yes.
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No. It can't learn Mega Drain but it can learn Giga Drain.
If your gloom had mega drain then it evolved vileplume should still have mega drain, all though maybe it can't learn mega drain i do know it can learn giga drain.
Gloom learns Mega Drain at level 23.
grotle learns mega drain at level 27
Shroomish learns the following moves before he evolves to Breloom: Absorb (Start) Tackle (lvl 4) Stun Spore (lvl7) Leech Seed (lvl 10) Mega Drain (lvl 16) Headbutt (lvl 22) But, if you stop its evolution which starts at level 23, he can also learn these moves: Poison Powder (lvl 28) Growth (lvl 36) Giga Drain (lvl 45) Spore (lvl 54) If you want a specialized GRASS Pokemon I would keep it a Shroomish for a while, but then you'll miss out on the FIGHTING type attacks that Breloom learns like Mach Punch and Sky Uppercut