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RTI-229

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Chemical compound

Pharmaceutical compound
RTI-229
Legal status
Legal status
  • In general: legal
Identifiers
IUPAC name
  • octan-2-yl]-pyrrolidin-1-ylmethanone
CAS Number
PubChem CID
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H25IN2O
Molar mass424.326 g·mol
3D model (JSmol)
SMILES
  • CN12CC1((C2)C3=CC=C(C=C3)I)C(=O)N4CCCC4
  (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.

Uses

RTI-229 is mainly used in scientific research into the dopamine reuptake transporter, with its extremely high DAT selectivity making it useful for distinguishing between DAT and NET binding sites in the brain to an even greater extent than related compounds such as RTI-121.

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

  1. 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.
  2. 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.
  3. Zhong D, Kotian P, Wyrick CD, Seltzman HH, Kepler JA, Kuhar MJ, Boja JW, Carroll FI (March 1999). "Synthesis of 3β-(4-iodophenyl)tropane-2β-pyrrolidine carboxamide (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

Stimulants
Adamantanes
Adenosine antagonists
Alkylamines
Ampakines
Arylcyclohexylamines
Benzazepines
Cathinones
Cholinergics
Convulsants
Eugeroics
Oxazolines
Phenethylamines
Phenylmorpholines
Piperazines
Piperidines
Pyrrolidines
Racetams
Tropanes
Tryptamines
Others
ATC code: N06B
Monoamine reuptake inhibitors
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
See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
Phenyltropanes (classifications)
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)
Categories:
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