2-Aminotetralin

2-Aminotetralin
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 1,2,3,4-tetrahydronaphthalen-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.019.067
Chemical and physical data
FormulaC10H13N
Molar mass147.221 g·mol−1
3D model (JSmol)
  • C1CC2=CC=CC=C2CC1N
  • 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)

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 core with an amine as substituent.

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. 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.

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