Talk:Piperidine

message: There is no mention that piperidine is a heterocyclic compound. I fix it.--84.163.86.13 00:03, 10 October 2006 (UTC)
thread_title:  Heterocyclic 

message: No, piperidine is not the same as piperidine compounds. Some editors are obsessed with the following idea:
Piperidine is a structural component of fireant venom.
Piperidine is a structural component of neuroleptics.
ergo: Neuroleptics cause symptoms like fireant venom
etc. See also article on phenothiazine:
Phenothiazine is an insecticide
Phenothiazine compounds are neuroleptics
ergo: Neuroleptics are bugspray and cause anticholinesterase toxicity.
etc. etc.
I have added a few more examples of piperidine toxic compounds to add to this kind of logic.
You can check it out.
And: Please don't revert edits without a comment. This is not a looney bin.
70.137.181.232 (talk) 09:24, 21 July 2008 (UTC)
thread_title: Piperidine compounds

message: I have just reinstated my recent edits that had been reverted (diff. Here are my detailed reasons:
* Quinine is a bad example, it contains quinuclidine, not piperidine
* The whole section about ditran has nothing to do with this article
* The rest of that section was written in a very unencyclopedic tone and/or had not much to do with piperidine itself
* The neuroleptics are not synthesized from piperidine and were clearly in the wrong section
* The piperidine structure is so common that it does not make sense to randomly list compounds that have it in their structure
Cacycle (talk) 02:50, 25 July 2008 (UTC)
replies: text: The only compound which contains piperidine is 1 - piperidine. If you misspoke, and meant "compounds containing the piperidine substructure", a search of PubChem shows 1249853 hits. So, either way doesn't work. --Rifleman 82 (talk) 04:24, 29 July 2008 (UTC)
replies: text: That does'nt however mean that there is 1249853 piperidine compounds however. 65.28.227.116 (talk) 04:33, 30 July 2008 (UTC)
replies: text: Pray tell, what does this 1249853 number represent then, in your opinion? --Rifleman 82 (talk) 05:39, 30 July 2008 (UTC)
thread_title:  Disgressions 

message: If piperidine is used as a precursor to commerically significant compounds, then this application merits mention, IMHO. The mere presence of the piperidine-skeleton is more questionable.  Otherwise the benzene article would or could indicate it is "in" thousands of compounds, which would be silly.  It is very possible that piperidine is a common pharmacophore, a concept that could be explained.  In WE-chem, we are constantly dealing with all sorts of editors, often from advocates for some political cause or conspiracy, who cannot suppress an urge to fill these pages with tangential information (e.g. that Socrates drank a tea containing a molecule related to piperidine!), the main virtue of such information being that it is merely true, vs pertinent and notable.--Smokefoot (talk) 17:23, 28 July 2008 (UTC)
replies: text: I think there is always some room in the articles about functional groups, heterocycles, and common ring systems, to discuss the properties that are general to the compounds having a given substructure, as well as some specific examples. However, the discussion needs to be focused and avoid too many random-looking examples, or even worse, a selection of not-so-random examples that gives wrong ideas to the reader. One of the statements that was removed during the edit war was that "Many pharmaceutical drugs contain a piperidine ring because the group tends to impart favorable pharmacokinetic properties such as water solubility and bioavailability. Most piperidines induce the liver enzyme CYP2D6, resulting in faster metabolism, such as in many beta-blockers and antiarrhythmics". This kind of information, if true, seems highly relevant, but can we have a reference, please? I did a quick search to see if I could find an article about piperidine as a building block in drug molecules, but I couldn't find it. --Itub (talk) 17:46, 28 July 2008 (UTC)
replies: text:  That cited part on pharmacokinetics is utter nonsense. That might actually be true for that unnamed class of compounds, but it is clearly not a general feature of the piperidine moiety. You could equally well attribute this to methylene groups. Cacycle (talk) 00:52, 29 July 2008 (UTC)

