(-)-2β-(1,2,4-oxadiazol-5-methyl)-3β-phenyltropane

Drugbox
IUPAC_name = (1R,2S,3S,5S)-8-methyl-2-(1,2,4-oxadiazol-5-methyl)-3-phenyl-8-azabicyclo [3.2.1] octane


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C=17 | H=21 | N=3 | O=1
molecular_weight = 283.367
smiles = CN2C1CCC2CC(c4ccccc4)C1c3nc(C)on3
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RTI-126, ((-)-2β-(1,2,4-oxadiazol-5-methyl)-3β-phenyltropane) is a phenyltropane derivative which acts as a potent monoamine reuptake inhibitor and stimulant drug. It is around 5x more potent a stimulant than cocaine, but is relatively unselective, binding to all three monoamine transporters although still with some selectivity for the dopamine transporter. [Carroll FI, Gray JL, Abraham P, Kuzemko MA, Lewin AH, Boja JW, Kuhar MJ. 3-Aryl-2-(3'-substituted-1',2',4'-oxadiazol-5'-yl)tropane analogues of cocaine: affinities at the cocaine binding site at the dopamine, serotonin, and norepinephrine transporters. "Journal of Medicinal Chemistry". 1993 Oct 1;36(20):2886-90. PMID 8411004] RTI-126 has a fast onset of effects and short duration of action, and its pharmacological profile in animals is among the closest to cocaine itself out of all the drugs in the RTI series. Its main application in scientific research has been in studies investigating the influence of pharmacokinetics on the abuse potential of stimulant drugs, with its rapid entry into the brain thought to be a key factor in producing its high propensity for development of dependence in animals. [Kimmel HL, Carroll FI, Kuhar MJ. Locomotor stimulant effects of novel phenyltropanes in the mouse. "Drug and Alcohol Dependence". 2001 Dec 1;65(1):25-36. PMID 11714587] [Kimmel HL, O'Connor JA, Carroll FI, Howell LL. Faster onset and dopamine transporter selectivity predict stimulant and reinforcing effects of cocaine analogs in squirrel monkeys. "Pharmacology, Biochemistry and Behaviour". 2007 Jan;86(1):45-54. PMID 17258302]

RTI-126 is not explicitly illegal anywhere in the world; its similar pharmacological activity to cocaine makes it possible that it could be considered a controlled substance analogue in countries such as the USA, Canada, Australia and New Zealand which have controlled substance analogue legislation, but the replacement of the 2β-carbomethoxy group with methyloxadiazole is a significant structural alteration and it is unclear whether it could be considered "substantially similar" in chemical structure so as to bring it within the definition of a controlled substance analogue. There is as yet no case law defining what constitutes a substantially similar chemical structure, and so it is not possible to say for certain whether RTI-126 would be an illegal drug or not.

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