Talk:Alkaloid

message: There's no reason to include a picture of a decapitated  and deformed animal in this article.  The image serves no educational or informative value for the subject at hand.  The article already clearly explains that the substance in question is known to cause deformities.  A reader does not gain any better education on the topic by being subjected to the image.  Its inclusion here serves NO purpose, other than to create shock.  — Preceding unsigned comment added by 2600:4040:B078:6C00:7CC0:956C:48D:58E4 (talk) 10:56, 5 July 2023 (UTC)
thread_title: Gruesome content provides no value

message: Why is this substance in two groups? __meco 01:34, 15 July 2006 (UTC)
replies: text: Because it has both a pyridine and a pyrrolidene group. Look at the molecule. —Keenan Pepper 02:13, 15 July 2006 (UTC)
replies: text: I'm not chemically conversant. I understand however that it's correct the way it currently reads. __meco 18:48, 15 July 2006 (UTC)
thread_title: Nicotine

message: I added an example and citation of an organism that uses alkaloids for protection: Utetheisa ornatrix to “The Biological Role” section. 
Kzyoung (talk) 20:18, 14 November 2013 (UTC)
thread_title: edits

message: The  box looks awful at the top. Can we please not put it there? —Keenan Pepper 09:52, 4 August 2006 (UTC)
replies: text: Moved back to where it belongs - bottom of article. __meco 11:32, 4 August 2006 (UTC)
thread_title:  Layout 

message: it does not appear naturally, so why is it included here? if noone objects, I'll remove it. -- Rwst 08:07, 7 August 2006 (UTC)
replies: text: I'm certainly no authority, however, if LSD is removed on the grounds of it being synthetic, then others must also be removed, for instance MDMA. __meco 23:08, 7 August 2006 (UTC)
thread_title:  LSD an alkaloid? 

message: The article on cocaine has "The name comes from the name of the coca plant plus the alkaloid suffix -ine". Can this suffix use be confirmed and documented here? TIA
Jerome Potts 03:35, 21 August 2006 (UTC)
thread_title:  the suffix "ine" 

message: I'm adding Category: Chemistry to this article, for obvious reasons. Mihovil 18:42, 30 August 2006 (UTC)
replies: text: There's no reason to. It's already in :Category:Chemistry via :Category:Alkaloids → :Category:Organic compounds → :Category:Organic chemistry → :Category:Chemistry. If you really want to put it in another category, why not something more specific, like :Category:Amines? —Keenan Pepper 04:42, 31 August 2006 (UTC)
thread_title:  Categories 

message: What about pyrrolizidine alkaloids? Does this category merit a mention in the list of 
alkaloid groups? They are of interest for their hepatotoxicity and have already been mentioned in a number of other articles- for example, borage, comfrey, fuki, Roger Adams. Krnntp 17:20, 1 September 2006 (UTC)
replies: text: It certainly does. As do the quinolizidines (e.g. the amphibian-derived homopumiliotoxins)Pikiwedian 08:39, 20 December 2006 (UTC)
thread_title:  Pyrrolizidine 

message: I am a novice on this area but would like someone to direct me what to analyse for (not myself but competent biochemists) if I would like to look at the metabolites of an alkaloid, mesembrine.  If I want to see if it was taken up in animal metabolic pathways when consumed, what would I look for.  or if I need to analyse for residues.  Could anyone give me clues? PstrydomPstrydom 13:59, 19 October 2006 (UTC)
thread_title:  Alkaloid metabolic pathways 

message: The classification section could use a bit of cleanup. It is not clear that the examples given are not exhaustive. Also, what are the criteria for choosing specific compounds to list as examples? If it is by their importance, I would suggest adding Synephrine. With the FDA's restrictions on Ephedrine, Synephrine is becoming a popular alternative despite the fact that it may be just as dangerous.  70.100.3.62 03:20, 2 November 2006 (UTC)
thread_title:  Examples in classification section 

message: If anyone has time, the  would really benefit from your expertise.  Thanks! :) Willow 19:07, 27 January 2007 (UTC)
thread_title: Template help