text: The sentence, as it is there now, suggests that the compound 'contains' piperidine ("Piperidine is found in the following drugs"), which is untrue (and that was true quite a couple of times in the edits).  It would be better to say that it is a structural component of the drug.  --Dirk Beetstra T C 14:51, 28 July 2008 (UTC)
replies: text: Perfect.--Stone (talk) 15:54, 30 July 2008 (UTC)
replies: text: Not really: see Beetstra's and Cacycle's comments.  Piperidine is NOT found in ANY drug. The presence of the piperidine skeleton is of no specific pharmacological significance: six membered hydrocarbons are routine as are amines, so inevitably the piperidine skeleton is pervasive.--Smokefoot (talk) 17:36, 30 July 2008 (UTC)
thread_title: Dispute on piperidine

message: Yes, the presence of the piperidine skeleton is of some pharmacological significance, however not in the way how some editors imagine (giving pharmaceuticals the properties of ant venom). The significance is that frequently a functional amino group is embedded into the semi-rigid conformation of the piperidine skeleton, to arrive at derivatives with altered pharmacological profile (keeping the distances to other functional groups constant): The alteration may stem from the semi-rigid conformation, or from the increased lipid solubility due to the 5-C chain, or from details in receptor binding affinity by the bulky ring addition, or from steric hindrance of metabolic attacks, to give examples. Or from a combination of the above and other factors.
Substance examples:
Phencyclidine vs. open chain analogs
Phenmetrazine vs. Methamphetamine
similar for Phendimetrazine
oooh, made a mistake there these have a morpholine ring. The corresponding piperidine analog is not commercialized, because it has an extremely long duration of action.
Thioridazine vs open chain neuroleptic analogs (increased central activity)
N-ethyl-Piperidil-3-benzilate vs. Benactyzine (increased central activity and duration of action)
Pethidine and derivatives vs. open chain analogs
You are however right, that no common simple property of the piperidine compounds is inherited from the parent compound, as naive editors assume. So there is a common theme of alterations which may be achieved by this embedding; but it has no single, simple and consistent explanation, more like a mix of the above mentioned possible mechanisms plus others, like change of metabolic pathways due to the steric hindrance of certain metabolic attacks in the open chain analog etc. and things become more complex if we take the possibility of active or toxic metabolites into account. Embedding the active amino group is simply one of the building blocks in drug design and individually leads itself to new SARs to play with. I would not call this "no significance".
:I've read a bit of medicinal chemistry myself as well, but the texts I saw generally talked in more general "rules of thumb". For example, if to increase hydrophobicity, add more carbons, as you say. To reduce flexibility, add a ring. If you need a hydrogen bond donor, add an amine or alcohol. If you need to protect something from oxidation, block it with something (maybe fluorine) or see if you can remove it. To increase solubility... and so on. But I've never seen a rule that says "add piperidine", although to some extent it may stem from the more general rules because it is a ring, it is an amine, and it has five methylenes. Of course, the books include specific case studies and some may include piperidine. But the ones I've seen don't focus the discussion on the piperidine itself. Is there really enough we can generalize? What references can you cite about it? Cacycle made a good point in comparing it with methylene: a vague statement such as "piperidine can improve pharmacokinetics" can be true of nearly any functional group found in a drug. Most groups are added either to improve pharmacokinetics or pharmacodynamics, but is this specific group notable enough to mention here? To give an example, I would say that trifluoromethyl is more notable because I've seen reviews focusing specifically on the use of trifluoromethyl in medicinal chemistry. I haven't seen anything like that for piperidine. If there is something, it would be a great source for this article. --Itub (talk) 05:58, 1 August 2008 (UTC)
thread_title: In reply: Piperidine, pharmacological significance

