AL-34662

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AL-34662
AL-34662 structure.png
Systematic (IUPAC) name
1-((S)-2-Aminopropyl)-1H-indazol-6-ol
Identifiers
CAS Number 210580-75-9 N
ChemSpider 21467821 YesY
ChEMBL CHEMBL371300 YesY
Chemical data
Formula C10H13N3O
Molecular mass 191.229 g/mol
  • CC(N)Cn1ncc2ccc(O)cc12
  • InChI=1S/C10H13N3O/c1-7(11)6-13-10-4-9(14)3-2-8(10)5-12-13/h2-5,7,14H,6,11H2,1H3/t7-/m0/s1 YesY
  • Key:WBYHTZYHAFNBKW-ZETCQYMHSA-N YesY
Physical data
Melting point 170 to 172 °C (338 to 342 °F)
 NYesY (what is this?)  (verify)

AL-34662 is an indazole derivative drug that is being developed for the treatment of glaucoma. It acts as a selective 5-HT2A receptor agonist, the same target as that of psychedelic drugs like psilocin, but unlike these drugs, AL-34662 was designed specifically as a peripherally selective drug, which does not cross the blood–brain barrier. This means that AL-34662 can exploit a useful side effect of the hallucinogenic 5-HT2A agonists, namely reduction in intra-ocular pressure and hence relief from the symptoms of glaucoma, but without causing the hallucinogenic effects that make centrally active 5-HT2A agonists unsuitable for clinical use.[1] In animal studies, AL-34662 has been shown to be potent and effective in the treatment of symptoms of glaucoma, with minimal side effects.[2]

Peripherally acting 5-HT2A agonists have been a rich field of research in recent years, with potential glaucoma treatments being the main proposed application for 5-HT2A agonists at present, as centrally acting agonists for this receptor tend to be hallucinogenic and thus have little medical use. While many novel, potent and selective 5-HT2A agonists have been developed for this application,[3][4][5][6][7][8][9][10] retaining peripheral selectivity can be a problem, and several of the more lipophilic compounds closely related to AL-34662 such as those shown below, did cross the blood–brain barrier and produced hallucinogen-appropriate responding in animals.[11]

Hallucinogenic indazoles.png

See also

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Jesse A. May, Paul W. Zinke. 5-Hydroxyl indole derivatives for treating glaucoma. US Patent 6806285
  5. ↑ Jesse A. May, Zixia Feng, Anura P. Dantanarayana. 6-hydroxy-indazole derivatives for treating glaucoma. US Patent 6956036
  6. ↑ Jesse A. May, Anura P. Dantanarayana. Fused indazoles and indoles and their use for the treatment of glaucoma. US Patent 6960608
  7. ↑ Jesse A. May, Zixia Feng. 5-Hydroxy indazole derivatives for treating glaucoma. US Patent 7005443
  8. ↑ Zixia Feng, Mark R. Hellberg. Benzodifuranimidazoline and benzofuranimidazoline derivatives and their use for the treatment of glaucoma. US Patent 7208512.
  9. ↑ Anura P. Dantanarayana, Jesse Albert May. Substituted (1,4)oxazino(2,3-g)indazoles for the treatment of glaucoma. US Patent 7268131
  10. ↑ Anura P. Dantanarayana, Jesse A. May. Substituted 1-alkylamino-1H-indazoles for the treatment of glaucoma. US Patent 7338972
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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