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69-05-6

69-05-6 structure
69-05-6 structure
  • Name: Quinacrine (dihydrochloride)
  • Chemical Name: Quinacrine Dihydrochloride Hydrate
  • CAS Number: 69-05-6
  • Molecular Formula: C23H32Cl3N3O
  • Molecular Weight: 472.88
  • Catalog: API Antiparasitic drug Antimalarial
  • Create Date: 2018-05-27 08:00:00
  • Modify Date: 2026-06-30 17:37:31
  • 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
Synonyms 2-Methoxy-6-chloro-9-[[4-(diethylamino)-1-methylbutyl]amino]acridine dihydrochloride
Quinacrine Dihydrochloride
palusan
ATABRINE HYDROCHLORIDE
3-chloro-7-methoxy-9-(1-methyl-4-diethylaminobutylamino)acridinedihydrochlor
Chinacrin hydrochloride
methoquine
3-Chloro-7-methoxy-9-[1-methyl-4-(diethylamino)butylamino]acridine dihydrochloride
ATEBRIN HYDROCHLORIDE
Erion
Atebrin dihydrochloride, Macrine dihydrochloride, 6-Chloro-9-(4-diethylamino-1-methylbutylamino)-2-methoxyacridine dihydrochloride
N-(6-Chloro-2-methoxy-9-acridinyl)-N,N-diethyl-1,4-pentanediamine dihydrochloride dihydrate
Quinacrine, DiHCl
metoquin
pentilen
ERION HYDROCHLORIDE
1,4-Pentanediamine, N-(6-chloro-2-methoxy-9-acridinyl)-N,N-diethyl-, hydrochloride, hydrate (1:2:2)
ATABRINE
3-chloro-9-(4’-diethylamino-1’-methylbutylamino)-7-methoxyacridinedihydrochl
malicida
metoquine
Acridine, 6-chloro-9-[[4-(diethylamino)-1-methylbutyl]amino]-2-methoxy-, dihydrochloride
CHEMIOCHIN HYDROCHLORIDE
Akrichin
ATEBRIN DIHYDROCHLORIDE
3-Chloro-9-[4'-(diethylamino)-1'-methylbutyl]amino]-7-methoxyacridine dihydrochloride
metochin
Italchin
chinacrin
Metochin
italchin
ICHIN HYDROCHLORIDE
6-CHLORO-9-(4-DIETHYLAMINO-1-METHYL-N-BUTYL)AMINO-2-METHOXYACRIDINE DIHYDROCHLORIDE
Quinacine dihydrochloride
QUINACRINE DIHYDROCHLORIDE CRYSTALLINE
Malaricida
crinodora
Atebrin hydrochloride
866 R.P.
Chemiochin
sn390
Acrichine
QUINACRINE
DL-QUINACRINE HYDROCHLORIDE
METOCHIN HYDROCHLORIDE
2-Chloro-5-[[.omega.-(diethylamino)-.alpha.-methylbutyl)amino]-7-methoxyacridine dihydrochloride
QUINACRINE DIHYDROCHLORIDE, FOR FLUORESC ENCE
Mepacrine dihydrochloride
MFCD00012659
1,4-Pentanediamine, N4-(6-chloro-2-methoxy-9-acridinyl)-N1,N1-diethyl-, dihydrochloride
2-methoxy-6-chloro-9-(4-diethylamino-1-methylbutylamino)acridinedihydrochlor
Mecryl
QUINACRINE DIHYDROCHLORIDE MAO INHIBITOR
Pentilen
Atebrine hydrochloride
MACRINE
866r.p
MACRINE HYDROCHLORIDE
mecryl
QUINACRINE DIHYDROCHLORIDE
Palusan
Crinodora
palacrin
erionHCl
CHINACRIN HYDROCHLORIDE
Metoquine
Palacrin
69-05-6 {Anhydrous}
6-CHLORO-9-(4-DIETHYLAMINO-1-METHYL-BUTYLAMINO)-2-METHOXYACRIDINE DIHYDROCHLORIDE
atabrinedihydrochloride
EINECS 200-700-8
chemiochin
1,4-Pentanediamine,N4-(6-chloro-2-methoxy-9-acridinyl)-N1,N1-diethyl-, hydrochloride (1:2)
Acriquine
2-chloro-5-(omega-diethylamino-alpha-methylbutylamino)-7-methoxyacridinedihy
MACRINE DIHYDROCHLORIDE
quinacrine2HCl
erion
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
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)

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
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
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title: CAS No. 69-05-6 | Chemsrc address: https://m.chemsrc.com/en/baike/1108924.html

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