Abstract: A syringe assembly (10) includes a syringe barrel (12) having a proximal end and a distal end (16), a needle hub (20) coupled to the distal end of the syringe barrel. A guide member (30) extends from the needle hub (20) for sliding in an axial opening (76, 118, 132) of an adapter (32, 100, 130) connected to the container (36) or vial containing a medication substance, drug, or pharmaceutical. The guide member (30) has a shape and length for mating with the axial opening (76, 118, 132) in the adapter to guide the needle of the syringe in straight line through a septum (42) in the container where the syringe can be filed and aspirated. In one embodiment, the guide member (30) has a plurality of radially extending ribs (52) mating with complementing axial channels or grooves in the axial opening (76, 118, 132) of the adapter (32).