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10262-69-8

10262-69-8 structure
10262-69-8 structure
  • Name: Maprotiline
  • Chemical Name: maprotiline
  • CAS Number: 10262-69-8
  • Molecular Formula: C20H23N
  • Molecular Weight: 277.40300
  • Catalog: API Nervous system medication Antidepressant, manic
  • Create Date: 2018-08-09 13:02:35
  • Modify Date: 2024-01-01 17:12:01
  • 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].
Name maprotiline
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
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
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.
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

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