An empty vial that once contained methadone prescribed to William Burroughs and a 1968 first edition of Tom Wolfe's book The Electric Kool-Aid Acid Test, signed by 45 stars of the 60s counterculture scene, are being auctioned in San Francisco next week as part of the sale of a unique collection of beat and avant-garde literature and ephemera.

One of the star items of the sale is a 1958 first edition paperback of Jack Kerouac's On the Road, inscribed by Neal Cassady – the real-life inspiration for Kerouac's drug-fuelled protagonist Dean Moriarty – with the words "Tell it John". The inscription is a message to Kerouac, and the book is expected to make between $8,000 and $12,000

The list of signatories to the copy of Wolfe's The Electric Kool-Aid Acid Test, his new journalism account of Ken Kesey and the Merry Pranksters' bus trip across America in 1964, reads like a who's who of 1960s US counterculture. They include Kesey, who wrote One Flew Over the Cuckoo's Nest, the novelist and activist Wendell Berry, who worked alongside Kesey at Stanford University, acid test participant Ken Babbs, and Dan Healy and Phil Lesh of the Grateful Dead. Its sale value is estimated at $7,000 - $10,000.

Counterculture collector and historian Rick Synchef, who is selling off the books and other items, told CollectorsWeekly: "These are my idols. I looked up to these people because they brought something so new to the country."

The empty vial once belonging to Burroughs has a list price of $300 (£185). The 1950s and 1960s paperbacks, which are being sold separately and together in small lots, include works by Charles Bukowski, Gary Snyder, Burroughs, Raymond Chandler and Allen Ginsberg. Most of the books are signed by the author, and many have additional signatures or inscriptions from others associated with the work.

The sale takes place at PBA Galleries in San Francisco on 10 October, and will be followed by a second auction in January 2014, focusing on books and other materials about drugs. A third sale will follow in May 2014.