SpAMDA

SpAMDA, also known as spiro-AMDA or as spiro[9,10-dihydroanthracene]-9,3'-pyrrolidine, is a serotonin 5-HT_2A 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]

Other namesSpiro[9,10-dihydroanthracene]-9,3'-pyrrolidine

Drug classSerotonin 5-HT_2A receptor antagonist

ATC code

• None

PubChem CID

• 10236153

Quick facts Clinical data, Other names ...

SpAMDA

Clinical data
Other names	Spiro[9,10-dihydroanthracene]-9,3'-pyrrolidine
Drug class	Serotonin 5-HT2A receptor antagonist
ATC code	None
Identifiers
IUPAC name spiro[9H-anthracene-10,3'-pyrrolidine]
PubChem CID	10236153
ChemSpider	8411641
ChEMBL	ChEMBL307956
Chemical and physical data
Formula	C17H17N
Molar mass	235.330 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1CNCC12C3=CC=CC=C3CC4=CC=CC=C24
InChI 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

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The drug shows high affinity for the serotonin 5-HT_2A receptor (K_i = 4 nM) and has 5-fold higher affinity than AMDA.^[1][2][3] Its A₂ value for serotonin 5-HT_2A receptor antagonism is 79 nM.^[2] In addition to the serotonin 5-HT_2A receptor, SpAMDA shows 6-fold lower affinity for the serotonin 5-HT_2C receptor (K_i = 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]