How to send email from MySQL 5.1

I would be very concerned about putting the load of sending e-mails on my database server (small though it may be). I might suggest one of these alternatives:

1. Have application logic detect the need to send an e-mail and send it.
2. Have a MySQL trigger populate a table that queues up the e-mails to be sent and have a process monitor that table and send the e-mails.

If you have an SMTP service running, you can outfile to the drop directory. If you have high volume, you may result with duplicate file names, but there are ways to avoid that.

Otherwise, you will need to create a UDF.

Here's a sample trigger solution:

CREATE TRIGGER test.autosendfromdrop BEFORE INSERT ON test.emaildrop
FOR EACH ROW BEGIN
      /* START THE WRITING OF THE EMAIL FILE HERE*/      
      SELECT  concat("To: ",NEW.To),
              concat("From: ",NEW.From),
              concat("Subject: ",NEW.Subject),
              NEW.Body
          INTO OUTFILE 
                   "C:\\inetpub\\mailroot\\pickup\\mail.txt" 
              FIELDS TERMINATED by '\r\n' ESCAPED BY '';            
END;

To markup the message body you will need something like this...

CREATE FUNCTION `HTMLBody`(Msg varchar(8192)) 
    RETURNS varchar(17408) CHARSET latin1 DETERMINISTIC
BEGIN
  declare tmpMsg varchar(17408);
  set tmpMsg = cast(concat(
      'Date: ',date_format(NOW(),'%e %b %Y %H:%i:%S -0600'),'\r\n',
      'MIME-Version: 1.0','\r\n',
      'Content-Type: multipart/alternative;','\r\n',
      ' boundary=\"----=_NextPart_000_0000_01CA4B3F.8C263EE0\"','\r\n',
      'Content-Class: urn:content-classes:message','\r\n',
      'Importance: normal','\r\n',
      'Priority: normal','\r\n','','\r\n','','\r\n',
      'This is a multi-part message in MIME format.','\r\n','','\r\n',
      '------=_NextPart_000_0000_01CA4B3F.8C263EE0','\r\n',
      'Content-Type: text/plain;','\r\n',
      '  charset=\"iso-8859-1\"','\r\n',
      'Content-Transfer-Encoding: 7bit','\r\n','','\r\n','','\r\n',
      Msg,
      '\r\n','','\r\n','','\r\n',
      '------=_NextPart_000_0000_01CA4B3F.8C263EE0','\r\n',
      'Content-Type: text/html','\r\n',
      'Content-Transfer-Encoding: 7bit','\r\n','','\r\n',
      Msg,
      '\r\n','------=_NextPart_000_0000_01CA4B3F.8C263EE0--'
      ) as char);
  RETURN tmpMsg;
END ;