7-OH-DPAT

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 addiction to cocaine.[8][9][10][11][12]

7-OH-DPAT
Kekulé, skeletal formula of 7-OH-DPAT
Names
IUPAC name
7-Hydroxy-N,N-dipropyl-2-aminotetralin
Systematic IUPAC name
7-(Dipropylamino)-5,6,7,8-tetrahydronaphthalen-2-ol[1]
Identifiers
3D model (JSmol)
Abbreviations 7-OH-DPAT
ChEMBL
ChemSpider
MeSH 7-Hydroxy-2-N,N-dipropylaminotetralin
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 checkY
    Key: BLYMJBIZMIGWFK-UHFFFAOYSA-N checkY
  • 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).
☒N verify (what is checkY☒N ?)
Infobox references

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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