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Basic Information
| CAS No.: | 10347-81-6 |
|---|---|
| Name: | Maprotiline hydrochloride |
| Molecular Structure: | |
|
|
|
| Formula: | C20H23N.HCl |
| Molecular Weight: | 313.87 |
| 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); |
| EINECS: | 233-758-8 |
| Melting Point: | 230-232 °C |
| Boiling Point: | 399.6 °C at 760 mmHg |
| Flash Point: | 187.7 °C |
| Solubility: | 50 mg/mL in water |
| Appearance: | Crystalline solid |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22 |
| Safety: | 7-16-36/37-45 |
| Transport Information: | UN 3249 |
| PSA: | 12.03000 |
| LogP: | 5.40430 |
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Synthetic route
- 10347-81-6
maprotiline hydrochloride
- 106-51-4
p-benzoquinone
Conditions
| Conditions | Yield |
|---|---|
| In dichloromethane for 24h; Ambient temperature; | 90% |
- 10347-81-6
maprotiline hydrochloride
- 5721-37-9
Desmethylmaprotiline
Conditions
| Conditions | Yield |
|---|---|
| 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
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 90 percent / CH2Cl2 / 24 h / Ambient temperature 2: CH2Cl2 / Ambient temperature View Scheme |
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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 Codes
XnRisk 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.