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

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

Legal status
Legal status	NZ: Temporary Class Drug
Identifiers
IUPAC name (2S,3S)-8-methyl-2-(3-methyl-1,2,4-oxadiazol-5-yl)-3-phenyl-8-azabicyclo[3.2.1]octane
CAS Number	146659-37-2 HCl: 147059-95-8
PubChem (CID)	71095000
Chemical and physical data
Formula	C17H21N3O
Molar mass	283.367 g/mol
3D model (Jmol)	Interactive image
SMILES CC1=NOC(=N1)[C@H]2[C@H](CC3CCC2N3C)C4=CC=CC=C4
InChI 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(-4229)-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 5 times more potent a stimulant than cocaine, but is relatively unselective. It binds to all three monoamine transporters, although still with some selectivity for the dopamine 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 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.^[2][3]

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

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

See also

• List of cocaine analogues

References

1. Carroll, FI; Gray, JL; Abraham, P; Kuzemko, MA; Lewin, AH; Boja, JW; Kuhar, MJ (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 (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 (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. Synthesis and nicotinic acetylcholine receptor binding affinities of 2- and 3-isoxazolyl-8-azabicyclo[3.2.1]octanes. Bioorganic and Medicinal Chemistry Letters. April 2004; 14(7):1775-1778. doi:10.1016/j.bmcl.2004.01.025 PMID 15026069