Title: Dimepheptanol
CAS Registry Number: 545-90-4
CAS Name: b-[2-(Dimethylamino)propyl]-a-ethyl-b-phenylbenzeneethanol
Additional Names: 6-(dimethylamino)-4,4-diphenyl-3-heptanol; 2-dimethylamino-4,4-diphenyl-5-heptanol; 3-hydroxy-4,4-diphenyl-6-dimethylaminoheptane; bimethadol
Trademarks: Methadol; Pangerin
Molecular Formula: C21H29NO
Molecular Weight: 311.46
Percent Composition: C 80.98%, H 9.38%, N 4.50%, O 5.14%
Literature References: Prepn of a-isomers by catalytic or lithium aluminum hydride reduction of methadone: Speeter et al., J. Am. Chem. Soc. 71, 57 (1949); Pohland et al., ibid. 460. Prepn of b-isomers by sodium propanol reduction of methadone: Eddy et al., J. Org. Chem. 17, 321 (1952); Clark, US 2565592 and US 2668814 (1951 and 1954 to Merck & Co.); Speeter, US 2649445 (1953 to Bristol). Stereochemistry: Portoghese, Williams, 152nd Am. Chem. Soc. Meet. (New York, Sept. 1966) Abstracts of Papers, p 5.
Derivative Type: b-dl-Form
Properties: mp 127-128°.
Melting point: mp 127-128°
Derivative Type: b-dl-Form Hydrochloride
Properties: Rods from acetone, mp 210-212°.
Melting point: mp 210-212°
Derivative Type: b-d-Form
Properties: Prisms from alc + water, mp 106-107°; [a]D20 +178° (c = 0.63 in alc).
Melting point: mp 106-107°
Optical Rotation: [a]D20 +178° (c = 0.63 in alc)
Derivative Type: b-d-Form Hydrochloride
Properties: Plates from acetone + ether, mp 206-208°. [a]D20 +73.9° (c = 0.69).
Melting point: mp 206-208°
Optical Rotation: [a]D20 +73.9° (c = 0.69)
Derivative Type: b-l-Form
Properties: Prisms, mp 105-107°. [a]D20 -178° (c = 1.04 in alc).
Melting point: mp 105-107°
Optical Rotation: [a]D20 -178° (c = 1.04 in alc)
Derivative Type: b-l-Form Hydrochloride
Properties: mp 206-208°. [a]D20 -74° (c = 0.94).
Melting point: mp 206-208°
Optical Rotation: [a]D20 -74° (c = 0.94)
Derivative Type: a-dl-Form Hydrochloride
Properties: mp 192-193°.
Melting point: mp 192-193°
Derivative Type: a-d-Form Hydrochloride
Properties: mp 169-171°. [a]D25 +34° (c = 0.26).
Melting point: mp 169-171°
Optical Rotation: [a]D25 +34° (c = 0.26)
Derivative Type: a-l-Form Hydrochloride
Properties: mp 169-171°. [a]D25 -35° (c = 0.30).
Melting point: mp 169-171°
Optical Rotation: [a]D25 -35° (c = 0.30)
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.11.
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).
Status: This monograph has been retired and is no longer subject to revision or update. |