Chemistry:2-Aminotetralin

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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]

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, and 7-AB.[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

  • Substituted 2-aminotetralin
  • 1-Aminotetralin
  • Aminoindane

References

  1. ↑ 1.0 1.1 1.2 1.3 "Structural variation and (+)-amphetamine-like discriminative stimulus properties". Pharmacology, Biochemistry, and Behavior 38 (3): 581–586. March 1991. doi:10.1016/0091-3057(91)90017-V. PMID 2068194. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=77437efa02b4a0f688e4038b153ddfafde6da614. "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. ↑ "Actions of dexamphetamine and amphetamine-like amines in chickens with brain transections". British Journal of Pharmacology 42 (4): 522–542. August 1971. doi:10.1111/j.1476-5381.1971.tb07138.x. PMID 5116035. 
  3. ↑ 3.0 3.1 3.2 "Structure-activity studies on amphetamine analogs using drug discrimination methodology". Pharmacol Biochem Behav 21 (6): 895–901. December 1984. doi:10.1016/s0091-3057(84)80071-4. PMID 6522418. 
  4. ↑ "A new, potent, conformationally restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene". Journal of Medicinal Chemistry 25 (5): 535–538. May 1982. doi:10.1021/jm00347a011. PMID 6123601. 
  5. ↑ "Evidence for inhibition of the reuptake of 5-hydroxytryptamine and noradrenaline by tetrahydronaphthylamine in rat brain". British Journal of Pharmacology 42 (2): 281–286. June 1971. doi:10.1111/j.1476-5381.1971.tb07109.x. PMID 5091160. 
  6. ↑ "Role of noradrenaline and 5-hydroxytryptamine in tetrahydronaphthylamine-induced temperature changes in the rat". British Journal of Pharmacology 43 (1): 1–9. September 1971. doi:10.1111/j.1476-5381.1971.tb07151.x. PMID 4257629. 
  7. ↑ "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. 1978. pp. 70–83. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=7ec3b34f01bca1140244abd0c87473cf38701e50#page=81. 
  8. ↑ "Potential psychotomimetics. 2. Rigid analogs of 2,5-dimethoxy-4-methylphenylisopropylamine (DOM, STP)". J Med Chem 17 (2): 161–166. February 1974. doi:10.1021/jm00248a004. PMID 4809251. 



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