2-Aminotetralin

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2-Aminotetralin
2-Aminotetralin Structure.svg
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 InfoCard 100.019.067 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C10H13N
Molar mass 147.221 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 Yes check.svgY
  • Key:LCGFVWKNXLRFIF-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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. [1] [2]

Contents

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-AB Tooltip 6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene, and 7-AB Tooltip 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

A number of derivatives of 2-aminotetralin exist, including:

See also

References

  1. 1 2 3 4 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. 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. 1 2 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.
  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.
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