page_title: List of phenyltropanes
section_title: p-methyl aryl front & back N-bridged phenyltropanes
hierarchical_section_title: List of phenyltropanes / 8-tropane (bridgehead) position modified / Bridged N-constrained phenyltropanes (fused/tethered) / p-methyl aryl front & back N-bridged phenyltropanes
caption_attribution_description: English: N-alkyl class front-bridged para-chloro phenyltropane of RTI's 4229 series, code-numbered 242
context_page_description: Phenyltropanes are a family of chemical compounds originally derived from structural modification of cocaine. The main feature differentiating phenyltropanes from cocaine is that they lack the ester functionality at the 3-position terminating in the benzene; and thusly the phenyl is attached direct to the tropane skeleton with no further spacer that the cocaine benzoyloxy provided. The original purpose of which was to extirpate the cardiotoxicity inherent in the local anesthetic "numbing" capability of cocaine while retaining stimulant function. These compounds present many different avenues of research into therapeutic applications, particularly in addiction treatment. Uses vary depending on their construction and structure-activity relationship ranging from the treating of cocaine dependency to understanding the dopamine reward system in the human brain to treating Alzheimer's & Parkinson's diseases. Certain phenyltropanes can even be used as a smoking cessation aid.
context_section_description: U.S. Patent 6,150,376
  ɑValue for displacement of [³H]WIN 35,428 binding @ DAT
  ᵇValue for displacement of [³H]paroxetine binding to SERT
  ᶜValue for displacement of [³H]nisoxetine from NET
  Fused tropane-derivatives as neurotransmitter reuptake inhibitors. Singh notes that all bridged derivatives tested displayed 2.5—104 fold higher DAT affinity than cocaine. The ones 2.8—190 fold more potent at DAT also had increased potency at the other two MAT sites (NET & SERT); NET having 1.6—78× increased activity. (+)-128 additionally exhibited 100× greater potency @ SERT, whereas 132a & 133a had 4—5.2× weaker 5-HTT (i.e. SERT) activity. Front-bridged (e.g. 128 & 129) had a better 5-HT/DA reuptake ratio in favor of SERT, while the back-bridged (e.g. 130—133) preferred placement with DAT interaction.U.S. Patent 5,998,405
caption: RTI-242
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