Pin Ring
A simple ring with a flip-up lid, below which is a needle capable of delivering a dose of poison (or drug) to the target. Stealthily sticking an unaware target would require a sleight of hand check vs the victim's passive Perception. If stuck, the victim would know they've been scatched/poked, but may not know where it came from (especially in a crowded area). It is up to the DM how to handle the situation. If a victim is aware of the assassin, then an attack roll would be needed.
The pin will not administer poison through any significant thickness of clothing.
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