CAS 10262-69-8|Maprotiline

Introduction：Basic information about CAS 10262-69-8|Maprotiline, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Maprotiline BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Synonyms

Common Name	Maprotiline
CAS Number	10262-69-8	Molecular Weight	277.40300
Density	1.08 g/cm3	Boiling Point	399.6ºC at 760 mmHg
Molecular Formula	C₂₀H₂₃N	Melting Point	/
MSDS	/	Flash Point	187.7ºC

Names

Name	maprotiline
Synonym	More Synonyms

Maprotiline BiologicalActivity

Description	Maprotiline is a highly selective noradrenergic reuptake blocker, has strong antidepressant efficacy. Maprotiline induces cancer cells apoptosis by targeting ERK signaling pathway and CRABP1. Maprotiline restrains cell proliferation and metastasis, exhibits anticancer effect[1][2].
Related Catalog	Research Areas >>CancerSignaling Pathways >>Autophagy >>AutophagyResearch Areas >>Neurological Disease
In Vitro	Maprotiline (10 μM) enhances the sensitivity of HCC cells to sorafenib (2 μM) and induces apoptosis[2]. Maprotiline (0, 10, or 20 μM for 72 h) works on ERK pathway and inhibits phosphorylation of SREBP2 in HepG2 and Huh7 cells[2]. Maprotiline may targets CRABP1 and regulate cholesterol biosynthesis in HCC cells[2]. Cell Invasion Assay[2] Cell Line: The human HCC cell lines Huh7 and HepG2 Concentration: 0, 10, 20 μM Incubation Time: 24 hours Result: Restrained HCC cells migration with inhibition of epithelial-mesenchymal transition (EMT). Cell Viability Assay[2] Cell Line: The human HCC cell lines Huh7 and HepG2 Concentration: 0, 10, 20 μM Incubation Time: 0, 24, 48, 72, 96, 120 hours Result: Triggered cell apoptosis and inhibited the cell viability of Huh7 and HepG2 cells in a dose- and time-dependent manner. Western Blot Analysis[2] Cell Line: The human HCC cell lines Huh7 and HepG2 Concentration: 0, 10, 20 μM Incubation Time: 72 hours Result: Inhibited cholesterol biosynthesis in HCC Cells.
In Vivo	Maprotiline (intraperitoneal injection; 3, 10, or 30 mg/kg) combinds with the synthetic cannabinoid WIN 55,212-2 and effectively reduces neuropathic pain[1]. Maprotiline (intraperitoneal injection; 0, 20, or 40 mg/kg; twice a week; 3 weeks) shows low toxicity and side effects on the organs, immune system and hematopoietic function[2]. Maprotiline (intraperitoneal injection; 0, 20, or 40 mg/kg; twice a week; 3 weeks) restrains cholesterol biosynthesis to inhibit growth and metastasis of HCC cells by interacting with CRABP1[2]. Animal Model: Male Balb-c mice (25–30 g)[1] Dosage: 3, 10, 30 mg/kg Administration: Intraperitoneal injection; evaluation 30 minutes after treatment Result: Attenuated pain-related behaviours in neuropathic mice. Animal Model: Nude mice (BALB/C nu/nu, 4–6 weeks old, female)[2] Dosage: 40 mg/kg Administration: Intraperitoneal injection; twice a week; 3 weeks Result: Decreased the cholesterol levels in serum and tumors and suppressed the growth of Huh7-derived tumor xenografts without obvious toxic effect.
References	[1]. Gunduz O, et al. Analysis of the anti-allodynic effects of combination of a synthetic cannabinoid and a selective noradrenaline re-uptake inhibitor in nerve injury-induced neuropathic mice. Eur J Pain. 2016 Mar. 20(3):465-71. [2]. Zheng C, et al. Maprotiline Suppresses Cholesterol Biosynthesis and Hepatocellular Carcinoma Progression Through Direct Targeting of CRABP1. Front Pharmacol. 2021 May 20. 12:689767.

