ACN

Modify Date: 2024-01-04 16:59:48

ACN Structure
ACN structure
 Common Name ACN
CAS Number 2797-51-5 Molecular Weight 207.613
Density 1.5±0.1 g/cm3 Boiling Point 310.2±42.0 °C at 760 mmHg
Molecular Formula C10H6ClNO2 Melting Point 198-200 °C
MSDS Chinese USA Flash Point 141.4±27.9 °C
Symbol GHS06 GHS09
GHS06, GHS09		 Signal Word Danger

 Use of ACN


Quinoclamine, a naphthoquinone derivative, is a NF-κB inhibitor. Quinoclamine exhibits anti-cancer activity[1][2].

 Names

Name quinoclamine
Synonym More Synonyms

 ACN Biological Activity

Description Quinoclamine, a naphthoquinone derivative, is a NF-κB inhibitor. Quinoclamine exhibits anti-cancer activity[1][2].
Related Catalog
Target

NF-κB[2]

In Vitro Quinoclamine causes differentiation of U-937 cells into macrophage-like cells[1]. Quinoclamine inhibits NF-κB activities in HepG2 cells, with an IC50 of 1.7 μM[2]. Quinoclamine (1-4 μM; 30 minutes ) suppresses endogenous NF-κB activity in HepG2 cells through the inhibition of IκB-α phosphorylation and p65 translocation[2]. Quinoclamine inhibits induced NF-κB activities in lung and breast cancer cell lines[2]. Quinoclamine affects the expression levels of genes involved in cell cycle or apoptosis[2]. Quinoclamine down-regulates the expressions of UDP glucuronosyltransferase genes involved in phase II drug metabolism[2]. Cell Viability Assay[2] Cell Line: HepG2 cells Concentration: 1 μM, 2 μM, 4 μM, 8 μM, 16 μM, 32 μM, 64 μM Incubation Time: 24 hours Result: Inhibited NF-κB activities in HepG2 cells. Western Blot Analysis[2] Cell Line: HepG2 cells Concentration: 0 μM, 1 μM, 2 μM, 4 μM Incubation Time: 30 minutes Result: Inhibited IκB-α phosphorylation and p65 translocation in HepG2 cells.
References

[1]. Kwon H ,et al. Induction of differentiation of U-937 cells by 2-chloro-3-amino-1,4-naphthoquinone. Res Commun Mol Pathol Pharmacol. 1997 Aug;97(2):215-27.

[2]. Cheng WY, et al. Comprehensive evaluation of a novel nuclear factor-kappaB inhibitor, quinoclamine, by transcriptomic analysis. Br J Pharmacol. 2009 Jul;157(5):746-56.

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Boiling Point 310.2±42.0 °C at 760 mmHg
Melting Point 198-200 °C
Molecular Formula C10H6ClNO2
Molecular Weight 207.613
Flash Point 141.4±27.9 °C
Exact Mass 207.008713
PSA 60.16000
LogP 1.31
Vapour Pressure 0.0±0.7 mmHg at 25°C
Index of Refraction 1.660
Storage condition 0-6°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QL7350000
CHEMICAL NAME :
1,4-Naphthoquinone, 2-amino-3-chloro-
CAS REGISTRY NUMBER :
2797-51-5
BEILSTEIN REFERENCE NO. :
2094762
LAST UPDATED :
199612
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C10-H6-Cl-N-O2
MOLECULAR WEIGHT :
207.62
WISWESSER LINE NOTATION :
L66 BV EVJ CZ DG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1360 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FMCHA2 Farm Chemicals Handbook. (Meister Pub., 37841 Euclid Ave., Willoughy, OH 44094) Volume(issue)/page/year: -,C208,1991
TYPE OF TEST :
LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>790 mg/m3/4H
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 18,S19,1993
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 18,S19,1993
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
315 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 18,S19,1993
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1260 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FMCHA2 Farm Chemicals Handbook. (Meister Pub., 37841 Euclid Ave., Willoughy, OH 44094) Volume(issue)/page/year: -,C208,1991
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 18,S19,1993
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
800 mg/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
REFERENCE :
JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 26,570,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
320 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#03360 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1080 mg/kg/90D-C
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in bladder weight Blood - changes in spleen
REFERENCE :
NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 18,S19,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
29528 mg/kg/2Y-C
TOXIC EFFECTS :
Behavioral - food intake (animal) Kidney, Ureter, Bladder - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 18,S19,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2160 mg/kg/90D-C
TOXIC EFFECTS :
Endocrine - changes in adrenal weight Blood - changes in spleen Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 18,S19,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
4550 mg/kg/2Y-C
TOXIC EFFECTS :
Liver - other changes Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
REFERENCE :
NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 18,S19,1993

 Safety Information

Symbol GHS06 GHS09
GHS06, GHS09
Signal Word Danger
Hazard Statements H302-H319-H331-H400
Precautionary Statements P261-P273-P305 + P351 + P338-P311
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes T: Toxic;
Risk Phrases R36/37/38
Safety Phrases S45-S37/39-S26
RIDADR 2811.0
RTECS QL7350000
HS Code 2922399021

 Synthetic Route

2,3-Dichlor-1,4-naphthochinone structure

2,3-Dichlor-1,4...

