RTI-229
From Wikipedia, the free encyclopedia
| Legal status | |
|---|---|
| Legal status |
|
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| UNII | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C19H25IN2O |
| Molar mass | 424.326 g·mol−1 |
| 3D model (JSmol) | |
| |
| (verify) | |
RTI-229, also known as (–)-3β-(4-iodophenyl)tropane-2β-pyrrolidine carboxamide and RTI-4229-229, is a potent and long-lasting stimulant drug which was developed in the 1990s as part of a large group of related analogues from the phenyltropane family. With the combination of two potent dopamine transporter (DAT) binding motifs attached to the tropane ring, the p-iodophenyl group at the 3β-position and a pyrrolidine carboxamide at 2β, RTI-229 has extremely high selectivity for the dopamine transporter (2600x and 4600x selective over NET and 5-HTT respectively) and is one of the most DAT-selective compounds in the RTI series.[1][2]
Legal Status
RTI-229 is legal throughout the world as of 2010. Some jurisdictions such as the United States, Australia and New Zealand might however consider RTI-229 to be a controlled substance analogue of cocaine on the grounds of its related chemical structure.
See also
References
- ↑ Carroll FI, Kotian P, Dehghani A, Gray JL, Kuzemko MA, Parham KA, et al. (January 1995). "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". Journal of Medicinal Chemistry. 38 (2): 379–88. doi:10.1021/jm00002a020. PMID 7830281.
- ↑ Singh S (March 2000). "Chemistry, design, and structure-activity relationship of cocaine antagonists". Chemical Reviews. 100 (3): 925–1024. doi:10.1021/cr9700538. PMID 11749256.
- ↑ Zhong D, Kotian P, Wyrick CD, Seltzman HH, Kepler JA, Kuhar MJ, Boja JW, Carroll FI (March 1999). "Synthesis of 3β-(4-[125I]iodophenyl)tropane-2β-pyrrolidine carboxamide ([125I]RTI-229)". Journal of Labelled Compounds and Radiopharmaceuticals. 42 (3): 281–286. doi:10.1002/(sici)1099-1344(199903)42:3<281::aid-jlcr188>3.3.co;2-o.
External links
| 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) | |