CAS 6151-30-0|Quinacrine Dihydrochloride Dihydrate

Introduction：Basic information about CAS 6151-30-0|Quinacrine Dihydrochloride Dihydrate, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

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

Common Name	Quinacrine Dihydrochloride Dihydrate
CAS Number	6151-30-0	Molecular Weight	508.909
Density	/	Boiling Point	557.1ºC at 760 mmHg
Molecular Formula	C₂₃H₃₆Cl₃N₃O₃	Melting Point	247 °C
MSDS	/	Flash Point	/

Names

Name	Mepacrine hydrochloride
Synonym	More Synonyms

Quinacrine Dihydrochloride Dihydrate BiologicalActivity

Description	Quinacrine hydrochloride hydrate (Mepacrine hydrochloride hydrate) is an antimalarial agent, which possess anticancer effect both in vitro and vivo. Quinacrine hydrochloride hydrate suppresses NF-κB and activates p53 signaling, which results in the induction of the apoptosis[1].
Related Catalog	Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>CancerResearch Areas >>InfectionSignaling Pathways >>Autophagy >>AutophagySignaling Pathways >>Autophagy >>Mitophagy
In Vitro	Quinacrine (5-20 μM; 24 hours) inhibits the growth of SGC-7901 cells[1]. Quinacrine (7.5 and 15 μM; 24 hours) induces apoptosis in SGC-7901 cells, which is associated with mitochondria-dependent signal pathway and involves p53 upregulation and caspase-3 activation pathway[1]. Quinacrine (15 μM; 24 hours) treatment significantly increased the levels of proapoptotic proteins, including cytochrome c, Bax, and p53, and decreased the levels of antiapoptotic protein Bcl-2, thus shifting the ratio of Bax/Bcl-2 in favor of apoptosis [1]. Cell Viability Assay[1] Cell Line: SGC-7901 cells Concentration: 0, 5, 10, 15, and 20 μM Incubation Time: 24 hours Result: Cell viability was inhibited in a dose-dependent manner, and the mean IC50 value is 16.18 μM. Apoptosis Analysis[1] Cell Line: SGC-7901 cells Concentration: 7.5 and 15 μM Incubation Time: 24 hours Result: The percentage of apoptotic cells, including the early phase and late phase apoptosis, increased to 26.30%, compared with control group of 3.37%. Western Blot Analysis[1] Cell Line: SGC-7901 cells Concentration: 15 μM Incubation Time: 24 hours Result: The relative quantity of cytochrome c protein was upregulated, increased from 0.10 to 0.24. The relative quantity of p53 protein was dramatically increased, from 0.06 to 0.19. The Bax/Bcl-2 ratio was dramatically elevated from 1.21 to 2.59.
In Vivo	Quinacrine (100 mg/kg three times per week for two consecutive weeks) significantly suppresses circulating blast cells at days 30/31 and increases the median survival time (MST). Quinacrine does not decrease the body weight of treated animals at the tested dose[2]. Animal Model: Female SCID mice with acute myeloid leukemia (AML)-PS model[2] Dosage: 100 mg/kg Administration: Administered by oral gavage (po); three times a week for two consecutive weeks Result: In the first AML mouse in vivo study, evaluation of circulating leukemic cells detected in blood samples (in percent of white blood cells (WBC)) at day 30/31 showed 72% human tumor cells in the control mice, whereas in mice treated with Quinacrine, this was only 2.2%. The MST of control mice was 34 days whereas it was 46 days in Quinacrine-treated mice.
References	[1]. Xiaoyang Wu, et al. Quinacrine Inhibits Cell Growth and Induces Apoptosis in Human Gastric Cancer Cell Line SGC-7901. Curr Ther Res Clin Exp. 2012 Feb;73(1-2):52-64. [2]. Anna Eriksson, et al. Towards repositioning of quinacrine for treatment of acute myeloid leukemia - Promising synergies and in vivo effects. Leuk Res. 2017 Dec;63:41-46.

Chemical & Physical Properties

Boiling Point	557.1ºC at 760 mmHg
Melting Point	247 °C
Molecular Formula	C₂₃H₃₆Cl₃N₃O₃
Molecular Weight	508.909
Exact Mass	507.182220
PSA	55.85000
LogP	7.52080
InChIKey	RZFNKJVCPDLQQA-UHFFFAOYSA-N
SMILES	CCN(CC)CCCC(C)Nc1c2ccc(Cl)cc2nc2ccc(OC)cc12.Cl.Cl.O.O
Storage condition	-20℃
Water Solubility	2.8 g/100 mL

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AR7876000

CHEMICAL NAME :: Acridine, 6-chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2- methoxy-, dihydrochloride, dihydrate

CAS REGISTRY NUMBER :: 6151-30-0

LAST UPDATED :: 199112

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C23-H30-Cl-N3-O.2Cl-H.2H2-O

MOLECULAR WEIGHT :: 507.96

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 37 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 44,225,1978 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intratesticular

DOSE :: 4 mg/kg

SEX/DURATION :: male 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 6,329,1972

Safety Information

Hazard Codes	Xn: Harmful;
Risk Phrases	R22;R36/37/38
Safety Phrases	S26-S37/39

Synonyms

Atebrin hydrochloride

Quinacrinehydrochlorid

MFCD00150069

866 R.P.

Chemiochin

Acrichine

mepacrinehydrochloridedihydrate

atabrinehydrochloridedihydrate

QuinacrineHCl

QUINACRINE,ATABRINE MEPACNINE

Mepacrine dihydrochloride

Chinacrin hydrochloride

hloride2h2-o

ochloride,dihydrate

Mecryl

Erion

Pentilen

mepacrinehcl

N-(6-Chloro-2-methoxy-9-acridinyl)-N,N-diethyl-1,4-pentanediamine dihydrochloride dihydrate

AtabrineMepacnine

QUINACRINE DIHYDROCHLORIDE

Palusan

1,4-Pentanediamine, N-(6-chloro-2-methoxy-9-acridinyl)-N,N-diethyl-, hydrochloride, hydrate (1:2:2)

Crinodora

Akrichin

Italchin

Metochin

Metoquine

Palacrin

69-05-6 {Anhydrous}

Acriquine

Malaricida

Recommended......