Talk:Bufotenin/Archives/2020/February

Synthesis
Would a synthesis section be useful? I found an article from Chemistry Quarterly that has a few synthesis for Bufotenin and I believe that would be something that should be included into the article. A picture of the synthesis can be created in ChemDraw and all the necessary information can be labeled.
 * I think a synthesis section would be potentially useful but only if it covers the topic broadly enough. For example, I'm guessing that there is more than one method for synthesis (although I could be wrong), so focusing on on only one method could be problematic (e.g., WP:BALANCE and WP:UNDUE. The ideal would be to have a sentence or two describing the major methods of synthesis that have been reported in the literature, preferably from a good review article. If structural diagrams were to be included, I would prefer that they be referenced to a source that provides the same schematic, so that it can be easily verified. If you were to draw all the structures on your own, it would be difficult to verify whether you had done so correctly in the absence of a verifiable schematic. It would treading, albeit lightly, into the area of WP:OR. BTW, you should always sign your posts using 4 tildes. Thanks and good luck. Rhode Island Red (talk) 23:07, 4 May 2015 (UTC)

Effects of Human Table
Would it be possible to change the Effects of Humans section into a table? I feel like it would be a better way to organize the information. The table could be organized in a way where we have different columns, one for who performed the experiment, when it was performed, the dosage of bufotenin used and then finally the effects of that dosage.
 * Not too keen on the table idea. I left a comment on my Talk page explaining why. Rhode Island Red (talk) 22:59, 4 May 2015 (UTC)
 * I went back and had a look at the table you crafted and the biggest problem with it is that it omits a lot of critical information that was in the text version, so I would have to say that I overwhelmingly prefer the latter. Rhode Island Red (talk) 23:12, 4 May 2015 (UTC)

Toads & Anadenanthera
I'm having a very difficult time deciding exactly what should go where. Bufotenin, Bufo Alvarius, Bufo toads, the Anadenanthera genus, and their history all seem very interconnected, and I'd like to make sure all the information falls on the right page. I'll spend some time in the future overhauling these pages and citing sources. If anyone has any suggestions on the organization of these articles, let me know.—Old american century 00:01, 2 March 2007 (UTC)
 * I think I've finished working on this article. It's beautiful now.  The rest of the articles above need touch-ups still. --'oac' (old american century) | Talk 21:42, 25 April 2007 (UTC)

In Humans
I added information and citations for bufotenin levels in humans (schizophrenics, violent offenders, etc). Much thanks to the anonymous contributor who initially raised concern over the fact that these studies are often inconclusive, which got me to finally compile all these texts into the article.--'oac' (old american century) | Talk 21:35, 6 May 2007 (UTC)

Sources from Ott, Torres and Repke Are Reliable
The tests performed by Ott were both self tests and were also administered to other individuals (except the rectal ones) who had identical results. Please read the source completely. Similar test results showing clear hallucinogenic activity for free base bufotenin were also confirmed separately and presented in Visionary Plant Of Ancient South America By Constantino by Torres and Repke. Also, keep in mind that we have thousands of years of confirmed hallucinogenic activity from shamans using bufotenin. People seem to want to discard this fact concerning bufotenin in favor of test results from injections of forms of bufotenin never used by the shamans. We cannot argue with thousands of years of use by shamans just because some tests of injected forms show different effects. To do so is to put our heads in the sand and ignore an important part of human history in South America. -FV 17:23, 9 August 2007 (UTC)


 * With regard to one of your points, we can't reasonably infer much about bufotenin based on historic accounts of use by shamans, since they were incapable of purifying bufotenin. Whatever shamans were using for thousands of years (e.g. Anadenanthera or toad venom preparations), it was not merely bufotenin, but rather a mixture of many different substances. Rhode Island Red 00:26, 11 August 2007 (UTC)


 * I must inform you that Anadenanthera colubrina beans used by shamans have been confirmed to contain only bufotenin in active amounts. No other compounds are present in active amounts. I can site many studies proving this to be the case. So yes we can infer much about bufotenin based on historic accounts of Vilca snuff and smoking powders used by shamans made solely from A. colubrina where bufotenin is the only active compound.


