Chemistry:9-Aminomethyl-9,10-dihydroanthracene

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AMDA, also known as 9-aminomethyl-9,10-dihydroanthracene, is a tricyclic compound and cyclized phenethylamine which acts as a potent and selective antagonist for the 5-HT2A receptor (Ki = 20 nM).[1][2] It has been used to help study the shape of the 5-HT2A protein,[3] and develop a large family of related derivatives with even higher potency and selectivity.[4][5][6][7][8]

File:AMDH structure.svg
AMDH structure.[1]

Another related compound is AMDH, in which the central cyclohexane ring of AMDA has instead been expanded into a cycloheptane ring.[1][9] As with AMDA, AMDH shows affinity for the serotonin 5-HT2A receptor (Ki = 112 nM).[1]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 (in de) Phenethylamine: von der Struktur zur Funktion. Nachtschatten-Science (1 ed.). Solothurn: Nachtschatten-Verlag. 2013. pp. 79, 275–286, 500–502. ISBN 978-3-03788-700-4. OCLC 858805226. https://books.google.com/books?id=-Us1kgEACAAJ. 
  2. ↑ "9-(Aminomethyl)-9,10-dihydroanthracene is a novel and unlikely 5-HT2A receptor antagonist". European Journal of Pharmacology 380 (1): R5–R7. September 1999. doi:10.1016/S0014-2999(99)00525-7. PMID 10513561. 
  3. ↑ "Geometry-affinity relationships of the selective serotonin receptor ligand 9-(aminomethyl)-9,10-dihydroanthracene". Journal of Medicinal Chemistry 45 (8): 1656–1664. April 2002. doi:10.1021/jm010354g. PMID 11931619. 
  4. ↑ "Spiro[9,10-dihydroanthracene]-9,3'-pyrrolidine-a structurally unique tetracyclic 5-HT2A receptor antagonist". European Journal of Pharmacology 482 (1–3): 335–337. December 2003. doi:10.1016/j.ejphar.2003.09.059. PMID 14660041. 
  5. ↑ "Structural determinants for high 5-HT(2A) receptor affinity of spiro[9,10-dihydroanthracene]-9,3(')-pyrrolidine (SpAMDA)". Bioorganic & Medicinal Chemistry Letters 14 (9): 2279–2283. May 2004. doi:10.1016/j.bmcl.2004.02.014. PMID 15081025. 
  6. ↑ "Methoxy-substituted 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives exhibit differential binding affinities at the 5-HT(2A) receptor". Bioorganic & Medicinal Chemistry Letters 18 (19): 5268–5271. October 2008. doi:10.1016/j.bmcl.2008.08.059. PMID 18774714. 
  7. ↑ "Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: a ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation". Journal of Medicinal Chemistry 51 (21): 6808–6828. November 2008. doi:10.1021/jm800771x. PMID 18847250. 
  8. ↑ "9-Aminomethyl-9,10-dihydroanthracene (AMDA) analogs as structural probes for steric tolerance in 5-HT2A and H1 receptor binding sites". Bioorganic & Medicinal Chemistry Letters 20 (3): 935–938. February 2010. doi:10.1016/j.bmcl.2009.12.064. PMID 20045641. 
  9. ↑ "PiHKAL·info". 12 June 2025. https://isomerdesign.com/pihkal/explore/12057. 



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