fbpx
Wikipedia

7-OH-DPAT

December 15, 2023

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
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
  • 74938-11-7 Y
3D model (JSmol)
  • Interactive image
  • Interactive image
Abbreviations 7-OH-DPAT
ChEMBL
  • ChEMBL285755 Y
ChemSpider
  • 1182 Y
  • 5036175 (R) Y
  • 950
MeSH 7-Hydroxy-2-N,N-dipropylaminotetralin
  • 1219
  • 6603867 (R)
  • 23928184 (S)
UNII
  • RR7D75YDF4 Y
  • DTXSID00874864
  • 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 Y
    Key: BLYMJBIZMIGWFK-UHFFFAOYSA-N Y
  • 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 YN ?)

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.


 

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

 

This article about an organic compound is a stub. You can help Wikipedia by expanding it.

December 15, 2023
dpat, synthetic, compound, that, acts, dopamine, receptor, agonist, with, reasonable, selectivity, receptor, subtype, affinity, serotonin, receptors, unlike, structural, isomer, dpat, self, administered, several, animal, models, used, study, addiction, cocaine. 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 NamesIUPAC name 7 Hydroxy N N dipropyl 2 aminotetralin citation needed Systematic IUPAC name 7 Dipropylamino 5 6 7 8 tetrahydronaphthalen 2 ol 1 IdentifiersCAS Number 74938 11 7 Y3D model JSmol Interactive imageInteractive imageAbbreviations 7 OH DPATChEMBL ChEMBL285755 YChemSpider 1182 Y5036175 R YIUPHAR BPS 950MeSH 7 Hydroxy 2 N N dipropylaminotetralinPubChem CID 12196603867 R 23928184 S UNII RR7D75YDF4 YCompTox Dashboard EPA DTXSID00874864InChI 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 YKey BLYMJBIZMIGWFK UHFFFAOYSA N YInChI 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 2H3Key BLYMJBIZMIGWFK UHFFFAOYAHSMILES CCCN CCC C1CCc2ccc O cc2C1CCCN CCC C1CCC2 C C1 C C O C C2PropertiesChemical formula C 16H 25N OMolar mass 247 382 g mol 1log P 3 653Acidity pKa 10 389Basicity pKb 3 608Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesSee also edit5 OH DPAT 8 OH DPAT PD 128 907 Rotigotine UH 232References edit 7 hydroxy 2 N N dipropylaminotetralin PubChem Public Chemical Database The PubChem Project USA National Center for Biotechnology Information 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 Levesque 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 Levesque 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 Arvidsson LE Johansson AM Hacksell U Nilsson JL Svensson K Hjorth S Magnusson T Carlsson A Andersson B Wikstrom 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 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 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 Acri J B Carter S R Alling K Geter Douglass B Dijkstra D Wikstrom 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 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 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 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 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 nbsp This drug article relating to the nervous system is a stub You can help Wikipedia by expanding it vte nbsp This article about an organic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title 7 OH DPAT amp oldid 1174878548, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.