 * Work by Ott, Torres and Repke has shown that insufflated freebase butotenin gives the complete hallucinogenic effects of Vilca snuff. The reason previous tests failed to show this was that they either used a water soluble salt or used free base bufotenin in doses too small to produces such effects instranasally. To produce the effects of Vilca snuff, you need to insufflate 50-100 mg of free base bufotenin, not IV, IM, or by using salts, etc. None of those other methods produce the effects of Vilca snuff. Your newly added old material clearly helps to back that up. All of those failed tests either used water soluble salts, doses too small, or non nasal or non vapor routes of administration. Its pretty clear if you examine all the data. If you exclude modern tests by Ott, Torres and Repke, then this isn’t clear. But now that we have them, it is very clear why earlier tests were inadequate.


 * I know first hand that the free base bufotenin work sited by Ott, Torres and Repke is credible. I personally know of several individuals in Mexico, who attempted to prove them wrong and were surprised when they duplicated their findings. However, I don’t personally know anyone who’s published their findings yet. It’s hard to get people who’ve been saying “bufotenin is not a hallucinogen” for so many years to suddenly reverse their opinions. Ott was himself one who said that bufotenin is not a hallucinogen. That was until he did the tests himself and proved himself wrong. After proving himself wrong he had the guts to publish his results. That takes a lot of character. We should commend him for that.


 * Anyway, if anyone finds it difficult to believe that insufflated free base bufotenin is indeed a powerful hallucinogen, bufotenin is currently legal in Mexico and in most countries in the world, so you can easily hire a qualified group to conduct such tests to verify their findings.


 * By the way, thanks for adding all the new material. It’s much appreciated! Ron Delipski 02:45, 14 August 2007 (UTC)

Modifications on 08/14/2007
FlowingVisions, I noticed you removed the citation tags I added without commenting on the edit summary or here on the talk page. I also had made substantial revisions to the text, which I explained clearly in my edit summaries, and the revisions were reverted without explanation. If you have objections, let's talk about them here before reverting good-faith edits. Rhode Island Red 01:40, 15 August 2007 (UTC)

Shultes Reference
Hallucinogenic Plants by Richard E. Shultes is not a sufficiently high-quality source, since none of the statements in the book are supported by references. Please refer to WP:RS. The sentence in question already has 3 other references to support it, so this isn't needed anyway. Rhode Island Red 02:30, 15 August 2007 (UTC)

Article Quality
A few observations and opinions towards further improving the quality of this article:

Over-reliance on Torres & Rapke Book
As I stated before, I see far too much reliance on the one reference by Torres & Rapke (reference #16:Anadenanthera: Visionary Plant Of Ancient South America. | ISBN0789026422 ), and the problem has now been exacerbated by the recent addition of several more citations to this book (it is now quoted 19 times -- nearly half of the article’s 41 references). Please refer to Wikipedia’s NPOV policy and consider the section on |Undue Weight as well as WP:EL, which states.


 * Avoid undue weight on particular points of view -- On articles with multiple points of view, the number of links dedicated to one point of view should not overwhelm the number dedicated to other equal points of view, nor give undue weight to minority views. Add comments to these links informing the reader of their point of view. If one point of view dominates informed opinion, that should be represented first. For more information, see Wikipedia:Neutral point of view—in particular, Wikipedia's guidelines on undue weight.

The undue weight in this case makes the article convey that the Torres & Rapke book is the single most important source to ever comment on bufotenin, which is misleading.

Bear in mind that Torres & Rapke’s’ book is essentially a review of the subject, and while this may have been a useful review, Torres & Rapke are only one of many groups to have written about bufotenine. Many other very credible sources have written excellent reviews and published primary research on the topic, and their contributions in the field should be given a more balanced representation in the article.

With respect to credibility, Torres is a Professor of Art & Art History at Florida International University, and co-author David Repke holds only a BSc. in medicinal chemistry. I would not suggest that they should be dismissed completely as credible sources when it comes to the science of bufotenin, but it can easily be argued that their book and credentials are not notable enough to warrant 19 citations, especially when other well-credentialed authorities (PhD.’s and MD’s) who have written on the subject are not cited at all.


