Salicylmethylecgonine

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Salicylmethylecgonine
Salicylecgonine.png
Systematic (IUPAC) name
methyl (1R,2R,3S,5S)-3-(2-hydroxybenzoyloxy)-8-methyl-8-azabicyclo[3.2.1] octane-2-carboxylate
Identifiers
PubChem CID 10519659
ChemSpider 8695057
Chemical data
Formula C17H21NO5
Molar mass 319.351 g/mol
  (verify)

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] Salicylmethylecgonine also shows increased behavioral stimulation compared to cocaine similar to the phenyltropanes.[4]

Binding comparison between cocaine and semi-synthetic derivative o-hydroxy-cocaine[4]
Compound DAT

[3H]WIN 35428

5-HTT

[3H]Paroxetine

NET

[3H]Nisoxetine

Selectivity

5-HTT/DAT

Selectivity

NET/DAT

Cocaine 89 ± 4.8 1045 ± 89 3298 ± 293 11.7 37.0
2′(ortho)-hydroxycocaine 25 ± 4 143 ± 21 48 ± 2 5.7 1.9

See also[edit]

References[edit]

  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
  4. ^ a b Chemistry, Design, and Structure-Activity Relationship of Cocaine Antagonists. Satendra Singh et al. Chem. Rev. 2000, 100. 925-1024. PubMed; Chemical Reviews (Impact Factor: 45.66). 04/2000; 100(3):925-1024 American Chemical Society; 2000 ISSN 0009-2665 ChemInform; May, 16th 2000, Volume 31, Issue 20, doi:10.1002/chin.200020238. Mirror hotlink.