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Substance Name: Maprotiline hydrochloride [USP:JAN]
RN: 10347-81-6
UNII: 7C8J54PVFI
InChIKey: NZDMFGKECODQRY-UHFFFAOYSA-N

Note

  • A bridged-ring tetracyclic antidepressant that is both mechanistically and functionally similar to the tricyclic antidepressants, including side effects associated with its use.

Molecular Formula

  • C20-H23-N.Cl-H

Molecular Weight

  • 313.8696
 

Classification Codes

  • Antidepressant
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Maprotiline hydrochloride [USP:JAN]

Synonyms

  • 1-(3-Methylaminopropyl)dibenzo(b,e)bicyclo(2.2.2)octadiene hydrochloride
  • 9-(gamma-Methylaminopropyl)-9,10-dihydro-9,10-ethanoanthracene hydrochloride
  • BA 34276
  • Ciba 34276 Ba
  • EINECS 233-758-8
  • Ludiomil
  • Maprotiline HCl
  • Maprotiline hydrochloride
  • N-Methyl-9,10-ethanoanthracene-9(10H)-propanamine hydrochloride
  • N-Methyl-9,10-ethanoanthracene-9(10H)-propylamine hydrochloride
  • Psymion
  • UNII-7C8J54PVFI

Systematic Names

  • 9,10-Ethanoanthracene-9(10H)-propanamine, N-methyl-, hydrochloride
  • 9,10-Ethanoanthracene-9(10H)-propylamine, N-methyl-, hydrochloride
  • Maprotiline hydrochloride

Registry Numbers

CAS Registry Number

  • 10347-81-6

FDA UNII

  • 7C8J54PVFI

Related Registry Number

  • 10262-69-8 (Parent)

System Generated Number

  • 0010347816

Molecular Formulas

Molecular Formula

  • C20-H23-N.Cl-H

Molecular Formula Fragments

  • C20-H23-N
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

InChI=1S/C20H23N.ClH/c1-21-14-6-12-20-13-11-15(16-7-2-4-9-18(16)20)17-8-3-5-10-19(17)20;/h2-5,7-10,15,21H,6,11-14H2,1H3;1H

InChIKey

NZDMFGKECODQRY-UHFFFAOYSA-N

Smiles

Cl.CNCCCC12CCC(c3ccccc13)c4ccccc24

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 30mg/kg (30mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Bollettino Chimico Farmaceutico. Vol. 112, Pg. 601, 1973.
cat LDLo oral > 300mg/kg (300mg/kg)   Bollettino Chimico Farmaceutico. Vol. 112, Pg. 601, 1973.
child TDLo oral 12mg/kg (12mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
American Journal of Emergency Medicine. Vol. 6, Pg. 247, 1988.
dog LDLo intravenous 20mg/kg (20mg/kg)   Bollettino Chimico Farmaceutico. Vol. 112, Pg. 782, 1973.
dog LDLo oral 20mg/kg (20mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Bollettino Chimico Farmaceutico. Vol. 112, Pg. 601, 1973.
human TDLo oral 17mg/kg (17mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
British Medical Journal. Vol. 1, Pg. 1573, 1977.
man TDLo oral 490ug/kg (0.49mg/kg) BEHAVIORAL: SLEEP Journal of Clinical Psychiatry. Vol. 47, Pg. 210, 1986.
man TDLo oral 391mg/kg/1Y-I (391mg/kg) KIDNEY, URETER, AND BLADDER: INCONTINENCE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Postgraduate Medical Journal. Vol. 55, Pg. 742, 1979.
mouse LD50 intraperitoneal 125mg/kg (125mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 229, Pg. 163, 1977.
mouse LD50 intravenous 31mg/kg (31mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Bollettino Chimico Farmaceutico. Vol. 112, Pg. 601, 1973.
mouse LD50 oral 480mg/kg (480mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. Vol. 1, Pg. 207, 1975.
mouse LD50 subcutaneous 310mg/kg (310mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. Vol. 1, Pg. 207, 1975.
rabbit LDLo intravenous 20mg/kg (20mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Bollettino Chimico Farmaceutico. Vol. 112, Pg. 601, 1973.
rabbit LDLo oral > 1gm/kg (1000mg/kg)   Bollettino Chimico Farmaceutico. Vol. 112, Pg. 601, 1973.
rat LD50 intraperitoneal 72mg/kg (72mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Bollettino Chimico Farmaceutico. Vol. 112, Pg. 601, 1973.
rat LD50 intravenous 35mg/kg (35mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE WEAKNESS
Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. Vol. 1, Pg. 207, 1975.
rat LD50 oral 760mg/kg (760mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Bollettino Chimico Farmaceutico. Vol. 112, Pg. 601, 1973.
rat LD50 subcutaneous 170mg/kg (170mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Bollettino Chimico Farmaceutico. Vol. 112, Pg. 601, 1973.
women LDLo oral 90mg/kg (90mg/kg) BEHAVIORAL: COMA Journal of Analytical Toxicology. Vol. 6, Pg. 199, 1982.
women TDLo oral 7mg/kg/1W-I (7mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) Journal of Clinical Pyschopharmacology. Vol. 3, Pg. 264, 1983.
women TDLo oral 20mg/kg (20mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
American Journal of Emergency Medicine. Vol. 2, Pg. 144, 1984.
women TDLo oral 63mg/kg/6W-I (63mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: GENERAL ANESTHETIC

KIDNEY, URETER, AND BLADDER: INCONTINENCE
Postgraduate Medical Journal. Vol. 55, Pg. 742, 1979.
women TDLo oral 75mg/kg (75mg/kg) BEHAVIORAL: COMA

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
Intensive Care Medicine. Vol. 11, Pg. 220, 1985.