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Substance Name: Dextrorphan [INN:BAN]
RN: 125-73-5
UNII: 04B7QNO9WS
InChIKey: JAQUASYNZVUNQP-PVAVHDDUSA-N

Note

  • Dextro form of levorphanol. It acts as a noncompetitive NMDA receptor antagonist, among other effects, and has been proposed as a neuroprotective agent. It is also a metabolite of DEXTROMETHORPHAN.

Molecular Formula

  • C17-H23-N-O

Molecular Weight

  • 257.375
 

Classification Codes

  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Excitatory Amino Acid Agents
  • Excitatory Amino Acid Antagonists
  • Neuroprotective Agents
  • Neurotransmitter Agents
  • Protective Agents
  • Reproductive Effect
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Names and Synonyms

Results Name

  • Dextrorphan [INN:BAN]

Name of Substance

  • Dextrorphan
  • Dextrorphan [INN:BAN]
  • Levorphanol d-form

MeSH Heading

  • Dextrorphan

Synonyms

  • (+)-cis-1,3,4,9,10,10a-Hexahydro-11-methyl-2H-10,4a-iminoethanophenanthren-6-ol
  • 2H-10,4a-(Iminoethano)phenanthren-6-ol, 1,3,4,9,10,10a-hexahydro-11-methyl-, (+)-
  • 4-21-00-01364 (Beilstein Handbook Reference)
  • BRN 0088093
  • d-3-Hydroxy-N-methylmorphinan
  • Destrorfano
  • Destrorfano [DCIT]
  • Dextrorfano
  • Dextrorfano [INN-Spanish]
  • Dextrorphan
  • Dextrorphane
  • Dextrorphane [INN-French]
  • Dextrorphanum
  • Dextrorphanum [INN-Latin]
  • EINECS 204-754-3
  • Morphinan, 3-hydroxy-N-methyl, (+)-
  • Ro 1-6794
  • UNII-04B7QNO9WS

Systematic Names

  • 9-alpha,13-alpha,14-alpha-Morphinan-3-ol, 17-methyl-
  • Dextrorphan
  • Morphinan-3-ol, 17-methyl-, (9alpha,13alpha,14alpha)-

Registry Numbers

CAS Registry Number

  • 125-73-5

FDA UNII

  • 04B7QNO9WS

System Generated Number

  • 0000125735

Structure Descriptors

InChI

1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m1/s1

InChIKey

JAQUASYNZVUNQP-PVAVHDDUSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 65mg/kg (65mg/kg)   Compilation of LD50 Values of New Drugs.
mouse LD50 oral 276mg/kg (276mg/kg)   Journal of Organic Chemistry. Vol. 22, Pg. 1370, 1957.
mouse LD50 subcutaneous 131mg/kg (131mg/kg)   Journal of Organic Chemistry. Vol. 22, Pg. 1370, 1957.
rabbit LD50 intravenous 28mg/kg (28mg/kg)   Compilation of LD50 Values of New Drugs.
rat LD50 intravenous 21mg/kg (21mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

MUSCULOSKELETAL: OTHER CHANGES		 Arzneimittel-Forschung. Drug Research. Vol. 45, Pg. 1188, 1995.
rat LD50 oral 584mg/kg (584mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: ATAXIA		 Arzneimittel-Forschung. Drug Research. Vol. 45, Pg. 1188, 1995.
rat LD50 subcutaneous 800mg/kg (800mg/kg)   Compilation of LD50 Values of New Drugs.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 3.11 (none)   EXP
Water Solubility 1840 mg/L 25 EST
Vapor Pressure 1.04E-06 mm Hg 25 EST
Henry's Law Constant 2.11E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.07E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.