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Substance Name: Naltrexone [USAN:INN:BAN]
RN: 16590-41-3
UNII: 5S6W795CQM
InChIKey: DQCKKXVULJGBQN-XFWGSAIBSA-N

Note

  • Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of NALOXONE. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence.

Molecular Formula

  • C20-H23-N-O4

Molecular Weight

  • 341.4047
 

Classification Codes

  • Antagonist (to Narcotics)
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Narcotic Antagonists
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sensory System Agents

Names and Synonyms

Name of Substance

  • Naltrexone
  • Naltrexone [USAN:INN:BAN]

MeSH Heading

  • Naltrexone

Synonyms

  • 17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-one
  • 17-(Cyclopropylmethyl)-4,5alpha-epoxy-3,14-dihydroxymorphinan-6-one
  • BRN 3596648
  • CCRIS 3506
  • Celupan
  • Depade
  • EINECS 240-649-9
  • EN-1639A [as hydrochloride]
  • HSDB 6750
  • N-Cyclopropylmethyl-14-hydroxydihydromorphinone
  • N-Cyclopropylmethylnoroxymorphone
  • Naltrexona
  • Naltrexona [INN-Spanish]
  • Naltrexone
  • Naltrexonum
  • Naltrexonum [INN-Latin]
  • ReVia
  • UM-792
  • UNII-5S6W795CQM
  • Vivitrex
  • Vivitrol

Systematic Names

  • Morphinan-6-one, 17-(cyclopropylmethyl)-4,5-alpha-epoxy-3,14-dihydroxy-
  • Morphinan-6-one, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-, (5alpha)-
  • Naltrexone

Registry Numbers

CAS Registry Number

  • 16590-41-3

FDA UNII

  • 5S6W795CQM

System Generated Number

  • 0016590413

Structure Descriptors

InChI

1S/C20H23NO4/c22-13-4-3-12-9-15-20(24)6-5-14(23)18-19(20,16(12)17(13)25-18)7-8-21(15)10-11-1-2-11/h3-4,11,15,18,22,24H,1-2,5-10H2/t15-,18+,19+,20-/m1/s1

InChIKey

DQCKKXVULJGBQN-XFWGSAIBSA-N

Smiles

Oc1ccc2C[C@H]3N(CC4CC4)CC[C@@]56[C@@H](Oc1c25)C(=O)CC[C@@]36O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 subcutaneous 551mg/kg (551mg/kg)   Annals of the New York Academy of Sciences. Vol. 281, Pg. 321, 1976.
women TDLo oral 8mg/kg/4D-I (8mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: TOXIC PSYCHOSIS

BEHAVIORAL: EXCITEMENT
American Journal of Psychiatry. Vol. 155, Pg. 447, 1998.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 168-170 deg C   EXP
log P (octanol-water) 1.92 (none)   EXP
Water Solubility 1630 mg/L 25 EST
Vapor Pressure 1.30E-11 mm Hg 25 EST
Henry's Law Constant 4.22E-19 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.74E-10 cm3/molecule-sec 25 EST

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