Dimepheptanol

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.
Dimestrol Dimetacrine Dimetan? Dimethadione Dimethazan

Dimepheptanol
Dimepheptanol.svg
Systematic (IUPAC) name
(±)-6-dimethylamino-4,4-diphenylheptan-3-ol
Clinical data
Legal status Prohibited (S9) (AU) Schedule I (US)
Identifiers
CAS number 545-90-4
ATC code None
UNII NNB4I01PA7 YesY
Chemical data
Formula C21H29NO 
Mol. mass 311.46 g/mol
 YesY (what is this?)  (verify)

Dimepheptanol (INN; Amidol, Pangerin), also known as methadol or racemethadol, is a synthetic opioid analgesic related to methadone. It has similar effects to other opioids, including analgesia, sedation and euphoria, as well as side effects like itching, nausea and respiratory depression.

Dimepheptanol is a mixture of two isomers, alphamethadol (α-methadol) and betamethadol (β-methadol).[1] These are also available separately, and this drug has three separate entries in many national and international lists of illegal drugs, which refer to the racemic mixture dimepheptanol, and the two optical isomers.[1] Each of these isomers is itself a mixture of two isomers, and so there are in fact four isomers of dimepheptanol in total; L-α-methadol, D-α-methadol, L-β-methadol and D-β-methadol.[1]

Methadol isomers.svg

The isomer L-α-methadol is the active metabolite of the long-acting opioid substitute drug levomethadyl acetate (LAAM), and has been used much more widely than β-methadol or the racemic mixture of dimepheptanol.