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Short description: Chemical compound
RTI-177 |
Identifiers |
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(1R,2S,3S,5S)-3-(4-chlorophenyl)-8-methyl-2-(3-phenyl-1,2-oxazol-5-yl)-8-azabicyclo[3.2.1]octane
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CAS Number | |
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PubChem CID | |
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ChemSpider | |
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ChEMBL | |
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Chemical and physical data |
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Formula | C23H23ClN2O |
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Molar mass | 378.90 g·mol−1 |
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3D model (JSmol) | |
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CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)C3=CC=C(C=C3)Cl)C4=CC(=NO4)C5=CC=CC=C5
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InChI=1S/C23H23ClN2O/c1-26-18-11-12-21(26)23(19(13-18)15-7-9-17(24)10-8-15)22-14-20(25-27-22)16-5-3-2-4-6-16/h2-10,14,18-19,21,23H,11-13H2,1H3/t18-,19+,21+,23-/m0/s1 Key:ZGCYMNJHHKQEGA-KPYOPSEVSA-N
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RTI(-4229)-177 (2β-(3-phenylisoxazol-5-yl)-3β-(4-chlorophenyl)tropane, β-CPPIT) is a synthetic stimulant drug from the phenyltropane family, which acts as a DRI with micromolar affinity for the SERT.[1] RTI-177 has an unusually long duration of action of 20 hours or more, substantially longer than the related compound RTI-336 from which it differs in molecular structure only by the absence of a p-methyl group.[2]
"the nonselective monoamine transporter inhibitor RTI-126 and the DAT-selective inhibitors RTI-150 and RTI-336 both had a faster rate of onset (30 min) and a short duration of action (4h). In contrast, the nonselective monoamine transporter inhibitor RTI-112 had a slower rate of onset (30–60 min) and a longer duration of action (10h). The DAT-selective inhibitors RTI-171 and RTI-177 also had slower rates of onset (30–120 min), but RTI-171 had a short duration of action (2.5 h) while RTI-177 had a very long duration of action (20 h)."[3]
Update
Lower reinforcing strength of the phenyltropane cocaine analogs RTI-336 and RTI-177 compared to cocaine in nonhuman primates.
Comparison of six MAT inhibitors
RTI
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X
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R
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[3H]CFT
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[3H]Nisoxetine
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[3H]Paroxetine
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Coc
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—
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—
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89.1
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3298 (1986)
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1045 (45)
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177
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Cl
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phenyl
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1.28
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504 (304)
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2420 (220)
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176
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Me
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phenyl
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1.58
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398 (239)
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5110 (465)
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354
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Me
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ethyl
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1.62
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299 (180)
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6400 (582)
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336
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Cl
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p-cresyl
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4.09
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1714 (1033)
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5741 (522)
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386
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Me
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p-anisoyl
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3.93
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756 (450)
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4027 (380)
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In the Lindsey paper, RTI-177 was wrongly considered to be a dual inhibitor of the NET, although this was later found out to be incorrect.[citation needed]
"In acute toxicity studies in male rats, 3β-(4-chlorophenyl)-2β-[3-(4’-methylphenyl)isoxazol-5-yl]tropane (RTI-336) possessed an LD50 of 180 mg/kg after oral administration, compared with 49 mg/kg for RTI-177 (unpublished results, Howell 2005; Table 9). These results suggested that RTI-336 was a better candidate than RTI-177 for further preclinical development."[2]
Also the potency of the heterocyclic compounds is not as great as would be predicted based on in vitro test results.
