Aminopentamide

Title: Aminopentamide
CAS Registry Number: 60-46-8
CAS Name: a-[2-(Dimethylamino)propyl]-a-phenylbenzeneacetamide
Additional Names: 4-dimethylamino-2,2-diphenylvaleramide; a,a-diphenyl-g-dimethylaminovaleramide; dimevamide
Manufacturers' Codes: BL-139
Molecular Formula: C19H24N2O
Molecular Weight: 296.41
Percent Composition: C 76.99%, H 8.16%, N 9.45%, O 5.40%
Literature References: Anticholinergic. Prepn similar to that of methadone, starts by condensing diphenylmethyl cyanide with chlorodimethylaminopropane: Walton, et al., J. Chem. Soc. 1949, 648; Cheney et al., J. Org. Chem. 17, 770 (1952); Specter, US 2647926 (1953 to Bristol). Prepn of optical isomers: Wheatley et al., J. Org. Chem. 19, 794 (1954). See also Moffett, Aspergren, J. Am. Chem. Soc. 79, 4451 (1957). Toxicity study: Cazort, J. Pharmacol. Exp. Ther. 100, 325 (1950).
Derivative Type: dl-Form
Properties: Long prisms from dilute alcohol, mp 183-184°. Practically insol in water.
Melting point: mp 183-184°
Derivative Type: d-Form
Properties: Crystals from petr ether, mp 136.5-137.5° (sintering). [a]D23 +98.9° (methanol).
Melting point: mp 136.5-137.5° (sintering)
Optical Rotation: [a]D23 +98.9° (methanol)
Derivative Type: l-Form
Properties: Crystals from petr ether, mp 136.5-137.5° (sintering). [a]D23 -101.9° (methanol).
Melting point: mp 136.5-137.5° (sintering)
Optical Rotation: [a]D23 -101.9° (methanol)
Derivative Type: dl-Form hydrochloride
Molecular Formula: C19H24N2O.HCl
Molecular Weight: 332.87
Percent Composition: C 68.56%, H 7.57%, N 8.42%, O 4.81%, Cl 10.65%
Properties: Slightly deliquescent leaflets from alcohol + ether, dec 190-191°. Bitter taste. Soluble in water, alcohol. A 1% aq soln has a pH of 6.8. LD50 in mice (mg/kg): 34.7 i.v.; 396 orally (Cazort).
Toxicity data: LD50 in mice (mg/kg): 34.7 i.v.; 396 orally (Cazort)
Derivative Type: dl-Form acid sulfate
Trademarks: Centrine (Fort Dodge)
Molecular Formula: C19H24N2O.H2SO4
Molecular Weight: 394.49
Percent Composition: C 57.85%, H 6.64%, N 7.10%, O 20.28%, S 8.13%
Properties: Deliquescent crystals from isopropanol + ethyl acetate, mp 185-187°. The commercial medicinal grade, mp 178-181°. Bitter taste. uv max (1% H2SO4): 258.5 nm (A1%1cm 10.3); min: 249 nm. Freely sol in water, alc. Very slightly sol in chloroform. Practically insol in ether. pH of 2.5% aq soln 1.3-2.2.
Melting point: mp 185-187°; mp 178-181°
Absorption maximum: uv max (1% H2SO4): 258.5 nm (A1%1cm 10.3)
Therap-Cat: Antispasmodic.
Therap-Cat-Vet: Antispasmodic; antiemetic.
Keywords: Antimuscarinic; Antispasmodic.
Aminophylline Aminopromazine Aminopropylon Aminopterin Aminopyrine