1)

Why will you be filled with intoxication and grief?

1.

Radak: The intoxication is the grief that will fill you. The cup and wine are a Mashal for afflictions.

2.

Malbim: The first time you will be full of intoxication, but not intoxication of wine that gladdens. Rather, it is a drink that inebriates and finishes off intellect and fills [the person] with grief. The second time you will drink a cup of desolation; the entire land will be desolate. The third time you will drink the cup of your sister Shomron, which was the capitol.

2)

What is "Shemamah"?

1.

Rashi: It is desolation.

Sefer: Perek: Pasuk:

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