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Salicylmethylecgonine

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Title: Salicylmethylecgonine  
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Subject: Salicylates, Aluminon, Ethenzamide, Salsalate, Caffeine
Collection: Dopamine Reuptake Inhibitors, Local Anesthetics, Methyl Esters, Salicylates, Stimulants, Tropanes
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Salicylmethylecgonine

Salicylmethylecgonine
Systematic (IUPAC) name
methyl (1R,2R,3S,5S)-3-(2-hydroxybenzoyloxy)-8-methyl-8-azabicyclo[3.2.1] octane-2-carboxylate
Clinical data
Legal status
?
Identifiers
ATC code ?
PubChem
ChemSpider
Chemical data
Formula C17H21NO5 
Mol. mass 319.351
 YesY   

Salicylmethylecgonine, (2'-Hydroxycocaine) is a tropane derivative drug which is both a synthetic analogue and a possible active metabolite of cocaine.[1] Its potency in vitro is around 10x that of cocaine,[2] although it is only around three times more potent than cocaine when administered to mice.[3]

See also

References

  1. ^ Singh S, Basmadjian GP, Avor K, Pouw B, Seale TW. A convenient synthesis of 2'- or 4'-hydroxycocaine. Synthetic Communications. 1997;27(22):4003-4012.
  2. ^ el-Moselhy TF, Avor KS, Basmadjian GP. 2'-substituted analogs of cocaine: synthesis and dopamine transporter binding potencies. Archiv der Pharmazie (Weinheim). 2001 Sep;334(8-9):275-8. PMID 11688137
  3. ^ Seale TW, Avor K, Singh S, Hall N, Chan HM, Basmadjian GP. 2'-Substitution of cocaine selectively enhances dopamine and norepinephrine transporter binding. Neuroreport. 10 November 1997;8(16):3571-5. PMID 9427328


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