2-Amino-1,2-dihydronaphthalene

2-Amino-1,2-dihydronaphthalene
Clinical data
Other names2-ADN; ADN
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 1,2-dihydronaphthalen-2-amine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H11N
Molar mass145.205 g·mol−1
3D model (JSmol)
  • c2ccc1c(\C=C/C(N)C1)c2
  • InChI=1S/C10H11N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-6,10H,7,11H2 checkY
  • Key:SHLZSYAMFQNEOF-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

2-Amino-1,2-dihydronapthalene (2-ADN or ADN) is a stimulant drug.[1][2] It is a rigid analogue of phenylisobutylamine and substitutes for amphetamine in rat drug discrimination tests, although at approximately one-fourth the potency.[1][2]

The drug is closely related to 2-aminotetralin (2-AT; 2-amino-1,2,3,4-tetrahydronaphthalene), which also substitutes for amphetamine, and is about twice as potent as 2-AT in substituting for amphetamine.[1][2] Other homologous and rigid analogues of amphetamine besides 2-ADN and 2-AT include 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][2]

See also

References

  1. ^ a b c Hathaway BA, Nichols DE, Nichols MB, Yim GK (May 1982). "A new, potent, conformationally restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene". Journal of Medicinal Chemistry. 25 (5): 535–538. doi:10.1021/jm00347a011. PMID 6123601.
  2. ^ a b c d Oberlender R, Nichols DE (March 1991). "Structural variation and (+)-amphetamine-like discriminative stimulus properties". Pharmacology, Biochemistry, and Behavior. 38 (3): 581–586. doi:10.1016/0091-3057(91)90017-V. PMID 2068194. S2CID 19069907.
  3. ^ Glennon RA, Young R, Hauck AE, McKenney JD (December 1984). "Structure-activity studies on amphetamine analogs using drug discrimination methodology". Pharmacol Biochem Behav. 21 (6): 895–901. doi:10.1016/s0091-3057(84)80071-4. PMID 6522418.