9-Aminomethyl-9,10-dihydroanthracene

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
PubChemCID	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)

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_2Areceptor.^[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 selectivity.^{[4][5][6][7][8]}

See also

• Cyclized phenethylamine
• Serotonin 5-HT_2A receptor antagonist
• 4-PhPr-PEA

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. pp. 79, 275–286, 500–502. ISBN 978-3-03788-700-4. OCLC 858805226.
2. 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–R7. doi:10.1016/S0014-2999(99)00525-7. PMID 10513561.
3. 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): 1656–1664. doi:10.1021/jm010354g. PMID 11931619.
4. 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.
5. 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. doi:10.1016/j.bmcl.2004.02.014. PMID 15081025.
6. 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): 5268–5271. doi:10.1016/j.bmcl.2008.08.059. PMC 3082371. PMID 18774714.
7. 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): 6808–6828. doi:10.1021/jm800771x. PMC 3088499. PMID 18847250.
8. 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): 935–938. doi:10.1016/j.bmcl.2009.12.064. PMC 3252747. PMID 20045641.