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	209.292 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 ; 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 (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.
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.
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.
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.
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.
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.
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 (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.

[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.