Talk:List of cocaine analogues/Archive 1

Archive 1

comment

So I read there's a whole series of 2-acetoxy-3-phenyltropane that are stimulant cocaine analogues. There really is a whole sea of chemicals wikipedia has yet to touch on. Nagelfar (talk) 02:57, 10 December 2007 (UTC)

Maybe as well, which are analogues in a larger scope and which are specifically homologues in structural change should be differentiated on this page. Someone who is a bit more astute than I would have to incorporate this classification however. Nagelfar (talk) 00:46, 18 April 2009 (UTC)

Clarification

There may be a technical difference between derivatives and analogues, in which case I'm sure many of those local anesthetics fall under the former category. Either someone could edit those out or we could have a page move to 'List of cocaine analogues & derivatives' or something of the like. Nagelfar (talk) 17:32, 9 January 2008 (UTC)

In addition, there may be the technicality that molecular structures with additions to them are considered "analogues" while ones with molecular aspects removed are not, this page should distinguish between these "technical" analogues and ones which are not so. Nagelfar (talk) 04:40, 13 January 2008 (UTC)

Maybe a short list at the bottom of the page of cocaine metabolites such as methylecgonidine could also be added, but the page name might need to be found to be more suitable in such a case. Nagelfar (talk) 20:16, 13 January 2008 (UTC)

Drugs which are analogues to other tropanes.

There may be some confusion on this page as to what drugs constitute "cocaine analogues" specifically. If anyone notices any that do not belong in this list please take corrective action. Other tropane related drugs, like Hyoscyamine, may appear to be cocaine analogues when in fact they are derivatives of a plant related to coca and not directly constructed from it (in the case of hyoscyamine, which is from Henbane). Nagelfar (talk) 23:42, 9 January 2008 (UTC)

Off site source for a lot of cocaine analogues yet on Wikipedia:

These are non-nitrogen bearing derivatives of cocaine, the first link has the most amount of derivatives:

Thioether derivatives which are DAT selective.

methylene derivatives with no heteroatom in the tropane ring.

There is also the drug tropoxane. Nagelfar (talk) 23:51, 3 November 2008 (UTC)

Thanks to user:Meodipt a good example of each of those were added… I recently came across "Isothiocyanate derivatives of cocaine: irreversible inhibition of ligand binding at the dopamine transporter" i.e. an example of a class of cocaine analogue which acts as a 'covalent binding' ligand. Anyone resourceful enough care to make an example page of one such chemical? Meodipt? Nagelfar (talk) 16:51, 4 January 2009 (UTC)

Molecule structure image of 4-Fluoro-Cocaine and a uploaded pdf file on the chemical structure citing it as 60 times the binding potency of cocaine. Nagelfar (talk) 16:35, 4 February 2009 (UTC)

A site on a patent for "novel cocaine compounds" that is titled "Cocaine receptor binding ligands" may have very useful information. Also this page has a two dimensional image of a benzoylthio cocaine analogue. ... Nagelfar (talk) 05:13, 11 February 2009 (UTC)

...

Apparently a 2'-MeO-derivative of cocaine was made and tested in vitro. The IC50 has been deemed to be far too high to suggest stimulant activity (46654 +/- 840 nM, which is in contrary to cocaine itself with an IC50 = 249 +/- 37; the 2'-OH-derivative however, having an IC50 of 25 +/- 4 nM) and potentially then showing more promise. The reference for this information being Arch Pharm 2001, 334(8-9), p.275 Nagelfar (talk) 11:34, 29 March 2010 (UTC)

...

Arylhydroxy Metabolites of Cocaine in the Urine of Cocaine Users & the thus already cited Hydroxymethoxybenzoylmethylecgonines: New Metabolites of Cocaine From Human Urine available to reference. Anyone who can avail themselves to such sources please add any potential notable substances to Wikipedia for the interest in this vein of study. Nagelfar (talk) 13:13, 20 March 2011 (UTC)

...

