1-Aminomethyl-5-methoxyindane

AMMI
Clinical data
Other names	AMMI
Drug class	Selective serotonin releasing agent (SSRA); Possible entactogen
ATC code	None;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name (5-Methoxy-2,3-dihydro-1H-inden-1-yl)methanamine;
CAS Number	1415750-28-5 N;
PubChem CID	45091234;
ChemSpider	24205063 Y;
UNII	585V6BDH9X;
CompTox Dashboard (EPA)	DTXSID801029881 ;
Chemical and physical data
Formula	C11H15NO
Molar mass	177.247 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES NCC1CCc2c1ccc(OC)c2;
	InChI InChI=1S/C11H15NO/c1-13-10-4-5-11-8(6-10)2-3-9(11)7-12/h4-6,9H,2-3,7,12H2,1H3 Y; Key:WPBKCMLYKMDWRD-UHFFFAOYSA-N Y;
	NY (what is this?) (verify)

Chemical compound

Pharmaceutical compound

1-Aminomethyl-5-methoxyindane (AMMI), is a drug developed by a team led by David E. Nichols at Purdue University, which acts as a selective serotonin releasing agent (SSRA) and binds to the serotonin transporter (SERT) with similar affinity relative to DFMDA (K_i = 2,000 nM).^[1]^[2]^[3]

References

↑ 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. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
↑ Roman DL, Saldaña SN, Nichols DE, Carroll FI, Barker EL (February 2004). "Distinct molecular recognition of psychostimulants by human and Drosophila serotonin transporters". The Journal of Pharmacology and Experimental Therapeutics. 308 (2): 679–687. doi:10.1124/jpet.103.057836. PMID 14593087. S2CID 6439942.
↑ Walline CC, Nichols DE, Carroll FI, Barker EL (June 2008). "Comparative molecular field analysis using selectivity fields reveals residues in the third transmembrane helix of the serotonin transporter associated with substrate and antagonist recognition". The Journal of Pharmacology and Experimental Therapeutics. 325 (3): 791–800. doi:10.1124/jpet.108.136200. PMC 2637348. PMID 18354055.