RTI-229

Chemical compound

RTI-229

Legal status
Legal status|

* In general: legal

Identifiers

IUPAC name

* [(1R,2S,3S,5S)-3-(4-Iodophenyl)-8-methyl-8-azabicyclo[3.2.1]octan-2-yl]-pyrrolidin-1-ylmethanone

CAS Number|

* 160948-17-4 Y

PubChem CID|

* 9910220

UNII|

* 4XC2A2NPZ2

CompTox Dashboard (EPA)|

* DTXSID10432717

Chemical and physical data
Formula| C19H25IN2O
Molar mass| 424.326 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* CN1[C@H]2CC[C@@H]1[C@H]([C@H](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.[1][2]

## Uses[edit]

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.[3]

## Legal Status[edit]

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[edit]

* RTI-55
* RTI-160
* List of Phenyltropanes

## References[edit]

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-[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[edit]

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* MeOPP
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Piperidines|

* 1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine
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* 3,4-Dichloromethylphenidate
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* 4-Fluoromethylphenidate
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Pyrrolidines|

* 2-Diphenylmethylpyrrolidine
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Racetams|

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Tropanes|

* 4-fluorotropacocaine
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ATC code: N06B

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Monoamine reuptake inhibitors

DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)|

* Piperazines: DBL-583
* GBR-12783
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* GBR-13098
* Nefazodone
* Vanoxerine

* Piperidines: 4-Fluoropethidine
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* Tesofensine
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* Dimethocaine
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* Modafinil
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* Nomifensine
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* Oroxylin A
* Perafensine
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* Norepinephrine–dopamine reuptake inhibitors: Amineptine
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* Serotonin–norepinephrine–dopamine reuptake inhibitors: 3,3-Diphenylcyclobutanamine
* Amifitadine
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* Bicifadine
* Brasofensine
* Centanafadine
* Cocaine
* Dasotraline
* Desmethylsertraline
* Desmethylsibutramine (BTS-54354)
* Diclofensine
* Didesmethylsibutramine (BTS-54505)
* DOV-102677
* DOV-216303
* EXP-561
* Fezolamine
* HDMP-28
* HP-505
* Indatraline
* JNJ-7925476
* JZ-IV-10
* Liafensine
* Mazindol
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* Nefopam
* NS-2359
* Perafensine
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* SEP-228431
* SEP-228432
* Sibutramine
* Tedatioxetine
* Tesofensine
* Threohydrobupropion
* Tropanes (e.g., cocaine)

* Tricyclic antidepressants: Amitriptyline
* Butriptyline
* Cianopramine
* Clomipramine
* Desipramine
* Dosulepin (dothiepin)
* Doxepin
* Imipramine
* Lofepramine
* Melitracen
* Nortriptyline
* Protriptyline
* Trimipramine

* Tetracyclic antidepressants: Amoxapine
* Maprotiline
* Mianserin
* Oxaprotiline
* Setiptiline

* Others: Antihistamines (e.g., brompheniramine, chlorphenamine, pheniramine, tripelennamine)
* Antipsychotics (e.g., loxapine, ziprasidone)
* Arylcyclohexylamines (e.g., ketamine, phencyclidine)
* Dopexamine
* Ephenidine
* Ginkgo biloba
* Indeloxazine
* Nefazodone
* Opioids (e.g., desmetramadol, methadone, pethidine (meperidine), tapentadol, tramadol, levorphanol)

SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)|

* Selective serotonin reuptake inhibitors: 6-Nitroquipazine
* Alaproclate
* Centpropazine
* Cericlamine
* Citalopram
* Dapoxetine
* Desmethylcitalopram
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* Escitalopram
* Femoxetine
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* Fluvoxamine
* Indalpine
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* Norfluoxetine
* Omiloxetine
* Panuramine
* Paroxetine
* PIM-35
* Pirandamine
* RTI-353
* Seproxetine
* Sertraline
* Zimelidine

* Selective serotonin reuptake inhibitors and serotonin receptor modulators: Etoperidone
* Litoxetine
* Lubazodone
* LY-393558
* Quipazine
* SB-649915
* TGBA01AD
* Trazodone
* Vilazodone
* Vortioxetine

* Serotonin–norepinephrine reuptake inhibitors: Atomoxetine (tomoxetine)
* Bicifadine
* CP-39332
* Desvenlafaxine
* Duloxetine
* Eclanamine
* Levomilnacipran
* McN5652
* Milnacipran
* N-Methyl-PPPA
* PPPA
* Tofenacin
* Venlafaxine

