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[ CAS No. 2251-50-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
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Chemical Structure| 2251-50-5
Chemical Structure| 2251-50-5
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Product Citations

Product Citations

Raithatha, Sheetal A. ; Hagel, Jillian M. ; Matinkhoo, Kaveh , et al. DOI: PubMed ID:

Abstract: The psychedelic prodrug psilocybin has shown therapeutic benefits for the treatment of numerous psychiatric conditions. Despite pos. clin. end points targeting depression and anxiety, concerns regarding the duration of the psychedelic experience produced by psilocybin, associated with enduring systemic exposure to the active metabolite psilocin, pose a barrier to its therapeutic application. Our objective was to create a novel prodrug of psilocin with similar therapeutic benefits but a reduced duration of psychedelic effects compared with psilocybin. Here, we report the synthesis and functional screening of 28 new chem. entities. Our strategy was to introduce a diversity of cleavable groups at the 4-hydroxy position of the core indole moiety to modulate metabolic processing. We identified several novel prodrugs of psilocin with altered pharmacokinetic profiles and reduced pharmacol. exposure compared with psilocybin. These candidate prodrugs have the potential to maintain the long term benefits of psilocybin therapy while attenuating the duration of psychedelic effects.

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Product Details of [ 2251-50-5 ]

CAS No. :2251-50-5 MDL No. :MFCD00000657
Formula : C7ClF5O Boiling Point : No data available
Linear Structure Formula :- InChI Key :MYHOHFDYWMPGJY-UHFFFAOYSA-N
M.W : 230.52 Pubchem ID :75256
Synonyms :

Safety of [ 2251-50-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P264-P301+P330+P331-P305+P351+P338-P363-P403-P501 UN#:3265
Hazard Statements:H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 2251-50-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 2251-50-5 ]

[ 2251-50-5 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 2251-50-5 ]
  • [ 16947-63-0 ]
  • N-(2,6-dimethyl-4-nitrophenyl)-2,3,4,5,6-pentafluorobenzamide [ No CAS ]
  • 2
  • [ 2251-50-5 ]
  • [ 193537-14-3 ]
  • 6-(tert-butyl) 3-ethyl 2-(perfluorobenzamido)-4,7-dihydrothieno[2,3-c]pyridine-3,6(5H)-dicarboxylate [ No CAS ]
  • 3
  • [ 22246-83-9 ]
  • [ 2251-50-5 ]
  • C26H18F5NO5 [ No CAS ]
  • 4
  • [ 22246-83-9 ]
  • [ 2251-50-5 ]
  • 8-methoxy-1-(perfluorobenzoyl)-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one [ No CAS ]
  • 5
  • [ 2251-50-5 ]
  • [ 19008-43-6 ]
  • benzyl 4-(perfluorobenzamido)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% In chloroform; at 100℃; for 1.5h;Microwave irradiation; Inert atmosphere; General procedure: The acid chloride or sulfonyl chloride (1.0-1.1 equiv.) was added in one go to a solution of the appropriate aniline (1.0-1.05 equiv.) in chloroform (0.1-0.5M) and irradiated in microwave initiator at 100C for 90min. Removal of the solvent in vacuo followed by column chromatography isolated the target compound.
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