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Substance Name: Dextromethorphan [USP:INN:BAN]
RN: 125-71-3
InChIKey: MKXZASYAUGDDCJ-NJAFHUGGSA-N

Note

  • Methyl analog of DEXTRORPHAN that shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist (RECEPTORS, N-METHYL-D-ASPARTATE) and acts as a non-competitive channel blocker. It is one of the widely used ANTITUSSIVES, and is also used to study the involvement of glutamate receptors in neurotoxicity.

Molecular Formula

  • C18-H25-N-O

Molecular Weight

  • 271.401
 

Classification Codes

  • Antitussive
  • Antitussive agents
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Excitatory Amino Acid Agents
  • Excitatory amino acid antagonists
  • Human Data
  • Neurotransmitter Agents
  • Respiratory System Agents

Names and Synonyms

Name of Substance

  • Dextromethorphan
  • Dextromethorphan [USP:INN:BAN]

MeSH Heading

  • Dextromethorphan

Synonyms

  • (+)-3-Methoxy-N-methylmorphinon
  • (+)-cis-1,3,4,9,10,10a-Hexahydro-6-methoxy-11-methyl-2H-10,4alpha-iminoethanophenanthren
  • 3-Methoxy-17-methyl-9alpha,13alpha,14alpha-morphinan
  • 4-21-00-01367 (Beilstein Handbook Reference)
  • 9alpha,13alpha,14alpha-Morphinan, 3-methoxy-17-methyl-
  • Albutussin
  • BA 2666
  • BRN 0088549
  • d-Methorphan
  • delta-Methorphan
  • Destrometerfano
  • Destrometerfano [DCIT]
  • Dextromethorfan
  • Dextromethorfan [Czech]
  • Dextromethorphan
  • Dextromethorphane
  • Dextromethorphane [INN-French]
  • Dextromethorphanum
  • Dextromethorphanum [INN-Latin]
  • Dextrometorfano
  • Dextrometorfano [INN-Spanish]
  • Dextromorphan
  • DXM [Antitussive]
  • EINECS 204-752-2
  • HSDB 3056
  • Morphinan, 3-methoxy-17-methyl-, (9alpha,13alpha,14alpha)-
  • UNII-7355X3ROTS

Systematic Names

  • 9-alpha,13-alpha,14-alpha-Morphinan, 3-methoxy-17-methyl-
  • Dextromethorphan
  • Morphinan, 3-methoxy-17-methyl-, (9-alpha,13-alpha,14-alpha)-
  • Morphinan, 3-methoxy-17-methyl-, (9alpha,13alpha,14alpha)-

Mixture Name

  • Delsym

Registry Numbers

CAS Registry Number

  • 125-71-3

Other Registry Numbers

  • 18046-32-7
  • 32062-10-5

Related Registry Numbers

  • 125-69-9 (hydrobromide)
  • 18609-21-7 (hydrochloride)
  • 6700-34-1 (hydrobromide, mono-hydrate)

System Generated Number

  • 0000125713

Structure Descriptors

InChI

1S/C18H25NO/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/t15-,17+,18+/m1/s1

InChIKey

MKXZASYAUGDDCJ-NJAFHUGGSA-N

Smiles

c12[C@]34[C@@H]([C@@H]([N@@](C)CC3)Cc1ccc(c2)OC)CCCC4

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 16mg/kg (16mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: ATAXIA
Pediatric Emergency Care. Vol. 7, Pg. 163, 1991.
Link to PubMed
child TDLo oral 38mg/kg (38mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Pediatric Emergency Care. Vol. 13, Pg. 214, 1997.
Link to PubMed
dog LDLo intravenous 22mg/kg (22mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 7, Pg. 372, 1959.
mouse LD50 oral 210mg/kg (210mg/kg)   Journal of Pharmaceutical Sciences. Vol. 60, Pg. 1523, 1971.
Link to PubMed
mouse LD50 subcutaneous 112mg/kg (112mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 7, Pg. 372, 1959.
rat LD50 intravenous 16286ug/kg (16.286mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

BEHAVIORAL: GENERAL ANESTHETIC
Arzneimittel-Forschung. Drug Research. Vol. 45, Pg. 1188, 1995.
Link to PubMed
rat LD50 oral 116mg/kg (116mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: ATAXIA
Arzneimittel-Forschung. Drug Research. Vol. 45, Pg. 1188, 1995.
Link to PubMed