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RTI-126

From Wikipedia, the free encyclopedia
Pharmaceutical drug
Pharmaceutical compound
RTI-126
Legal status
Legal status
Identifiers
  • (2S,3S)-8-Methyl-2-(3-methyl-1,2,4-oxadiazol-5-yl)-3-phenyl-8-azabicyclo[3.2.1]octane
CAS Number
PubChemCID
UNII
Chemical and physical data
FormulaC17H21N3O
Molar mass283.375 g·mol−1
3D model (JSmol)
  • CC1=NOC(=N1)[C@H]2[C@H](CC3CCC2N3C)C4=CC=CC=C4
  • InChI=1S/C17H21N3O/c1-11-18-17(21-19-11)16-14(12-6-4-3-5-7-12)10-13-8-9-15(16)20(13)2/h3-7,13-16H,8-10H2,1-2H3/t13?,14-,15?,16+/m1/s1
  • Key:QSHBOMWRGOGQOF-KNIAUWFNSA-N

RTI-126 (RTI-4229-126 or(–)-2β-(1,2,4-oxadiazol-5-methyl)-3β-phenyltropane) is aphenyltropane derivative which acts as a potentmonoaminereuptake inhibitor andstimulant drug, and has been sold as adesigner drug. It is around 5 times more potent thancocaine at inhibiting monoamine reuptakein vitro, but is relatively unselective. It binds to all three monoamine transporters, although still with some selectivity for thedopamine transporter.[1] 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 ofpharmacokinetics 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.[2][3]

The structurally related compound (–)-2β-(3-methyl-5-isoxazolyl)nortropane is a potent and selective agonist fornicotinic acetylcholine receptors, with twice the potency ofnicotine.[4]

(–)-2β-(3-methyl-5-isoxazolyl)nortropane

See also

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References

[edit]
  1. ^Carroll FI, Gray JL, Abraham P, Kuzemko MA, Lewin AH, Boja JW, Kuhar MJ (October 1993). "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.36 (20):2886–90.doi:10.1021/jm00072a007.PMID 8411004.
  2. ^Kimmel HL, Carroll FI, Kuhar MJ (December 2001). "Locomotor stimulant effects of novel phenyltropanes in the mouse".Drug and Alcohol Dependence.65 (1):25–36.doi:10.1016/S0376-8716(01)00144-2.PMID 11714587.
  3. ^Kimmel HL, O'Connor JA, Carroll FI, Howell LL (January 2007)."Faster onset and dopamine transporter selectivity predict stimulant and reinforcing effects of cocaine analogs in squirrel monkeys".Pharmacology, Biochemistry, and Behavior.86 (1):45–54.doi:10.1016/j.pbb.2006.12.006.PMC 1850383.PMID 17258302.
  4. ^Cheng J, Izenwasser S, Zhang C, Zhang S, Wade D, Trudell ML (April 2004). "Synthesis and nicotinic acetylcholine receptor binding affinities of 2- and 3-isoxazolyl-8-azabicyclo[3.2.1]octanes".Bioorganic & Medicinal Chemistry Letters.14 (7):1775–8.doi:10.1016/j.bmcl.2004.01.025.PMID 15026069.
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DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
Others
2-Carboxymethyl Esters
(3,4-Disubstituted Phenyl)-tropanes
Arylcarboxy
Carboxyalkyl
Acyl
β,α Stereochemistry
α,β Stereochemistry
Heterocycles: 3-Substituted-isoxazol-5-yl
Heterocycles: 3-Substituted-1,2,4-oxadiazole
N-alkyl
N-replaced (S,O,C)
Irreversible
Nortropanes (N-demethylated)
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