How are synthetic alkynes used for birth control?
1 Answer
Some synthetic alkynes are modifications of naturally-occurring female hormones.
Estradiol and progesterone are two naturally-occurring female hormones.
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Ethinylestradiol, norethindrone, levonorgestrel, and mifepristone are four synthetic alkynes that are used in birth control pills.
Ethinylestradiol
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Estradiol cannot be administered orally because it is rapidly oxidized by the liver.
To prevent oxidation, the 2° alcohol is converted to a 3° alcohol.
Estrone is ethynylated in one step by reaction with ethyne, sodium and sodium amide.
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Ethinylestradiol prevents ovulation.
Norethindrone
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Norethindrone makes it difficult for a fertilized egg to attach to the wall of the uterus.
Levonorgestrel
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Levonorgestrel inhibits ovulation.
Mifepristone
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Mifepristone is often used as a "morning after" pill. If taken before ovulation, it can prevent ovulation and so prevent pregnancy.