Bicyclo[3.2.1]octanes & 2-Carbomethoxy-3-aryl-8-thiabicyclo[3.2.1]octane analogues of cocaine articles have quite a few that could be added. Nagelfar (talk) 04:13, 11 August 2011 (UTC)

General cocaine molecular alteration SAR information:

"Structure-activity relationships for cocaine and analog binding at the dopamine, norepinephrine and serotonin transporters were determined. Cocaine inhibition of ligand binding to each of these sites has a stereospecific requirement for the levorotatory isomer. Binding potencies of cocaine derivatives involving N-substitution, C2 and C3 substituent modifications, however, revealed differences in structure-activity relationships for cocaine binding at the transporters. Removal of the N-methyl groups produced little change in binding potency at the dopamine transporter site but produced increases in binding potency at norepinephrine and serotonin transporter sites. Changes in structure at the C2 substituent produced changes in binding potency at the dopamine transporter which were generally similar in direction, but not necessarily in magnitude at the norepinephrine and serotonin transporters. Modifications to the C3 substituent, especially substitution of a hydroxyl moiety, produce changes in affinity at norepinephrine and serotonin transporters which are much larger than those observed at dopamine transporters. In general, our results indicate that unique structural requirements exist for each transporter site, but that cocaine binding at norepinephrine and dopamine transporters can be described by more similar structure-activity relationships than those found for the serotonin transporter. Requirements for cocaine binding to the dopamine transporter, which we have previously shown to be associated with the reinforcing effects of cocaine, include levorotatory stereospecificity, the benzene ring at C3, at least some portions of the tropane ring, and the presence of the C2 methyl ester group in the beta conformation." Source: Cocaine inhibition of ligand binding at dopamine, norepinephrine and serotonin transporters: a structure-activity study. Ritz M C; Cone E J; Kuhar M J. Life sciences 1990;46(9):635-45. Nagelfar (talk) 17:02, 4 January 2009 (UTC)

Also, a page showing an image overlay for the mechanism of DAT ligand activity using cocaine and its analogue CFT as examples in relation to the dopamine chemical & its transporter. Maybe someone could redraw such an image and release it unto the public domain for this page &/or the cocaine page or similar? Showing the molecule as a 'DAT ligand' specifically in an image may convey a better difference of the unique mode of action that such a dopamine reuptake inhibitor drug has in relation others of that type, better than the current image on the cocaine page showing the difference between cocaine and amphetamine which only serves to make cocaine look like it has a simpler mode of action to the layperson. Nagelfar (talk) 17:23, 4 January 2009 (UTC)

What makes cocaine so incredibly lipid/water soluble?

Please see the gist of my question and why I believe it is so important for SAR on the List of phenyltropanes discussion page here which I posted while not logged in. Nagelfar (talk) 19:16, 2 July 2010 (UTC)

Classes of 'cocaine analogues' proper as per S. Singh et al.

"...Cocaine analogues retain 3β-benzoyloxy or similar functionality unlike phenyltropanes. This series consists of the following compounds: a) stereoisomers of cocaine, (b) 3β-phenyl ring substituted analogues, (c) 2β-substituted analogues, (d) N-modified analogues of cocaine, (e) 3β-carbamoyl analogues, (f) 3β-alkyl-3-benzyl tropanes, (g) 6/7-subtituted cocaines, (h) 6-alkyl-3-benzyl tropanes, and (i) piperidine homologues of cocaine..." Final paragraph pg. 45 Nagelfar (talk) 03:06, 9 August 2011 (UTC)

At least one example of each of these should be put into the "sensu stricto" section. Any suggestions for articles to transclude or examples of any with extant pages would be welcome. Nagelfar (talk) 22:29, 2 November 2011 (UTC)

Some 17 full .pdf papers on cocaine analogs, with a vast swath of information which could be incorporated into this article, is available here. Nagelfar (talk) 08:16, 10 November 2011 (UTC)

Split to methylphenidate analogues list page

The eventual goal of this page should be to get ever more specific to its topic. Certainly since this page could become as in depth as the phenyltropanes list (and, along with it, ever much more so), a (list of) methylphenidate analogues page will eventually need be made; having the MPH data here transcluded to there. Nagelfar (talk) 03:36, 14 November 2011 (UTC)

Comments

Although most references note that Ecgonine Cinnamate and Ecgonine Truxillates are inactive, studies commissioned by anti-drug agencies imply that they are active when smoked e.g. as part of "Crack" Cocaine.

Arecoline would be an Ecgonine analog. There are U.S. import restrictions.

Dyclonine has been used in Cocaine diluent ("Cut") formulations and has stimulant properties. Since removed from hemorrhoid formulations. (Why non-stimulant anesthetic but not for stimulant anesthetics.) Also, Phenacaine (Holocaine) and Cocaine are the only approved anesthetics for ophthalmic use. Should show Phenacaine on anesthetics list.

