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Substance Name: Maprotiline [USAN:INN:BAN]
RN: 10262-69-8
UNII: 2U1W68TROF
InChIKey: QSLMDECMDJKHMQ-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

Molecular Weight

  • 277.4087
 

Classification Codes

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

Names and Synonyms

Name of Substance

  • Maprotiline
  • Maprotiline [USAN:INN:BAN]

MeSH Heading

  • Maprotiline

Synonyms

  • 276-Ba
  • 3-(9,10-Dihydro-9,10-ethanoanthracen-9-yl)propylmethylamine
  • Ba-34,276 [as hydrochloride]
  • BRN 2385493
  • EINECS 233-599-4
  • Maprotilina
  • Maprotilina [INN-Spanish]
  • Maprotiline
  • Maprotilinum
  • Maprotilinum [INN-Latin]
  • Maprotylina
  • Maprotylina [Polish]
  • N-Methyl-9,10-ethanoanthracene-9(10H)-propylamine
  • UNII-2U1W68TROF

Systematic Names

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

Registry Numbers

CAS Registry Number

  • 10262-69-8

FDA UNII

  • 2U1W68TROF

Related Registry Numbers

  • 10347-81-6 (hydrochloride)
  • 58902-67-3 (mesylate)

System Generated Number

  • 0010262698

Structure Descriptors

InChI

InChI=1S/C20H23N/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

InChIKey

QSLMDECMDJKHMQ-UHFFFAOYSA-N

Smiles

CNCCCC12CCC(c3ccccc13)c4ccccc24

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 26mg/kg (26mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: COMA

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION		 British Medical Journal. Vol. 2, Pg. 260, 1977.
mouse LD50 intraperitoneal 140mg/kg (140mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)		 Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 40, Pg. 235, 1983.
mouse LD50 intravenous 31mg/kg (31mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: MUSCLE WEAKNESS		 Handbook of Experimental Pharmacology. Vol. 55, Pg. 527, 1980.
mouse LD50 oral 660mg/kg (660mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: ATAXIA

BEHAVIORAL: MUSCLE WEAKNESS		 Handbook of Experimental Pharmacology. Vol. 55, Pg. 527, 1980.
rat LD50 intraperitoneal 105mg/kg (105mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: MUSCLE WEAKNESS		 Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 40, Pg. 235, 1983.
rat LD50 intravenous 38mg/kg (38mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: MUSCLE WEAKNESS		 Handbook of Experimental Pharmacology. Vol. 55, Pg. 527, 1980.
rat LD50 oral 760mg/kg (760mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: ATAXIA		 Handbook of Experimental Pharmacology. Vol. 55, Pg. 527, 1980.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 93 deg C   EXP
log P (octanol-water) 4.520 (none)   EST
Atmospheric OH Rate Constant 9.41E-11 cm3/molecule-sec 25 EST

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