4NQ

3-methoxy-17-methyl-9alpha,13alpha,14alpha-morphinan

Created:2015-04-21
Last modified:  2025-09-17

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Chemical Details

Formal Charge0
Atom Count45
Chiral Atom Count3
Bond Count48
Aromatic Bond Count6
2D diagram of 4NQ

Chemical Component Summary

Name3-methoxy-17-methyl-9alpha,13alpha,14alpha-morphinan
Systematic Name (OpenEye OEToolkits)(1~{S},9~{S},10~{S})-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene
FormulaC18 H25 N O
Molecular Weight271.397
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs14.52COc1ccc2CC3C4CCCCC4(CCN3C)c2c1
SMILESCACTVS3.385COc1ccc2C[CH]3[CH]4CCCC[C]4(CCN3C)c2c1
SMILESOpenEye OEToolkits3.1.0.0CN1CCC23CCCCC2C1Cc4c3cc(cc4)OC
Canonical SMILESCACTVS3.385 COc1ccc2C[C@H]3[C@H]4CCCC[C@@]4(CCN3C)c2c1
Canonical SMILESOpenEye OEToolkits3.1.0.0 CN1CC[C@@]23CCCC[C@@H]2[C@@H]1Cc4c3cc(cc4)OC
InChIInChI1.06 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
InChIKeyInChI1.06 MKXZASYAUGDDCJ-NJAFHUGGSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
DrugBank IDDB00514 
NameDextromethorphan
Groups approved
DescriptionDextromethorphan is a levorphanol derivative and codeine analog commonly used as a cough suppressant and also a drug of abuse.[A215412] Although similar in structure to other opioids, it has minimal interaction with opioid receptors.[A215412] Dextromethorphan was granted FDA approval before 3 December 1957.[A215412,L14997]
Synonyms
  • (+)-dextromethorphan
  • Dextromethorphan hydrobromide
  • Dextromethorphanum
  • Dextromethorphan hydrochloride
  • Dex
Brand Names
  • Broncho-grippol-DM
  • Cough & Chest Congestion Regular Strength
  • Smart Sense Nighttime Cough
  • Vicks DayQuil and Vicks NyQuil Cherry Cold and Flu
  • Mucinex Childrens Cough
IndicationDextromethorphan is indicated in combination with [brompheniramine] and [pseudoephedrine] in the treatment of coughs and upper respiratory symptoms associated with allergies or the common cold.[L14366] Dextromethorphan is also used in combination with [guaifenesin] as an over-the-counter product to relieve a cough.[L14369] Dextromethorphan in combination with [quinidine] is indicated in the treatment of pseudobulbar affect.[L14363]
Categories
  • Alkaloids
  • Anticholinergic Agents
  • Antidepressive Agents
  • Antitussive Agents
  • Central Nervous System Agents
ATC-Code
  • N06AX62
  • R05DA09
  • N07XX59
CAS number125-71-3

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
NameTarget SequencePharmacological ActionActions
Sigma non-opioid intracellular receptor 1MQWAVGRRWAWAALLLAVAAVLTQVVWLWLGTQSFVFQREEIAQLARQYA...unknownagonist
AromataseMVLEMLNPIHYNITSIVPEAMPAATMPVLLLTGLFLLVWNYEGTSSIPGP...unknowninhibitor
Glutamate receptor ionotropic, NMDA 3AMRRLSLWWLLSRVCLLLPPPCALVLAGVPSSSSHPQPCQILKRIGHAVRV...unknownantagonist
Neuronal acetylcholine receptor subunit alpha-2MGPSCPVFLSFTKLSLWWLLLTPAGGEEAKRPPPRAPGDPLSSPSPTALP...unknownantagonist
Sodium-dependent serotonin transporterMETTPLNSQKQLSACEDGEDCQENGVLQKVVPTPGDKVESGQISNGYSAV...unknowninhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL52440
PubChem 5360696
ChEMBL CHEMBL52440
ChEBI CHEBI:92579, CHEBI:4470