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SpAMDA, also known as spiro-AMDA or as spiro[9,10-dihydroanthracene]-9,3′-pyrrolidine, is a serotonin 5-HT2A receptor antagonist of the phenethylamine family.[1][2][3] It is a tricyclic and spiro cyclized phenethylamine and is an analogue of AMDA.[1][2][3]

The drug shows high affinity for the serotonin 5-HT2A receptor (Ki = 4 nM) and has 5-fold higher affinity than AMDA.[1][2][3] Its A2 value for serotonin 5-HT2A receptor antagonism is 79 nM.[2] In addition to the serotonin 5-HT2A receptor, SpAMDA shows 6-fold lower affinity for the serotonin 5-HT2C receptor (Ki = 24 nM), but no affinity for several other targets, such as the dopamine D2 receptor among others.[3]

The chemical synthesis of SpAMDA has been described.[2][3] Various analogues of SpAMDA have been described.[1][3]

SpAMDA was first described in the scientific literature by Richard Glennon and Bryan L. Roth and colleagues in 2003.[1][2][3]

See also

References

  1. ^ a b c d e Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
  2. ^ a b c d e f Peddi S, Roth BL, Glennon RA, Westkaemper RB (December 2003). “Spiro[9,10-dihydroanthracene]-9,3′-pyrrolidine-a structurally unique tetracyclic 5-HT2A receptor antagonist”. European Journal of Pharmacology. 482 (1–3): 335–337. doi:10.1016/j.ejphar.2003.09.059. PMID 14660041.
  3. ^ a b c d e f g Peddi S, Roth BL, Glennon RA, Westkaemper RB (May 2004). “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. Bibcode:2004BMCL…14.2279P. doi:10.1016/j.bmcl.2004.02.014. PMID 15081025.