Constellation Brands (NYSE: STZ) appears to have walked away from the idea of investing further dollars into Canopy Growth (TSX: WEED). The company on Wednesday saw its Tranche A warrants held in the company expire, ending future investment opportunities in the company under its original investment agreement from 2018.

As of November 1, 88.5 million Tranche A warrants, which contained an exercise price of $50.40, have expired unexercised. While it was rather obvious that the warrants would not be exercised at this price, given the company closed Wednesday’s session at just $0.83 per share, it’s noteworthy that Constellation was seemingly disinterested in revising the warrant pricing prior to expiry.

With the Tranche A warrants expiring unexercised, the vesting terms of Tranche B warrants, which contain an exercise price of $76.68 per share, were not met, and as a result have expired as well. 12.8 million Tranche C warrants have likewise expired. Collectively, the three tranches of warrants would have enabled Constellation to increase its stake in the cannabis operator by a combined 16.9%.

As of Friday’s close, Constellation, through Greenstar Canada Investment Limited Partnership, owns 171.5 million shares of Canopy as well as $100.0 million in principal of promissory notes due 2024.

Constellation initially invested $5.0 billion in Canopy back in 2018, in what was a cornerstone investment for the cannabis industry as a whole. The investment at the time resulted in the company owning a 37% stake in the issuer, and with related warrants provided a path for the beverage alcohol company to secure a majority stake in Canopy.

READ: Canopy Growth Collects $53 Million From Sale Of Hershey Drive Facility

Continued failures by Canopy however have forced Constellation to take writedowns on its investment, with Constellation recording over $1.0 billion in impairments in a single quarter last year. Canopy Growth meanwhile, despite the several billion investment, today has a market valuation of just $713 million, and as of June 30 had a cash balance of just $533.3 million.

Canopy Growth last traded at $0.86 on the TSX.

Information for this briefing was found via Sedar and the sources mentioned. The author has no securities or affiliations related to the organizations discussed. Not a recommendation to buy or sell. Always do additional research and consult a professional before purchasing a security. The author holds no licenses.