Shjacks45 (talk) 11:41, 5 February 2012 (UTC)

Cocaine stereoisomers image error

The name of two of the isomers are given as "Allocaine" (which is procaine) when the name should be "Allococaine". If someone has the ability, please fix this in the image. Nagelfar (talk) 23:45, 16 February 2012 (UTC)

Corrected. My thanks to whomever corrected this. 66.96.79.221 (talk) 20:01, 17 February 2015 (UTC)

'Synthesis of novel spirocyclic cocaine analogs using the Suzuki coupling'

"Spirocyclic cocaine analogs" can be referenced at the aforementioned link for possible inclusion by anyone who has an account at the given site. Nagelfar (talk) 20:37, 23 February 2015 (UTC)

More pages of interest

Analog patents Nagelfar (talk) 18:53, 27 February 2015 (UTC)

Research needed for inclusion.

File:Cocamentholene.jpg

cocaine analog with complex alcohol "menthol" substitution at the methyl group on the end of the 2-beta position.

Instability of Cocaine and Derivatives that have been Mixed with Analgesics and Menthol. Not quite a discussion on the analog capacity of such a substitution on the molecular level but it does bring up the interesting possibility. Nagelfar (talk) 23:25, 9 March 2015 (UTC)

More metabolites than given on parent page:

A list of cocaine metabolites, treating mainly rat & mouse metabolism and their differences, can be found at the article Characterization of Differential Cocaine Metabolism in Mouse and Rat through Metabolomics-Guided Metabolite Profiling. They include quite a few others than mentioned as the metabolites on the cocaine page. Whether this is due to differences in rat & human or simply an omission I haven't delved deeply enough to know:

Norecgonine methyl ester, Ecgonine methyl ester, Benzoylnorecgonine, Benzoylecgonine, Norcocaine, Hydroxybenzoylnorecgonine, N-Hydroxybenzoylnorecgonine, Hydroxybenzoylecgonine, Hydroxynorcocaine, Hydroxycocaine, Cocaine-N-oxide, Dihydroxycocaine, Hydroxymethoxybenzoylecgonine, Hydroxymethoxynorcocaine, Hydroxymethoxycocaine, Dihydroxymethoxycocaine, Hydroxydimethoxynorcocaine, Hydroxydimethoxycocaine, N-hydroxybenzoylnorecgonine glucoside, Hydroxymethoxynorcocaine glucuronide, Hydroxymethoxycocaine glucuronide, Dihydroxymethoxycocaine glucuronide, Hydroxydimethoxynorcocaine glucuronide, Hydroxydimethoxycocaine glucuronide. Nagelfar (talk) 00:44, 10 March 2015 (UTC)

Reagents

Does anybody know anything about the reagents (structure, IUPAC, etc.) of [²H₅-phenyl]-cocaine & [²H₃-N-methyl]-cocaine? Nagelfar (talk) 00:44, 11 March 2015 (UTC)

WP:OR?

Nagelfar you are putting a ton of work into this, and quite logically too, but this seems to me, to be all WP:OR.... (I do appreciate the work and your effort and expertise, of course!) just wondering how this fits in WP. Jytdog (talk) 20:10, 11 March 2015 (UTC)

Not at all. How is it original research? Most of this is from Satendra Singh's paper on cocaine "antagonists", the other few compounds currently not from that paper are cited. (e.g. methylvanillinecgonine, and methylbenzoylthioecgonine). Nagelfar (talk) 20:24, 11 March 2015 (UTC)

great! i wasn't catching it, that it was all sourced. Thanks for creating this resource. Jytdog (talk) 20:41, 11 March 2015 (UTC)

No problem. Perhaps I should make a generic entry that unless otherwise cited, the material is from that aforementioned publishing; to call attention to the issue if you thought it could have been OR. Nagelfar (talk) 22:05, 11 March 2015 (UTC)

I think the sourcing you are doing is great. thanks for the great work Jytdog (talk) 19:56, 14 March 2015 (UTC)

From 1st archival storage:

I had a few pertinent questions that were recently archived shortly after adding them, so I am going to replace them here: I found a list of cocaine metabolites, treating mainly rat & mouse metabolism and their differences, it can be found at the article Characterization of Differential Cocaine Metabolism in Mouse and Rat through Metabolomics-Guided Metabolite Profiling. They include quite a few others than mentioned as the metabolites on the cocaine page. Whether this is due to differences in rat & human or simply an omission I haven't delved deeply enough to know:

