$500 Provincial debenture 1862

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It's on eBay right now. Province of Canada, 1862. Face proof.

Anyone ever heard of this before? It's not in the Charlton.

If memory serves, there were about six of these in the Christie's ABN Archives Sale.  They are not -- and should not be -- listed in Charlton because they are not notes.  Bonds, stock certificates, debentures and the like lie outside the scope of the catalogue.  This is, just like the poster said, a Provincial Debenture proof.  Lovely, historic and very collectable nonetheless.

Thanks for the info. It is a fascinating piece.

Debentures from about a decade earlier than this one are listed in the Charlton right at the beginning of the Province of Canada section, and prices are given for face proofs.

You are correct, of course, but in that instance they were "transferable and reissuable", and known to have circulated as currency, unlike debentures in general.