9-Aminomethyl-9,10-dihydroanthracene

9-Aminomethyl-9,10-dihydroanthracene
Identifiers
	IUPAC name 1-(9,10-Dihydroanthracen-9-yl)methanamine;
CAS Number	22136-76-1 ;
PubChem CID	10398175;
ChemSpider	8573613 ;
ChEMBL	ChEMBL47482 ;
CompTox Dashboard (EPA)	DTXSID80439253 ;
Chemical and physical data
Formula	C15H15N
Molar mass	209.286 g/mol 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 ; Key:GEICAQNIOJFRQN-UHFFFAOYSA-N ;
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AMDA (9-Aminomethyl-9,10-dihydroanthracene) is an organic compound which acts as a potent and selective antagonist for the 5-HT_2A receptor.[1] It has been used to help study the shape of the 5-HT_2A protein,[2] and develop a large family of related derivatives with even higher potency and selectivity.[3][4][5][6][7]

References

Westkaemper, RB; Runyon, SP; Bondarev, ML; Savage, JE; Roth, BL; Glennon, RA (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.
Runyon, SP; Peddi, S; Savage, JE; Roth, BL; Glennon, RA; Westkaemper, RB (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.
Peddi, S; Roth, BL; Glennon, RA; Westkaemper, RB (2003). "Spiro9,10-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.
Peddi, S; Roth, BL; Glennon, RA; Westkaemper, RB (2004). "Structural determinants for high 5-HT(2A) receptor affinity of spiro9,10-dihydroanthracene-9,3(')-pyrrolidine (SpAMDA)". Bioorganic & Medicinal Chemistry Letters. 14 (9): 2279–83. doi:10.1016/j.bmcl.2004.02.014. PMID 15081025.
Dewkar, GK; Peddi, S; Mosier, PD; Roth, BL; Westkaemper, RB (2008). "Methoxy-substituted 9-Aminomethyl-9,10-dihydroanthracene (AMDA) Derivatives Exhibit Differential Binding Affinities at the 5-HT2A Receptor". Bioorganic & Medicinal Chemistry Letters. 18 (19): 5268–71. doi:10.1016/j.bmcl.2008.08.059. PMC 3082371. PMID 18774714.
Runyon, SP; Mosier, PD; Roth, BL; Glennon, RA; Westkaemper, RB (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.
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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[1] Westkaemper, RB; Runyon, SP; Bondarev, ML; Savage, JE; Roth, BL; Glennon, RA (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 (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 (2003). "Spiro9,10-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 (2004). "Structural determinants for high 5-HT(2A) receptor affinity of spiro9,10-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 (2008). "Methoxy-substituted 9-Aminomethyl-9,10-dihydroanthracene (AMDA) Derivatives Exhibit Differential Binding Affinities at the 5-HT2A 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 (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.

[pmid20045641-7] 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.