Talk:Indole

Reactions

I will hold off on adding more to this page until Cacycle and K have finished adding stuff, I don't want to find myself duplicating others' work, and I have to give three exams in the next week anyway! Thanks for the excellent additions, Walkerma 03:54, 5 August 2005 (UTC)

I'm done for now. Over the next few weeks, I plan to add ===Oxidation of indole=== and ===Reduction of indole=== sections. My understanding of these two subjects is sketchy and I need to do some reading. Therefore, if you (or anyone else) would like to start these sections before me, please do so. ~K 03:02, 9 August 2005 (UTC)

Six-membered vs. six-member ring

An anonymous user has twice edited the text "six-membered ring" (and five-membered ring) to lose the "ed" at the end. I reverted this the first time, pointing out that the ed ending is usual in chem texts (I checked in a couple of books to confirm this). Can I get some consensus from other chemists before I revert this again? Please give your preference below, thanks. Walkerma 20:24, 28 December 2005 (UTC)

As a practicing organic chemist, I can attest that "membered" is by far the more commonly used word in this situation. Edgar181 01:11, 29 December 2005 (UTC)

Yes, rings are membered. ~K 02:29, 29 December 2005 (UTC)

This is a common grammatical error: for the time being, "member" is a noun and "membered" is the corresponding adjective. Hence six-membered ring. Physchim62 (talk) 18:05, 29 December 2005 (UTC)

Metabolic waste product

My Norwegian encyclopedia states among other things about indole that it "..is also a physiological product, in that it arises during decomposition and during digestion in the gastrointestinal tract. It is therefore also to be found in human ecscrement". Should this not be mentioned in the article? __meco 14:37, 20 April 2006 (UTC)

Thanks for that, it's a useful snippet to make this a little more interesting for the general reader. I did a quick Google search and found the top hit was the Wikipedia page on feces! I'll add a short section. Thanks, Walkerma 14:43, 20 April 2006 (UTC)

What that same work also states is that the fecal odour is due to indole being contaminated by skatole. Could this be correct? __meco 14:54, 20 April 2006 (UTC)

I think it's almost certainly true. The fecal odour is made up of lots of things, including thiols as well, indole is just once component. I think we probably need a separate section in this article on indole and its derivatives in nature, that could go into more detail. I was trying to keep my edit VERY succinct, because the lead section is already very long. Walkerma 15:01, 20 April 2006 (UTC)

The article leads me to believe that Indole is present only in human feces. Is it present in the feces of other living things too?? -- Kevin ^(TALK)_(MUSIC) 01:44, 18 March 2007 (UTC)

The article does not say only human feces, it does not exclude othe species! You're right, though, it would be nice to find out, but I don't have access to those books right now. Walkerma 02:04, 18 March 2007 (UTC)

Indole in Pasteurella multocida

How does Pasteurella multocida produce indole?

Redirect?

Someone please redirect indoyl here. I don't know how. 129.98.212.55 16:06, 17 January 2007 (UTC)

You mean indolyl. Cacycle 03:17, 18 March 2007 (UTC)

Googling the two terms yields 66,000 hits for indoyl and 1.2 million for indolyl. From that I would surmise that both are valid names. __meco 07:42, 18 March 2007 (UTC)

They are both terms for the indole moeity as part of the structure of the molecule. So, the redirect is right. --Rifleman 82 08:28, 18 March 2007 (UTC)

intramolecular substitution

It says that the ring must be substituted on N1, C2 and C3 before the benzene ring can be substituted. Is this really true for say, tryptophan, if say the C2 site is already occupied? Acylation of the benzene ring (by tryptophan's on COOH group, activated maybe by thionyl chloride) would seem to be the only process giving unstrained, aromatic product. John Riemann Soong (talk) 15:09, 19 January 2010 (UTC)

Component of body odor

It seems that "indole, a chemical that is responsible for 30 percent of the "volatile headspace," or scent, of human sweat. ", and that it is used by mosquitoes to zero in on a human target. Source: Ars technica quoting a Nature paper. —Preceding unsigned comment added by 81.194.32.45 (talk) 12:54, 5 February 2010 (UTC)

Catalyst

What catalyst is used in the synthesis of indole from phenylamine and ethane-1,2-diol? Jamez Z23 (talk) 14:19, 16 August 2015 (UTC)

Typically for alkylation of amines by alcohols, industrial routes employ certain forms of alumina. The catalyst helps alkylate the aniline and would also help cyclize the hydroxyethylamine. Both reactions release water. --Smokefoot (talk) 15:56, 16 August 2015 (UTC)

Literature for this example also has dozens of metal-catalyst options, including copper, silver, zirconium, ruthenium, tin. DMacks (talk) 16:04, 16 August 2015 (UTC)

I would recommend adding a couple of examples of catalysts. Jamez Z23 (talk) 22:36, 17 August 2015 (UTC)

At very low concentrations, however, it has a flowery smell,

Mistake!: Indole has only an unpleasant super strong feces smell. HOWEVER ! it is used in perfume industry as a "contrast agent" It means that a fine fair blossom smell will be more pregnant for the some final smell the perfume maker will use less flower aromatic oil (very expensive) It is a perfumers trick. Dr. Gheorghe Plesea Romania — Preceding unsigned comment added by 82.208.135.53 (talk) 13:29, 14 May 2016 (UTC)

Melatonin not a neurotransmitter

Although very closely related to serotonin in structure and synthesis, melatonin is not a neurotransmitter. It's synthesized in the pineal gland (and other tissues) and signals distant cells after being released into circulatrion, not into a synaptic cleft. It's a small point, but I thought it best to edit the article for accuracy. I added a citation for its role as a hormone (the paper calls it a neurotransmitter-like hormone), but I think it's clunky where it is, mid-sentence. If it's kept as a cit, it doesn't support the main point of the sentence, so that's really where it has to be. I don't think a cit should be required for this point, but my experience has been that without a cit, the most trivial edits often get reverted. I'll add the cite here, in case it gets removed from the article (for readability) but some future editor doubts the statement: Dcs002 (talk) 19:07, 11 June 2022 (UTC)

References

Hydrogenation

the last reaction is a hydrogenation of an indolenine, not an indole 2A02:908:D42:8E40:55C:313:1463:40EC (talk) 04:26, 9 January 2023 (UTC)