Talk:List of phenyltropanes

Position-labels in the tables
How do the "X", "2", "8", and "config" values relate to the structures? If these are going to be useful and intelligible details, the image for the section should be drawn using the same generic groups and with the relevant positions labeled rather than just a single example that only serves as decoration for the section. DMacks (talk) 20:36, 16 September 2009 (UTC)
 * Nuklear, I can work on this later, didn't want to jump into the middle of your long edit session. DMacks (talk) 20:57, 16 September 2009 (UTC)

Lede image
The thumb for the article itself is confusing! Which of the two structures is a "Phenyltropane"? This "list of" isn't about a reaction at all, so the image is pretty far from representative of this article. Should be just an image of a specific compound of this class. DMacks (talk) 20:39, 16 September 2009 (UTC)


 * Replaced with Nuklear's nice rotating gif of troparil which is more or less the prototypical phenyltropane and so a much more appropriate lede image. Meodipt (talk) 02:53, 17 September 2009 (UTC)
 * Nice! DMacks (talk) 02:56, 17 September 2009 (UTC)

Technically cocaine *not* a phenyltropane?
So technically cocaine itself is not a 'phenyltropane', out of simply a technicality most likely, and the topical anesthetic quality being removed in the series of tropane research chemicals (RCs) called "phenyltropane" defined themselves as having no anesthetic qualtity for simplicities sake. Thus relating to cocaine as the tropane stimulant action purely (in the manner of cocaine, rather than stimulant action in the manner of amphetamine or nicotine or another form of CNS stimulation) are then the definition of "phenyltropanes" (cocaine stimulation without cocaine anesthetic) am I correct in this assertion?

Yet are there no class of artificial / man-made altered stimulant of cocaine that maintains said extra ester link that gives the anesthetic sodium channel blocking quality of cocaine to a research tropane stimulant? (cocaine molecule altered, but with related stimulation effect & related anesthetic effect). I have read many research papers noting the convulsant qualities of the external sodium channeling blocking that is innate to the local anesthetic natural to the cocaine numbing effect; and that the stimulant sensitization may indeed relate to this local anesthetic action and be key to the mediating of some sort of reinforcement or the like to the stimulation of the cocaine DARI stimulation itself... Has there not been RCs of the phenyltropane (or whatever it may be called) with the local anesthetic kept intact and engaged in different manners to see how the sodium channel extra-cellar anesthetic effect, affects stimulation while intact, to see if indeed such aesthetic sodium channel blocking effects on the brain relates to mediating the stimulation of DARI binding?

If papers were released to this effect I may readily guess that such chemicals of said properties have been produced. If not I am surprised; if they have been or would be, would they still be classed as "phenyltropanes", or more direct cocaine homologue/analogues of another sort? (They'd share even more in common with cocaine than phenyltropanes themselves if phenyltropanes are thus defined as being DARIs without the local anesthetic, they'd instead be "coca-tropanes" of sorts). Could anyone furnish me any information on any of what I here inquire? Nagelfar (talk) 09:24, 4 October 2009 (UTC)


 * With a little bit of self-study ones finds the term for cocaine would be a benzoyltropane (rather than phenyltropane). So benzoyltropane cocaine analogues may be the field of interest that I am seeking. Other (other alternate prefix-)-tropane analogues as well too possibly. (the technical term for any other non-specific type would be allo-, possibly? An Allotropane?) There doesn't seem to be much literature online about benzoyltropanes other than cocaine, and maybe two instances of published works referring to cocaine specifically as one. Though a few other natural benzoyltropanes, like ferrugine, are mentioned. Nagelfar (talk) 11:41, 27 October 2009 (UTC)

Compound table inconsistency,
Currently as it stands on this table: DA is usually first, but 5-HT & NE are oft reversed in the tables as to which comes next. So when visually scrolling down and scanning for affinity in relation to NE & 5-HT, the information becomes confused for ease of reference. Nagelfar (talk) 08:34, 12 October 2009 (UTC)

