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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|D<sub>3</sub> receptor]] subtype,<ref name="pmid2830544">{{cite journal |vauthors=Mulder TB, de Vries JB, Dijkstra D, Wiechers JW, Grol CJ, Horn AS |title=Further in vitro and in vivo studies with the putative presynaptic dopamine agonist N,N-dipropyl-7-hydroxy-2-aminotetralin |journal=Naunyn-Schmiedeberg's Archives of Pharmacology |volume=336 |issue=5 |pages=494–501 |date=November 1987 |pmid=2830544 |doi= 10.1007/bf00169305|s2cid=20846810 }}</ref><ref name="pmid1518841">{{cite journal |vauthors=Lévesque D, Diaz J, Pilon C, Martres MP, Giros B, Souil E, Schott D, Morgat JL, Schwartz JC, Sokoloff P |title=Identification, characterization, and localization of the dopamine D3 receptor in rat brain using 7-[3H]hydroxy-N,N-di-n-propyl-2-aminotetralin |journal=Proceedings of the National Academy of Sciences of the United States of America |volume=89 |issue=17 |pages=8155–9 |date=September 1992 |pmid=1518841 |pmc=49875 |doi= 10.1073/pnas.89.17.8155|bibcode=1992PNAS...89.8155L |doi-access=free }}</ref><ref name="pmid8759022">{{cite journal |author =Lévesque D |title=Aminotetralin drugs and D3 receptor functions. What may partially selective D3 receptor ligands tell us about dopamine D3 receptor functions? |journal=[[Biochemical Pharmacology (journal)|Biochemical Pharmacology]] |volume=52 |issue=4 |pages=511–8 |date=August 1996 |pmid=8759022 |doi= 10.1016/0006-2952(96)00239-0}}</ref> and low affinity for [[serotonin receptor]]s, unlike its [[structural isomer]] [[8-OH-DPAT]].<ref name="pmid2959776">{{cite journal |vauthors=Arvidsson LE, Johansson AM, Hacksell U, Nilsson JL, Svensson K, Hjorth S, Magnusson T, Carlsson A, Andersson B, Wikström H |title=(+)-cis-8-Hydroxy-1-methyl-2-(di-n-propylamino)tetralin: a potent and highly stereoselective 5-hydroxytryptamine receptor agonist |journal=Journal of Medicinal Chemistry |volume=30 |issue=11 |pages=2105–9 |date=November 1987 |pmid=2959776 |doi= 10.1021/jm00394a029}}</ref><ref name="pmid8078492">{{cite journal |vauthors=Malmberg A, Nordvall G, Johansson AM, Mohell N, Hacksell U |title=Molecular basis for the binding of 2-aminotetralins to human dopamine D2A and D3 receptors |journal=Molecular Pharmacology |volume=46 |issue=2 |pages=299–312 |date=August 1994 |pmid=8078492 }}</ref><ref name="pmid11472307">{{cite journal |vauthors=Eltayb A, Lindblom S, Oerther S, Ahlenius S |title=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 |journal=Acta Physiologica Scandinavica |volume=172 |issue=3 |pages=205–9 |date=July 2001 |pmid=11472307 |doi= 10.1046/j.1365-201x.2001.00858.x}}</ref> 7-OH-DPAT is self-administered in several animal models, and is used to study addiction to [[cocaine]].<ref>{{Cite journal
'''7-OH-DPAT''' is a synthetic compound that acts as a [[dopamine receptor]] [[agonist]] with reasonable selectivity for the [[D3 receptor|D<sub>3</sub> receptor]] subtype,<ref name="pmid2830544">{{cite journal |vauthors=Mulder TB, de Vries JB, Dijkstra D, Wiechers JW, Grol CJ, Horn AS |title=Further in vitro and in vivo studies with the putative presynaptic dopamine agonist N,N-dipropyl-7-hydroxy-2-aminotetralin |journal=Naunyn-Schmiedeberg's Archives of Pharmacology |volume=336 |issue=5 |pages=494–501 |date=November 1987 |pmid=2830544 |doi= 10.1007/bf00169305|s2cid=20846810 }}</ref><ref name="pmid1518841">{{cite journal |vauthors=Lévesque D, Diaz J, Pilon C, Martres MP, Giros B, Souil E, Schott D, Morgat JL, Schwartz JC, Sokoloff P |title=Identification, characterization, and localization of the dopamine D3 receptor in rat brain using 7-[3H]hydroxy-N,N-di-n-propyl-2-aminotetralin |journal=Proceedings of the National Academy of Sciences of the United States of America |volume=89 |issue=17 |pages=8155–9 |date=September 1992 |pmid=1518841 |pmc=49875 |doi= 10.1073/pnas.89.17.8155|bibcode=1992PNAS...89.8155L |doi-access=free }}</ref><ref name="pmid8759022">{{cite journal |author =Lévesque D |title=Aminotetralin drugs and D3 receptor functions. What may partially selective D3 receptor ligands tell us about dopamine D3 receptor functions? |journal=[[Biochemical Pharmacology (journal)|Biochemical Pharmacology]] |volume=52 |issue=4 |pages=511–8 |date=August 1996 |pmid=8759022 |doi= 10.1016/0006-2952(96)00239-0}}</ref> and low affinity for [[serotonin receptor]]s, unlike its [[structural isomer]] [[8-OH-DPAT]].<ref name="pmid2959776">{{cite journal |vauthors=Arvidsson LE, Johansson AM, Hacksell U, Nilsson JL, Svensson K, Hjorth S, Magnusson T, Carlsson A, Andersson B, Wikström H |title=(+)-cis-8-Hydroxy-1-methyl-2-(di-n-propylamino)tetralin: a potent and highly stereoselective 5-hydroxytryptamine receptor agonist |journal=Journal of Medicinal Chemistry |volume=30 |issue=11 |pages=2105–9 |date=November 1987 |pmid=2959776 |doi= 10.1021/jm00394a029}}</ref><ref name="pmid8078492">{{cite journal |vauthors=Malmberg A, Nordvall G, Johansson AM, Mohell N, Hacksell U |title=Molecular basis for the binding of 2-aminotetralins to human dopamine D2A and D3 receptors |journal=Molecular Pharmacology |volume=46 |issue=2 |pages=299–312 |date=August 1994 |pmid=8078492 }}</ref><ref name="pmid11472307">{{cite journal |vauthors=Eltayb A, Lindblom S, Oerther S, Ahlenius S |title=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 |journal=Acta Physiologica Scandinavica |volume=172 |issue=3 |pages=205–9 |date=July 2001 |pmid=11472307 |doi= 10.1046/j.1365-201x.2001.00858.x}}</ref> 7-OH-DPAT is self-administered in several animal models, and is used to study its addiction effects to [[cocaine]].<ref>{{Cite journal
| doi = 10.1016/0014-2999(95)00411-D
| doi = 10.1016/0014-2999(95)00411-D
| last1 = Acri | first1 = J. B.
| last1 = Acri | first1 = J. B.

Revision as of 02:43, 26 January 2024

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)
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 ?)

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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