 * This is a very poorly constructed attack on their book. It’s basically an encyclopedia drawing from hundreds of other sources obtained from highly qualified people, all of which are given credit in the back of their book. Honestly, it doesn't matter who wrote the book. The shear wealth of studies cited in this book makes it the single most important book on the subject. No other book on the subject comes even close to this one. If you're going to attack their work, at least have something more to say, something with some meat. Attacking their credibility holds no water. They didn't do the tests cited! If you don’t believe in a particular study that was performed, attack the people who did the study, not Torres and Rapke who merely included their study in their book. This book shows many conflicting studies and attempts to show all points of view. It’s a great book. Ron Delipski 22:47, 22 August 2007 (UTC)


 * The main argument is one of undue weight on a single source, which is a fundamental WP policy and a cornerstone principle of NPOV writing. Torres and Rapke's lack of crednetials related to bufotenin pharmacology is a secondary (although relevant) issue. Even though Torres and Rapke's book is a review and cites many secondary references, it is still their interpretation of those references that is being presented and we have no way of knowing whether they have cited the information correctly. The original sources should be cited so that others can check whether Torres & Rapke interpreted and summarized them correctly. It is also customary to indicate that specific statements in the text of the WP article refer to a source as described by another source; for example, we would say “Turner and Merlis (1956) noted that…[Torres & Rapke, 2007]". Citing Torres & Rapke alone would make it seem that they conducted the original research. This needs fixing ASAP. Rhode Island Red 00:34, 24 August 2007 (UTC)

Lastly, for most of the Torres & Rapke citations (references #16 a-q), page numbers have not been included, which makes it exceedingly difficult to verify statements. This is inconsistent with WP:CIT and the references may be challenged and/or removed. Because this book is not readily accessible online, it might help if someone could quote a few relevant passages here on the talk page so that others can assess the validity and interpretation. Also, if the book is being used to cite other primary/secondary references, it would be helpful to list those references so that they too can be verified and/or mentioned.


 * No. You are just plain wrong. If you bothered to check you would find much of the book is available on-line to view for free at http://books.google.com and http://www.amazon.com Ron Delipski 22:47, 22 August 2007 (UTC)


 * After reading this Wiki article last week I went to Amazon. They let you read a lot of it for free before buying it. I got my copy right in my hand this week! This book is full of lots of references that are easily verified. I also updated some of the stuff in this article based on that book. Like he says, its practically an encyclopedia on the subject, drawing from sources all around the world. They did a lot of research. It must have taken them years to put the book together. Torres is THE SNUFF EXPERT. You will not believe how much information is in this book. It’s mind boggling. Books like this one about snuff and bufotenin don’t come along that often. It’s a rarely studied area. Being the most up to date book on the subject, its no wonder most of this article references that book. If it didn't, the article would be out dated. —The preceding unsigned comment was added by A C Williams (talk • contribs).
 * You both still seem to be missing the point about undue weight. The WP article is about bufotenin, not bufotenin according to Torres & Rapke. Their book is clearly given undue weight in the WP article. Some of the book is available for free online but most of the section on bufotenin is not. Only 1 page of the bibliography section is available online, which makes this online resource essentially useless for cross checking references. Overall, I'm a lot less impressed with the book than you. It's a decent review on the anthropological and ethnobotanical aspects of Anadenanthera but the section on bufotenin was not overly impressive and certainly not original. Also, if I want to know information about pharmacology, I would seek out a pharmacologist, not an art history major (ie. Torres). The WP article will never acheive top-rated status as long as the undue weight issue goes unresolved. Rhode Island Red 00:34, 24 August 2007 (UTC)

Bufotenin vs. Bufotenine-containing Extracts
We should be careful to restrict this article mainly to what is known about bufotenine itself, rather than the effects of extracts of toad venom or anadenanthera seeds, which contain mixtures of compounds, making it impossible to attribute effects directly to bufotenin. Bear in mind that there are already articles on psychoactive toad, Anadenanthera peregrina and Anadenanthera colubrina, so information that relates to these subjects, but not directly to bufotenine, should be moved/merged into those other articles. For example, the description of the methods of snuff preparation; other than perhaps a very, very brief synopsis, this really doesn’t merit mention in this article, although it is relevant to the articles on Anadenanthera.

