Quinacrine (dihydrochloride)

Modify Date: 2024-01-02 19:11:15

Quinacrine (dihydrochloride) structure	Common Name	Quinacrine (dihydrochloride)
	CAS Number	69-05-6	Molecular Weight	472.88
	Density	1.2962 (rough estimate)	Boiling Point	N/A
	Molecular Formula	C₂₃H₃₂Cl₃N₃O	Melting Point	ca. 248 - 250ºC (decomposes)
	MSDS	Chinese USA	Flash Point	N/A
	Symbol	GHS07	Signal Word	Warning

Use of Quinacrine (dihydrochloride)

Quinacrine is a fluorescent probe for the conformational transitions of the cholinergic receptor protein. Quinacrine shows activity in the low μM range with a mean IC50 of 2.30 μM In the patient AML cells.IC50 value: 2.30 μM (for AML cells)Target:in vitro: Quinacrine is a fluorescent probe for the conformational transitions of the cholinergic receptor protein in its membrane-bound state.[1] In the patient AML samples, Quinacrine showed activity in the low μM range with a mean IC50 of 2.30 μM, statistically significantly lower than that of normal PBMCs; 3.54 μM (P=0.0327; Student's t-test). Samples from patients with chronic lymphocytic, acute myeloid and lymphocytic leukemias as well as peripheral blood mononuclear cells (PBMC) were tested in response to 1266 compounds from the LOPAC1280 library. 25 compounds were defined as hits with activity in all leukemia subgroups (<50% cell survival compared with control) at 10 μM drug concentration. Only Quinacrine showed concurrent high activity in all leukemia subgroups and low activity in normal PBMCs and was, therefore, selected for further preclinical evaluation. Quinacrine also induced early inhibition of both DNA and protein synthesis. Quinacrine have repositioning potential for treatment of acute myeloid leukemia by targeting of ribosomal biogenesis.[2]

Name	Quinacrine Dihydrochloride Hydrate
Synonym	More Synonyms

Description	Quinacrine is a fluorescent probe for the conformational transitions of the cholinergic receptor protein. Quinacrine shows activity in the low μM range with a mean IC50 of 2.30 μM In the patient AML cells.IC50 value: 2.30 μM (for AML cells)Target:in vitro: Quinacrine is a fluorescent probe for the conformational transitions of the cholinergic receptor protein in its membrane-bound state.[1] In the patient AML samples, Quinacrine showed activity in the low μM range with a mean IC50 of 2.30 μM, statistically significantly lower than that of normal PBMCs; 3.54 μM (P=0.0327; Student's t-test). Samples from patients with chronic lymphocytic, acute myeloid and lymphocytic leukemias as well as peripheral blood mononuclear cells (PBMC) were tested in response to 1266 compounds from the LOPAC1280 library. 25 compounds were defined as hits with activity in all leukemia subgroups (<50% cell survival compared with control) at 10 μM drug concentration. Only Quinacrine showed concurrent high activity in all leukemia subgroups and low activity in normal PBMCs and was, therefore, selected for further preclinical evaluation. Quinacrine also induced early inhibition of both DNA and protein synthesis. Quinacrine have repositioning potential for treatment of acute myeloid leukemia by targeting of ribosomal biogenesis.[2]
Related Catalog	Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Autophagy >> Mitophagy Signaling Pathways >> Metabolic Enzyme/Protease >> Phospholipase Research Areas >> Cancer
References	[1]. Grünhagen HH, et al. Studies on the electrogenic action of acetylcholine with Torpedo marmorata electric organ. IV. Quinacrine: a fluorescent probe for the conformational transitions of the cholinergic receptor protein in its membrane-bound state. J Mol Biol. 1976 Sep 25;106(3):497-516. [2]. Eriksson A, et al. Drug screen in patient cells suggests quinacrine to be repositioned for treatment of acute myeloid leukemia.Blood Cancer J. 2015 Apr 17;5:e307.

