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Maprotiline Hydrochloride

Names

[ CAS No. ]:
10347-81-6

[ Name ]:
Maprotiline Hydrochloride

[Synonym ]:
Deprilept
N-Methyl-3-(tetracyclo[6.6.2.0.0]hexadeca-2,4,6,9,11,13-hexaen-1-yl)propan-1-amine hydrochloride (1:1)
9,10-Ethanoanthracene-9(10H)-propanamine, N-methyl-, hydrochloride (1:1)
Maprotiline hydrochloride
N-Methyl-3-(tetracyclo[6.6.2.0.0]hexadeca-2,4,6,9,11,13-hexaen-1-yl)-1-propanamine hydrochloride (1:1)
9-(g-Methylaminopropyl)-9,10-dihydro-9,10-ethanoanthracene Hydrochloride
N-Methyl-3-tetracyclo[6.6.2.0.0]hexadeca-2,4,6,9,11,13-hexaen-1-ylpropan-1-aminhydrochlorid
EINECS 233-758-8
3-(9,10-ethanoanthracen-9(10H)-yl)-N-methylpropan-1-amine hydrochloride (1:1)
MFCD00079464
N-methyl-3-tetracyclo[6.6.2.0.0]hexadeca-2,4,6,9,11,13-hexaen-1-ylpropan-1-amine hydrochloride
N-méthyl-3-tétracyclo[6.6.2.0.0]hexadéca-2,4,6,9,11,13-hexaén-1-ylpropan-1-amine chlorhydrate
Psymion
9-(γ-Methylaminopropyl)-9,10-dihydro-9,10-ethanoanthracene Hydrochloride

Biological Activity

[Description]:

Maprotiline HCl is a selective noradrenalin re-uptake inhibitor and a tetracyclic antidepressant.Target: OthersMaprotiline (sold as Deprilept, Ludiomil, Psymion) is a tetracyclic antidepressant (TeCA). However, Maprotiline's fourth ring is spurious, as formed by a bridge across the central tricyclic ring. It is a strong norepinephrine reuptake inhibitor with only weak effects on serotonin and dopamine reuptake. It exerts strong blocking effect at H1 receptors, moderate at 5-HT2 and alpha1 and weak blocking effect at D2 and mACh postsynaptic receptors [1, 2].

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy
Research Areas >> Neurological Disease

[References]

[1]. Peng, W.H., et al., Berberine produces antidepressant-like effects in the forced swim test and in the tail suspension test in mice. Life Sci, 2007. 81(11): p. 933-8.

[2]. http://en.wikipedia.org/wiki/Maprotiline


[Related Small Molecules]

Rapamycin (Sirolimus) | MG-132 | Cycloheximide | 3-Methyladenine | LY294002 | TAK-242 | (+)-JQ1 | SB203580 | Pyrazolanthrone (SP600125) | U0126-EtOH | Actinomycin D | Chloroquine diphosphate | CHIR-99021 (CT99021) | MK-2206 2HCl | Dorsomorphin dihydrochloride

Chemical & Physical Properties

[ Boiling Point ]:
399.6ºC at 760 mmHg

[ Melting Point ]:
230-232ºC

[ Molecular Formula ]:
C20H24ClN

[ Molecular Weight ]:
313.864

[ Flash Point ]:
187.7ºC

[ Exact Mass ]:
313.159729

[ PSA ]:
12.03000

[ LogP ]:
5.40430

[ Vapour Pressure ]:
9.8E-08mmHg at 25°C

[ Storage condition ]:
Store at RT

[ Water Solubility ]:
H2O: 50 mg/mL | Soluble to 50mg/ml in water. Soluble in ethanol at 10mM

