Pharmacology - N-propanol & N-butanol

[Piglet]

Has anyone else tried N-propanol (not IPA!) and N-butanol? They are, respectivly, 4 & 9 times stronger than ethanol. No hangover after being totally blitzed. Shorter T1/2 obviously, but it saves the liver...

[b3ni]

SWIMs chemistry tutor has always told SWIM that Propan-1-ol is toxic.

[shivakiva2112]

OH well, it doesn't save the liver as the metabolic routes are the same. I couldn't find any information that indicates that either propanol or butanol are appreciably more toxic than EtOH.

b3ni, it would make sense that SWIY tutor would say such things, propanol, butanol, and ethanol are all fairly toxic, but considering how many millions of doses of ethanol are consumed on a daily basis and considering that the two longer chain alcohols aren't much more toxic, I think it's safe to assume that propanol and butanol aren't gonna kill anybody in low doses.

OP I take it SWIY has already tried this by the wording in the OP? Interesting experiment.

[Piglet]

Propan-2-ol is toxic since the body oxidises it to acetone, propan-1-ol goes the same way as ethanol but being stronger, you use less...

[shivakiva2112]

Would the propan-1-ol metabolites be propylaldehyde (propaldehyde?) and propanoic acid? Oh, organic chemistry memories, where art thou?

Sounds as if someone who isn't piglet has been imbibing in their lab...tsk, tsk... Do tell...

Any ideas about the mechanism of action? I know EtOH's mech. still isn't fully elucidated, but is something like prolonging or increasing the frequency of chloride channel opening subsequent to GABA binding to GABA A I think, I always get the details of benzo, barbiturate, and EtOH psychopharmacology mixed up.

[hobgoblin]

Originally Posted by shivakiva2112

Would the propan-1-ol metabolites be propylaldehyde (propaldehyde?) and propanoic acid? Oh, organic chemistry memories, where art thou?

Yes the metabolites would be propanal (propylaldehyde's IUPAC name) and propanoic acid, as propan-1-ol is a primary alcohol it oxidises to a aldehyde and then to a carboxylic acid.