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Maprotiline hydrochloride

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Name

Maprotiline hydrochloride

EINECS 233-758-8
CAS No. 10347-81-6 Density N/A
PSA 12.03000 LogP 5.40430
Solubility 50 mg/mL in water Melting Point 230-232 °C
Formula C20H23N.HCl Boiling Point 399.6 °C at 760 mmHg
Molecular Weight 313.87 Flash Point 187.7 °C
Transport Information UN 3249 Appearance Crystalline solid
Safety 7-16-36/37-45 Risk Codes 22
Molecular Structure Molecular Structure of 10347-81-6 (Maprotiline hydrochloride) Hazard Symbols HarmfulXn
Synonyms

9,10-Ethanoanthracene-9(10H)-propanamine,N-methyl-, hydrochloride (9CI);9,10-Ethanoanthracene-9(10H)-propylamine,N-methyl-, hydrochloride (7CI,8CI);9,10-Dihydro-9-(3-methylaminopropyl)-9,10-ethanoanthracene hydrochloride;9-[g-(Methylamino)propyl]-9,10-dihydro-9,10-ethanoanthracenehydrochloride;CIBA 34,276Ba;CIBA 34276 hydrochloride;Ladiomil;Ludiomil;Psymion;9,10-Ethanoanthracene-9(10H)-propanamine,N-methyl-, hydrochloride (1:1);

 

Maprotiline hydrochloride Synthetic route

10347-81-6

maprotiline hydrochloride

106-51-4

p-benzoquinone

N-Methyl-3-(9,10-dihydro-9,10-ethano-anthr-9-yl)-propylamino-1,4-benzochinon

Conditions
ConditionsYield
In dichloromethane for 24h; Ambient temperature;90%
10347-81-6

maprotiline hydrochloride

5721-37-9

Desmethylmaprotiline

Conditions
ConditionsYield
With human liver microsomes; NADPH-generating system In phosphate buffer at 37℃; for 0.25h; pH=7.4; Enzyme kinetics; Further Variations:; Solvents;
10347-81-6

maprotiline hydrochloride

2,5-Bis--1,4-benzochinon

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / CH2Cl2 / 24 h / Ambient temperature
2: CH2Cl2 / Ambient temperature
View Scheme

Maprotiline hydrochloride Specification

1. Introduction of Maprotiline hydrochloride
Maprotiline hydrochloride is one kind of crystalline solid. Its chemical name is N-methyl-9,10-ethanoanthracene-9(10H)-propylamine hydrochloride. Besides, Maprotiline hydrochloride belongs to Active Pharmaceutical Ingredients;Chemical Amines;Amines;Intermediates & Fine Chemicals;Pharmaceuticals;Adrenoceptor. In addition, the Classification Code of it is Antidepressant; Drug / Therapeutic Agent; Human Data; Reproductive Effect. And its solubility in H2O is 50 mg/mL.

2. Properties of Maprotiline hydrochloride
Physical properties about Maprotiline hydrochloride are:
(1)Flash Point: 187.7 °C; (2)Enthalpy of Vaporization: 65.04 kJ/mol; (3)Boiling Point: 399.6 °C at 760 mmHg; (4)Vapour Pressure: 1.35E-06 mmHg at 25°C; (5)Melting point: 230-232°C; (6)H-Bond Donor: 2; (7)H-Bond Acceptor: 1; (8)Rotatable Bond Count: 4; (9)Exact Mass: 313.159727; (10)MonoIsotopic Mass: 313.159727; (11)Topological Polar Surface Area: 12; (12)Heavy Atom Count: 22; (13)Formal Charge: 0; (14)Complexity: 339; (15)Isotope Atom Count: 0; (16)Defined Atom Stereocenter Count: 0; (17)Undefined Atom Stereocenter Count: 0; (18)Defined Bond Stereocenter Count: 0; (19)Undefined Bond Stereocenter Count: 0; (20)Covalently-Bonded Unit Count: 2.

3. Structure Descriptors of Maprotiline hydrochloride
(1)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
(2)InChIKey: NZDMFGKECODQRY-UHFFFAOYSA-N
(3)Canonical SMILES : CNCCCC12CCC(C3=CC=CC=C31)C4=CC=CC=C24.Cl
(4)Smiles: c1cc2c(cc1)C1CCC2(CCCNC)c2ccccc12.Cl

4. Toxicity of Maprotiline hydrochloride

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) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
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)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Bollettino Chimico Farmaceutico. Vol. 112, Pg. 601, 1973.
human TDLo oral 17mg/kg (17mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
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) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

KIDNEY, URETER, AND BLADDER: INCONTINENCE
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) 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.
mouse LD50 oral 480mg/kg (480mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE WEAKNESS

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

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
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)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
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) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
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)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
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: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
American Journal of Emergency Medicine. Vol. 2, Pg. 144, 1984.
women TDLo oral 63mg/kg/6W-I (63mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

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.

5. Safety information of Maprotiline hydrochloride
Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Human systemic effects: arrhythmias, coma, convulsions, distorted perceptions, general anesthesia, hallucinations, pulse rate increase, respiration changes. An experimental teratogen. Experimental reproductive effects. An antidepressant. When heated to decomposition it emits toxic fumes of NOx and HCl.
Hazard CodesHarmfulXn
Risk Statements 22
R22:Harmful if swallowed.
RIDADR 3249
WGK Germany 3
RTECS KJ4555000
HazardClass 6.1(b)
PackingGroup III

6. Uses of Maprotiline hydrochloride
Maprotiline hydrochlorid (CAS NO.10347-81-6) is antidepressant. It is a selective noradrenalin re-uptake inhibitor. It can be made into the maprotiline hydrochloride tablet. Maprotiline hydrochloride tablets are indicated for the treatment of depressive illness in patients with depressive neurosis (dysthymic disorder) and manic depressive illness, depressed type (major depressive disorder). Maprotiline is also effective for the relief of anxiety associated with depression.

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