List of rat & mouse cocaine metabolites (possibly human & common-among-mammalian metabolites)

Norecgonine methyl ester, Ecgonine methyl ester, Benzoylnorecgonine, Benzoylecgonine, Norcocaine, Hydroxybenzoylnorecgonine, N-Hydroxybenzoylnorecgonine, Hydroxybenzoylecgonine, Hydroxynorcocaine, Hydroxycocaine, Cocaine-N-oxide, Dihydroxycocaine, Hydroxymethoxybenzoylecgonine, Hydroxymethoxynorcocaine, Hydroxymethoxycocaine, Dihydroxymethoxycocaine, Hydroxydimethoxynorcocaine, Hydroxydimethoxycocaine, N-hydroxybenzoylnorecgonine glucoside, Hydroxymethoxynorcocaine glucuronide, Hydroxymethoxycocaine glucuronide, Dihydroxymethoxycocaine glucuronide, Hydroxydimethoxynorcocaine glucuronide, Hydroxydimethoxycocaine glucuronide.

_Nagelfar (talk) 19:11, 29 March 2015 (UTC)

Trademark thing

About this. Wierd. I see where MOS:TM] says that. It is not good in my view. Am opening a discussion at WP:MED to get more thoughts on this. Will ping in the pharmacology project too. Jytdog (talk) 19:46, 12 August 2015 (UTC)

done Wikipedia_talk:WikiProject_Medicine#Trademarks.3F Jytdog (talk) 19:51, 12 August 2015 (UTC)

btw, Nagelfar it is not clear to me what confusion you are wanting to avoid with using the TM in these specific cases ... but I am curious what the outcome of the discussion is. Jytdog (talk) 19:52, 12 August 2015 (UTC)

The edits in question are not distinguishing between generic and brand names. There is no unavoidable necessity here and the use of ™ serves no purpose. The exemption given in the MOS does not mean that every time we mention a brand name drug we should gratuitously insert ™; it is there for cases where there is a difference between some property of "BrandDrug™" (the branded version) and that property in "BrandDrug" (the generic version), and we need to identify which is which. --RexxS (talk) 10:21, 13 August 2015 (UTC)

Agree with User:RexxS. IMO we do not need to list the brands at all. There are dozens. We should just go with the generic. Doc James (talk · contribs · email) 12:53, 13 August 2015 (UTC)

My thinking was that common generics and brands listed, solely in a list capacity, side by side would warrant that method of distinguishing, instead of having to head each one as "brand" or "generic", regardless, I have capitulated to the consensus. Nagelfar (talk) 20:15, 14 August 2015 (UTC)

We don't really need to list brands, per se - although "other common names" could be considered useful (as is done in List of local anesthetics). I've gone ahead and re-vamped the layout (two columns created by using a table is messy on a narrow screen). It really should contain just the INN in the first column, so I'll have another look tomorrow. --RexxS (talk) 00:23, 15 August 2015 (UTC)

if you're using high-resolution screens, as I do, you won't normally be reading Wikipedia at full width because the eye does not follow onto the next line of text comfortably once the line length gets beyond a certain size, which varies from person to person. It's not our job to fill in white space for readers who deliberately choose to use very wide viewports, because the moment we try to do that, we introduce problems for readers using mobile devices with narrow screens as well as for readers using assistive technology. Yes, we could break up a list into say, three separate lists and float them with divs to fill up HD screens, but then a screen reader user is left asking "Why am I reading three separate lists? Aren't these all supposed to be in the same list?" And why would we stop there? I use dual monitors so I could view a Wikipedia page at twice high-resolution - why not get rid of the whitespace for that setup as well? And what about when I upgrade to 4K monitors? Realistically we should be keeping it simple: a list should be marked up as a single list and two-dimensional list should be marked up as a single table. There just aren't any good reasons to do it differently. --RexxS (talk) 22:19, 16 August 2015 (UTC)

I'm going by Fort Vancouver Regional Library screen resolution; I don't know whether they use some set standard for the current resolution or not; but the page is aligned accordingly to the public access computers in my county of residence. Nagelfar (talk) 22:27, 17 August 2015 (UTC)

