page_title: List of cocaine analogues
section_title: Bioisostere 2-position carbmethoxy-ester functional replacements
hierarchical_section_title: List of cocaine analogues / Analogs sensu stricto / 2β-substitutions (including transesterification metabolite substitution cocaethylene) / Bioisostere 2-position carbmethoxy-ester functional replacements
caption_attribution_description: English: 2-((2-methoxy-2-oxoethoxy)methyl) cocaine analogue from Carroll patent (U.S. Patent 6,479,509)
context_page_description: This is a list of cocaine analogues. A cocaine analogue is a artificial construct of a novel chemical compound from cocaine's molecular structure, with the result product sufficiently similar to cocaine to display similarity in, but alteration to, its chemical function. Within the scope of analogous compounds created from the structure of cocaine, so named "cocaine analogues" retain 3β-benzoyloxy or similar functionality on a tropane skeleton, as compared to other stimulants of the kind. Many of the semi-synthetic cocaine analogues proper which have been made & studied have consisted of among the nine following classes of compounds:
  stereoisomers of cocaine
  3β-phenyl ring substituted analogues
  2β-substituted analogues
  N-modified analogues of cocaine
  3β-carbamoyl analogues
  3β-alkyl-3-benzyl tropanes
  6/7-substituted cocaines
  6-alkyl-3-benzyl tropanes
  piperidine homologues of cocaine
  However strict analogues of cocaine would also include such other potential combinations as phenacyltropanes & other carbon branched replacements not listed above.
context_section_description: Benzoylecgonine, i.e. compound 197e, (differing from its cocaine parent only by de-methylation of the C2 carbmethoxy to that of a carboxy) has an extreme loss in potency (its approximate affinity being 195,000 nM) as displayed by in vitro methodologies for determining binding efficacy (wherein BBB penetration does not factor-in on the matter in the manner as in vivo studies) and is posited to be due possibly to zwitterion formation.
caption: 2-[(2-methoxy-2-oxoethoxy)methyl] cocaine analogue.[17]
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