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Substance Name: Nalorphine [INN:BAN]
RN: 62-67-9
UNII: U59WB2WRY2
InChIKey: UIQMVEYFGZJHCZ-SSTWWWIQSA-N

Note

  • A narcotic antagonist with some agonist properties. It is an antagonist at mu opioid receptors and an agonist at kappa opioid receptors. Given alone it produces a broad spectrum of unpleasant effects and it is considered to be clinically obsolete.

Molecular Formula

  • C19-H21-N-O3

Molecular Weight

  • 311.3789
 

Classification Codes

Classification Codes

  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Narcotic Antagonists
  • Peripheral Nervous System Agents
  • Sensory System Agents

Superlist Classification Code

  • DEA Schedule III
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Names and Synonyms

Results Name

  • Nalorphine [INN:BAN]

Name of Substance

  • Nalorphine
  • Nalorphine [INN:BAN]

MeSH Heading

  • Nalorphine

Synonyms

  • 7,8-Didehydro-4,5-epoxy-17-(2-propenyl)morphinan-3,6-diol
  • Acetorfin
  • Acetorfin [Czech]
  • Allorphine
  • Anarcon
  • Anthorphine
  • Antorfin
  • Antorphin
  • Antorphine
  • EINECS 200-546-1
  • HSDB 3278
  • Morphinan-3,6-alpha-diol, 17-allyl-7,8-didehydro-4,5-alpha-epoxy-
  • Morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-(2-propenyl)-, (5alpha,6alpha)-
  • N-Allyl-7,8-dehydro-4,5-epoxy-3,6-dihydroxymorphinan
  • N-Allyl-N-desmethylmorphine
  • N-Allylnormorphine
  • Nallin
  • Nalline
  • Nalorfina
  • Nalorfina [DCIT]
  • Nalorphin
  • Nalorphine
  • Nalorphinium
  • Nalorphinum
  • Nalorphinum [INN-Latin]
  • NANM
  • Norfin
  • Normorphine, N-allyl-
  • UNII-U59WB2WRY2

Systematic Names

  • Morphinan-3,6-alpha-diol, 17-allyl-7,8-didehydro-4,5-alpha-epoxy-
  • Morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-(2-propenyl)-, (5alpha,6alpha)-
  • Nalorphine

Superlist Names

  • DEA No. 9400
  • Nalorphine

Registry Numbers

CAS Registry Number

  • 62-67-9

FDA UNII

  • U59WB2WRY2

Related Registry Numbers

  • 1041-90-3 (hydrobromide)
  • 57-29-4 (hydrochloride)
  • 97889-94-6 (L-tartrate (1:1))

System Generated Number

  • 0000062679

Structure Descriptors

InChI

InChI=1S/C19H21NO3/c1-2-8-20-9-7-19-12-4-6-15(22)18(19)23-17-14(21)5-3-11(16(17)19)10-13(12)20/h2-6,12-13,15,18,21-22H,1,7-10H2/t12-,13+,15-,18-,19-/m0/s1

InChIKey

UIQMVEYFGZJHCZ-SSTWWWIQSA-N

Smiles

O[C@H]1C=C[C@H]2[C@H]3Cc4ccc(O)c5O[C@@H]1[C@]2(CCN3CC=C)c45

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo parenteral 200ug/kg (0.2mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: EXCITEMENT
Pharmacological Reviews. Vol. 8, Pg. 175, 1956.
human TDLo subcutaneous 71ug/kg (0.071mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: TREMOR

BEHAVIORAL: ANTIANXIETY
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 15, Pg. 442, 1956.
monkey LDLo intravenous 100mg/kg (100mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 13, Pg. 369, 1954.
monkey LDLo subcutaneous 400mg/kg (400mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 13, Pg. 369, 1954.
mouse LD50 intraperitoneal 492mg/kg (492mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

BEHAVIORAL: EXCITEMENT
Pharmacological Reviews. Vol. 8, Pg. 175, 1956.
mouse LD50 intravenous 127mg/kg (127mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 165, Pg. 112, 1967.
mouse LD50 oral 1140mg/kg (1140mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 268, 1972.
mouse LD50 parenteral 670mg/kg (670mg/kg) BEHAVIORAL: EXCITEMENT

BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Pharmacological Reviews. Vol. 8, Pg. 175, 1956.
mouse LD50 subcutaneous 500mg/kg (500mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 165, Pg. 112, 1967.
rabbit LDLo intravenous 50mg/kg (50mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: EXCITEMENT

BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS
Pharmacological Reviews. Vol. 8, Pg. 175, 1956.
rat LD50 intravenous 226mg/kg (226mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 165, Pg. 112, 1967.
rat LD50 subcutaneous 474mg/kg (474mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 165, Pg. 112, 1967.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 208-209 deg C   EXP
pKa Dissociation Constant 7.64 (none)   EXP
log P (octanol-water) 1.86 (none)   EXP
Water Solubility 2770 mg/L 25 EST
Vapor Pressure 2.78E-10 mm Hg 25 EST
Henry's Law Constant 1.75E-16 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.98E-10 cm3/molecule-sec 25 EST

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