8-OH-DPAT

8-OH-DPAT
Nazewnictwo
	Nomenklatura systematyczna (IUPAC)
	7-(dipropyloamino)-5,6,7,8-tetrahydronaftalen-1-ol
	Inne nazwy i oznaczenia
	8-hydroksy-2-(di-n-propyloamino)tetralina
	Ogólne informacje
Wzór Hilla	C16H25NO
Masa molowa	247,38 g/mol
	Identyfikacja
Numer CAS	78950-78-4
PubChem	1220
SMILES
	CCCN(CCC)C1CCc2cccc(O)c2C1
InChI
	InChI=1S/C16H25NO/c1-3-10-17(11-4-2)14-9-8-13-6-5-7-16(18)15(13)12-14/h5-7,14,18H,3-4,8-12H2,1-2H3
	InChIKey
	ASXGJMSKWNBENU-UHFFFAOYSA-N
Niebezpieczeństwa
	Globalnie zharmonizowany system; klasyfikacji i oznakowania chemikaliów
	Wiarygodne źródła oznakowania tej substancji; według kryteriów GHS są niedostępne.

8-OH-DPAT – organiczny związek chemiczny, pochodna 2-aminotetraliny, agonista receptora serotoninowego 5-HT_1A, opracowany w latach 80. XX wieku i szeroko stosowany w badaniu funkcji tego receptora^[1]. Był to jeden z pierwszych wykorzystywanych pełnych agonistów receptora 5-HT_1A.

Początkowo uważano, że 8-OH-DPAT działa selektywnie na receptor 5-HT_1A, później jednak odkryto, że działa również jako agonista receptora serotoninowego 5-HT₇ oraz inhibitor wychwytu zwrotnego serotoniny lub środek uwalniający ją^[2]^[3]^[4]^[5]^[6].

W badaniach na zwierzętach wykazano, że 8-OH-DPAT ma działanie przeciwdepresyjne^[7], przeciwlękowe^[8], uspokajające^[9], anorektyczne^[10], przeciwwymiotne^[11], hipotermiczne^[12], hipotensyjne^[13], hamujące bradykardię^[13], hiperwentylujące^[14]^[15]^[16], i przeciwbólowe^[17].