Phenyltropane that is an 'amphetaminergic DA releaser'? (c.f. 'DA reuptake inhibitor')
Exo-2-phenyl-7-azabicyclo [ 2.2.1 heptane - (IMAGE)] My Source. In addition to being the regular DARI that phenyltropane drugs are most usually, this is a DARA (releasing agent) much like the amphetamine class of drugs. Nagelfar (talk) 13:40, 15 October 2009 (UTC)


 * Phenyltropane that also has opioid activity: 3-(3-methoxyphenyl)-3-ethoxycarbonyltropane ... 3-(3-methoxyphenyl)-tropane derivatives supposedly are opiates in addition to being DARIs? Information on either of these would be quite interesting. Nagelfar (talk) 12:34, 16 October 2009 (UTC)
 * Many years later, I upload this: Exo-2-phenyl-7-azabicyclo(2.2.1)heptane.png


 * Anyone have access to the paper(s) ( exo-2-Phenyl-7-azabicyclo [ 2.2.1 heptane-1-carboxylic Acid: A New Constrained Proline Analogue] of course, the "...-1-carboxylic Acid" is left off of the above referenced)? Nagelfar (talk) 21:49, 6 October 2015 (UTC)

Speed on onset?
A lot of articles speak of "slower" or "faster" speed on onset relative to cocaine. etc. Is this rated and could that go on the tables when known? Nagelfar (talk) 11:49, 16 October 2009 (UTC)


 * Also the table maybe needs a place for notes so that it can easily be seen from this page which phenyltropanes have been recorded as having which special properties: such as the "...uniform downregulation of tyrosine hydroxylase protein and activity gene expression with a regimen of use..." which is "...In contrast to the findings of cocaine effects" inherent to WF-11/PTT or that RTI-371 "displayed actions at the cannabinoid receptor" making one assume it works as THC/marijuana. These type of facets would be great to reference from this "list" page itself rather than browsing through every link to find such pertinent differences. Nagelfar (talk) 13:38, 16 October 2009 (UTC)

RTI-371 listed twice.
As a N-methylphenyltropanes with 1R β,β stereochemistry. of the 3-Substituted-isoxazol-5-yl type and under the 3-Substituted-1,2,4-oxadiazole. Does it fit both criteria? Even so, most Wikipedia articles do not Wikify the second instance. 4.242.174.75 (talk) 12:10, 19 October 2009 (UTC)

What makes cocaine so incredibly lipid/water soluble?
Does the phenyl- replacing the benzoyl- (as per this class of cocaine analogues) create, as a usual staple/ubiquitous factor, a less lipid/water soluble substance? (And therefore one that will cross the blood-brain barrier more slowly, resulting in decreased "rush" subjective experience i.e. onset of euphoria from DAT DRI activation overcoming the equilibrium that metabolic osmosis would initiate to counteract the effect of the drug regardless of other affinity. - likely the source of the superior 'rush' experience / perception from IV administration of cocaine itself.) If so would not the addictive properties of cocaine be targeted not by less water soluble analogues but more greatly soluble analogues which simply have longer duration to replicate what is found particularly & peculiarly addictive about cocaine over for instance dextro-methamphetamine? 184.76.53.217 (talk) 18:46, 2 July 2010 (UTC)

Alternate conformation in 2D of any of these phenyltropanes.


