7-OH-DPAT

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7-OH-DPAT
IUPAC name

7-Hydroxy-N,N-dipropyl-2-aminotetralin[citation needed]

Systematic name

7-(Dipropylamino)-5,6,7,8-tetrahydronaphthalen-2-ol[1]

Identifiers
Abbreviations 7-OH-DPAT
CAS number 74938-11-7 N
PubChem 1219, 6603867 (R), 23928184 (S)
ChemSpider 1182 YesY, 5036175 (R) YesY
MeSH 7-Hydroxy-2-N,N-dipropylaminotetralin
ChEMBL CHEMBL285755 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C16H25NO
Molar mass 247.38 g mol−1
log P 3.653
Acidity (pKa) 10.389
Basicity (pKb) 3.608
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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]

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. PMID 2830544. 
  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. 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. PMID 8739545. 
  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. PMID 8724444. 
  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. 
  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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