Sometime before stardate 4978, Harry Mudd sold a love potion to a thousand people on Sirius IX. When they became ill, Mudd quickly left the planet. (TAS: "Mudd's Passion"; Star Trek VI: The Undiscovered Country, production art)
The Enterprise computer's star chart was a drawing by Rick Sternbach that had originally been published in 1979 on page 77. This chart showed Earth commercial and exploration routes after the use of warp drive began. Sirius A was a destination on an exploration route.
"The Explored Galaxy"
"The Explored Galaxy" was a map of charted space in the Alpha Quadrant. Sirius was located between the Tholian Assembly and Romulus. Both locations were identified in DS9: "The Search, Part II", "Call to Arms" as being located in this quadrant. This star chart was also seen in several Star Trek: The Next Generation and Star Trek: Deep Space Nine episodes set in the 24th century, from the year 2364 to 2370. These were: TNG: "Conspiracy", "The Measure Of A Man", "The Emissary", "The Mind's Eye", "The Game" and DS9: "In the Hands of the Prophets", "Cardassians".