1-Aminomethylindane

1-Aminomethylindane
Names
	IUPAC name 2,3-dihydro-1H-inden-1-ylmethanamine
	Other names 1-AMI
Identifiers
CAS Number	54949-92-7;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL4569715;
ChemSpider	11365763;
EC Number	832-793-1;
PubChem CID	14348692;
CompTox Dashboard (EPA)	DTXSID80559228 ;
	InChI InChI=1S/C10H13N/c11-7-9-6-5-8-3-1-2-4-10(8)9/h1-4,9H,5-7,11H2 Key: QBHALBZXAXQBOY-UHFFFAOYSA-N;
	SMILES C1CC2=CC=CC=C2C1CN;
Properties
Chemical formula	C10H13N
Molar mass	147.221 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H315, H318, H335
Precautionary statements	P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1-Aminomethylindane (1-AMI) is a chemical compound and derivative of indane. It can also be thought of as a cyclized phenethylamine or β-phenethylamine derivative in which the side chain is cyclized with the benzene ring. 1-AMI is the parent compound of a group of psychedelic- and entactogen-related drugs that includes 1-aminomethyl-5-methoxyindane (1-AMMI; related to para-methoxyamphetamine (PMA)), 2CB-Ind (related to 2C-B), jimscaline (related to mescaline), and bromojimscaline (related to 2-bromomescaline).^[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. Retrieved 31 January 2025.
↑ Blaazer AR, Smid P, Kruse CG (September 2008). "Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT(2A) receptors". ChemMedChem. 3 (9): 1299–1309. doi:10.1002/cmdc.200800133. PMID 18666267.
↑ McLean TH, Chambers JJ, Parrish JC, Braden MR, Marona-Lewicka D, Kurrasch-Orbaugh D, Nichols DE (July 2006). "C-(4,5,6-trimethoxyindan-1-yl)methanamine: a mescaline analogue designed using a homology model of the 5-HT2A receptor". J Med Chem. 49 (14): 4269–4274. doi:10.1021/jm060272y. PMID 16821786.