Jonathan Ott’s Self-Administration Study
First, while Ott’s self-authored self-administration study is interesting, I have several concerns about the study itself and some of the statements made about the research in our WP article. First, he used a study population consisting of one person (himself) and it is difficult to reach firm conclusions on that basis. The study also seems to have been conducted without coauthors, academic affiliations, or oversight of any kind. Ott seems to be a well-educated and highly motivated ethnobotany enthusiast who undertook some interesting experiments on himself, but his scientific authority and credibility seems lacking.


 * OH MY WORD! THAT IS COMPLETELY WRONG! For your information, his tests were performed on several people. He clearly states that in his work. How can you say such a thing and post it here for everyone in the world to see? Aren’t you at all concerned about your own credibility? READ THE ARTICLE LIKE I DID! READ ALL OF IT! Then come back and make some comments about Ott! A C Williams 03:25, 23 August 2007 (UTC)


 * Reply -- My first piece of advice is to avoid all caps for emphasis, in keeping with WP policy (see WP:TPG). Shouting (which all caps denote) doesn't make one's argument any more compelling. Secondly, I perused the article completely. Clearly, the article indicated that majority of tests were performed by Ott alone. He used 5 routes of administration (nasal, rectal, oral, sublingual, and smoked). He was the sole subject for the sublingual, oral and intrarectal routes; one additional subject was included for nasal administration, and an unspecified number of subjects for smoked buftenin. Ott stated:


 * ''In snuff bioassays, I first washed my nose with saline solution, which was exsufflated followed by drying with tissue. Alkaloids were insufflated bilaterally through a short glass tube, after which I reclined until the peak effects were perceived, at times elevating my head to ensure the material did not enter my throat. For sublingual bioassays, the alkaloids were again finely powdered on a glassine weighing paper from which they were dropped under my tongue, which was first lowered to smear them around, after which I would recline with my head propped up, my tongue positioned in the back of my mouth to obviate salivary dilution, again until experiencing peak effects. Oral experiments involved simply swallowing the encapsulated alkaloids. For inhaled-vapor tests, bufotenine was weighed on a square of heavy-gauge aluminum foil subsequently fashioned as a ball, into the opening of which the flared end of a female ball-jointed glass tube would just fit. The material was vaporized over an alcohol lamp, and the vapor retained for 45-60 seconds. Both foil and tube were later weighed to ensure I had absorbed the entire dose. The bufotenine suppositories (in pharmaceutical cocoa butter) were simply inserted intrarectally.


 * Careful notes were made of each experiment. At least a full day passed between bioassays. My aim was always to ascertain the threshold dose for unmistakable visionary effects (auditory and visual), so to minimize subjectivity in evaluating the results - the threshold can be noted accurately, whereas comparing stronger effects implies subjective guesswork. Visionary effects of insufflated bufotenine were verified by one colleague well experienced with Anadenanthera snuff, those of vaporized bufotenine by several volunteers. As yet, effects of sublingual, oral and intrarectal bufotenine are unreplicated.'' Rhode Island Red 00:55, 24 August 2007 (UTC)

Second, according to Ott's article, he synthesized the bufotenin analogs himself, and although he described the methodology, he presented no evidence to confirm that his syntheses were successful (i.e. that he obtained pure salts, free base etc.). He did not show any purity testing results nor did he indicate that he had submitted his samples for independent analysis and confirmation of purity. Who knows what Ott might have been taking?


 * You've got to be joking! It was clearly bufotenin. That's the only compound in the seeds of Anadenanthera colubrina present in those amounts. He didn’t synthesize anything. He used a published extraction technique and verified the melting points of bufotenin. It couldn't be something else. A C Williams 03:25, 23 August 2007 (UTC)


 * No, I'm totally serious. Anandenanthera seeds contain bioactive compounds other than bufotenin, and this has been well documented by other sources (e.g. see Chamakura 1994). Ott did the extraction himself rather than obtaining it from a reliable manufacturer who could assess and confirm the purity of the compound. Ott presented no data that confirms the purity of the compound he alleges was bufotenin free base. It could easily be something other than bufotenin that he administered. As near as I can tell, Ott is an amateur and has no legitimate credentials as a chemist or pharmacologist, which certainly raises red flags about the reliability of his study. Rhode Island Red 01:05, 24 August 2007 (UTC)

