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List of phenyltropanes
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List of phenyltropanes
Phenyltropanes (PTs) 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; thus, the phenyl is attached direct to the tropane skeleton (hence the name "phenyl"-tropane) with no further spacer that the cocaine benzoyloxy provided. The original purpose of phenyltropane-related research was to extirpate the cardiotoxicity inherent in the local anesthetic "numbing" capability of cocaine (which stems from the methylated benzoate ester being essential to cocaine's blockage of sodium channels, and which causes topical anesthesia) while retaining stimulant function.
Phenyltropane compounds present promising avenues of research into therapeutic applications, particularly in regard to addiction treatment. These compounds' 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 and Parkinson's diseases. (Since 2008 there have been continual additions to the list and enumerations of the plethora of types of chemicals that fall into the category of this substance profile.) Certain phenyltropanes can even be used as a smoking cessation aid (cf. RTI-29). Many of the compounds were first elucidated in published material by the Research Triangle Institute and are thus named with "RTI" serial-numbers (in this case the long form is either RTI-COC-n, for 'cocaine' "analog", or specifically RTI-4229-n of the subsequent numbers given below in this article) Similarly, a number of others are named for Sterling-Winthrop pharmaceuticals ("WIN" serial-numbers) and Wake Forest University ("WF" serial-numbers). The following includes many of the phenyltropane class of drugs that have been made and studied.
Like cocaine, phenyltropanes are considered a 'typical' or 'classical' (i.e. "cocaine-like") DAT re-uptake pump ligands in that they stabilize an "open-to-out" conformation on the dopamine transporter; despite the extreme similarity to phenyltropanes, benztropine and others are in suchwise not considered "cocaine-like" and are instead considered atypical inhibitors insofar as they stabilize what is considered a more inward-facing (closed-to-out) conformational state.
Considering the differences between PTs and cocaine: the difference in the length of the benzoyloxy and the phenyl linkage contrasted between cocaine and phenyltropanes makes for a shorter distance between the centroid of the aromatic benzene and the bridge nitrogen of the tropane in the latter PTs. This distance being on a scale of 5.6 Å for phenyltropanes and 7.7 Å for cocaine or analogs with the benzoyloxy intact. The manner in which this sets phenyltropanes into the binding pocket at MAT is postulated as one possible explanation to account for PTs increased behavioral stimulation profile over cocaine.
Blank spacings within tables for omitted data use "no data", "?", "-" or "—" interchangeably.
ɑN=2
ɑN=2
Use of a cyclopropyl ester appears to enable better MAT retention than does the choice of isopropyl ester.
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List of phenyltropanes
Phenyltropanes (PTs) 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; thus, the phenyl is attached direct to the tropane skeleton (hence the name "phenyl"-tropane) with no further spacer that the cocaine benzoyloxy provided. The original purpose of phenyltropane-related research was to extirpate the cardiotoxicity inherent in the local anesthetic "numbing" capability of cocaine (which stems from the methylated benzoate ester being essential to cocaine's blockage of sodium channels, and which causes topical anesthesia) while retaining stimulant function.
Phenyltropane compounds present promising avenues of research into therapeutic applications, particularly in regard to addiction treatment. These compounds' 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 and Parkinson's diseases. (Since 2008 there have been continual additions to the list and enumerations of the plethora of types of chemicals that fall into the category of this substance profile.) Certain phenyltropanes can even be used as a smoking cessation aid (cf. RTI-29). Many of the compounds were first elucidated in published material by the Research Triangle Institute and are thus named with "RTI" serial-numbers (in this case the long form is either RTI-COC-n, for 'cocaine' "analog", or specifically RTI-4229-n of the subsequent numbers given below in this article) Similarly, a number of others are named for Sterling-Winthrop pharmaceuticals ("WIN" serial-numbers) and Wake Forest University ("WF" serial-numbers). The following includes many of the phenyltropane class of drugs that have been made and studied.
Like cocaine, phenyltropanes are considered a 'typical' or 'classical' (i.e. "cocaine-like") DAT re-uptake pump ligands in that they stabilize an "open-to-out" conformation on the dopamine transporter; despite the extreme similarity to phenyltropanes, benztropine and others are in suchwise not considered "cocaine-like" and are instead considered atypical inhibitors insofar as they stabilize what is considered a more inward-facing (closed-to-out) conformational state.
Considering the differences between PTs and cocaine: the difference in the length of the benzoyloxy and the phenyl linkage contrasted between cocaine and phenyltropanes makes for a shorter distance between the centroid of the aromatic benzene and the bridge nitrogen of the tropane in the latter PTs. This distance being on a scale of 5.6 Å for phenyltropanes and 7.7 Å for cocaine or analogs with the benzoyloxy intact. The manner in which this sets phenyltropanes into the binding pocket at MAT is postulated as one possible explanation to account for PTs increased behavioral stimulation profile over cocaine.
Blank spacings within tables for omitted data use "no data", "?", "-" or "—" interchangeably.
ɑN=2
ɑN=2
Use of a cyclopropyl ester appears to enable better MAT retention than does the choice of isopropyl ester.
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