CAS#:117-80-6

~77%

ACN Structure

ACN

CAS#:2797-51-5

Literature: Hodnett, Ernest M.; Wongwiechintana, Chinda; Dunn, William J.; Marrs, Pam Journal of Medicinal Chemistry, 1983 , vol. 26, # 4 p. 570 - 574
1,4-Naphthalenedione,2-amino- structure

1,4-Naphthalene...

CAS#:2348-81-4

~95%

ACN Structure

ACN

CAS#:2797-51-5

Literature: Thapliyal, Prakash Chander Synthetic Communications, 1998 , vol. 28, # 7 p. 1123 - 1126
1H-Pyrazole-1-carboximidamide hydrochloride structure

1H-Pyrazole-1-c...

CAS#:4023-02-3

~%

ACN Structure

ACN

CAS#:2797-51-5

Literature: ENZON PHARMACEUTICALS, INC. Patent: US2011/305769 A1, 2011 ;
1-Naphthalenol structure

1-Naphthalenol

CAS#:90-15-3

~%

ACN Structure

ACN

CAS#:2797-51-5

Literature: Ullmann; Ettisch Chemische Berichte, 1921 , vol. 54, p. 271
2-chloro-3-piperazin-1-ylnaphthalene-1,4-dione structure

2-chloro-3-pipe...

CAS#:104309-89-9

~%

ACN Structure

ACN

CAS#:2797-51-5

5-chloro-3,4-dihydro-2H-benzo[f]quinoxalin-6-one structure

5-chloro-3,4-di...

CAS#:75473-67-5

Literature: Shishkina, R. P.; Berezhnaya, V. N.; Fokin, E. P. Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1985 , vol. 34, # 10 p. 2160 - 2164 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1985 , # 10 p. 2332 - 2337
2,3-Dichlor-1,4-naphthochinone structure

2,3-Dichlor-1,4...

CAS#:117-80-6

Ethanol structure

Ethanol

CAS#:64-17-5

Ammonia structure

Ammonia

CAS#:7664-41-7

~%

ACN Structure

ACN

CAS#:2797-51-5

Literature: Fries; Ochwat Chemische Berichte, 1923 , vol. 56, p. 1298 Full Text Show Details Ullmann; Ettisch Chemische Berichte, 1921 , vol. 54, p. 271
2,3-Dichlor-1,4-naphthochinone structure

2,3-Dichlor-1,4...

CAS#:117-80-6

Ammonia structure

Ammonia

CAS#:7664-41-7

nitrobenzene structure

nitrobenzene

CAS#:98-95-3

~%

ACN Structure

ACN

CAS#:2797-51-5

Literature: Fries; Ochwat Chemische Berichte, 1923 , vol. 56, p. 1298 Full Text Show Details Ullmann; Ettisch Chemische Berichte, 1921 , vol. 54, p. 271

 Customs

HS Code 2922399021
Summary 2922399021 2-amino-3-chloronaphthalene-1,4-dione。supervision conditions:s(import or export registration certificate for pesticides)。VAT:17.0%。tax rebate rate:9.0%。MFN tarrif:6.5%。general tariff:30.0%

 Articles2

More Articles
Induction of differentiation of U-937 cells by 2-chloro-3-amino-1,4-naphthoquinone.

Res. Commun. Mol. Pathol. Pharmacol. 97(2) , 215-27, (1997)

Naphthoquinone compounds have various pharmacological effects such as antiviral, antifungal and anticancer activities. We demonstrated the differentiation of the inducing effect of a naphthoquinone de...

Differentiation inducing effects of 2-chloro-3-amino-1,4-naphthoquinone on human leukemia HL-60.

Biol. Pharm. Bull. 19(6) , 824-7, (1996)

There are some highly cytotoxic anticancer compounds inducing differentiation of cancer cells to normal cells at below highly cytotoxic concentration. Naphthoquinone derivatives having cytotoxic effec...

 Synonyms

Quinoclamin
Quinoclamine
EINECS 220-529-2
2-AMINO-3-CHLORO-1,4-NAPHTHOQUINONE
ACN
2-amino-3-chloro-naphthoquinone
2-Amino-3-chlor-1,4-naphthochinone
06K-Quinone
2-amino-3-chloronaphthalene-1,4-dione
MFCD00001680
Mogeton
1,4-Naphthalenedione, 2-amino-3-chloro-
2-amino-3-chloro-1,4-dihydro-1,4-dioxonaphthalene
ACNQ
Mogeton granule
O 6K-quinone
2-amino-3-chloro-1,4-naphthalenedione
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