|Systematic (IUPAC) name|
|Pregnancy cat.||C: (United States)|
|Legal status||Prescription Only (S4) (AU) Schedule II (US)
Schedule III international
|Mol. mass||217.264 g/mol|
|(what is this?)|
Glutethimide is a hypnotic sedative that was introduced in 1954 as a safe alternative to barbiturates to treat insomnia. Before long, however, it had become clear that glutethimide was just as likely to cause addiction and caused similarly severe withdrawal symptoms. Doriden was the brand-name version of the drug; it was also available under the brand names Elrodorm, Noxyron, Glimid and others. Both the generic and brand-name forms are very rarely prescribed today.
Long term use
In long term use rebound effects, which resembled those seen in withdrawal, have anecdotally been described in patients, who were still taking a stable dose of the drug. The symptoms included delirium, hallucinosis, convulsions and fever.
Glutethimide is a CYP2D6 enzyme inducer. When taken with codeine, it enables the body to convert higher amounts of the codeine (higher than the average 5 - 10%) to morphine. The general sedative effect also adds to the effect of the combination.
Glutethimide is a Schedule II drug under the Convention on Psychotropic Substances. It was originally a Schedule III drug in the United States under the Controlled Substances Act, but in 1991 it was upgraded to Schedule II, after it was discovered that misuse combined with codeine increased the effect of the codeine and deaths had resulted from the combination.
Glutethimide (2-ethyl-2-phenylgutarimide) is synthesized by addition of 2-phenylbutyronitrile to the methylacrylate (Michael reaction), and the subsequent alkaline hydrolysis of the nitrile group in the obtained compound into an amide group, and the subsequent acidic cyclization of the product into the desired glutethimide. The (R) isomer has a faster onset and more potent anticonvulsant activity in animal models than the (S) isomer.
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