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
KJ4555000
CHEMICAL NAME :
9,10-Ethanoanthracene-9(10H)-propylamine, N-methyl-, hydrochloride
CAS REGISTRY NUMBER :
10347-81-6
LAST UPDATED :
199706
DATA ITEMS CITED :
31
MOLECULAR FORMULA :
C20-H23-N.Cl-H
MOLECULAR WEIGHT :
313.90
WISWESSER LINE NOTATION :
L6 H666/GP 2AF P&&TTJ G3M1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
20 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Cardiac - arrhythmias (including changes in conduction) Cardiac - pulse rate increase, without fall in BP
REFERENCE :
AJEMEN American Journal of Emergency Medicine. (WB Saunders, Philadelphia, PA) V.1- 1983- Volume(issue)/page/year: 2,144,1984
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
7 mg/kg/1W-I
TOXIC EFFECTS :
Behavioral - muscle contraction or spasticity
REFERENCE :
JCPYDR Journal of Clinical Pyschopharmacology. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1981- Volume(issue)/page/year: 3,264,1983
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
490 ug/kg
TOXIC EFFECTS :
Behavioral - sleep
REFERENCE :
JCLPDE Journal of Clinical Psychiatry. (Physicians Postgraduate Press, Inc., POB 240008, Memphis, TN 38124) V.39- 1978- Volume(issue)/page/year: 47,210,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
17 mg/kg
TOXIC EFFECTS :
Behavioral - general anesthetic Behavioral - hallucinations, distorted perceptions Behavioral - convulsions or effect on seizure threshold
REFERENCE :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 1,1573,1977
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
75 mg/kg
TOXIC EFFECTS :
Behavioral - coma Cardiac - pulse rate increase, without fall in BP
REFERENCE :
ICMED9 Intensive Care Medicine. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.3- 1977- Volume(issue)/page/year: 11,220,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
12 mg/kg
TOXIC EFFECTS :
Cardiac - pulse rate increase, without fall in BP Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
REFERENCE :
AJEMEN American Journal of Emergency Medicine. (WB Saunders, Philadelphia, PA) V.1- 1983- Volume(issue)/page/year: 6,247,1988
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
90 mg/kg
TOXIC EFFECTS :
Behavioral - coma
REFERENCE :
JATOD3 Journal of Analytical Toxicology. (Preston Pub. Inc., POB 48312, Niles, IL 60648) V.1- 1977- Volume(issue)/page/year: 6,199,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
760 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 112,601,1973
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
72 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 112,601,1973
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
170 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 112,601,1973
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
35 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - muscle weakness Lungs, Thorax, or Respiration - respiratory stimulation
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 1,207,1975
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
480 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - muscle weakness Lungs, Thorax, or Respiration - respiratory stimulation
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 1,207,1975
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
125 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 229,163,1977
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
310 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - muscle weakness Lungs, Thorax, or Respiration - respiratory stimulation
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 1,207,1975
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
31 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 112,601,1973
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
20 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 112,601,1973
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
20 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 112,782,1973
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
>300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 112,601,1973
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
30 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 112,601,1973
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 112,601,1973
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
20 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 112,601,1973 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
10950 mg/kg/52W-I
TOXIC EFFECTS :
Related to Chronic Data - death
REFERENCE :
BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 112,782,1973
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2800 mg/kg/28D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in bladder weight Endocrine - changes in spleen weight Related to Chronic Data - changes in testicular weight
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 1,207,1975
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
10920 mg/kg/26W-I
TOXIC EFFECTS :
Liver - fatty liver degeneration Endocrine - changes in spleen weight Related to Chronic Data - changes in prostate weight
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 1,207,1975 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
15 mg/kg
SEX/DURATION :
female 13 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - breasts, lactation (prior to or during pregnancy)
REFERENCE :
AJPSAO American Journal of Psychiatry. (American Psychiatric Assoc., Circulation Dept., 1400 K St., NW, Washington, DC 20005) V.78- 1921- Volume(issue)/page/year: 140,641,1983
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
420 mg/kg
SEX/DURATION :
female 17-22 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 15,567,1978
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
210 mg/kg
SEX/DURATION :
female 9-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 2,69,1976
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
105 mg/kg
SEX/DURATION :
female 7-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - stillbirth
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 2,69,1976
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
210 mg/kg
SEX/DURATION :
female 7-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 2,69,1976
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
32500 ug/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 15,555,1978 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4986 No. of Facilities: 58 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 1657 (estimated) No. of Female Employees: 895 (estimated)

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
7-16-36/37-45

[ RIDADR ]:
UN 3249

[ WGK Germany ]:
3

[ RTECS ]:
KJ4555000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2921499090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2921499090

[ Summary ]:
2921499090 other aromatic monoamines and their derivatives; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

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