The toxicity of acetylenic alcohols to the fathead minnow, Pimephales promelas: narcosis and proelectrophile activation.

Abstract

1. 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. 2. 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 alpha,beta-unsaturated propargylic aldehydes or ketones is proposed to account for the increased toxicity. 3. 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.

• Authors: G D Veith, R L Lipnick, C L Russom
• Journal: Xenobiotica; the fate of foreign compounds in biological systems (Xenobiotica) Vol. 19 Issue 5 Pg. 555-65 (May 1989) ISSN: 0049-8254 [Print] England
• PMID: 2750212 (Publication Type: Journal Article)

Chemical References

• Fatty Alcohols
• Narcotics

Topics

• Animals
• Biotransformation
• Chemical Phenomena
• Chemistry
• Cyprinidae (metabolism)
• Fatty Alcohols (pharmacokinetics, toxicity)
• Narcotics
• Structure-Activity Relationship