Third, I have not seen any other reliable sources who have echoed the quote attributed to Ott that bufotenin “is the primary active component” of Anadenanthera snuff and that it alone is responsible for the snuff’s alleged hallucinogenic effects. As such, this assertion represents a minority opinion and should therefore not be given undue weight (see WP:REDFLAG) or presented as fact. Instead, this should be qualified as Ott’s opinion, if it is to be mentioned at all. Several other sources have identified other psychoactive components in Anadenanthera snuffs and/or have suggested that these components also contribute to the snuff’s psychoactive effects. [e.g. see (a) Torres et al. Snuff powders from Pre-Hispanic San Pedro de Atacama: chemical and contextual analysis. Current Anthropology. 1991;32(5):640-649; and (b) Chamakura 1994). Others have stated that bufotenin is not the active ingredient in Cohoba snuffs (see Turner and Merlis, 1956).


 * WHAT? You are completely wrong! Check with the DEA why don't you! They've tested these seeds many times and find bufotenin to be the main active chemical. All the modern tests show this. Not just tests performed by 1 guy. Show me 1 study done in this century that shows anything else. Just 1 study! I'd like to see it. I TRUST THE DEA IS RIGHT ABOUT THIS and some test done back in 1956 is probably not. We are much better at detecting chemical compounds these days. The year is currently 2007. Show me a modern test from at least 10 years ago that says what that old obsolete 1956 test says. Show me one PLEASE. I would love to see it. Then we can add it to the article to make your point. Otherwise, forget it. No one is going to believe that 1956 test is more accurate than tests done in this century. A C Williams 03:25, 23 August 2007 (UTC)


 * Would you like me to phone the DEA and ask or might you be able to provide a verifiable reference, as would be the norm when substantiating information in Wikipedia? My point was that if we are to include any statement to the effect that bufotenin is the sole psychoactive ingredient in snuffs, it needs to be verifiable, and others sources (mentioned above) who have stated that it is not the sole psychoactive ingredient need to be included as well for fair balance. Rhode Island Red 01:12, 24 August 2007 (UTC)

Furthermore, other studies have shown that the alkaloids in the snuffs are not stable over time, so it is difficult when analyzing archeological snuff samples, to determine exactly which alkaloids they contained when fresh. Chamkura (1994) highlighted a study by world-renowned authority Richard Schultes indicating that DMT and 5-MeO-DMT were not stable in Anadenanthera seed samples; the concentrations in freshly prepared samples declined to zero over a two-year span while bufotenin remained stable. This explains why bufotenine is the only alkaloid detectable in archaelogical samples of snuff and seeds.


 * True. DMT and 5-MeO-DMT are unstable. But DEA tests of fresh seeds show bufotenin is the main active compound, so what's your point? Are we to ingore all modern evidence? A C Williams 03:25, 23 August 2007 (UTC)


 * Again, if you have a verifiable reference to studies by the DEA that show this, please provide it. Rhode Island Red 01:14, 24 August 2007 (UTC)

Lastly, Ott's article, originally published in the Journal of Psychedelic Drugs, is hyperlinked in the WP bufotenin article. Journal articles are typically copyrighted works belonging to the journal published, and there is no indication that copyright permission was obtained to re-post the article online. As such, we may have a copyright issue about linking to an unauthorized online copy, according to WP:EL, which states;
 * Restrictions on Linking - For policy or technical reasons, editors are restricted from linking to the following, without exception: Sites that violate the copyrights of others per contributors' rights and obligations should not be linked. Linking to websites that display copyrighted works is acceptable as long as the website has licensed the work. Knowingly directing others to a site that violates copyright may be considered contributory infringement. If you know that an external Web site is carrying a work in violation of the creator's copyright, do not link to that copy of the work. Linking to a page that illegally distributes someone else's work sheds a bad light on Wikipedia and its editors. Rhode Island Red 05:33, 15 August 2007 (UTC)


