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10262-69-8

Basic Information
CAS No.: 10262-69-8
Name: 9,10-Ethanoanthracene-9(10H)-propanamine,N-methyl-
Article Data: 5
Cas Database
Molecular Structure:
Molecular Structure of 10262-69-8 (9,10-Ethanoanthracene-9(10H)-propanamine,N-methyl-)
Formula: C20H23N
Molecular Weight: 277.409
Synonyms: 9,10-Ethanoanthracene-9(10H)-propylamine,N-methyl- (7CI,8CI);Maprotiline;N-Methyl-9,10-ethanoanthracene-9(10H)-propylamine;
EINECS: 233-599-4
Density: 1.081 g/cm3
Melting Point: 92-94°
Boiling Point: 399.615 °C at 760 mmHg
Flash Point: 187.657 °C
Solubility: 833.4ug/L(22.5 oC)
Appearance: N/A
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: UN 3249
PSA: 12.03000
LogP: 4.60230
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History

 Ludiomil (10262-69-8) was developed and has been marketed by the Swiss manufacturer Geigy (now Novartis) since the early 1980s under the brand name Ludiomil. Generics are widely available

Specification

The CAS register number of Maprotiline is 10262-69-8. It also can be called as N-Methyl-9,10-ethanoanthracene-9(10H)-propanamine and the systematic name about this chemical is 3-(9,10-ethanoanthracen-9(10H)-yl)-N-methylpropan-1-amine. The molecular formula about this chemical is C20H23N and the molecular weight is 277.41. Classification code about this chemical are Adrenergic Agents, Adrenergic uptake inhibitors, Antidepressant, Antidepressive Agents, Antidepressive agents, second-generation, Central Nervous System Agents, Drug / Therapeutic Agent, Human Data, Neurotransmitter Agents, Neurotransmitter Uptake Inhibitors and Psychotropic Drugs. This chemical is a bridged-ring tetracyclic antidepressant that is both mechanistically and functionally similar to the tricyclic antidepressants, including side effects associated with its use.

Physical properties about Maprotiline are: (1)ACD/LogP: 4.51; (2)ACD/LogD (pH 5.5): 1.41; (3)ACD/LogD (pH 7.4): 1.65; (4)ACD/BCF (pH 5.5): 1.26; (5)ACD/BCF (pH 7.4): 2.2; (6)ACD/KOC (pH 5.5): 5.43; (7)ACD/KOC (pH 7.4): 9.44; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 3.24Å2; (12)Index of Refraction: 1.599; (13)Molar Refractivity: 87.77 cm3; (14)Molar Volume: 256.7 cm3; (15)Polarizability: 34.79x10-24cm3; (16)Surface Tension: 46.4 dyne/cm; (17)Enthalpy of Vaporization: 65.04 kJ/mol; (18)Boiling Point: 399.6 °C at 760 mmHg; (19)Vapour Pressure: 1.35E-06 mmHg at 25°C.

The Maprotiline is a tetracyclic antidepressant (TeCA). It is a strong norepinephrine reuptake inhibitor with only weak effects on serotonin and dopamine reuptake.it causes a strong initial sedation (first 2 to 3 weeks of therapy) and is therefore indicated to treat agitated patients or those with suicidal risks. It causes anticholinergic side effects with a lower incidence than Amitritypline. Originally, the manufacturer claimed that Maprotiline is better tolerated than other tri-/tetrcyclic drugs. This is not the case because seizures, leukopenia and skin reactions occur more often with Maprotiline than with comparable drugs like Amitriptyline.

The reduction of β-(9 - anthryl) propionic acid can get 9 - (3 - hydroxy-propyl) methylamine, and it can condensation with anthracene to produce β-[(9 - anthryl) propyl] methylamine, then condensation with ethylene to get Maprotiline.

Uses of Maprotiline: it can be used to produce 3-Chlor-2-[N-methyl-3-(9,10-dihydro-9,10-ethano-anthr-9-yl)-propylamino]-1,4-naphthoχnon with 2,3-dichloro-[1,4]naphthoquinone. This reaction will need solvent CH2Cl2 with reaction time of 18 hours. The yield is about 65%.

You can still convert the following datas into molecular structure:
(1)SMILES: c1ccc3c(c1)C4c2ccccc2C3(CC4)CCCNC
(2)InChI: InChI=1/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
(3)InChIKey: QSLMDECMDJKHMQ-UHFFFAOYAS
(4)Std. 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
(5)Std. InChIKey: QSLMDECMDJKHMQ-UHFFFAOYSA-N

The toxicity data is as follows:

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) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 40, Pg. 235, 1983.
mouse LD50 intravenous 31mg/kg (31mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

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

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

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

BEHAVIORAL: MUSCLE WEAKNESS

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

BEHAVIORAL: ATAXIA

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

BEHAVIORAL: ATAXIA

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Handbook of Experimental Pharmacology. Vol. 55, Pg. 527, 1980.