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Substance Name: Apomorphine [BAN]
RN: 58-00-4
UNII: N21FAR7B4S
InChIKey: VMWNQDUVQKEIOC-CYBMUJFWSA-N

Note

  • A derivative of morphine that is a dopamine D2 agonist. It is a powerful emetic and has been used for that effect in acute poisoning. It has also been used in the diagnosis and treatment of parkinsonism, but its adverse effects limit its use.

Molecular Formula

  • C17-H17-N-O2

Molecular Weight

  • 267.3263
 

Classification Codes

  • Anti-Dyskinesia Agents
  • Antiparkinson Agents
  • Autonomic Agents
  • Central Nervous System Agents
  • Dopamine Agents
  • Dopamine Agonists
  • Drug / Therapeutic Agent
  • Emetics
  • Gastrointestinal Agents
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Apomorphine
  • Apomorphine [BAN]

MeSH Heading

  • Apomorphine

Synonyms

  • (-)-10,11-Dihydroxyaporphine
  • (-)-Apomorphine
  • (6aR)-5,6,6a,7-Tetrahydro-6-methyl-4H-dibenzo(de,g)chinolin-10,11-diol
  • (R)-(-)-Apomorphine
  • 4H-Dibenzo(de,g)quinoline-10,11-diol, 5,6,6a,7-tetrahydro-6-methyl-, (R)-
  • 6abeta-Aporphine-10,11-diol
  • Apokyn
  • Apomorfin
  • Apomorphin
  • Apomorphine
  • EINECS 200-360-0
  • HSDB 3289
  • Ixense
  • L-Apomorphine
  • R-(-)-Apomorphine
  • UNII-N21FAR7B4S
  • Uprima

Systematic Names

  • 4H-Dibenzo(de,g)quinoline-10,11-diol, 5,6,6a,7-tetrahydro-6-methyl-, (R)- (9CI)
  • 6a-beta-Aporphine-10,11-diol
  • Apomorphine

Registry Numbers

CAS Registry Number

  • 58-00-4

FDA UNII

  • N21FAR7B4S

Related Registry Numbers

  • 314-19-2 (hydrochloride anhydrous)
  • 41372-20-7 (hydrochloride hemihydrate)

System Generated Number

  • 0000058004

Structure Descriptors

InChI

1S/C17H17NO2/c1-18-8-7-10-3-2-4-12-15(10)13(18)9-11-5-6-14(19)17(20)16(11)12/h2-6,13,19-20H,7-9H2,1H3/t13-/m1/s1

InChIKey

VMWNQDUVQKEIOC-CYBMUJFWSA-N

Smiles

CN1CCc2cccc-3c2[C@H]1Cc4c3c(c(cc4)O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo rectal 50mg/kg (50mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
dog LDLo subcutaneous 50mg/kg (50mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
frog LDLo subcutaneous 300mg/kg (300mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
mouse LD50 intraperitoneal 160mg/kg (160mg/kg)   Journal of Medicinal Chemistry. Vol. 15, Pg. 348, 1972.
mouse LD50 intravenous 56mg/kg (56mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03170,
mouse LD50 oral > 100mg/kg (100mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: MUSCLE WEAKNESS
Farmaco, Edizione Scientifica. Vol. 35, Pg. 951, 1980.
mouse LDLo subcutaneous 13mg/kg (13mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
pigeon LDLo subcutaneous 200mg/kg (200mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rabbit LDLo intravenous 10mg/kg (10mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rabbit LDLo subcutaneous 5mg/kg (5mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rat LDLo intravenous 40mg/kg (40mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: TREMOR
Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 1003, 1960.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 195 dec deg C   EXP
pKa Dissociation Constant 8.92 (none)   EXP
log P (octanol-water) 2.3 (none)   EXP
Water Solubility 1.66E+04 mg/L 16 EXP
Vapor Pressure 1.27E-09 mm Hg 25 EST
Henry's Law Constant 5.80E-16 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.61E-10 cm3/molecule-sec 25 EST

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