On all operating systems that are commonly in use, there exists the ability to view browser windows at a smaller width than the full width of the screen. I'd recommend asking the librarian to set it at a comfortable width for you. Trying to read lines of text that have more than about a dozen words is conventionally considered problematical; indeed Bringhurst, Robert (2004). The Elements of Typographic Style. ISBN 978-0881792065. – which is often quoted as authoritative – states that "Anything from 45 to 75 characters is widely-regarded as a satisfactory length of line for a single-column page set in a serifed text face in a text size. The 66-character line (counting both letters and spaces) is widely regarded as ideal." More recent studies suggest that web pages may be still be readable with as much as twice that length, but that still implies that Wikipedia pages are read most efficiently using the standard vector skin at 100% zoom when the width of the browser window is limited to rather less than 1500 pixels. 1500 pixels would allow a line length of around 150 characters and I have found no source endorsing anything as wide as that. Even at that width, I don't find the space surrounding the table in Local anesthetics (not usually CNS stimulants) a problem: there's no more space in that section than in the next section, Analogues for other purposes, and I wouldn't be considering forcing that into two columns just to fill it up. --RexxS (talk) 23:58, 17 August 2015 (UTC)

isomers

The S. Singh paper names eight isomers of cocaine, however chemicalize.org on "cocaine" gives 16. Which is correct? How is one omitted or in error if so? Nagelfar (talk) 18:28, 13 December 2015 (UTC)

Articles of interest.

Tropanyl that acts of allosteric modulator at SERT, (that is doi:10.1016/j.bmc.2012.09.004) may well fall within the spectrum of analogous compounds. See also the Talk:List of cocaine analogues/Archive 1 for more such others not yet transcluded. Nagelfar (talk) 20:40, 7 October 2015 (UTC)

cf. Synthesis of novel spirocyclic cocaine analogs using the Suzuki coupling (i.e. doi:10.1016/S0040-4039(00)00113-1] Nagelfar (talk) 21:58, 2 January 2016 (UTC)

Categories

@Nagelfar: The problem with categorizing structural classes with drug effect (e.g., nootropic, stimulant, anaesthetic, euphoriant) categories is that its inclusion in the category ambiguously implies that either every compound in the structural class has that property or at least some of the compounds in the class, but not all, have that property. Unless this is covered in the text, it's unclear which of these is the case; assuming the latter case is correct, it's unclear which compounds do and do not have the property. Moreover, I literally know of no other structural class article on wikipedia that is included in a drug effect category. If you want to ensure that compounds in this structural class are included in those categories, it would be better to categorize the appropriate compound articles individually instead of this article in order to address these ambiguity issues.

If you insist on categorizing structural class articles in drug effect categories anyway, keep in mind that you do actually have to satisfy WP:V and cite a reference in the article that supports its inclusion in a category (i.e., see WP:Categorization#Articles or the associated maintenance tag {{Category unsourced}}). Seppi333 (Insert 2¢) 02:29, 6 June 2016 (UTC)

How would you like to address this? Seppi333 (Insert 2¢) 04:19, 6 June 2016 (UTC)

My point is only the first section is structural, the 2nd is intermediate and largest section, the third, is functional. So it's not purely a structural list page, is my point. But its a reference, if reference requiring discrimination, wherein one might find functional drugs not having their own page to reference, such as the spiro-cyclic allosteric modulator of SERT which hasn't it own page and cannot be found by category unless via this list page. Nagelfar (talk) 20:07, 6 June 2016 (UTC)

However if you feel they are unprecedented as categories for this kind of page and so inclined as your certainty of this fact and edit it as such again I will not revert a second time. Cheers. Nagelfar (talk) 01:04, 8 June 2016 (UTC)

It's not a big deal so I'm probably just going to leave it as is. At the moment, the inclusion of this page in those categories is useful to the average person though because it's not clear which compounds are relevant to those categories. Seppi333 (Insert 2¢) 01:58, 8 June 2016 (UTC)

Articles for ref. later;

Faster onset and dopamine transporter selectivity predict stimulant and reinforcing effects of cocaine analogs in squirrel monkeys 10.1016/j.pbb.2006.12.006 Some info on the fast onset (mostly it seems phenyltropanes) Nagelfar (talk) 21:47, 14 June 2016 (UTC)

ChEMBL compound turns up first for search of the word simply "cocaine"

Wonder what it could be? Nagelfar (talk) 01:21, 23 June 2016 (UTC)

'closed-to-out', 'open-to-out', et 'other'

C1 analog, benztropine and traditional cocaine binding conformations @ DAT graph Nagelfar (talk) 21:30, 1 August 2016 (UTC)

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