message: Currently the article opens as follows:
:An alkaloid, strictly speaking, is a naturally-occurring amine produced by a plant,[1] but amines produced by animals and fungi are also called alkaloids. (...) The name derives from the word alkaline; originally, the term was used to describe any nitrogen-containing base.
The wording of the first sentence seems to suggest that the "strict" definition (must be found in plants) is the most correct somehow, but the third sentence suggests that this interpretation was predated by a much broader one (any nitrogen-containing base). My feeling is that we should go by usage and not by someone's conservative interpretation of what should "strictly" be called an alkaloid. If "alkaloid" is widely used in scientific literature to describe nitrogen-containing bases that have been found in animals or fungi but not (or not yet) in plants, then I think those chemicals are alkaloids. This usage might be considered mildly controversial by some, which is worth noting, but I don't think we're justified in implying it's not "strictly" correct.
from Wiktionary:alkaloid:
:Any of many organic heterocyclic bases, that occur in nature and often have medicinal properties.
The "heterocyclic" qualifier is interesting. Phenethylamine alkaloids like mescaline have only carbons in their rings, and I'd guess there are many other example non-heterocyclic alkaloids. Are there alkaloids with no rings at all? It seems like most have some type of ring structure. --Eloil 09:51, 1 April 2007 (UTC)
replies: text: Yes, please try to clarify. I read this article to try and understand what an alkaloid is, but the definition is WAY to loose to be useful. By the current definition, why wouldn't an amino acid be called an alkaloid? ike9898 (talk) 22:36, 21 February 2008 (UTC)

text: there is a whole class of alkaloids called protoalkaloids that contains nitrogen atom but not in a heterocyclic ring--7amada'sback:) (talk) 17:59, 5 January 2009 (UTC)
thread_title:  alkaloid definition 

message: Mesembrine is Alkaloid which can be added.  —Preceding unsigned comment added by 196.209.60.35 (talk) 17:36, 7 June 2008 (UTC)
thread_title:  Mesembrine 

message: I think the classification in the article needs some revising. Namely, the quaternary ammonium salts are listed as if they were part of steroids... and they aren't:) In either way they're not terpenoids so they would better fit under separate entry somewhere below.
And also the Indolic alkaloids. Reserpine and yohimbine have no more relation to beta-carbolines than to simple tryptamines. They'd better be listed as a separate subgroup amongst other indoles, possibly "Yohimbans". Mytraginine has also much similarity to that particular structure.
Vinca alkaloids are too indolic, so why not place them as a sub to indoles? Same about Strychnine and Ibogaine, they deserve a mention as structurally unrelated Indoles.
And also, capsaicin is not an alkaloid at all, it's a vanilloid, not an amine (it's rather an amide) and thus not basic.
Correct me if I'm wrong.
Angsaar (talk) 20:26, 18 July 2008 (UTC)
thread_title:  Classificating list 

message: Fixed that, now saying it is a "steroid alkaloid", containing both a nitrogen, and a steroid skeleton as components of the structure. Linking them to "steroid" is misleading.
70.137.149.127 (talk) 11:13, 5 August 2008 (UTC)
thread_title: Solanine

message: Regardless of the synthesis pathway, these three differ so much from the structure of the other isoquinoline alkaloids, that a separate category is justified.
70.137.149.127 (talk) 12:26, 5 August 2008 (UTC)
thread_title: Phenanthrene alkaloids

message: Acoording to this ref
http://www.pnas.org/content/103/36/13315.full
capsaicin is an alkaloid, synthesized from vanillylamine by capsaicin synthase. There you are. No OR.
70.137.143.23 (talk) 18:40, 11 September 2008 (UTC)
replies: text:  Vanillylamine is not a close analog of capsaicin, it is a precursor. An amine as a precursor does not make any biosynthetical product an alkaloid. Cacycle (talk) 00:50, 12 September 2008 (UTC)
thread_title: Capsaicin is an alkaloid: YES, Sir

message: According to this review article
But see also the book sources above. (They are not hippie books, how to grow your own etc. or popular science)
Cacycle: What you are doing here is WP:Synth from the IUPHARM/IUPAC definition, which is rather mushy. (*are NORMALLY not regarded..*)
Now don't tell me all these sources are wrong: 2 teaching books, one peer reviewed primary source, one peer reviewed review article.
70.137.143.23 (talk) 19:14, 11 September 2008 (UTC)
replies: text:  You (or that outdated source) might have confused hydrolysis with salt formation. Piperine does not form salts (at least under normal conditions). Also, randomly citing books on alkaloids that merely mention certain compounds is not convincing. Find current and explicit definitions. Cacycle (talk) 00:58, 12 September 2008 (UTC)

text: I think that numeric data may shed some light on this question. The pKa of piperine is reported to be 1.98 (see the ref. I added to the article). With that pKa, it should be possible to protonate it with a strong acid and form a salt. Piperine turned out to be more basic than caffeine! --Itub (talk) 12:33, 12 September 2008 (UTC)
thread_title: Piperine is an alkaloid: Yes, Sir

message: I have added some Literary references to alkaloids as seen in some famous novels. I thought this would broaden this interesting topic. I hope no one has a problem with it being included. Please add more to it. Proquence (talk) 18:31, 22 November 2008 (UTC)
thread_title:  Cultural references 

message: just raised the importance rating from mid to top.personally I don't know how anybody see this topic as mid importance!!!
alkaloids are a major class in both pharmaceutical and phytochemistry that include very important drugs like morphine,quinidine and many others in a very long and ever expanding list.
I am know jammed with exams so as soon as they are over I'll work on improving it--7amada'sback:) (talk) 17:59, 5 January 2009 (UTC)
thread_title: Importance