Przypisy

↑ Richard A.R.A. Glennon Richard A.R.A., Concepts for the design of 5-HT 1A serotonin agonists and antagonists, „Drug Development Research”, 26 (3), 1992, s. 251–274, DOI: 10.1002/ddr.430260306 (ang.).
↑ L.G.L.G. Larsson L.G.L.G., LucyL. Rényi LucyL., S.B.S.B. Ross S.B.S.B., B.B. Svensson B.B., KristinaK. Ängeby-Möller KristinaK., Different effects on the responses of functional pre- and postsynaptic 5-HT_1A receptors by repeated treatment of rats with the 5-HT_1A receptor agonist 8-OH-DPAT, „Neuropharmacology”, 29 (2), 1990, s. 85–91, DOI: 10.1016/0028-3908(90)90047-U (ang.).
↑ JeffreyJ. Sprouse JeffreyJ., LindaL. Reynolds LindaL., XingfangX. Li XingfangX., JohnJ. Braselton JohnJ., AnneA. Schmidt AnneA., 8-OH-DPAT as a 5-HT₇ agonist: phase shifts of the circadian biological clock through increases in cAMP production, „Neuropharmacology”, 46 (1), 2004, s. 52–62, DOI: 10.1016/j.neuropharm.2003.08.007 (ang.).
↑ 5-HT₇ receptor, [w:] IUPHAR/BPS Guide to Pharmacology [online] [dostęp 2009-09-23] [zarchiwizowane z adresu 2016-03-04] (ang.).
↑ Marie-BernadetteM.B. Assié Marie-BernadetteM.B., WouterW. Koek WouterW., Possible in vivo 5-HT reuptake blocking properties of 8-OH-DPAT assessed by measuring hippocampal extracellular 5-HT using microdialysis in rats, „British Journal of Pharmacology”, 119 (5), 1996, s. 845–850, DOI: 10.1111/j.1476-5381.1996.tb15749.x, PMID: 8922730, PMCID: PMC1915946 (ang.).
↑ ReinhardR. Wölfel ReinhardR., Karl-HeinzK.H. Graefe Karl-HeinzK.H., Evidence for various tryptamines and related compounds acting as substrates of the platelet 5-hydroxytryptamine transporter, „Naunyn-Schmiedeberg’s Archives of Pharmacology”, 345 (2), 1992, s. 129–136, DOI: 10.1007/BF00165727 (ang.).
↑ Graham P.G.P. Luscombe Graham P.G.P., Keith F.K.F. Martin Keith F.K.F., Lisa J.L.J. Hutchins Lisa J.L.J., JaneJ. Gosden JaneJ., David J.D.J. Heal David J.D.J., Mediation of the antidepressant-like effect of 8-OH-DPAT in mice by postsynaptic 5-HT_1A receptors, „British Journal of Pharmacology”, 108 (3), 1993, s. 669–677, DOI: 10.1111/j.1476-5381.1993.tb12859.x, PMID: 8467355, PMCID: PMC1908013 (ang.).
↑ RudyR. Schreiber RudyR., Jean DeJ.D. Vry Jean DeJ.D., Neuronal circuits involved in the anxiolytic effects of the 5-HT_1A receptor agonists 8-OH-DPAT, ipsapirone and buspirone in the rat, „European Journal of Pharmacology”, 249 (3), 1993, s. 341–351, DOI: 10.1016/0014-2999(93)90531-L (ang.).
↑ Sietse F. deS.F. Boer Sietse F. deS.F., Jaap M.J.M. Koolhaas Jaap M.J.M., 5-HT_1A and 5-HT_1B receptor agonists and aggression: A pharmacological challenge of the serotonin deficiency hypothesis, „European Journal of Pharmacology”, 526 (1–3), 2005, s. 125–139, DOI: 10.1016/j.ejphar.2005.09.065 (ang.).
↑ C.T.C.T. Dourish C.T.C.T., P.H.P.H. Hutson P.H.P.H., G.G. Curzon G.G., Characteristics of feeding induced by the serotonin agonist 8-hydroxy-2-(di-n-propylamino) tetralin (8-OH-DPAT), „Brain Research Bulletin”, 15 (4), 1985, s. 377–384, DOI: 10.1016/0361-9230(85)90005-X (ang.).
↑ James B.J.B. Lucot James B.J.B., Antiemetic effects of flesinoxan in cats: comparisons with 8-hydroxy-2-(di-n-propylamino)tetralin, „European Journal of Pharmacology”, 253 (1–2), 1994, s. 53–60, DOI: 10.1016/0014-2999(94)90756-0 (ang.).
↑ M.T.M.T. O’Connell M.T.M.T., G.S.G.S. Sarna G.S.G.S., G.G. Curzon G.G., Evidence for postsynaptic mediation of the hypothermic effect of 5-HT_1A receptor activation, „British Journal of Pharmacology”, 106 (3), 1992, s. 603–609, DOI: 10.1111/j.1476-5381.1992.tb14382.x (ang.).
1 2 John R.J.R. Fozard John R.J.R., Anis K.A.K. Mir Anis K.A.K., Derek N.D.N. Middlemiss Derek N.D.N., Cardiovascular Response to 8-Hydroxy-2-(di-n-Propylamino) Tetralin (8-OH-DPAT) in the Rat: Site of Action and Pharmacological Analysis, „Journal of Cardiovascular Pharmacology”, 9 (3), 1987, s. 328–347, DOI: 10.1097/00005344-198703000-00010 (ang.).
↑ NiazN. Sahibzada NiazN., ManuelM. Ferreira ManuelM., Adam M.A.M. Wasserman Adam M.A.M., Angelo M.A.M. Taveira-DaSilva Angelo M.A.M., Richard A.R.A. Gillis Richard A.R.A., Reversal of Morphine-Induced Apnea in the Anesthetized Rat by Drugs that Activate 5-Hydroxytryptamine_1A Receptors, „The Journal of Pharmacology and Experimental Therapeutics”, 292 (2), 2000, s. 704–713, DOI: 10.1016/S0022-3565(24)35342-X (ang.).
↑ Leith C.R.L.C.R. Meyer Leith C.R.L.C.R., AndreaA. Fuller AndreaA., DuncanD. Mitchell DuncanD., Zacopride and 8-OH-DPAT reverse opioid-induced respiratory depression and hypoxia but not catatonic immobilization in goats, „American Journal of Physiology-Regulatory, Integrative and Comparative Physiology”, 290 (2), 2006, s. R405–R413, DOI: 10.1152/ajpregu.00440.2005 (ang.).
↑ UlfU. Guenther UlfU. i inni, The Counteraction of Opioid-Induced Ventilatory Depression by the Serotonin 1A-Agonist 8-OH-DPAT Does Not Antagonize Antinociception in Rats In Situ and In Vivo, „Anesthesia & Analgesia”, 108 (4), 2009, s. 1169–1176, DOI: 10.1213/ane.0b013e318198f828 (ang.).
↑ W.W. Xu W.W., X.C.X.C. Qiu X.C.X.C., J.S.J.S. Han J.S.J.S., Serotonin receptor subtypes in spinal antinociception in the rat, „The Journal of Pharmacology and Experimental Therapeutics”, 269 (3), 1994, s. 1182–1189, DOI: 10.1016/S0022-3565(25)38857-9 (ang.).

