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TOXICITY OF ACETYLENIC ALCOHOLS TO THE FATHEAD MINNOW, PIMEPHALES PROMELAS: NARCOSIS AND PROELECTROPHILE ACTIVATION
Citation:
Veith, G., R. Lipnick, AND C. Russom. TOXICITY OF ACETYLENIC ALCOHOLS TO THE FATHEAD MINNOW, PIMEPHALES PROMELAS: NARCOSIS AND PROELECTROPHILE ACTIVATION. U.S. Environmental Protection Agency, Washington, D.C., EPA/600/J-89/084 (NTIS PB90103672).
Description:
The 96-h LC50 values for 16 acetylenic alcohols in the fathead minnow (Pimephales promelas) were determined using continuous-flow diluters. The measured LC50 values for seven tertiary propargylic alcohols agreed closely with the QSAR predictions based upon data for other organic non-electrolytes acting by a narcosis mechanism.Four primary and four secondary propargylic alcohols were 7 to 4600 times more toxic than the respective narcotic toxicity estimated by QSAR. Metabolic activation to electrophilic a,B-unsaturated propargylic aldehydes or ketones is proposed to account for the increased toxicity. 3-Butyn-1-ol and 4-pentyn-2-ol, primary and secondary homopropargylic alcohols, were 320 and 160, respectively, times more toxic than predicted. In this case an activation step involving biotransformation to an allenic electrophile intermediate was proposed.