message: Morphine etc. is sometimes grouped with the benzylisoquinoline alkaloids because of its natural synthesis pathway. Morphine, codeine, thebaine, oripavine are however so different in structure from the other opium alkaloids, that they are usually grouped together as phenanthrene alkaloids.
They are also pharmacologically different from the others (narcotine, papaverine...) in that they are opioid agonists, while the others are not. Looking at the structure, they are more related to each other than to narcotine etc.
See entry "phenanthrene alkaloids" in the list
70.137.172.47 (talk) 05:02, 21 September 2009 (UTC)
replies: text: I find this distinction somewhat problematic. Clearly, the naturally occurring opium alkaloids are closely related by biosynthetic origin being all derived from L-tyrosine via L-DOPA and tyramine. Since even very slight variation in structure, eg. between isomers, can have drastic effects on biological activity, employing a distinguishing nomenclature based on receptor-binding activity is imprecise. There are several articles that group morphine with the benzylisoquinolines (see eg. here), as does the Morphine entry. I think one way to address this could be to tally up usage of benzylisoquinoline alkaloids vs phenanthrene alkaloids in the context of morphine and related compounds, and state the caveat that chemists, pharmacologists, and biochemists may use different nomenclatures. Otherwise I'd feel inclined to place morphine back (supported by the above reference). Many thanks! Malljaja (talk) 18:12, 21 September 2009 (UTC)

text: There needs to be a good and current reference for this. I'm not a chemist or pharmacologist, so I'm not privy to their preferred grouping. Ergo I have to take your word for it at this point. However, the distinction based on biological activity, while convenient, is somewhat questionable. By analogy, there are, e.g., isoflavones that interact with the estrogen receptor, but they are not steroidal compounds like estrogen, so no one with a biochemical/chemical background would lump the estrogenic isoflavones together with steroidal estrogens. So my feeling is that the phenanthrene grouping for morphine and structurally similar quinolines is outdated, since the common biosynthetic origin of all of the benzylisoquinolines is now well established. It is also seems slightly inaccurate in that phenanthrene is a tricyclic aromatic compound, whereas morphine is a tetracyclic one with only one aromatic ring. It would be advantageous to find a recent reference that discusses this, but it'll probably take some digging. Malljaja (talk) 20:35, 22 September 2009 (UTC)

text: I by no means suggest that you have invented the classification of morphine as phenanthrene alkaloids. You misunderstood me—I am aware of this classification in some parts of the literature. What I am advocating is that the prevailing classification in the literature is stated with a proper reference (citation from a book or peer-reviewed publication). The reference you gave is a start, albeit the wording in it is rather woolly. The authors refer to the opium alkaloids as phenanthrene alkaloids. Though they also appear to state that the opium alkaloids are grouped in the benzylisoquinolines because of their biogenic origin, but this is unclear (they say "opium alkaloids are included in this group", and from the preceding sentence it appears that by "group" they mean the benzylisoquinolines). So this is not very useful, as it does not establish a clear hierarchy in nomenclature. Again, phenanthrene alkaloids strikes me as an outdated classification, based on structure and biological activity only, but having said that, I am well aware that this would also need a proper ref. Hence my earlier suggestion to scan the literature for the most common classification of the opium-type and other benzylisoquinoline alkaloids. Malljaja (talk) 22:06, 23 September 2009 (UTC)
thread_title: Morphine etc., isoquinoline alkaloids

message: Since when bufotenine is a poison? Tryptamines (talk) 09:34, 29 March 2012 (UTC)
replies: text: It's found in the secretion of toads as well as a constituent in some plants, most likely as a defensive compound, ergo one that negatively affects those that try to eat its producer. It's LC50 is several 100 mg/kg in mice, which is relatively high, but it goes to show that it can kill mice with a greater potency than, say, sugar. So it stands to reason that it can be described as a poison. Malljaja (talk) 20:57, 29 March 2012 (UTC)
replies: text:  Well, sola dosis facit venenum. What about closely related psilocin - would you call it a poison, or rather a psychedelic drug? Though of course it can kill, if one takes enough. I'll change from 'poison' to 'alkaloid' - eventually this is what this article is on. ;) Tryptamines (talk) 05:04, 18 April 2012 (UTC)
thread_title:  Bufotenine 

