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Chemical Compound Review

Aminotetralin     1,2,3,4-tetrahydronaphthalen- 1-amine

Synonyms: zlchem 415, PubChem14041, SureCN40422, ACMC-1BMQF, AG-E-62211, ...
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Disease relevance of Tetrahydro-beta-naphthylamine


Psychiatry related information on Tetrahydro-beta-naphthylamine


High impact information on Tetrahydro-beta-naphthylamine

  • The fact that 11 (Ki = 206 microM) is more potent than analogues 4 (Ki = 1296 microM) and 5 (Ki = 479 microM), with a half-boat 2AT moiety, suggests that PNMT preferentially binds the half-chair conformation of 2AT at the active site [3].
  • The results of the present study show that this bulky functionality is also tolerated by the receptor when incorporated into examples of all other major classes of 5-HT1A agents (e.g., 2-aminotetralin, phenylalklamine, indolylalkylamine, and (aryloxy)alkylamine derivatives) [4].
  • The corresponding trans isomer 10 is not a substrate, in spite of enhanced active site interactions with respect to the parent analogue (2-aminotetralin, 4) [5].
  • An improved route to 2-aminotetralin systems has been utilized for some of the compounds, which involves Pummerer rearrangement and cyclization of beta-keto sulfoxides and reductive amination of beta-tetralones with a NaBH4-carboxylic acid complex [6].
  • In our attempts to elucidate the prolactin release inhibiting pharmacophore within the ergoline structure, we have prepared one indolealkylamine and several 2-aminotetralin derivatives [7].

Biological context of Tetrahydro-beta-naphthylamine


Anatomical context of Tetrahydro-beta-naphthylamine


Associations of Tetrahydro-beta-naphthylamine with other chemical compounds

  • These findings led us to synthesize a series of polyamine derivatives of 1-aminoindan and 1-aminotetralin and to determine their effects in several in vitro and in vivo models of neurotrauma [15].
  • Thus, a series of 35 differently substituted 2-aminotetralin-derived substituted benzamides was synthesized and the compounds were evaluated for their ability to compete for [3H]-raclopride binding to cloned human dopamine D2A and D3 receptors, and for [3H]-8-OH-DPAT binding to rat serotonin 5-HT1A receptors in vitro [16].

Analytical, diagnostic and therapeutic context of Tetrahydro-beta-naphthylamine


  1. Stereoselective metabolism of two keto-pyrrol analogues of 8-hydroxy-2-dipropyl-aminotetralin by freshly isolated rat hepatocytes. Wood, S.A., Parton, A.H., Simmonds, R.J., Stevenson, D. Chirality. (1996) [Pubmed]
  2. Comparison of the anorectic and motor activity effects of some aminoindanes, 2-aminotetralin and amphetamine in the rat. Mrongovius, R.I., Bolt, A.G., Hellyer, R.O. Clin. Exp. Pharmacol. Physiol. (1978) [Pubmed]
  3. Conformational and steric aspects of phenylethanolamine and phenylethylamine analogues as substrates or inhibitors of phenylethanolamine N-methyltransferase. Grunewald, G.L., Ye, Q., Sall, D.J., Criscione, K.R., Wise, B. Mol. Pharmacol. (1989) [Pubmed]
  4. N-(phthalimidoalkyl) derivatives of serotonergic agents: a common interaction at 5-HT1A serotonin binding sites? Glennon, R.A., Naiman, N.A., Pierson, M.E., Smith, J.D., Ismaiel, A.M., Titeler, M., Lyon, R.A. J. Med. Chem. (1989) [Pubmed]
  5. Conformational requirements of substrates for activity with phenylethanolamine N-methyltransferase. Grunewald, G.L., Ye, Q., Kieffer, L., Monn, J.A. J. Med. Chem. (1988) [Pubmed]
  6. Cerebral dopamine agonist properties of some 2-aminotetralin derivatives after peripheral and intracerebral administration. Cannon, J.G., Lee, T., Goldman, H.D. J. Med. Chem. (1977) [Pubmed]
  7. Ergoline congeners as potential inhibitors of prolactin release. 2. Rusterholz, D.B., Barfknecht, C.F., Clemens, J.A. J. Med. Chem. (1976) [Pubmed]
  8. Inhibition of norepinephrine transport into synaptic vesicles by amphetamine analogs. Knepper, S.M., Grunewald, G.L., Rutledge, C.O. J. Pharmacol. Exp. Ther. (1988) [Pubmed]
  9. Oxidative deamination of alicyclic primary amines by liver microsomes from rats and rabbits. Kurebayashi, H., Tanaka, A., Yamaha, T., Tatahashi, A. Xenobiotica (1988) [Pubmed]
  10. Antinicotinic activity of some 2-aminotetralin derivatives. A structure-activity relationship study. Babaoglu, M.O., Aydos, T.R., Orer, H.S., Ilhan, M. Arzneimittel-Forschung. (1999) [Pubmed]
  11. Differential activation by some 2-aminotetralin derivatives of the receptor mechanisms in the nucleus accumbens of rats which mediate hyperactivity and stereotyped biting. Costall, B., Naylor, R.J., Cannon, J.G., Lee, T. Eur. J. Pharmacol. (1977) [Pubmed]
  12. Interaction of dihydroxy-2-aminotetralin derivatives at sites labelled with [3H]clonidine, [3H]prazosin and [3H]spiperone in rat brain membranes. Chatterjee, T.K., Bhatnagar, R.K., Cannon, J.G., Long, J.P. Eur. J. Pharmacol. (1984) [Pubmed]
  13. Effects of semirigid methoxamine analogs on vascular smooth muscle: studies of methoxy-2-aminotetralin and 2-aminoindane derivatives. Arnerić, S.P., Roetker, A., Long, J.P., Mott, J., Barfknecht, C.F. Archives internationales de pharmacodynamie et de thérapie. (1982) [Pubmed]
  14. Effects of a new 2-piperazinotetralin on alpha-1 and alpha-2 adrenergic receptors in isolated rat vas deferens. Mutafova-Yambolieva, V., Staneva-Stoytcheva, D., Ivanov, D. Methods and findings in experimental and clinical pharmacology. (1985) [Pubmed]
  15. Novel polyamine derivatives as neuroprotective agents. Gilad, G.M., Gilad, V.H. J. Pharmacol. Exp. Ther. (1999) [Pubmed]
  16. 2-aminotetralin-derived substituted benzamides with mixed dopamine D2, D3, and serotonin 5-HT1A receptor binding properties: a novel class of potential atypical antipsychotic agents. Homan, E.J., Copinga, S., Elfström, L., van der Veen, T., Hallema, J.P., Mohell, N., Unelius, L., Johansson, R., Wikström, H.V., Grol, C.J. Bioorg. Med. Chem. (1998) [Pubmed]
  17. Optimisation of the enantiomeric separation of 12 2-aminotetralin analogues using Chiral AGP high-performance liquid chromatography by simultaneous factorial design. Wood, S.A., Long, J.M., Simmonds, R.J., Bridges, J.W., Stevenson, D. Journal of pharmaceutical and biomedical analysis. (1997) [Pubmed]
  18. Circular dichroism studies of imide derivatives of amines. Ghislandi, V., La Manna, A. Il Farmaco; edizione scientifica. (1976) [Pubmed]
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