Massachusetts Friday filed an administrative complaint against Merrill Lynch & Co. for state securities law violations in regards to risky collateralized debt obligation investments the firm made on behalf of Springfield — investments that dropped in value by more than $12 million in nine months.

The securities division of the office of the secretary of the commonwealth filed an administrative complaint a day after Springfield officials, along with state Attorney General Martha Coakley, announced an agreement in which Merrill will pay the city $13.9 million, the total amount of CDOs that Springfield purchased through the firm, along with $150,000 in outside legal fees.

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