2-Aminotetralin

2-Aminotetralin (2-AT), also known as 1,2,3,4-tetrahydronaphthalen-2-amine (THN), is a stimulant drug of the 2-aminotetralin family with a chemical structure consisting of a tetralin core with an amine as substituent.^[1][2]

Other names2-AT; 1,2,3,4-Tetrahydronaphthalen-2-amine; THN

Routes of
administrationOral

Drug classNorepinephrine–dopamine releasing agent; Stimulant

ATC code

• None

Quick facts Clinical data, Other names ...

2-Aminotetralin

Clinical data
Other names	2-AT; 1,2,3,4-Tetrahydronaphthalen-2-amine; THN
Routes of administration	Oral
Drug class	Norepinephrine–dopamine releasing agent; Stimulant
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 Y
PubChem CID	34677
ChemSpider	31912 Y
UNII	LGX8T83G7X
ChEMBL	ChEMBL30294 Y
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 Y Key:LCGFVWKNXLRFIF-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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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]