9-Aminomethyl-9,10-dihydroanthracene

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-HT_2A receptor (K_i = 20 nM).^[1][2] It has been used to help study the shape of the 5-HT_2A protein,^[3] and develop a large family of related derivatives with even higher potency and/or selectivity.^{[4][5][6][7][8]}

Other names9-Aminomethyl-9,10-dihydroanthracene

Drug classSerotonin 5-HT_2A receptor antagonist

ATC code

• None

CAS Number

• 22136-76-1 ^N

Quick facts Clinical data, Other names ...

AMDA

Clinical data
Other names	9-Aminomethyl-9,10-dihydroanthracene
Drug class	Serotonin 5-HT2A receptor antagonist
ATC code	None
Identifiers
IUPAC name 1-(9,10-dihydroanthracen-9-yl)methanamine
CAS Number	22136-76-1 N
PubChem CID	10398175
ChemSpider	8573613 Y
UNII	JG5GX32FDE
ChEMBL	ChEMBL47482 Y
CompTox Dashboard (EPA)	DTXSID80439253
Chemical and physical data
Formula	C15H15N
Molar mass	209.292 g·mol−1
3D model (JSmol)	Interactive image
SMILES c3cccc1c3Cc2ccccc2C1CN
InChI InChI=1S/C15H15N/c16-10-15-13-7-3-1-5-11(13)9-12-6-2-4-8-14(12)15/h1-8,15H,9-10,16H2 Y Key:GEICAQNIOJFRQN-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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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 good affinity for the serotonin 5-HT_2A receptor (K_i = 112 nM).^[1]