message: So, kinnings, I am running out of patience. Here my take:
The inclusion of natural "piperidine alkaloids", like solenopsin, anabasin, coniine, conhydrine is fully justified, as in the usual alkaloid classification in literature historically such distinction is being made, and such classification is being used. The addition of "unencyclopedic tangential" information, like that Socrates was executed by coniine, or anabasine is a nicotine like alkaloid, used as an insecticide, doesn't harm and adds a little to historical and everyday life context for the lay reader. We really don't need to encrypt this article to be readable or at least partially understandable only for chemists. I will be glad to point to scientific teaching materials (The chemistry of the plant alkaloids), which gladly include such slightly tangential information, historical information and case reports. We don't need to be more catholic than the pope here.
Regarding examples of the occurence of the piperidine structural motif in pharmaceuticals: Yes, give a few examples. Why not also include the JB-329 piperidilbenzilates, even if somebody, somewhere may wonder how everything is apparently connected to everything in the universe. No need to censor that. Of course these really include the "structural motif", not piperidine. And the structural motif is present in 1 Mio (!) other chemicals, so we have to focus on a few more commonly used pharmaceuticals there. My focus on toxic examples was "all true". but biased by selection, in an attempt of a "reductio ad absurdum".
Now kinnings: A serious word to Dr Carebear and another anon editor:
Chemistry doesn't work like cooking chicken soup.
In chicken soup you cook a soup on chicken, then it is a chicken soup and tastes like chicken. If you add salt it becomes more salty, if you add pepper it becomes more peppery. It is a mixture of the components. (Chicken, salt, pepper)
In chemistry this is not true for chemical compounds and chemical components. Ordinary salt is Sodium chloride, a compound of the flammable metal Sodium and the toxic Chlorine gas. But it retains none of these properties.
Anon: you said "containing piperidine" and "including the piperidine structure" would be the same, and I am mincing words. No I am not mincing words, but you need a chemistry class, as seen by the example of ordinary salt, which is not chlorine poison gas any more. I told you to discuss, others have told you the same. You are a candidate for blocking for vandalism, see your talk page.
Carebear: I have explained (for Phenothiazine) that in friendly words on your talk page, and you are still reversing edits without comment and discussion. This is mental. Stop it. Your neuroleptic bugspray theory is crap, for the same reason, why table salt is not poison gas, in the same logic.
Discuss further edits. This has been explained to you since a year, by reasonable people, on your talk page. If you don't listen then it is either vandalism, or lack of intellectual capacity, or hooliganism. I would propose you abstain from editing chemical articles.
70.137.164.136 (talk) 07:36, 31 July 2008 (UTC)
thread_title: Article, remarks

message: Piperidine (itself, not piperine) has been obtained from pepper (Spaeth and Englaender, Ber.1935,68, 2218; cf. Pictet and Pictet, Helv. Chim. Acta, 1927, 10, 593),from Psilocaulon absimile N.E.Br (Aizoaceae) in which it occurs to the extent of 4.5% (Rimington, S. Afr. J. Sci, 1934, 31, 184), and in Petrosimonia monandra (Juraschewski and Stepanov, J. Gen. Chem., U.R.S.S., 1939, 9, 1687)
(from ref below)
:I think this is worth including in the article. --Itub (talk) 16:38, 31 July 2008 (UTC)
thread_title: Piperidine, natural occurence

message: The Lobeline group belongs also to the Piperidine alkaloids.
(ref Book: The Plant Alkaloids, Thomas Anderson Henry (Formerly Director Wellcome Chemical Research Laboratories and Superintendent of Laboratories, the Imperial Institute London), 4th ed. 1949, The Blakiston Company)
This book is also a rich source of "unencyclopedic information" about the effects on frogs, extraction, plant synthesis pathways, commercial and historical importance. And it is written in "unencyclopedic tone". It is instead cacyclopedic.
Download from this site (very interesting website for WP freaks)
http://www.sciencemadness.org/library/index.html
70.137.164.136 (talk) 08:40, 31 July 2008 (UTC)
thread_title: Piperidine alkaloids

message: And cacycle may please explain, what he means by "unencyclopedic tone". More catholic than the pope?
I still believe that many things in scientific articles can be explained in plain english, for plain people. I know that we have to deprogram fresh academics from their academic babble until they finally notice that they are not writing on their damn thesis any more. Keep it educational for plain people too. e.g. "Scientific American" is also readable for normal educated people, WP should learn from that. (or if that is too prole for you, think you write for your CEO)
70.137.164.136 (talk) 09:03, 31 July 2008 (UTC)
thread_title: unencyclopedic?

