9-Aminomethyl-9,10-dihydroanthracene

AMDA (9-Aminomethyl-9,10-dihydroanthracene) is an organic compound which acts as a potent and selective antagonist for the 5-HT2A receptor.[1] It has been used to help study the shape of the 5-HT2A protein,[2] and develop a large family of related derivatives with even higher potency and selectivity.[3][4][5][6][7]

9-Aminomethyl-9,10-dihydroanthracene
Identifiers
IUPAC name
  • 1-(9,10-Dihydroanthracen-9-yl)methanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H15N
Molar mass209.292 g·mol−1
3D model (JSmol)
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)

References
  1. Westkaemper RB, Runyon SP, Bondarev ML, Savage JE, Roth BL, Glennon RA (September 1999). "9-(Aminomethyl)-9,10-dihydroanthracene is a novel and unlikely 5-HT2A receptor antagonist". European Journal of Pharmacology. 380 (1): R5-7. doi:10.1016/S0014-2999(99)00525-7. PMID 10513561.
  2. Runyon SP, Peddi S, Savage JE, Roth BL, Glennon RA, Westkaemper RB (April 2002). "Geometry-affinity relationships of the selective serotonin receptor ligand 9-(aminomethyl)-9,10-dihydroanthracene". Journal of Medicinal Chemistry. 45 (8): 1656–64. doi:10.1021/jm010354g. PMID 11931619.
  3. 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): 335–7. doi:10.1016/j.ejphar.2003.09.059. PMID 14660041.
  4. 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): 2279–83. doi:10.1016/j.bmcl.2004.02.014. PMID 15081025.
  5. Dewkar GK, Peddi S, Mosier PD, Roth BL, Westkaemper RB (October 2008). "Methoxy-substituted 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives exhibit differential binding affinities at the 5-HT(2A) receptor". Bioorganic & Medicinal Chemistry Letters. 18 (19): 5268–71. doi:10.1016/j.bmcl.2008.08.059. PMC 3082371. PMID 18774714.
  6. Runyon SP, Mosier PD, Roth BL, Glennon RA, Westkaemper RB (November 2008). "Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: a ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation". Journal of Medicinal Chemistry. 51 (21): 6808–28. doi:10.1021/jm800771x. PMC 3088499. PMID 18847250.
  7. Shah JR, Mosier PD, Peddi S, Roth BL, Westkaemper RB (February 2010). "9-Aminomethyl-9,10-dihydroanthracene (AMDA) analogs as structural probes for steric tolerance in 5-HT2A and H1 receptor binding sites". Bioorganic & Medicinal Chemistry Letters. 20 (3): 935–8. doi:10.1016/j.bmcl.2009.12.064. PMC 3252747. PMID 20045641.
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