive;Opioid ligand

Uses

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

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

Dextromethorphan hydrobromide monohydrate(6700-34-1)Related Product Information

• MELIBIOSE
• Dextromethorphan
• D-Glucose monohydrate
• Citric acid monohydrate
• 3-Isobutyl-1H-pyrazole-5-carboxylic acid
• 1,4,5,6-TETRAHYDRO-CYCLOPENTAPYRAZOLE-3-CARBOXYLIC ACID
• Ethyl 3-n-propylpyrazole-5-carboxylate
• 1-METHYL-4-NITRO-3-PROPYL-1H-PYRAZOLE-5-CARBOXYLIC ACID
• 3-CYCLOPROPYLPYRAZOLE-5-CARBOXYLIC ACID
• 1-METHYL-3-PROPYLPYRAZOLE-5-CARBOXYLIC ACID
• Dextromethorphan Hydrobromide
• INDAZOLE-3-CARBOXYLIC ACID
• Hydrogen bromide
• 4,5,6,7-TETRAHYDRO-1H-INDAZOLE-3-CARBOXYLIC ACID ETHYL ESTER
• 1H-Pyrazole-3-carboxylicacid,1-methyl-5-propyl-,ethylester(9CI)
• 2-METHYL-4,5,6,7-TETRAHYDRO-2H-INDAZOLE-3-CARBOXYLIC ACID
• 4,5,6,7,8,9-HEXAHYDRO-1H-CYCLOOCTAPYRAZOLE-3-CARBOXYLIC ACID
• 1H-Pyrazole-3-carboxylicacid,1-methyl-5-propyl-(9CI)