Structural Formula Vector Image
Title: p-Aminopropiophenone
CAS Registry Number: 70-69-9
CAS Name: 1-(4-Aminophenyl)-1-propanone
Additional Names: ethyl p-aminophenyl ketone; PAPP
Molecular Formula: C9H11NO
Molecular Weight: 149.19
Percent Composition: C 72.46%, H 7.43%, N 9.39%, O 10.72%
Literature References: Pretreatment antidote to cyanide; activity probably through the formation of methemoglobin, which has a higher affinity for cyanide than mitochondrial cytochrome oxidase. Prepd by the action of propionyl chloride on aniline in carbon bisulfide in the presence of aluminum chloride: Kunckell, Ber. 33, 2641 (1900); Derrick, Bornemann, J. Am. Chem. Soc. 35, 1283 (1913); Hartung, Foster, J. Am. Pharm. Assoc. 35, 15 (1946). Antidotal activity: C. L. Rose et al., J. Pharmacol. Exp. Ther. 89, 109 (1947). Toxicity study: J. W. Scawin et al., Toxicol. Lett. 23, 359 (1984). Review of pharmacology of cyanide detoxification: S. I. Baskin, R. F. Fricke, Cardiovasc. Drug Rev. 10, 358-375 (1992).
Properties: Yellow needles from water, mp 140°. Sol in water, alc, DMSO. LD50 in male, female mice (mg/kg): 145, 200 i.v.; in female mice, guinea pigs, rats, male rats (mg/kg): >5000, 1020, 223.7, 475 orally (Scawin).
Melting point: mp 140°
Toxicity data: LD50 in male, female mice (mg/kg): 145, 200 i.v.; in female mice, guinea pigs, rats, male rats (mg/kg): >5000, 1020, 223.7, 475 orally (Scawin)
Derivative Type: Hydrochloride
CAS Registry Number: 6170-25-8
Molecular Formula: C9H11NO.HCl
Molecular Weight: 185.65
Percent Composition: C 58.23%, H 6.52%, N 7.54%, O 8.62%, Cl 19.10%
Properties: Needles, yellowish cast, mp 198-199°. Freely sol in water. LD50 i.v. in dogs: 7.15 ±0.89 mg/kg (Rose).
Melting point: mp 198-199°
Toxicity data: LD50 i.v. in dogs: 7.15 ±0.89 mg/kg (Rose)
Derivative Type: Sulfate
Molecular Formula: (C9H11NO)2.H2SO4
Molecular Weight: 396.46
Percent Composition: C 54.53%, H 6.10%, N 7.07%, O 24.21%, S 8.09%
Properties: Yellow plates from alcohol, dec 25°.
Therap-Cat: Antidote (cyanide).
Keywords: Antidote (Cyanide).

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