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[Glennon_1992-1] Richard A.R.A. Glennon Richard A.R.A., Concepts for the design of 5-HT 1A serotonin agonists and antagonists, „Drug Development Research”, 26 (3), 1992, s. 251–274, DOI: 10.1002/ddr.430260306 (ang.).

[Larsson_1990-2] L.G.L.G. Larsson L.G.L.G., LucyL. Rényi LucyL., S.B.S.B. Ross S.B.S.B., B.B. Svensson B.B., KristinaK. Ängeby-Möller KristinaK., Different effects on the responses of functional pre- and postsynaptic 5-HT_1A receptors by repeated treatment of rats with the 5-HT_1A receptor agonist 8-OH-DPAT, „Neuropharmacology”, 29 (2), 1990, s. 85–91, DOI: 10.1016/0028-3908(90)90047-U (ang.).

[Sprouse_2004-3] JeffreyJ. Sprouse JeffreyJ., LindaL. Reynolds LindaL., XingfangX. Li XingfangX., JohnJ. Braselton JohnJ., AnneA. Schmidt AnneA., 8-OH-DPAT as a 5-HT₇ agonist: phase shifts of the circadian biological clock through increases in cAMP production, „Neuropharmacology”, 46 (1), 2004, s. 52–62, DOI: 10.1016/j.neuropharm.2003.08.007 (ang.).

[urlIUPHAR_DATABASE_-_5-Hydroxytryptamine_receptors_-_5-HT7-4] 5-HT₇ receptor, [w:] IUPHAR/BPS Guide to Pharmacology [online] [dostęp 2009-09-23] [zarchiwizowane z adresu 2016-03-04] (ang.).

[Assie_1996-5] Marie-BernadetteM.B. Assié Marie-BernadetteM.B., WouterW. Koek WouterW., Possible in vivo 5-HT reuptake blocking properties of 8-OH-DPAT assessed by measuring hippocampal extracellular 5-HT using microdialysis in rats, „British Journal of Pharmacology”, 119 (5), 1996, s. 845–850, DOI: 10.1111/j.1476-5381.1996.tb15749.x, PMID: 8922730, PMCID: PMC1915946 (ang.).

[Wolfel_1992-6] ReinhardR. Wölfel ReinhardR., Karl-HeinzK.H. Graefe Karl-HeinzK.H., Evidence for various tryptamines and related compounds acting as substrates of the platelet 5-hydroxytryptamine transporter, „Naunyn-Schmiedeberg’s Archives of Pharmacology”, 345 (2), 1992, s. 129–136, DOI: 10.1007/BF00165727 (ang.).

[Luscombe_1993-7] Graham P.G.P. Luscombe Graham P.G.P., Keith F.K.F. Martin Keith F.K.F., Lisa J.L.J. Hutchins Lisa J.L.J., JaneJ. Gosden JaneJ., David J.D.J. Heal David J.D.J., Mediation of the antidepressant-like effect of 8-OH-DPAT in mice by postsynaptic 5-HT_1A receptors, „British Journal of Pharmacology”, 108 (3), 1993, s. 669–677, DOI: 10.1111/j.1476-5381.1993.tb12859.x, PMID: 8467355, PMCID: PMC1908013 (ang.).

[Schreiber_1993-8] RudyR. Schreiber RudyR., Jean DeJ.D. Vry Jean DeJ.D., Neuronal circuits involved in the anxiolytic effects of the 5-HT_1A receptor agonists 8-OH-DPAT, ipsapirone and buspirone in the rat, „European Journal of Pharmacology”, 249 (3), 1993, s. 341–351, DOI: 10.1016/0014-2999(93)90531-L (ang.).

