View source for Commons:Deletion requests/File:Cannabicyclohexanol.png

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=== [[:File:Cannabicyclohexanol.png]] ===
Wrong enantiomer, see e.g. [http://www.chemspider.com/Chemical-Structure.26668381.html ChemSpider]. Replaced by [[:File:Cannabicyclohexanol.svg]]. [[User:Leyo|Leyo]] 15:40, 4 November 2015 (UTC)
:Please replace usage first. --[[User:Denniss|Denniss]] ([[User talk:Denniss|<span class="signature-talk">{{int:Talkpagelinktext}}</span>]]) 10:56, 5 November 2015 (UTC)
::Not necessarily ''first'', see [[COM:Redundant]]. --[[User:Leyo|Leyo]] 13:22, 5 November 2015 (UTC)
:[[:en:Cannabicyclohexanol]] also agrees, via it being an analog of what [https://pubchem.ncbi.nlm.nih.gov/compound/125835 PubChem says] is the other enantiomer. PubChem for this compound itself doesn't have stereo ([https://pubchem.ncbi.nlm.nih.gov/compound/12788230]), but using the definitely opposite one of the analog is at best misleading even if we were just picking one arbitrarily to use to represent the structure. Several other "CP 47,497" analogs in [[:Category:Cannabinoids]] have the same stereo mistake (and some even do have specific PubChem contradiction). Many of these are cited to ChemSpider, which does have the other stereo. But it uses the other stereo in its name as well. Each ref has self-consistent name and image. Need to figure out what the actual chemical is... [[User:DMacks|DMacks]] ([[User talk:DMacks|<span class="signature-talk">{{int:Talkpagelinktext}}</span>]]) 15:29, 5 November 2015 (UTC)
::[https://www.jstage.jst.go.jp/article/yakushi/131/7/131_7_1141/_pdf This paper, ''Isomeric Analysis of Synthetic Cannabinoids Detected as Designer Drugs'' (PDF)] refers to both enantiomeres as (+ and -) cannabicyclohexanol on page two. I can not read japanese, but the structures speak for themselves. If others agree, I would mention that in the article and refer to the paper. {{Autotranslate|base=Unsigned|1=Nothingserious|2=|3=}}
:::{{ping|Nothingserious}} The link is dead. --[[User:Leyo|Leyo]] 11:33, 6 November 2015 (UTC)
::::{{ping|Leyo}} PMID 21720146. --[[User:Nothingserious|Nothingserious]] ([[User talk:Nothingserious|<span class="signature-talk">{{int:Talkpagelinktext}}</span>]]) 17:22, 6 November 2015 (UTC)
:::::Thank you. I notified the original uploader, [[User:Meodipt|Meodipt]], on his talk page in en.wikipedia. Let's see if he can help. --[[User:Leyo|Leyo]] 19:59, 8 November 2015 (UTC)
: Hmm, I'm not convinced ChemSpider has this correct. Various isomers of this compound have been identified in illicit products (both cis and trans), but I was sure the "correct" most active enantiomer from the original Pfizer research was the one I had drawn, as then the stereochemistry matches other related cannabinoids like CP 55,940 , CP 55,244 and HU-243. The enantiomer you and Chemspider have shown, instead matches the stereochemistry of the non-cannabinoid compound HU-211 or the weaker enantiomer CP 55,243. My reference textbook on this shows the stereochemistry the way I had drawn it (for the original CP 47,497 anyway, and I'm sure the C8 homologue has the same stereochemistry.) Ref: Eric Stern and Didier Lambert. Cannabinoids in Nature and Medicine. Medicinal Chemistry Endeavors around the Phytocannabinoids. pp 5, 130. {{ISBN|978-3-906390-56-7}} [[User:Meodipt|Meodipt]] ([[User talk:Meodipt|<span class="signature-talk">{{int:Talkpagelinktext}}</span>]]) 08:33, 9 November 2015 (UTC)
:: The original reference is Pharmacol Biochem Behav 1991; 40: 471-478., compound VII. Also I would note that the website for CaymanChem, a major supplier of analytical reference standards for forensic use, shows the same enantiomer I drew on their product page for this compound [https://www.caymanchem.com/app/template/Product.vm/catalog/13216] [[User:Meodipt|Meodipt]] ([[User talk:Meodipt|<span class="signature-talk">{{int:Talkpagelinktext}}</span>]]) 08:48, 9 November 2015 (UTC)
:::[https://www.caymanchem.com/app/template/Product.vm/catalog/13216 CaymanChem] refers to this substance as (±)-CP 47,497; and as Formal Name: '' '''rel'''-2-[(1S,3R)-3-hydroxycyclohexyl]-5-(2-methylnonan-2-yl)phenol'', which means: [http://goldbook.iupac.org/R05260.html IUPAC Gold Book], so both enantiomeres. I've learned something today. --[[User:Nothingserious|Nothingserious]] ([[User talk:Nothingserious|<span class="signature-talk">{{int:Talkpagelinktext}}</span>]]) 10:04, 9 November 2015 (UTC)
:::: Sure, because it is a lot easier to make the mixture of ''cis'' isomers than it is to make the pure active enantiomer, and for analytical purposes it doesn't matter that much as they will look practically identical on GCMS or NMR. In terms of pharmacology though there is a massive difference, CP 55,244 is ~7000x more tightly binding than CP 55,243 and while the difference is probably not so dramatic with (C8)-CP 47,497 (due to less stereocenters), it will surely follow the same trend. Wikipedia convention is generally to show the most active enantiomer when it is known, unless the compound is always found as a mixture (which I'll admit could arguably be the case here). When the enantiomer is specified though, it should not be the inactive one. The Japanese reference you posted has it correct, (-)-Cannabicyclohexanol should be the image we have on the page, not the (+)-Cannabicyclohexanol that Leyo has drawn. Surely we should be trusting the scientific literature over collated databases like PubChem and ChemSpider. [[User:Meodipt|Meodipt]] ([[User talk:Meodipt|<span class="signature-talk">{{int:Talkpagelinktext}}</span>]]) 18:06, 9 November 2015 (UTC)
:::::I haven't been following this discussion so I won't comment on which version is the correct one, but I would like to concur wholeheartedly with Meodipt's last comment:  "Surely we should be trusting the scientific literature over collated databases like PubChem and ChemSpider".  Ed ([[User talk:Edgar181|Edgar181]]) 18:18, 9 November 2015 (UTC)

