2-Aminotetralin

2-Aminotetralin
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name 1,2,3,4-tetrahydronaphthalen-2-amine;
CAS Number	2954-50-9 ;
PubChem CID	34677;
ChemSpider	31912 ;
UNII	LGX8T83G7X;
ChEMBL	ChEMBL30294 ;
CompTox Dashboard (EPA)	DTXSID10903058 ;
ECHA InfoCard	100.019.067
Chemical and physical data
Formula	C10H13N
Molar mass	147.221 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CC2=CC=CC=C2CC1N;
	InChI InChI=1S/C10H13N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4,10H,5-7,11H2 ; Key:LCGFVWKNXLRFIF-UHFFFAOYSA-N ;
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2-Aminotetralin (2-AT), also known as 1,2,3,4-tetrahydronaphthalen-2-amine (THN), is a stimulant drug with a chemical structure consisting of a tetralin group combined with an amine.^[1]^[2]

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2-AT is a rigid analogue of phenylisobutylamine and fully substitutes for d-amphetamine in rat drug discrimination tests, although at one-half to one-eighth the potency.^[1]^[3] It showed greater potency than a variety of other amphetamine homologues, including 2-amino-1,2-dihydronapthalene (2-ADN), 2-aminoindane (2-AI), 1-naphthylaminopropane (1-NAP), 2-naphthylaminopropane (2-NAP), 1-phenylpiperazine (1-PP), 6-ABTooltip 6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene, and 7-ABTooltip 7-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene.^[3]^[1]^[4]

2-AT has been shown to inhibit the reuptake of serotonin and norepinephrine, and might induce their release as well.^[5]^[6] It is also likely to act on dopamine on account of its full substitution of d-amphetamine in rodent studies.^[1]^[3]

Chemical derivatives