Description

Related Catalog

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Autophagy >> Mitophagy

Signaling Pathways >> Metabolic Enzyme/Protease >> Phospholipase

Research Areas >> Cancer

References

[1]. Grünhagen HH, et al. Studies on the electrogenic action of acetylcholine with Torpedo marmorata electric organ. IV. Quinacrine: a fluorescent probe for the conformational transitions of the cholinergic receptor protein in its membrane-bound state. J Mol Biol. 1976 Sep 25;106(3):497-516.

[2]. Eriksson A, et al. Drug screen in patient cells suggests quinacrine to be repositioned for treatment of acute myeloid leukemia.Blood Cancer J. 2015 Apr 17;5:e307.

Density	1.2962 (rough estimate)
Melting Point	ca. 248 - 250ºC (decomposes)
Molecular Formula	C₂₃H₃₂Cl₃N₃O
Molecular Weight	472.88
PSA	37.39000
LogP	6.84740
Index of Refraction	1.6300 (estimate)

Quinacrine (dihydrochloride) MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AR7875000

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

CAS REGISTRY NUMBER :: 69-05-6

LAST UPDATED :: 199806

DATA ITEMS CITED :: 43

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

MOLECULAR WEIGHT :: 472.93

WISWESSER LINE NOTATION :: T C666 BNJ EG IMY1&3N2&2 LO1 &GH 2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 34 mg/kg/8D-I

TOXIC EFFECTS :: Behavioral - toxic psychosis

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 18 mg/kg/3D-I

TOXIC EFFECTS :: Behavioral - toxic psychosis

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 660 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 29 mg/kg

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

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

ROUTE OF EXPOSURE :: Intrauterine

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 557 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 189 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 212 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - respiratory depression

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 38 mg/kg

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

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 20 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Vascular - other changes Lungs, Thorax, or Respiration - other changes

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 15 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression Immunological Including Allergic - anaphylaxis

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Behavioral - excitement Gastrointestinal - hypermotility, diarrhea Gastrointestinal - other changes

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Liver - other changes Kidney, Ureter, Bladder - other changes

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 10 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Behavioral - convulsions or effect on seizure threshold Gastrointestinal - changes in structure or function of salivary glands

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 433 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 9 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex)

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 14 mg/kg

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

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 80 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - gerbil

DOSE/DURATION :: 70 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2520 mg/kg/7D-C

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intrauterine

DOSE :: 15 mg/kg

SEX/DURATION :: female 3 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intracervical

DOSE :: 20 mg/kg

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

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intrauterine

DOSE :: 50 mg/kg

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

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intrauterine

DOSE :: 2 mg/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intrauterine

DOSE :: 200 mg/kg

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

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intrauterine

DOSE :: 80 mg/kg

SEX/DURATION :: female 1 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intratesticular

DOSE :: 20 mg/kg

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

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intrauterine

DOSE :: 7200 ug/kg

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

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 375 mg/kg

SEX/DURATION :: female 25 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Maternal Effects - menstrual cycle changes or disorders

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TYPE OF TEST :: Specific locus test

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Micronucleus test

MUTATION DATA

TYPE OF TEST :: DNA adduct

TEST SYSTEM :: Mammal - species unspecified Lymphocyte

DOSE/DURATION :: 1 mmol/L

REFERENCE :: CHROAU Chromosoma. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1939- Volume(issue)/page/year: 49,17,1974 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4102 No. of Facilities: 66 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 987 (estimated) No. of Female Employees: 508 (estimated)

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302-H315-H319-H335
Precautionary Statements	P261-P305 + P351 + P338
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xn
Risk Phrases	22-36/37/38
Safety Phrases	S36/S37/S39
RIDADR	NONH for all modes of transport
RTECS	AR7875000

Precursor 0
DownStream 7
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CAS#:854892-24-3 6-chloro-9-[(4-... CAS#:83196-72-9 N4,N4-diethyl-N... CAS#:3407-99-6 ACRIDINE, 9-AMI...

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Product Name: 1,4-Pentanediamine,N4-(6-chloro-2-methoxy-9-acridinyl)-N1,N1-diethyl-, hydrochloride (1:2)
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