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Substance Name: Levallorphan [INN:BAN]
RN: 152-02-3
UNII: 353613BU4U
InChIKey: OZYUPQUCAUTOBP-QXAKKESOSA-N

Note

  • An opioid antagonist with properties similar to those of NALOXONE; in addition it also possesses some agonist properties. It should be used cautiously; levallorphan reverses severe opioid-induced respiratory depression but may exacerbate respiratory depression such as that induced by alcohol or other non-opioid central depressants. (From Martindale, The Extra Pharmacopoeia, 30th ed, p683)

Molecular Formula

  • C19-H25-N-O

Molecular Weight

  • 283.4125
 

Classification Codes

  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Narcotic Antagonists
  • Peripheral Nervous System Agents
  • Sensory System Agents
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Names and Synonyms

Results Name

  • Levallorphan [INN:BAN]

Name of Substance

  • Levallorphan
  • Levallorphan [INN:BAN]

MeSH Heading

  • Levallorphan

Synonyms

  • (-)-3-Hydroxy-N-allylmorphinan
  • 17-Allylmorphinan-3-ol
  • EINECS 205-799-1
  • HSDB 2148
  • L-N-Allyl-3-hydroxymorphinan
  • Levallofano
  • Levallofano [DCIT]
  • Levallorphan
  • Levallorphane
  • Levallorphane [INN-French]
  • Levallorphanum
  • Levallorphanum [INN-Latin]
  • Levalorfano
  • Levalorfano [INN-Spanish]
  • levo-3-Hydroxy-N-allyl morphinan
  • Morphinan, 17-allyl-3-hydroxy-
  • Morphinan-3-ol, 17-(2-propenyl)-
  • Morphinan-3-ol, 17-allyl-
  • N-Allyl-3-hydroxymorphinan
  • Naloxiphan
  • Ro-1-7700
  • UNII-353613BU4U

Systematic Names

  • Levallorphan
  • Morphinan-3-ol, 17-(2-propenyl)-
  • Morphinan-3-ol, 17-allyl-, (-)-

Registry Numbers

CAS Registry Number

  • 152-02-3

FDA UNII

  • 353613BU4U

System Generated Number

  • 0000152023

Structure Descriptors

InChI

1S/C19H25NO/c1-2-10-20-11-9-19-8-4-3-5-16(19)18(20)12-14-6-7-15(21)13-17(14)19/h2,6-7,13,16,18,21H,1,3-5,8-12H2/t16-,18+,19+/m0/s1

InChIKey

OZYUPQUCAUTOBP-QXAKKESOSA-N

Smiles

Oc1ccc2C[C@@H]3[C@@H]4CCCC[C@]4(CCN3CC=C)c2c1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 184mg/kg (184mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. -, 1965.
mouse LD50 subcutaneous 200mg/kg (200mg/kg)   Annals of the New York Academy of Sciences. Vol. 281, Pg. 321, 1976.
rat LD50 intraperitoneal 185mg/kg (185mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 140, 1973.
rat LD50 oral 949mg/kg (949mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. -, 1965.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 181 deg C   EXP
log P (octanol-water) 3.48 (none)   EXP
Water Solubility 633 mg/L 25 EST
Vapor Pressure 1.87E-07 mm Hg 25 EST
Henry's Law Constant 2.77E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.40E-10 cm3/molecule-sec 25 EST

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