The above is cocaine (a benzoyltropane) in the two-dimensional graph of the style unlike the totality of the given phenyltropanes shewn within the article to this discussion page. Could anyone with the diagram making skills of molecules in 2D remake any of the article's given phenyltropane chemicals in the style above instead of the one they are presented in currently? I find the above style to be rather more symmetrical, simple, straight-forward and therefore easily apprehended due to its straighter orientation. Which I dare say has the same advantage of 2D over 3D rotating ball & stick images on the 2D medium of a regular computer screen in general, and this style/type is more conducive to two dimensions in general therefore in all ways. Nagelfar (talk) 10:03, 30 July 2010 (UTC)

Phenyltropanes Discrimination Ratios?
Does anybody have literature on the 'discrimination ratios' of these phenyltropanes and which have lower discrimination ratios than cocaine itself / possibly faster onset of action, as well? Maybe a list page with DRIs of greater abuse potential than cocaine (itself).(?) 184.76.53.217 (talk) 04:27, 29 December 2010 (UTC)

SAR of cocaine analogs paper.
This paper contains quite a bit of information on phenyltropanes that would be of great use to this article & the cocaine analogues page. Pg. 38 (962) has on table 22 the 6/7 subtituted 3-butyl phenyltropane "121f" given above on the previous page in figure 24 & scheme 32. Also just below is the bridged phenyltropanes, esp. "128" also in table 23 below. 121f & 128: I'd like to see these touched on specifically in this article due to their higher affinities than cocaine alone, I would gladly assist anyone else interested in making a venture of it to transclude the information here. The piperidine analogs of phenyltropanes are equally worth the while for inclusion. In terms of cocaine analogs, 198a should be added in my opinion for the same reasons. Nagelfar (talk) 02:50, 9 August 2011 (UTC)

Singh's phenyltropanes
Does anybody notice any tables in this: phenyltropane & etc. paper of Mr. Singh of phenyltropanes that aren't already included here? Tell me which table and I'll add it here under it's proper section. I'm not savvy enough to notice which ones have been classified other ways here already or not. Nagelfar (talk) 00:11, 18 March 2015 (UTC)

SDRI PTs without NET
Development of 3-Phenyltropane Analogs with High Affinity for the Dopamine and Serotonin Transporters and Low Affinity for the Norepinephrine Transporter if someone could add the aforementioned compounds it'd be quite the boon to the article Nagelfar (talk) 17:26, 22 October 2015 (UTC)
 * Did one table myself, need to get to work on this next. Nagelfar (talk) 00:43, 11 January 2016 (UTC)
 * Someone could probably help clear it up, but those two tables are now transcluded. Nagelfar (talk) 02:31, 13 January 2016 (UTC)

RTI-4229-xxx
As per RTI's on-going patent of the institutes 4229 series, it claims those selected are those with a slower onset than cocaine. Perhaps someone with info on the 4229 series or contact info for RTI could get the numbers of compounds that are omitted from the given patent due to quicker onset (i.e. RTI-4229-n of which are not included in this patent due to not fitting that criteria) since such still are pertinent to this article despite not fitting the purposes of a likely drug candidate for those reasons/purposes. Nagelfar (talk) 19:08, 1 April 2016 (UTC)

C3 naphthyl-substitutions:
of 2β-Acyl-3β-(substituted naphthyl)-8-azabicyclo [3.2.1 octanes and Their Binding Affinities at Dopamine and Serotonin Transport Sites]

(image of substitution pattern) Nagelfar (talk) 01:12, 12 May 2016 (UTC)

PTs to be incorporated into article.

 * 3β-(4-alkylthio, -methylsulfinyl, and -methylsulfonylphenyl)tropane and 3β-(4-alkylthiophenyl)nortropane derivatives DONE

Just added a to-do list here. Nagelfar (talk) 20:36, 9 June 2016 (UTC)

p-nitro
The simple p-nitro phenyltropane has to be attested to somewhere in the literature, can someone locate it?

Nagelfar (talk) 20:36, 10 February 2020 (UTC)

Synthesis and Receptor Binding Properties of 2β-Alkynyl and 2β-(1,2,3-Triazol)substituted 3β-(substituted phenyl)tropane Derivatives
doi: 10.1016/j.bmc.2008.04.008 doesn't appear to be covered in list. It's been so long since I've championed this list. Someone surprise me and add it before I do. ;-j Nagelfar (talk) 23:08, 7 March 2020 (UTC)