message: It is of nobody's interest that the article is protected indefinitely. Can we come up with a consensus version which most, if not all of us can agree with? 
I will start with 
(Adapted from article text.) I left the second sentence out because it is IMHO patently false.
--Rifleman 82 (talk) 07:03, 1 August 2008 (UTC)
replies: text: Which sentence are you talking about? Hundreds of drugs do include a piperidine moiety, although as 70.(and basically everyone else) said above, "piperidine is not the same as piperidine compounds". I wouldn't like to see this article without any mention of "piperidine-containing" drugs; I'd like to see it free of fallacious arguments that have been pushed before on other articles (such as phenothiazine). Fvasconcellos (t·c) 14:40, 1 August 2008 (UTC)

text: Calling patently false a statement that can be corrected by adding two words is a bit too strong IMO. It's just an imprecision. The names of heterocycles are also commonly used as if they were functional groups. For example, the article on pyridine in Encyclopaedia Britannica begins with the words:  "any of a class of organic compounds of the aromatic heterocyclic series characterized by a six-membered ring structure composed of five carbon atoms and one nitrogen atom. The simplest member of the pyridine family is pyridine itself, a compound with molecular formula C5H5N."  Sometimes it is obvious from the context whether one is talking about the specific compound or the family, and sometimes it is a good idea to be explicit. --Itub (talk) 10:03, 4 August 2008 (UTC)
thread_title:  Consensus version 

message: The mention of Socrates in this article has been the subject of much ridicule, and now it has been deleted. Yet I think such a mention was useful. The article still mentions coniine and poison hemlock, but now many readers will wonder what the hell those things are. A good principle for making technical writing comprehensible is to try to connect the things that readers may not know yet with those that they are likely to know. I think readers are more likely to know about Socrates and his death than to remember the name of the plant that was used to kill him. Therefore adding a short phrase about Socrates makes the article more likely to grab the reader's attention. I agree that we may be trying to be more Catholic than the Pope here in avoiding interesting "trivia". I've seen countless perfectly serious chemistry textbooks, review articles, and research papers that include this type of "trivia" to help put things into perspective, or just to make the writing more interesting. --Itub (talk) 11:44, 4 August 2008 (UTC)
replies: text: To show how many book authors have thought it was worth mentioning Socrates in the context of piperidine and piperidine alkaloids in particular, see . --Itub (talk) 11:49, 4 August 2008 (UTC)
replies: text: Agree - I was one of the ridiculers, but I concede the point.  I did not think that any C-substituted piperidines should be developed much less mentioned as "see also"'s (the piperidinyl tetrasulfide is made from piperidine, so it is actually a derivative operationally).  But given that many cmpds containing the piperidine skeleton are mentioned, it may be useful to mention that one such species was in Socrates tea. This derivtive vs skeleton angle has recently been developed for ethanolamine and ethylenediamine by another editor.  It's not my preference (cup of tea, shall we say) for all the reasons we wrangled with, but the info is there and perhaps welcome.--Smokefoot (talk) 12:24, 4 August 2008 (UTC)
thread_title:  Why mentioning Socrates can be a good idea 

message: on this page it says that Piperidine smells like pepper but my own experience and everyone i have discussed it with has described the smell as that of semen. when i tried to include this interesting factoid into the article my edit has been reverted and called vandalism. wtf?  —Preceding unsigned comment added by 203.217.76.219 (talk) 11:39, 18 October 2010 (UTC)
replies: text: Correct! Some open chained polyamines have a similar odor (triethylenetetramine (TETA) e.g.). I guess the aliphatic amine forms a H-bridged ring so it fits the same odor receptor as piperidine or pyrrolidine (smells similar to piperidine). --FK1954 (talk) 10:40, 13 July 2016 (UTC)
replies: text: I have to add that piperidine does NOT smell like pepper. Not a bit. And to find a similarity to the odor of ammonia you need a lot of fantasy... --FK1954 (talk) 10:44, 13 July 2016 (UTC)
thread_title:  odor 

message: Hello fellow Wikipedians,
I have just modified  on Piperidine. Please take a moment to review my edit. If you have any questions, or need the bot to ignore the links, or the page altogether, please visit this simple FaQ for additional information. I made the following changes:
*Added archive https://web.archive.org/web/20080227224025/http://www.incb.org/pdf/e/list/red.pdf to http://www.incb.org/pdf/e/list/red.pdf
When you have finished reviewing my changes, please set the checked parameter below to true or failed to let others know (documentation at ).
Cheers.—InternetArchiveBot (Report bug) 22:56, 8 September 2016 (UTC)
thread_title:  External links modified