Cinchophen

NEEDLES FROM METHANOL OR DILUTED ALCOHOL

WHITE OR YELLOWISH CRYSTALS OR POWDER

SMALL, WHITE, NEEDLE-LIKE CRYSTALS

RAPIDLY LOSES WATER OF CRYSTALLIZATION ON EXPOSURE TO AIR; SOL IN WATER, ALC; PRACTICALLY INSOL IN ETHER /LITHIUM SALT OCTAHYDRATE/

SOLUBLE IN HOT ALCOHOL, ALKALI; SLIGHTLY SOL IN HOT ACETONE, HOT BENZENE; INSOLUBLE IN PETROLEUM ETHER, WATER

1 G DISSOLVES IN ABOUT: 400 ML CHLOROFORM, 100 ML ETHER, 120 ML ALCOHOL

INDEX OF REFRACTION IN ORTHORHOMBIC SYSTEM: 1.545 (ALPHA), 1.575 (BETA), EXCEEDS 1.734 (GAMMA); INDEX OF REFRACTION IN TRICLINIC SYSTEM: 1.545 (ALPHA), 1.590 (BETA), 1.630 (GAMMA); INDEX OF REFRACTION IN TRICLINIC SYSTEM: 1.545 (ALPHA), 1.590 (BETA), 1.630 (GAMMA)

156.6 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID0040705]；161.4 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID0040705]；156.2 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID0040705]；170.4 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID0040705]

165.67 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；165.35 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；153.79 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；146.44 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

154.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

OPTIC SIGN: +; ELONGATION: +; AXIAL ANGLE: 2V= 45 DEG /ORTHORHOMBIC SYSTEM/

OPTIC SIGN: -; AXIAL ANGLE: LARGE /TRICLINIC SYSTEM/

YELLOW CRYSTALLINE POWDER; SLIGHTLY BITTER, ASTRINGENT TASTE; MP: 223 °C; PRACTICALLY INSOL IN WATER; SLIGHTLY SOL IN ALCOHOL; SOL IN CHLOROFORM, ETHER /HYDROCHLORIDE/

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 45 reports by companies from 2 notifications to the ECHA C&L Inventory.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Drug Induced Liver Injury Rank (DILIrank 2.0)

Cinchophen

vMost-DILI-concern

8

Withdrawn

DOI:10.1016/j.drudis.2016.02.015

DOSES OF 1 G/KG BY MOUTH ARE LETHAL TO RABBITS... LETHAL DOSE RANGE OF CINCHOPHEN FOR FROGS, MICE, RATS & GUINEA PIGS BY VARIETY OF ROUTES LIES BETWEEN 0.5 & 1.0 G/KG. DEATH APPEARS TO RESULT FROM RESPIRATORY PARALYSIS.

INDUCTION OF UDP-GLUCURONYL TRANSFERASE ACTIVITY IN RAT EXTRAHEPATIC TISSUES HAS BEEN REPORTED FOLLOWING CINCHOPHEN...ADMIN...

CINCHOPHEN, 3-HYDROXYCINCHOPHEN, 6-HYDROXYCINCHOPHEN, 7-HYDROXYCINCHOPHEN, & 8-HYDROXYCINCHOPHEN INHIBITED RAT LIVER GLUTAMATE-PYRUVATE TRANSAMINASE MORE THAN GLUTAMATE-OXALACETATE TRANSAMINASE.

IV ADMIN OF CINCHOPHEN CAUSED ULCERATIVE ENTEROCOLITIS IN DOGS. ULCERS WERE CLOSELY ASSOCIATED WITH PEYER'S PATCHES. GRANULOMATA WERE OCCASIONALLY SEEN IN MUCOSA & ADJACENT MESENTERIC NODES ALSO.

For more Non-Human Toxicity Excerpts (Complete) data for CINCHOPHEN (6 total), please visit the HSDB record page.

M - Musculo-skeletal system；M04 - Antigout preparations；M04A - Antigout preparations；M04AC - Preparations with no effect on uric acid metabolism；M04AC02 - Cinchophen

QM - Musculo-skeletal system；QM04 - Antigout preparations；QM04A - Antigout preparations；QM04AC - Preparations with no effect on uric acid metabolism；QM04AC02 - Cinchophen

2% 2-O-OXYPHENYLQUINOLINE-4-CARBOXYLIC ACID WAS EXCRETED IN URINE FROM HUMANS AFTER DOSAGE WITH CINCHOPHEN. /FROM TABLE/

YIELDS 8-HYDROXY-2-PHENYLQUINOLINE-4-CARBOXYLIC ACID & 2-(P-HYDROXYPHENYL)QUINOLINE-4-CARBOXYLIC ACID IN DOG: HARTIALA, K, TERHO, T & HAKKINEN, I; BIOCHEM PHARMAC, 16, 843 (1967). /FROM TABLE/

PREPARED BY HEATING PYRUVIC ACID WITH ANILINE & BENZALDEHYDE OR WITH BENZYLIDENE ANILINE IN ABSOLUTE ALCOHOL: DOEBNER, GIESEKE, ANN 242, 290 (1887). ALSO FROM ACETOPHENONE & ISATINIC ACID IN ALCOHOLIC KOH: PFITZINGER, J PRAKT CHEM 38, 582 (1882); 56, 293 (1897).