[de_Boer_2005-9] Sietse F. deS.F. Boer Sietse F. deS.F., Jaap M.J.M. Koolhaas Jaap M.J.M., 5-HT_1A and 5-HT_1B receptor agonists and aggression: A pharmacological challenge of the serotonin deficiency hypothesis, „European Journal of Pharmacology”, 526 (1–3), 2005, s. 125–139, DOI: 10.1016/j.ejphar.2005.09.065 (ang.).

[Dourish_1985-10] C.T.C.T. Dourish C.T.C.T., P.H.P.H. Hutson P.H.P.H., G.G. Curzon G.G., Characteristics of feeding induced by the serotonin agonist 8-hydroxy-2-(di-n-propylamino) tetralin (8-OH-DPAT), „Brain Research Bulletin”, 15 (4), 1985, s. 377–384, DOI: 10.1016/0361-9230(85)90005-X (ang.).

[Lucot_1994-11] James B.J.B. Lucot James B.J.B., Antiemetic effects of flesinoxan in cats: comparisons with 8-hydroxy-2-(di-n-propylamino)tetralin, „European Journal of Pharmacology”, 253 (1–2), 1994, s. 53–60, DOI: 10.1016/0014-2999(94)90756-0 (ang.).

[OConnell_1992-12] M.T.M.T. O’Connell M.T.M.T., G.S.G.S. Sarna G.S.G.S., G.G. Curzon G.G., Evidence for postsynaptic mediation of the hypothermic effect of 5-HT_1A receptor activation, „British Journal of Pharmacology”, 106 (3), 1992, s. 603–609, DOI: 10.1111/j.1476-5381.1992.tb14382.x (ang.).

[Fozard_1987-13] 1 2 John R.J.R. Fozard John R.J.R., Anis K.A.K. Mir Anis K.A.K., Derek N.D.N. Middlemiss Derek N.D.N., Cardiovascular Response to 8-Hydroxy-2-(di-n-Propylamino) Tetralin (8-OH-DPAT) in the Rat: Site of Action and Pharmacological Analysis, „Journal of Cardiovascular Pharmacology”, 9 (3), 1987, s. 328–347, DOI: 10.1097/00005344-198703000-00010 (ang.).

[Sahibzada_2000-14] NiazN. Sahibzada NiazN., ManuelM. Ferreira ManuelM., Adam M.A.M. Wasserman Adam M.A.M., Angelo M.A.M. Taveira-DaSilva Angelo M.A.M., Richard A.R.A. Gillis Richard A.R.A., Reversal of Morphine-Induced Apnea in the Anesthetized Rat by Drugs that Activate 5-Hydroxytryptamine_1A Receptors, „The Journal of Pharmacology and Experimental Therapeutics”, 292 (2), 2000, s. 704–713, DOI: 10.1016/S0022-3565(24)35342-X (ang.).

[Meyer_2006-15] Leith C.R.L.C.R. Meyer Leith C.R.L.C.R., AndreaA. Fuller AndreaA., DuncanD. Mitchell DuncanD., Zacopride and 8-OH-DPAT reverse opioid-induced respiratory depression and hypoxia but not catatonic immobilization in goats, „American Journal of Physiology-Regulatory, Integrative and Comparative Physiology”, 290 (2), 2006, s. R405–R413, DOI: 10.1152/ajpregu.00440.2005 (ang.).

[Guenther_2009-16] UlfU. Guenther UlfU. i inni, The Counteraction of Opioid-Induced Ventilatory Depression by the Serotonin 1A-Agonist 8-OH-DPAT Does Not Antagonize Antinociception in Rats In Situ and In Vivo, „Anesthesia & Analgesia”, 108 (4), 2009, s. 1169–1176, DOI: 10.1213/ane.0b013e318198f828 (ang.).

[Xu_1994-17] W.W. Xu W.W., X.C.X.C. Qiu X.C.X.C., J.S.J.S. Han J.S.J.S., Serotonin receptor subtypes in spinal antinociception in the rat, „The Journal of Pharmacology and Experimental Therapeutics”, 269 (3), 1994, s. 1182–1189, DOI: 10.1016/S0022-3565(25)38857-9 (ang.).

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