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2-Aminotetralin

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
2-Aminotetralin
Clinical data
Other names2-AT; 1,2,3,4-Tetrahydronaphthalen-2-amine; THN
Routes of
administration
Oral
Drug classNorepinephrine–dopamine releasing agent;Stimulant
ATC code
  • None
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 1,2,3,4-tetrahydronaphthalen-2-amine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.019.067Edit this at Wikidata
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 checkY
  • Key:LCGFVWKNXLRFIF-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

2-Aminotetralin (2-AT), also known as1,2,3,4-tetrahydronaphthalen-2-amine (THN), is astimulantdrug of the2-aminotetralin family with achemical structure consisting of atetralin core with anamine assubstituent.[1][2]

2-AT is a rigidanalogue ofphenylisobutylamine and fully substitutes ford-amphetamine in ratdrug discrimination tests, although at one-half to one-eighth thepotency.[1][3] It showed greater potency than a variety of other amphetamine homologues, including2-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, and7-ABTooltip 7-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene.[3][1][4]

2-AT has been shown toinhibit thereuptake ofserotonin andnorepinephrine, and might induce theirrelease as well.[5][6] It is also likely to act ondopamine on account of its full substitution of d-amphetamine inrodent studies.[1][3]

Chemical derivatives

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A number ofderivatives of 2-aminotetralin exist, including:

See also

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References

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  1. ^abcdOberlender 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.In previous studies, 2-AT either did not stimulate spontaneous motor activity in mice (1,8), or it had 10% of the activity of amphetamine (24). Yet, in the present study, it mimicked (+)-amphetamine as a DS in rats, in agreement with the results of Glennon et al. (7). However, 2-AT was one-half as potent as (+)-amphetamine in that study but only one-eighth as potent as (+)-amphetamine in the present experiment.
  2. ^Marley E, Stephenson JD (August 1971)."Actions of dexamphetamine and amphetamine-like amines in chickens with brain transections".British Journal of Pharmacology.42 (4):522–542.doi:10.1111/j.1476-5381.1971.tb07138.x.PMC 1665761.PMID 5116035.
  3. ^abcGlennon 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.
  4. ^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.
  5. ^Bruinvels J (June 1971)."Evidence for inhibition of the reuptake of 5-hydroxytryptamine and noradrenaline by tetrahydronaphthylamine in rat brain".British Journal of Pharmacology.42 (2):281–286.doi:10.1111/j.1476-5381.1971.tb07109.x.PMC 1667157.PMID 5091160.
  6. ^Bruinvels J, Kemper GC (September 1971)."Role of noradrenaline and 5-hydroxytryptamine in tetrahydronaphthylamine-induced temperature changes in the rat".British Journal of Pharmacology.43 (1):1–9.doi:10.1111/j.1476-5381.1971.tb07151.x.PMC 1665934.PMID 4257629.
  7. ^Nichols DE, Weintraub HJ, Pfister WR, Yim GK (1978)."The Use of Rigid Analogues to Probe Hallucinogen Receptors".QuaSAR, Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. Department of Health, Education, and Welfare, Public Health Service, Alcohol, Drug Abuse, and Mental Health Administration. pp. 70–83.
  8. ^Nichols DE, Barfknecht CF, Long JP, Standridge RT, Howell HG, Partyka RA, Dyer DC (February 1974). "Potential psychotomimetics. 2. Rigid analogs of 2,5-dimethoxy-4-methylphenylisopropylamine (DOM, STP)".J Med Chem.17 (2):161–166.doi:10.1021/jm00248a004.PMID 4809251.

External links

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