Article · Wikipedia archive · Last revised Jun 17, 2026

SpAMDA

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. It is a tricyclic and spiro cyclized phenethylamine and is an analogue of AMDA.

Last revised
Jun 17, 2026
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≈ 1 min
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SpAMDA
Clinical data
Other namesSpiro[9,10-dihydroanthracene]-9,3'-pyrrolidine
Drug classSerotonin 5-HT2A receptor antagonist
ATC code
  • None
Identifiers
  • spiro[9H-anthracene-10,3'-pyrrolidine]
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC17H17N
Molar mass235.330 g·mol−1
3D model (JSmol)
  • C1CNCC12C3=CC=CC=C3CC4=CC=CC=C24
  • InChI=1S/C17H17N/c1-3-7-15-13(5-1)11-14-6-2-4-8-16(14)17(15)9-10-18-12-17/h1-8,18H,9-12H2
  • Key:LKSUTFUZSGZMOS-UHFFFAOYSA-N

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.123 It is a tricyclic and spiro cyclized phenethylamine and is an analogue of AMDA.123

The drug shows high affinity for the serotonin 5-HT2A receptor (Ki = 4 nM) and has 5-fold higher affinity than AMDA.123 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.23 Various analogues of SpAMDA have been described.13

SpAMDA was first described in the scientific literature by Richard Glennon and Bryan L. Roth and colleagues in 2003.123

See also

See also

References

References

  1. 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. 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. 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.
External links