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SpAMDA

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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.[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

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References

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  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.
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