Talk:Troparil

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I hereby award this page, (-)-2β-Carbomethoxy-3β-phenyltropane, the prestigious Strangest Article Name Ever™ award. Congratulations. Picaroon 02:48, 21 April 2007 (UTC)


Its the name of the compound the page is about. Whats so strange about that? Meodipt 13:46, 24 April 2007 (UTC)

In the section on legality, with regard to how the difference between Cocaine and this compound is the same as the difference between GHB and ethanol: this isn't exactly correct. The point is still somewhat valid though. If you want to avoid a lot of ugly chemistry talk, skip the next paragraph.

  • begin chemistry rant*

Substitutional analogues, which were once the bread and butter of the "designer drug" chemist, now rendered illegal by a certain analogue drug act passed not too long ago, did indeed evade the law by *adding* functional groups, or making subtle alterations to the chemical structure, while maintaining an identical "backbone". This rather difficult to pronounce chemical is *NOT* made by taking cocaine and removing a functional group, at least if those molecule graphics are correct. For that matter, the functional group "removed" (a type of ester linkage) isn't even the same one as the one "removed" from GHB! In the case of GHB, you're removing a carboxilic acid group (which is, admittedly, similar to an ester group) AND youre also removing a carbon! (which would actually be difficult to do, carbon carbon bonds are tough to break) The moral of the story is that these two pairs of molecules have similar but different backbones.

  • end chemistry rant*

The point made that this molecule and cocaine might be too dissimilar to be considered analogues has some merit. It wouldn't hold up in court if it came down to it. In the end, the point is moot, because, too my knowledge the controlled substances analogue act specifically states that the drug must be similar in chemical structure and/or effect to an illegal drug. Its a stupid law though because its so vague. Caffeine has carbon, nitrogen and oxygen atoms too, and its also a stimulant, which could be argued to fit both of the requirements for that law. For more discussion on that law, see PIKHAL and TIHKAL by alexander shulgin. -an interested chemical engineer


Canada has been removed from the analogue*suspect countries as the Controlled Drugs and Substances Act does not mention analogue of cocaine merely :

"Coca (Erythroxylon), its preparations, derivatives, alkaloids and salts, including:

(1) Coca leaves

(2) Cocaine (benzoylmethylecgonine)

(3) Ecgonine (3–hydroxy–2–tropane carboxylic acid) " —Preceding unsigned comment added by JohnStuartMill (talkcontribs) 22:37, 3 February 2009 (UTC)

Capable of metabolism to something similar to ethylphenidate / cocaethylene?[edit]

Is there any note, source or study stating the existence or name of such a substance in the conversion of troparil with ethyl alcohol? The "trans-esterification" via carboxylesterase in vivo would presumably, due to the same structural attributes, do as it would to troparil the same as it does to methylphenidate & cocaine (that produces ethylphenidate / cocaethylene respectively) though I would not want to impose original research on to wikipedia of course, but if it is obscure yet attested to I think it would be a worthy addition due to its obscurity. (The same may similarly be true to less widely used cocaine analogues like Tropoxane, but whether they are attested to or not I am unaware, please let me know here.) Nagelfar (talk) 09:40, 16 September 2009 (UTC)

Removed content: methylphenidate overlap to troparil, etc.[edit]

The below was removed from a previous edit, though I still found some comparisons / information interesting enough as it stands to add here to the discussion page for reference:

...


Troparil is the only regular phenyltropane having a NET affinity that exceeds the DAT affinity.

Comparison of In Vitro Data taken from Rats brains[1]
Compound [3H]CFT [3H]DA [3H]Nisoxetine [3H]NE [3H]Paroxetine [3H]5-HT
Cocaine[2] 89.1 275 c.f. 241 3300 (1990) 119 c.f. 161 1050 (45) 177 c.f. 112
WIN 35065-2 23 49.8 920 (550) 37.2 1960 (178) 173
(±)-TMP[3] 57.0 152 351 ND >10K >10K

Troparil is structurally similar to dexmethylphenidate. Indeed, it is possible to superimpose the structure of both these compounds to get very close overlap of the relevant pharmacophores.

Troparil and Dexidate

The reason why drugs like norcocaine and N-methyl ritalin are both weaker than the drugs from which they are derived still needs clarifying.

  1. ^ Carroll FI, Kotian P, Dehghani A, Gray JL, Kuzemko MA, Parham KA, Abraham P, Lewin AH, Boja JW, Kuhar MJ. Cocaine and 3 beta-(4'-substituted phenyl)tropane-2 beta-carboxylic acid ester and amide analogues. New high-affinity and selective compounds for the dopamine transporter. J Med Chem. 1995 Jan 20;38(2):379-88. PMID 7830281
  2. ^ Kozikowski AP, Johnson KM, Deschaux O, Bandyopadhyay BC, Araldi GL, Carmona G, Munzar P, Smith MP, Balster RL, Beardsley PM, Tella SR. Mixed cocaine agonist/antagonist properties of (+)-methyl 4beta-(4-chlorophenyl)-1-methylpiperidine-3alpha-carboxylate, a piperidine-based analog of cocaine. J Pharmacol Exp Ther. 2003 Apr;305(1):143-50. PMID 12649362
  3. ^ Ukairo OT, Bondi CD, Newman AH, Kulkarni SS, Kozikowski AP, Pan S, Surratt CK. Recognition of benztropine by the dopamine transporter (DAT) differs from that of the classical dopamine uptake inhibitors cocaine, methylphenidate, and mazindol as a function of a DAT transmembrane 1 aspartic acid residue. J Pharmacol Exp Ther. 2005 Aug;314(2):575-83. PMID 15879005

...

Nagelfar (talk) 11:55, 17 September 2009 (UTC)

DOI of ref 3 is dead[edit]

DOI of ref 3 (10.2165/00129784-200909030-00005) is dead but matches the one posted at Pubmed Bstard12 (talk) 21:46, 23 August 2012 (UTC)