* Serotonin–norepinephrine–dopamine reuptake inhibitors: 3,3-Diphenylcyclobutanamine
* Amifitadine
* Ansofaxine
* Bicifadine
* Brasofensine
* Centanafadine
* Cocaine
* Dasotraline
* Desmethylsertraline
* Desmethylsibutramine (BTS-54354)
* Diclofensine
* Didesmethylsibutramine (BTS-54505)
* DOV-102677
* DOV-216303
* EXP-561
* Fezolamine
* HDMP-28
* HP-505
* Indatraline
* JNJ-7925476
* JZ-IV-10
* Liafensine
* Mazindol
* Naphyrone
* Nefazodone
* Nefopam
* NS-2359
* Perafensine
* PRC200
* Pridefine
* SEP-228431
* SEP-228432
* Sibutramine
* Tedatioxetine
* Tesofensine
* Threohydrobupropion
* Tropanes (e.g., cocaine)

* Tricyclic antidepressants: Amitriptyline
* Cianopramine
* Clomipramine
* Cyanodothiepin
* Desipramine
* Dosulepin (dothiepin)
* Doxepin
* Imipramine
* Lofepramine
* Nortriptyline
* Pipofezine
* Protriptyline

* Others: A-80426
* Amoxapine
* Antihistamines (e.g., brompheniramine, chlorphenamine, dimenhydrinate, diphenhydramine, mepyramine (pyrilamine), pheniramine, tripelennamine)
* Antipsychotics (e.g., loxapine, ziprasidone)
* Arylcyclohexylamines (e.g., 3-MeO-PCP, esketamine, ketamine, methoxetamine, phencyclidine)
* Cyclobenzaprine
* Delucemine
* Dextromethorphan
* Dextrorphan
* Efavirenz
* Hypidone
* Medifoxamine
* Mesembrine
* Mifepristone
* MIN-117 (WF-516)
* N-Me-5-HT
* Opioids (e.g., dextropropoxyphene, methadone, pethidine (meperidine), levorphanol, tapentadol, tramadol)
* Roxindole

VMATsTooltip Vesicular monoamine transporters|

* Amiodarone
* Amphetamines (e.g., amphetamine, methamphetamine, MDMA)
* APP
* AZIK
* Bietaserpine
* Deserpidine
* Deutetrabenazine
* Dihydrotetrabenazine
* Efavirenz
* GBR-12935
* GZ-793A
* Ibogaine
* Ketanserin
* Lobeline
* Methoxytetrabenazine
* Reserpine
* Rose bengal
* Tetrabenazine
* Valbenazine
* Vanoxerine (GBR-12909)

Others|

* DAT enhancers: Luteolin

* DAT modulators: Agonist-like: SoRI-9804
* SoRI-20040; Antagonist-like: SoRI-20041

See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins

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Phenyltropanes (classifications)

2-Carboxymethyl Esters|

* Troparil
* WIN 35428
* RTI-31
* RTI-32
* RTI-51
* RTI-55
* RTI-83

(3,4-Disubstituted Phenyl)-tropanes|

* Dichloropane
* RTI-112
* RTI-353

Arylcarboxy|

* RTI-113
* RTI-120

Carboxyalkyl|

* RTI-121
* RTI-150

Acyl|

* PTT/WF-11
* WF-23
* PIT/WF-21
* WF-33

β,α Stereochemistry|

* RTI-352
* RTI-274

α,β Stereochemistry|

* Brasofensine
* Tesofensine
* NS2359

Heterocycles: 3-Substituted-isoxazol-5-yl|

* RTI-177
* RTI-336
* RTI-371

Heterocycles: 3-Substituted-1,2,4-oxadiazole|

* RTI-126
* RTI-371

N-alkyl|

* FP-β-CPPIT
* FE-β-CPPIT
* Altropane
* Ioflupane (123I)

N-replaced (S,O,C)|

* Tropoxane

Irreversible|

* RTI-76

Nortropanes (N-demethylated)|

* NS2359 (GSK-372,475)

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
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*[e]: Edit this template
*[DAT]: Dopamine transporter
*[DRIs]: Dopamine reuptake inhibitors
*[NET]: Norepinephrine transporter
*[NRIs]: Norepinephrine reuptake inhibitors
*[SERT]: Serotonin transporter
*[SRIs]: Serotonin reuptake inhibitors
*[VMATs]: Vesicular monoamine transporters