message: Is it necessary to have the picture of cyclopia in a sheep in this article? I'm sure I'm not the only person who doesn't like to see unexpected body horror in academic articles! Obviously, the story about the lambs receiving birth defects as a result of their mother eating the alkaloid is important - but does the picture need to be on this page? Is there some way in wiki markup to hide it, on the basis that it might be upsetting to some viewers, so you have to consciously click to see it? Baratron (talk) 00:43, 24 June 2014 (UTC)
replies: text: There were general discussions elsewhere on how to hide potentially shocking images - I don't know the outcome. In general, wikipedia is not censored, meaning images that are needed to illustrate the concept should be included even if they might disturb someone. In this particular case, I think just saying "cyclopia" won't tell people how bad it is, and this is not sensationalism - up to 25% of lambs born by sheep that had grazed on corn lily had serious facial deformations. Materialscientist (talk) 00:55, 24 June 2014 (UTC)
replies: text: WP:NOTCENSORED is a policy. It essentially forbids using "offensive" as the criterion for removal of encyclopediac images. DMacks (talk) 16:35, 28 July 2014 (UTC)

text: Agree completely. And what concept about alkaloids is "illustrated" by such a picture? None, really, except that they can have profound biological effects. This article isn't a forum to raise consciousness about the plight of sheep eating corn lilies. 205.232.191.2 (talk) 16:15, 28 July 2014 (UTC)
replies: text: The article is exactly to discuss various aspects of alkaloids, including their natural occurrence and diverse biological effects. DMacks (talk) 16:28, 28 July 2014 (UTC)
thread_title:  Gross-out Pictures in Wiki Articles? 

message: Hello fellow Wikipedians,
I have just added archive links to  on Alkaloid. Please take a moment to review my edit. If necessary, add  after the link to keep me from modifying it. Alternatively, you can add  to keep me off the page altogether. I made the following changes:
*Added archive https://web.archive.org/20130130101146/http://www.drugbank.ca/drugs/DB01392 to http://www.drugbank.ca/drugs/DB01392
Cheers.—cyberbot IITalk to my owner:Online 20:28, 13 July 2015 (UTC)
thread_title:  External links modified 

message: I changed the solubility description. was originally: 
:Caffeine,[156] cocaine,[157] codeine[158] and nicotine[159] are water-soluble (with a solubility of ≥1g/L), whereas others, including morphine[160] and yohimbine[161] are highly water-soluble (0.1–1 g/L).
Changed it to slightly and very slightly soluble in water (for the alkaloids, not the salts), corresponding to the Remington's table (http://pharmlabs.unc.edu/labs/solubility/intro.htm, or http://www.sigmaaldrich.com/united-kingdom/technical-services/solubility.html):
Descriptive term                  	Volume (ml) of Solvent Needed to Dissolve 1g of Solute
Very soluble                      	< 1
Freely soluble                    	1-10
Soluble                           	10-30
Sparingly soluble                 	30-100
Slightly soluble                  	100-1000
Very slightly soluble             	1000-10,000
Practically insoluble or insoluble	> 10,000
In a medical context these substances might be considered highly soluble by some ( for example: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3399483/ "Solubility is based on the highest-dose strength of an immediate release product. A drug is considered highly soluble when the highest dose strength is soluble in 250 mL or less of aqueous media over the pH range of 1 to 7.5."), but I doubt this definition is widely used (and is only useful for oral medication, you don't inject someone with 250 ml... ).  Prevalence (talk) 15:17, 22 December 2015 (UTC)
thread_title:  Solubility 

message: The Actions of Ergot Alkaloids in the table under the Applications heading is completely false.
Whether this is by accident or ignorance, it is very misleading and may undermine the credibility of Wikipedia.
Specifically, ergot alkaloids are seldom if ever "sympathomimetic".   There are no ergot alkaloids listed within the article Sympathomimetics.
Second, ergot alkaloids are predominantly vasoconstricting, not vasodialating.  For example, Ergotism is a disease marked by acute and chronic vasoconstriction leading to dry gangrene and vascular dementia after consumption of the alkaloids of the ergot fungus.
Third, ergot alkaloids, causing vasoconstriction, are not antihypertensive. The vasoconstriction they cause increases blood pressure directly.
I'll fix it myself in a few weeks if no-one can argue why I shouldn't.
69.92.196.11 (talk) 18:58, 16 November 2017 (UTC)
thread_title:  Actions of Ergot Alkaloids? 

message: I'm looking around for sources that would support the statement with citation [12] in the article that was marked as failed verification. This article implies that a typical alkaloid that inhibits hyperglycemia/diabetes through insulin stimulation is berberine, though that isn't mentioned among the many purported health effects that haven't been tested in humans for that chemical, and it's from J Diabetes Metab Disorder which is cited 4 times on Wikipedia in total. This article from Molecules (journal) says pretty much the same as the previous article, listing all the same alkaloids. Do either of these seem like plausible supporting evidence for the statement that alkaloids are effective against hyperglycemia or diabetes mellitus? Reconrabbit (talk|edits) 20:25, 15 December 2023 (UTC)
replies: text: The statement has been modified from piperine to berberine. Reconrabbit 14:59, 11 January 2024 (UTC)
thread_title:  Unverified statement on antihyperglycemic effects