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7-OH-DPAT

From Wikipedia, the free encyclopedia
Dopamine receptor agonist compound
7-OH-DPAT
Kekulé, skeletal formula of 7-OH-DPAT
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
MeSH7-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 mass247.382 g·mol−1
logP3.653
Acidity (pKa)10.389
Basicity (pKb)3.608
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

7-OH-DPAT is a synthetic compound that acts as adopamine receptoragonist with reasonable selectivity for theD3 receptor subtype,[2][3][4] and low affinity forserotonin receptors, unlike itsstructural isomer8-OH-DPAT.[5][6][7] 7-OH-DPAT is self-administered in several animal models, and is used to study its addiction effects tococaine.[8][9][10][11][12]

See also

[edit]

References

[edit]
  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.
D1-like
Agonists
PAMs
Antagonists
D2-like
Agonists
Antagonists


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