> そんなに絶望的な顔を **しちゃア** 、妾の涎が止まらなくなっちまうじゃあなィか **い** ♪

I don't understand what that means. What is しちゃア and the last い ?

I assume it means something like :

> I can't stop drooling if you keep making that desesperate face.
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meaning sentence
Trouble understanding しちゃア　and ending かい
It looks like manga-style sentence attempting to represent the way people
speak. I suspect the しちゃア is a contraction of してしまう, which is often contracted
to しちゃう in everyday speech, in a dialect where that last う becomes an ア sound.

The last い simply looks like one of the many occasions where the regular か for
questions becomes かい in speech.

Your translation might work if the speaker is the concubine/mistress (妾), but
without further context, I'm hard pressed to understand why a concubine
(several concubines?) would be drooling over someone looking especially down.
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> そんなに絶望的｛ぜつぼうてき｝な顔｛かお｝をし **ちゃア** 、妾｛わらわ｝の涎｛よだれ｝が止｛と｝まらなくなっ **ちまう** **じゃあ** 「
> **なィかい♪** 」

It could be said formally like:

> そんなに絶望的｛ぜつぼうてき｝な顔｛かお｝をし **たら** 、妾｛わらわ｝の涎｛よだれ｝が止｛と｝まらなくなっ **てしまう** **では**
> 「ないかい♪」
>
> そんなに絶望的｛ぜつぼうてき｝な顔｛かお｝をし **たら** 、妾｛わらわ｝の涎｛よだれ｝が止｛と｝まらなくなっ **てしまう** 。「
> **そうは思わないかい？** / **そうだよね。** 」

_I couldn't stop drooling if you keep making that hopeless/desperate face.
Don't you think so?_  
_I couldn't stop drooling if you keep making that hopeless/desperate
face,right?_

* * *

> 「わらは」（妾・私）は、武家時代、女が自分をへりくだっていう語（『広辞苑』）

妾｛わらわ｝ or 私｛わらわ｝ is a word that a woman calls herself humbly in the feudal
period in Japan.
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