References
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Adamantanes | |
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Adenosine antagonists | |
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Alkylamines | |
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Ampakines | |
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Arylcyclohexylamines | |
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Benzazepines | |
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Cholinergics | |
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Convulsants | |
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Eugeroics | |
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Oxazolines | |
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Phenethylamines |
- 1-(4-Methylphenyl)-2-aminobutane
- 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane
- 2-Fuoroamphetamine
- 2-Fuoromethamphetamine
- 2-OH-PEA
- 2-Phenyl-3-aminobutane
- 2,3-MDA
- 3-Fuoroamphetamine
- 3-Fluoroethamphetamine
- 3-Fluoromethcathinone
- 3-Methoxyamphetamine
- 3-Methylamphetamine
- 3,4-DMMC
- 4-BMC
- 4-CMC
- 4-Fluoroamphetamine
- 4-Fluoromethamphetamine
- 4-MA
- 4-Methylbuphedrone
- 4-Methylcathinone
- 4-MEAP
- 4-MMA
- 4-Methylpentedrone
- 4-MTA
- 6-FNE
- AL-1095
- Alfetamine
- a-Ethylphenethylamine
- Amfecloral
- Amfepentorex
- Amfepramone
- Amidephrine
- 2-Amino-1,2-dihydronaphthalene
- 2-Aminoindane
- 5-(2-Aminopropyl)indole
- 2-Aminotetralin
- Acridorex
- Amphetamine (Dextroamphetamine, Levoamphetamine)
- Amphetaminil
- Arbutamine
- β-Methylphenethylamine
- β-Phenylmethamphetamine
- Benfluorex
- Benzedrone
- Benzphetamine
- BDB
- BOH
- 3-Benzhydrylmorpholine
- BPAP
- Buphedrone
- Bupropion
- Butylone
- Camfetamine
- Cathine
- Cathinone
- Chlorphentermine
- Cilobamine
- Cinnamedrine
- Clenbuterol
- Clobenzorex
- Cloforex
- Clortermine
- Cypenamine
- D-Deprenyl
- Denopamine
- Dimethoxyamphetamine
- Dimethylamphetamine
- Dimethylcathinone
- Dobutamine
- DOPA (Dextrodopa, Levodopa)
- Dopamine
- Dopexamine
- Droxidopa
- EBDB
- Ephedrine
- Epinephrine
- Epinine
- Etafedrine
- Ethcathinone
- Ethylnorepinephrine
- Ethylone
- Etilamfetamine
- Etilefrine
- Famprofazone
- Fencamfamin
- Fencamine
- Fenethylline
- Fenfluramine (Dexfenfluramine, Levofenfluramine)
- Fenproporex
- Feprosidnine
- Flephedrone
- Fludorex
- Formetorex
- Furfenorex
- Gepefrine
- Hexapradol
- Hexedrone
- HMMA
- Hordenine
- 4-Hydroxyamphetamine
- 5-Iodo-2-aminoindane
- Ibopamine
- Indanylamphetamine
- Iofetamine
- Isoetarine
- Isoethcathinone
- Isoprenaline
- L-Deprenyl (Selegiline)
- Lefetamine
- Lisdexamfetamine
- Lophophine
- MBDB
- MDA (tenamfetamine)
- MDBU
- MDEA
- MDMA (midomafetamine)
- MDMPEA
- MDOH
- MDPR
- MDPEA
- Mefenorex
- Mephedrone
- Mephentermine
- Metanephrine
- Metaraminol
- Mesocarb
- Methamphetamine (Dextromethamphetamine, Levomethamphetamine)
- Methoxamine
- Methoxyphenamine
- MMA
- Methcathinone
- Methedrone
- Methoxyphenamine
- Methylenedioxycathinone
- Methylone
- Mexedrone
- MMDA
- MMDMA
- MMMA
- Morforex
- N,alpha-Diethylphenylethylamine
- N-Ethylbuphedrone
- N-Ethylhexedrone
- N,N-Dimethylphenethylamine
- Naphthylamphetamine
- Nisoxetine
- Norepinephrine
- Norfenefrine
- Norfenfluramine
- Normetanephrine
- L-Norpseudoephedrine
- Octopamine (drug)
- Orciprenaline
- Ortetamine
- Oxifentorex
- Oxilofrine
- PBA
- PCA
- PCMA
- PHA
- Pentorex
- Pentedrone
- Pentylone
- Phenatine
- Phenpromethamine
- Phentermine
- Phenylalanine
- Phenylephrine
- Phenylpropanolamine
- Pholedrine
- PIA
- PMA
- PMEA
- PMMA
- PPAP
- Phthalimidopropiophenone
- Prenylamine
- Propylamphetamine
- Pseudoephedrine
- Ropinirole
- Salbutamol (Levosalbutamol)
- Sibutramine
- Solriamfetol
- Synephrine
- Theodrenaline
- Tiflorex
- Tranylcypromine
- Tyramine
- Tyrosine
- Xylopropamine
- Zylofuramine
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Phenylmorpholines | |
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Piperazines | |
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Piperidines | |
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Pyrrolidines | |
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Racetams | |
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Tropanes | |
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Tryptamines | |
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Others | |
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DAT (DRIs) | |
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NET (NRIs) | | | | | | |
- 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|Desmetramadol]]]], methadone, pethidine (meperidine), tapentadol, tramadol, Levorphanol
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SERT (SRIs) | |
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VMATs | |
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Others | |
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2-Carboxymethyl Esters | |
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(3,4-Disubstituted Phenyl)-tropanes | |
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Arylcarboxy | |
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Carboxyalkyl | |
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Acyl | |
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β,α Stereochemistry | |
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α,β Stereochemistry | |
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Heterocycles: 3-Substituted-isoxazol-5-yl | |
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Heterocycles: 3-Substituted-1,2,4-oxadiazole | |
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N-alkyl | |
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N-replaced (S,O,C) | |
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Irreversible | |
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Nortropanes (N-demethylated) | |
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| Original source: https://en.wikipedia.org/wiki/RTI-177. Read more |