Chemical & Physical Properties

Density	1.08 g/cm3
Boiling Point	399.6ºC at 760 mmHg
Molecular Formula	C₂₀H₂₃N
Molecular Weight	277.40300
Flash Point	187.7ºC
Exact Mass	277.18300
PSA	12.03000
LogP	4.60230
Vapour Pressure	1.35E-06mmHg at 25°C
Index of Refraction	1.599
InChIKey	QSLMDECMDJKHMQ-UHFFFAOYSA-N
SMILES	CNCCCC12CCC(c3ccccc31)c1ccccc12

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KJ4552000

CHEMICAL NAME :: 9,10-Ethanoanthracene-9(10H)-propylamine, N-methyl-

CAS REGISTRY NUMBER :: 10262-69-8

LAST UPDATED :: 199612

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C20-H23-N

MOLECULAR WEIGHT :: 277.44

WISWESSER LINE NOTATION :: L6 H666/GP 2AF P&&TTJ O3M1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - child

DOSE/DURATION :: 26 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - coma Vascular - BP elevation not characterized in autonomic section

REFERENCE :: BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 2,260,1977

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 760 mg/kg

TOXIC EFFECTS :: Behavioral - muscle weakness Behavioral - ataxia Behavioral - muscle contraction or spasticity

REFERENCE :: HEPHD2 Handbook of Experimental Pharmacology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.50- 1978- Volume(issue)/page/year: 55,527,1980

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 105 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - muscle weakness Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: APPHAX Acta Poloniae Pharmaceutica. For English translation, see APPFAR. (Ars Polona, POB 1001, 00-680 Warsaw 1, Poland) V.1- 1937- Volume(issue)/page/year: 40,235,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 38 mg/kg

TOXIC EFFECTS :: Behavioral - muscle weakness Behavioral - ataxia Behavioral - muscle contraction or spasticity

REFERENCE :: HEPHD2 Handbook of Experimental Pharmacology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.50- 1978- Volume(issue)/page/year: 55,527,1980

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 660 mg/kg

TOXIC EFFECTS :: Behavioral - muscle weakness Behavioral - ataxia Behavioral - muscle contraction or spasticity

REFERENCE :: HEPHD2 Handbook of Experimental Pharmacology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.50- 1978- Volume(issue)/page/year: 55,527,1980

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 140 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: APPHAX Acta Poloniae Pharmaceutica. For English translation, see APPFAR. (Ars Polona, POB 1001, 00-680 Warsaw 1, Poland) V.1- 1937- Volume(issue)/page/year: 40,235,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 31 mg/kg

TOXIC EFFECTS :: Behavioral - muscle weakness Behavioral - ataxia Behavioral - muscle contraction or spasticity

REFERENCE :: HEPHD2 Handbook of Experimental Pharmacology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.50- 1978- Volume(issue)/page/year: 55,527,1980 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5760 mg/kg/22W-I

TOXIC EFFECTS :: Cardiac - EKG changes not diagnostic of specified effects Related to Chronic Data - death

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 30,1709,1980

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 650 mg/kg/7W-I

TOXIC EFFECTS :: Cardiac - EKG changes not diagnostic of specified effects

REFERENCE :: ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 51,43,1982

Safety Information

RIDADR	3249
Packaging Group	III
Hazard Class	6.1(b)
HS Code	2921499090

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%

Synonyms

3-(9,10-Dihydro-9,10-ethanoanthracen-9-yl)-N-methylpropan-1-amine

Deprilept

Dibencycladine

N-methyl-9,10-ethanoanthracene-9(10H)-propanamine

Maprotilina

Maprotylina [Polish]

Maprotilinum

MFCD00661057

Maprotilin

Maprotilinum [INN-Latin]

EINECS 233-599-4

9-[3-(methylamino)propyl]-9,10-dihydro-9,10-ethanoanthracene

Maprotilina [INN-Spanish]

Maprotylina

[14C]-Maprotiline

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