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Substance Name: Amoxapine [USAN:USP:INN:BAN:JAN]
RN: 14028-44-5
UNII: R63VQ857OT
InChIKey: QWGDMFLQWFTERH-UHFFFAOYSA-N

Note

  • The N-demethylated derivative of the antipsychotic agent LOXAPINE that works by blocking the reuptake of norepinephrine, serotonin, or both. It also blocks dopamine receptors.

Molecular Formula

  • C17-H16-Cl-N3-O

Molecular Weight

  • 313.7864
 

Classification Codes

  • Adrenergic Agents
  • Adrenergic Uptake Inhibitors
  • Antidepressant
  • Antidepressive Agents
  • Antidepressive Agents, Second-Generation
  • Central Nervous System Agents
  • Dopamine Agents
  • Dopamine Antagonists
  • Drug / Therapeutic Agent
  • Human Data
  • Membrane Transport Modulators
  • Neurotransmitter Agents
  • Neurotransmitter Uptake Inhibitors
  • Psychotropic Drugs
  • Serotonin Agents
  • Serotonin Uptake Inhibitors

Names and Synonyms

Name of Substance

  • Amoxapine
  • Amoxapine [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Amoxapine

Synonyms

  • 2-Chlor-11-(1-piperazinyl)dibenz(b,f)(1,4)oxazepin
  • 2-Chloro-11-(1-piperazinyl)dibenz(b,f)(1,4)oxazepine
  • Amoxan
  • Amoxapina
  • Amoxapina [INN-Spanish]
  • Amoxapine
  • Amoxapinum
  • Amoxapinum [INN-Latin]
  • Asendin
  • BRN 0832057
  • CL 67,772
  • CL 67772
  • Demolox
  • Desmethylloxapin
  • Dibenz(b,f)(1,4)oxazepine, 2-chloro-11-(1-piperazinyl)-
  • EINECS 237-867-1
  • Moxadil
  • UNII-R63VQ857OT

Systematic Names

  • Amoxapine
  • Dibenz(b,f)(1,4)oxazepine, 2-chloro-11-(1-piperazinyl)-

Superlist Name

  • Amoxapine

Registry Numbers

CAS Registry Number

  • 14028-44-5

FDA UNII

  • R63VQ857OT

System Generated Number

  • 0014028445

Structure Descriptors

InChI

1S/C17H16ClN3O/c18-12-5-6-15-13(11-12)17(21-9-7-19-8-10-21)20-14-3-1-2-4-16(14)22-15/h1-6,11,19H,7-10H2

InChIKey

QWGDMFLQWFTERH-UHFFFAOYSA-N

Smiles

Clc1ccc2Oc3ccccc3N=C(N4CCNCC4)c2c1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD unreported > 20mg/kg (20mg/kg) BEHAVIORAL: IRRITABILITY

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR
Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 1, 1979.
child LDLo oral 25mg/kg (25mg/kg)   Southern Medical Journal. Vol. 76, Pg. 543, 1983.
child LDLo oral 25mg/kg (25mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE
Southern Medical Journal. Vol. 76, Pg. 543, 1983.
child TDLo oral 10mg/kg (10mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP JAMA, Journal of the American Medical Association. Vol. 250, Pg. 1069, 1983.
dog LD unreported > 20mg/kg (20mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: IRRITABILITY
Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 1, 1979.
dog LDLo intraperitoneal 20mg/kg (20mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 1, 1979.
man TDLo oral 4285ug/kg/2D- (4.285mg/kg) BEHAVIORAL: EXCITEMENT American Journal of Psychiatry. Vol. 140, Pg. 115, 1983.
man TDLo oral 4286ug/kg (4.286mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: REGIDITY
Southern Medical Journal. Vol. 77, Pg. 94, 1984.
man TDLo oral 14mg/kg (14mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" JAMA, Journal of the American Medical Association. Vol. 248, Pg. 3141, 1982.
man TDLo oral 27mg/kg (27mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION
Pharmacotherapy Vol. 15, Pg. 528, 1995.
man TDLo oral 70mg/kg/3W-I (70mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Clinical Psychiatry. Vol. 45, Pg. 358, 1984.
man TDLo unreported 5714ug/kg/2D- (5.714mg/kg) PERIPHERAL NERVE AND SENSATION: FASCICULATIONS

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Southern Medical Journal. Vol. 76, Pg. 1077, 1983.
monkey LD unreported > 20mg/kg (20mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 1, 1979.
mouse LD50 intraperitoneal 112mg/kg (112mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: REGIDITY
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 233, Pg. 107, 1978.
mouse LD50 oral 104mg/kg (104mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 1, 1979.
mouse LD50 subcutaneous 385mg/kg (385mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1852, 1971.
rat LD50 intraperitoneal 201mg/kg (201mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: REGIDITY
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 233, Pg. 107, 1978.
rat LD50 oral 313mg/kg (313mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1852, 1971.
rat LD50 subcutaneous > 4500mg/kg (4500mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1852, 1971.
women LDLo oral 40mg/kg (40mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

CARDIAC: CHANGE IN RATE

CARDIAC: OTHER CHANGES
Annals of Emergency Medicine. Vol. 17, Pg. 274, 1988.
women LDLo oral 40mg/kg (40mg/kg) BEHAVIORAL: COMA

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
JAMA, Journal of the American Medical Association. Vol. 250, Pg. 1069, 1983.
women LDLo oral 75953ug/kg (75.953mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

CARDIAC: OTHER CHANGES

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
Forensic Science International. Vol. 26, Pg. 33, 1984.
women TDLo oral 5mg/kg (5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD JAMA, Journal of the American Medical Association. Vol. 250, Pg. 1069, 1983.
women TDLo oral 15mg/kg/5D-I (15mg/kg) ENDOCRINE: HYPERGLYCEMIA Journal of Clinical Psychiatry. Vol. 44, Pg. 347, 1983.
women TDLo oral 17mg/kg (17mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: COMA
Journal of Toxicology, Clinical Toxicology. Vol. 20, Pg. 101, 1983.
women TDLo oral 30mg/kg (30mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

BEHAVIORAL: COMA
JAMA, Journal of the American Medical Association. Vol. 248, Pg. 1092, 1982.
women TDLo oral 50mg/kg (50mg/kg) BEHAVIORAL: COMA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Ugeskrift for Laeger. Doctor's Weekly. Vol. 146, Pg. 3285, 1984.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 175.5 deg C   EXP
log P (octanol-water) 3.380 (none)   EST
Atmospheric OH Rate Constant 1.79E-10 cm3/molecule-sec 25 EST

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