{{info}} The reason for having a closer look at the structure, was that structural formula and the name in the en.wikipedia article ([[:en:Special:PermaLink/685401434]]) did not match, i.e. (1''S'',3''R'') vs. (1''R'',3''S'') isomer. --[[User:Leyo|Leyo]] 18:22, 9 November 2015 (UTC)

: Ah right. Well, I sometimes get mixed up with that R/S nomenclature so I won't comment about that. And it is easy to see how there could be confusion here when this compound has been identified in so many different isomeric forms (pretty sure both ''cis'' isomers, both ''trans'' isomers, and the diastereomeric mixtures of the two ''cis'' isomers and the two ''trans'' isomers have all been identified at different times). However I am certain that the stereochemistry in the image that I drew for this compound, matches the stereochemistry depicted for the most active enantiomer in all of the literature sources I have access to. Happy to look up some more references for this if you like. [[User:Meodipt|Meodipt]] ([[User talk:Meodipt|<span class="signature-talk">{{int:Talkpagelinktext}}</span>]]) 20:07, 9 November 2015 (UTC)
::I think there's no need to. The issue was - as it turned out - mainly with the german article, which has the wrong enantiomere mentioned in it's info box. My proposal would be that we (or I) leave the old structural formula, remove the deletion request, I revert my edits in [[:w:Cannabicyclohexanol]] and [[:d:Q1033359]], ''and'' the IUPAC-name in [[:de:Cannabicyclohexanol]] should be changed. Agreed? 
::I am vectorizing some of the structural formulae and started the discussion in the first place. By the way I later found out that there is already an svg version of Cannabicyclohexanol, only as [[:File:CP-47,497.svg]]. --[[User:Nothingserious|Nothingserious]] ([[User talk:Nothingserious|<span class="signature-talk">{{int:Talkpagelinktext}}</span>]]) 06:47, 10 November 2015 (UTC)
:: Sounds good. It is important to make sure the chemical name matches the image. Also probably worth noting in the article about the varied mixtures of isomers found in illicit samples of this compound. And note that CP 47,497 as shown in that svg is a slightly different compound again, the side chain is one carbon shorter. Cannabicyclohexanol is (C8)-CP 47,497 with 1,1-dimethyloctyl side chain instead of 1,1-dimethylheptyl. [[User:Meodipt|Meodipt]] ([[User talk:Meodipt|<span class="signature-talk">{{int:Talkpagelinktext}}</span>]]) 08:37, 10 November 2015 (UTC)
:::What about having an image of both enantiomers (example: [[:File:MDMA-Formel.png]] or other images in [[:Category:Racemic mixture]]) in the box? --[[User:Leyo|Leyo]] 11:38, 10 November 2015 (UTC)
All four isomers have been reported though, ''trans'' as well as ''cis''...maybe put the most active one in the infobox, then add a section lower down saying how the illicit samples are usually a mixture of isomers, with a picture of all four of them? [[User:Meodipt|Meodipt]] ([[User talk:Meodipt|<span class="signature-talk">{{int:Talkpagelinktext}}</span>]]) 18:49, 10 November 2015 (UTC)
:OK. --[[User:Leyo|Leyo]] 23:41, 10 November 2015 (UTC)
:: Ok, I have fixed all the names and added a blurb to the cannabicyclohexanol page explaining about the different enantiomers. Thanks Edgar181 for explaining the naming confusion for me, and please check to make sure everything is all correct now. [[User:Meodipt|Meodipt]] ([[User talk:Meodipt|<span class="signature-talk">{{int:Talkpagelinktext}}</span>]]) 21:08, 15 November 2015 (UTC)
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'''Deleted:''' Replaced it with the SVG. [[User:Natuur12|Natuur12]] ([[User talk:Natuur12|<span class="signature-talk">{{int:Talkpagelinktext}}</span>]]) 13:40, 20 November 2015 (UTC) 
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