7-OH-DPAT

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7-OH-DPAT
Kekule, skeletal formula of 7-OH-DPAT 7-OH-DPAT Structure.svg
Kekulé, skeletal formula of 7-OH-DPAT
Names
IUPAC name
7-Hydroxy-N,N-dipropyl-2-aminotetralin[ citation needed ]
Systematic IUPAC name
7-(Dipropylamino)-5,6,7,8-tetrahydronaphthalen-2-ol [1]
Identifiers
3D model (JSmol)
Abbreviations7-OH-DPAT
ChEMBL
ChemSpider
MeSH 7-Hydroxy-2-N,N-dipropylaminotetralin
PubChem CID
UNII
  • InChI=1S/C16H25NO/c1-3-9-17(10-4-2)15-7-5-13-6-8-16(18)12-14(13)11-15/h6,8,12,15,18H,3-5,7,9-11H2,1-2H3 Yes check.svgY
    Key: BLYMJBIZMIGWFK-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C16H25NO/c1-3-9-17(10-4-2)15-7-5-13-6-8-16(18)12-14(13)11-15/h6,8,12,15,18H,3-5,7,9-11H2,1-2H3
    Key: BLYMJBIZMIGWFK-UHFFFAOYAH
  • CCCN(CCC)C1CCc2ccc(O)cc2C1
  • CCCN(CCC)C1CCC2=C(C1)C=C(O)C=C2
Properties
C16H25NO
Molar mass 247.382 g·mol−1
log P 3.653
Acidity (pKa)10.389
Basicity (pKb)3.608
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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7-OH-DPAT is a synthetic compound that acts as a dopamine receptor agonist with reasonable selectivity for the D3 receptor subtype, [2] [3] [4] and low affinity for serotonin receptors, unlike its structural isomer 8-OH-DPAT. [5] [6] [7] 7-OH-DPAT is self-administered in several animal models, and is used to study its addiction effects to cocaine. [8] [9] [10] [11] [12]

See also

References

  1. ↑ "7-hydroxy-2-N,N-dipropylaminotetralin - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
  2. ↑ Mulder TB, de Vries JB, Dijkstra D, Wiechers JW, Grol CJ, Horn AS (November 1987). "Further in vitro and in vivo studies with the putative presynaptic dopamine agonist N,N-dipropyl-7-hydroxy-2-aminotetralin". Naunyn-Schmiedeberg's Archives of Pharmacology. 336 (5): 494–501. doi:10.1007/bf00169305. PMID   2830544. S2CID   20846810.
  3. ↑ Lévesque D, Diaz J, Pilon C, Martres MP, Giros B, Souil E, Schott D, Morgat JL, Schwartz JC, Sokoloff P (September 1992). "Identification, characterization, and localization of the dopamine D3 receptor in rat brain using 7-[3H]hydroxy-N,N-di-n-propyl-2-aminotetralin". Proceedings of the National Academy of Sciences of the United States of America. 89 (17): 8155–9. Bibcode:1992PNAS...89.8155L. doi: 10.1073/pnas.89.17.8155 . PMC   49875 . PMID   1518841.
  4. ↑ Lévesque D (August 1996). "Aminotetralin drugs and D3 receptor functions. What may partially selective D3 receptor ligands tell us about dopamine D3 receptor functions?". Biochemical Pharmacology . 52 (4): 511–8. doi:10.1016/0006-2952(96)00239-0. PMID   8759022.
  5. ↑ Arvidsson LE, Johansson AM, Hacksell U, Nilsson JL, Svensson K, Hjorth S, Magnusson T, Carlsson A, Andersson B, Wikström H (November 1987). "(+)-cis-8-Hydroxy-1-methyl-2-(di-n-propylamino)tetralin: a potent and highly stereoselective 5-hydroxytryptamine receptor agonist". Journal of Medicinal Chemistry. 30 (11): 2105–9. doi:10.1021/jm00394a029. PMID   2959776.
  6. ↑ Malmberg A, Nordvall G, Johansson AM, Mohell N, Hacksell U (August 1994). "Molecular basis for the binding of 2-aminotetralins to human dopamine D2A and D3 receptors". Molecular Pharmacology. 46 (2): 299–312. PMID   8078492.
  7. ↑ Eltayb A, Lindblom S, Oerther S, Ahlenius S (July 2001). "Additive hypothermic effects of the 5-HT1A receptor agonist 8-OH-DPAT and the dopamine D2/3 receptor agonist 7-OH-DPAT in the rat". Acta Physiologica Scandinavica. 172 (3): 205–9. doi:10.1046/j.1365-201x.2001.00858.x. PMID   11472307.
  8. ↑ Acri, J. B.; Carter, S. R.; Alling, K.; Geter-Douglass, B.; Dijkstra, D.; Wikström, H.; Katz, J. L.; Witkin, J. M. (1995). "Assessment of cocaine-like discriminative stimulus effects of dopamine D3 receptor ligands". European Journal of Pharmacology. 281 (2): R7 –R9. doi:10.1016/0014-2999(95)00411-D. PMID   7589197.
  9. ↑ Lamas, X.; Negus, S. S.; Nader, M. A.; Mello, N. K. (1996). "Effects of the putative dopamine D3 receptor agonist 7-OH-DPAT in rhesus monkeys trained to discriminate cocaine from saline". Psychopharmacology. 124 (4): 306–314. doi:10.1007/bf02247435. PMID   8739545. S2CID   27951018.
  10. ↑ Nader, M. A.; Mach, R. H. (1996). "Self-administration of the dopamine D3 agonist 7-OH-DPAT in rhesus monkeys is modified by prior cocaine exposure". Psychopharmacology. 125 (1): 13–22. doi:10.1007/bf02247388. PMID   8724444. S2CID   10593118.
  11. ↑ Barrett, A. C.; Miller, J. R.; Dohrmann, J. M.; Caine, S. B. (2004). "Effects of dopamine indirect agonists and selective D1-like and D2-like agonists and antagonists on cocaine self-administration and food maintained responding in rats". Neuropharmacology. 47: 256–273. doi:10.1016/j.neuropharm.2004.07.007. PMID   15464142. S2CID   2959198.
  12. ↑ Collins, G. T.; Butler, P.; Wayman, C.; Ratcliffe, S.; Gupta, P.; Oberhofer, G.; Caine, S. B. (2012). "Lack of abuse potential in a highly selective dopamine D3 agonist, PF-592,379, in drug self-administration and drug discrimination in rats". Behavioural Pharmacology. 23 (3): 280–291. doi:10.1097/FBP.0b013e3283536d21. PMC   3365486 . PMID   22470105.


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