 * You just keep going on and on with so many complains about Ott! This is hilarious! Are there more complaints to come?
 * Many editors on WP take policy seriously, and this includes copyright violations. If you have an argument to present as to why linking to this article does not violate WP copyright policy (WP:EL), please provide it. My other complaint about Ott is, once again, related to undue weight. It is cited 7 times, second only to Torres & Rapke. The issues about NPOV and avoiding undue weight are very simple ones and they need to be resolved. Rhode Island Red 01:20, 24 August 2007 (UTC)

Information Added to Toxicity Section Seems Redundant
Please consider that much of the newly added information under Toxicity about effects in humans is duplicative of exisiting material in the sections Bufotenin Salts vs. Free Base and Effects in Humans. The section also strikes me as obscure and difficult to follow for most readers, and it seems out of sequence with respect to the broader discussion of Effects in Humans that follows. We really should try to make the article as informative and detailed, but also as concise and easy to read, as possible. Rhode Island Red 03:40, 16 August 2007 (UTC)

It seems that the reference to morphine's LD50 in rats seems rather high. Whether or not the figure is accurate, a dose well below 200-300mg/kg in an opioid-tolerant human would still be fatal. I believe this gives the impression that this substance is much more toxic than test would indicate. Perhaps the level can be compared to a substance that is known to reflect the equivalent in humans. Stabwestrhcp (talk) 08:05, 10 March 2008 (UTC)stabwestrhcp

Anadenanthera: Visionary Plant Of Ancient South America by Torres & Rapke
There is a reason this article makes heavy use of this book as a reference. Much of the book is available on-line to view for free at http://books.google.com and http://www.amazon.com

The vast majority of the studies sited by Torres and Rapke appear in dozens of other publications and they are not the work of Torres and Rapke. A large portion of the book is a collection of work by other highly qualified people. Torres and Rapke basically took tons of studies published by others and crammed it into their book making it conveniently available to us all. From this single book you get references to work done by tons of other people. It's a great book and it is the single most important book on the subject because it draws from nearly every study ever done on the subject up until 2006. There is no other book as complete as this one. Check the back and you'll see an amazing amount of references to studies cited in the book. The references cited span centuries of work.Ron Delipski 23:04, 22 August 2007 (UTC)

If anyone has time to make the references more clear by citing the actual individuals responsible for the studies shown in this book, rather than simply this book, please do so.

Thanks. Ron Delipski 23:04, 22 August 2007 (UTC)


 * I have the book. I just got it Monday. It makes this article look like its written for children. Its full of all kinds of information. I recommend it to anyone interested in bufotenin or Yopo. Its a must have book. I'm also looking for a copy of Shamanic Snuffs or Entheogenic Errhines by Jonathan Ott. I can't find any available. If anyone has it and wants to sell it, please let me know! I WANT IT! A C Williams 03:33, 23 August 2007 (UTC)
 * I must admit that I becoming uncomfortable with what appear to be commercial plugs to buy Torres & Rapke's book, especially in light of the undue weight this book has been given in the WP article by some of the contributing editors. The purpose of the talk page is to discuss ways to improve the article. Please bear that in mind that encouraging people to buy a book does not serve that objective (see WP:SOAP). Rhode Island Red 01:30, 24 August 2007 (UTC)

The DEA source Rhode Island Red was looking for
http://www.usdoj.gov/dea//programs/forensicsci/microgram/journal_v4_num14/pg1.html

This graphic in particular: http://www.usdoj.gov/dea//programs/forensicsci/microgram/journal_v4_num14/image_007.gif

--88.1.38.80 (talk) 16:16, 17 November 2007 (UTC)


 * This is an interesting study but it is in no way definitive. To clarify the issue I think you would need a much larger sample of yopo seeds - these seeds may all have been from the same tree.  More importantly, if DMT and 5MeODMT are unstable than these results are rendered entirely inconclusive because nothing is known about the age of the seeds or their storage conditions.  I think to be conclusive you would need to use seeds with a known pedigree and origin.  —Preceding unsigned comment added by Psychopharmacology (talk • contribs) 09:40, 14 January 2009 (UTC)

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State of confusion
I did a bit of editing from an unfamiliar platform, then got concerned that i needed to switch back to finish my task. Perhaps edit conflict with myself reflects just race condition between platforms. I'll review intentions and results after taking time out for personal mental maintenance. --Jerzy•t 09:43, 2 May 2017 (UTC)