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Substance Name: Dextromethorphan [USP:INN:BAN]
RN: 125-71-3
UNII: 7355X3ROTS
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
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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)-
- NSC 751452
- 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
FDA UNII
- 7355X3ROTS
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
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/s1InChIKey
MKXZASYAUGDDCJ-NJAFHUGGSA-NSmiles
COc1ccc2C[C@H]3[C@H]4CCCC[C@@]4(CCN3C)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. |
| 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. |
| 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. | |
| 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. |
| 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. |