8-OH-DPAT

Last updated
8-OH-DPAT
8-OH-DPAT.svg
Names
Systematic IUPAC name
7-(Dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-ol [1]
Identifiers
3D model (JSmol)
Abbreviations8-OH-DPAT
ChEBI
ChEMBL
ChemSpider
MeSH 8-Hydroxy-2-(di-n-propylamino)tetralin
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: ASXGJMSKWNBENU-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/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
    Key: ASXGJMSKWNBENU-UHFFFAOYAY
  • CCCN(CCC)C1CCc2cccc(O)c2C1
  • CCCN(CCC)C1CCC2=C(C1)C(O)=CC=C2
Properties
C16H25NO
Molar mass 247.382 g·mol−1
log P 3.711
Acidity (pKa)10.539
Basicity (pKb)3.458
Pharmacology
Pharmacokinetics:
1.5 hours
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

8-OH-DPAT is a research chemical of the aminotetralin chemical class which was developed in the 1980s and has been widely used to study the function of the 5-HT1A receptor. It was one of the first major 5-HT1A receptor full agonists to have been discovered.

Contents

Originally believed to be selective for the 5-HT1A receptor, 8-OH-DPAT was later found to act as a 5-HT7 receptor agonist and serotonin reuptake inhibitor/releasing agent as well. [2] [3] [4] [5] [6]

In animal studies, 8-OH-DPAT has been shown to possess antidepressant, [7] anxiolytic, [8] serenic, [9] anorectic, [10] antiemetic, [11] hypothermic, [12] hypotensive, [13] bradycardic, [13] hyperventilative, [14] [15] [16] and analgesic effects. [17]

See also

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References

  1. ↑ "8-hydroxy-2-(di-n-propylamino)tetralin - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
  2. ↑ Larsson LG; Rényi L; Ross SB; Svensson B; Angeby-Möller K (February 1990). "Different effects on the responses of functional pre- and postsynaptic 5-HT1A receptors by repeated treatment of rats with the 5-HT1A receptor agonist 8-OH-DPAT". Neuropharmacology. 29 (2): 85–91. doi:10.1016/0028-3908(90)90047-U. PMID   1691832. S2CID   39066002.
  3. ↑ Sprouse J; Reynolds L; Li X; Braselton J; Schmidt A (January 2004). "8-OH-DPAT as a 5-HT7 agonist: phase shifts of the circadian biological clock through increases in cAMP production". Neuropharmacology. 46 (1): 52–62. doi:10.1016/j.neuropharm.2003.08.007. PMID   14654097. S2CID   41623573.
  4. ↑ "IUPHAR DATABASE - 5-Hydroxytryptamine receptors - 5-HT7". Archived from the original on 2016-03-03. Retrieved 2009-09-23.
  5. ↑ Assié MB; Koek W (November 1996). "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): 845–50. doi:10.1111/j.1476-5381.1996.tb15749.x. PMC   1915946 . PMID   8922730.
  6. ↑ Wölfel R; Graefe KH (February 1992). "Evidence for various tryptamines and related compounds acting as substrates of the platelet 5-hydroxytryptamine transporter". Naunyn-Schmiedeberg's Archives of Pharmacology. 345 (2): 129–36. doi:10.1007/BF00165727. PMID   1570019. S2CID   2984583.
  7. ↑ Luscombe GP; Martin KF; Hutchins LJ; Gosden J; Heal DJ (March 1993). "Mediation of the antidepressant-like effect of 8-OH-DPAT in mice by postsynaptic 5-HT1A receptors". British Journal of Pharmacology. 108 (3): 669–77. doi:10.1111/j.1476-5381.1993.tb12859.x. PMC   1908013 . PMID   8467355.
  8. ↑ Schreiber R; De Vry J (November 1993). "Neuronal circuits involved in the anxiolytic effects of the 5-HT1A receptor agonists 8-OH-DPAT ipsapirone and buspirone in the rat". European Journal of Pharmacology. 249 (3): 341–51. doi:10.1016/0014-2999(93)90531-L. PMID   7904566.
  9. ↑ de Boer SF; Koolhaas JM (December 2005). "5-HT1A and 5-HT1B receptor agonists and aggression: a pharmacological challenge of the serotonin deficiency hypothesis". European Journal of Pharmacology. 526 (1–3): 125–39. doi:10.1016/j.ejphar.2005.09.065. PMID   16310183.
  10. ↑ Dourish CT; Hutson PH; Curzon G (October 1985). "Characteristics of feeding induced by the serotonin agonist 8-hydroxy-2-(di-n-propylamino) tetralin (8-OH-DPAT)". Brain Research Bulletin. 15 (4): 377–84. doi:10.1016/0361-9230(85)90005-X. PMID   2933126. S2CID   11047288.
  11. ↑ Lucot JB (February 1994). "Antiemetic effects of flesinoxan in cats: comparisons with 8-hydroxy-2-(di-n-propylamino)tetralin". European Journal of Pharmacology. 253 (1–2): 53–60. doi:10.1016/0014-2999(94)90756-0. PMID   8013549.
  12. ↑ O'Connell MT; Sarna GS; Curzon G (July 1992). "Evidence for postsynaptic mediation of the hypothermic effect of 5-HT1A receptor activation". British Journal of Pharmacology. 106 (3): 603–9. doi:10.1111/j.1476-5381.1992.tb14382.x. PMC   1907559 . PMID   1387027.
  13. 1 2 Fozard JR; Mir AK; Middlemiss DN (March 1987). "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): 328–47. doi: 10.1097/00005344-198703000-00010 . PMID   2437400. S2CID   24327371.
  14. ↑ Sahibzada N; Ferreira M; Wasserman AM; Taveira-DaSilva AM; Gillis RA (February 2000). "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): 704–13. PMID   10640309.
  15. ↑ Meyer LC; Fuller A; Mitchell D (February 2006). "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): R405–13. doi:10.1152/ajpregu.00440.2005. PMID   16166206. S2CID   224414.
  16. ↑ Guenther U; Manzke T; Wrigge H; Dutschmann M; Zinserling J; Putensen C; Hoeft A (April 2009). "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 and Analgesia. 108 (4): 1169–76. doi: 10.1213/ane.0b013e318198f828 . PMID   19299781. S2CID   25951835.
  17. ↑ Xu W; Qiu XC; Han JS (June 1994). "Serotonin receptor subtypes in spinal antinociception in the rat". The Journal of Pharmacology and Experimental Therapeutics. 269 (3): 1182–9. PMID   8014862.



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