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

Related Research Articles

<span class="mw-page-title-main">5-HT receptor</span> Class of transmembrane proteins

5-HT receptors, 5-hydroxytryptamine receptors, or serotonin receptors, are a group of G protein-coupled receptor and ligand-gated ion channels found in the central and peripheral nervous systems. They mediate both excitatory and inhibitory neurotransmission. The serotonin receptors are activated by the neurotransmitter serotonin, which acts as their natural ligand.

<span class="mw-page-title-main">Azapirone</span> Drug class of psycotropic drugs

Azapirones are a class of drugs used as anxiolytics, antidepressants, and antipsychotics. They are commonly used as add-ons to other antidepressants, such as selective serotonin reuptake inhibitors (SSRIs).

<span class="mw-page-title-main">Pindolol</span> Chemical compound

Pindolol, sold under the brand name Visken among others, is a nonselective beta blocker which is used in the treatment of hypertension. It is also an antagonist of the serotonin 5-HT1A receptor, preferentially blocking inhibitory 5-HT1A autoreceptors, and has been researched as an add-on therapy to various antidepressants, such as clomipramine and the selective serotonin reuptake inhibitors (SSRIs), in the treatment of depression and obsessive-compulsive disorder.

<span class="mw-page-title-main">5-Methoxytryptamine</span> Chemical compound

5-Methoxytryptamine (5-MT), also known as mexamine, is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin. 5-MT has been shown to occur naturally in the body in low levels. It is formed via the deacetylation of melatonin in the pineal gland.

5-HT<sub>1A</sub> receptor Serotonin receptor protein distributed in the cerebrum and raphe nucleus

The serotonin 1A receptor is a subtype of serotonin receptors, or 5-HT receptors, that binds serotonin, also known as 5-HT, a neurotransmitter. 5-HT1A is expressed in the brain, spleen, and neonatal kidney. It is a G protein-coupled receptor (GPCR), coupled to the Gi protein, and its activation in the brain mediates hyperpolarization and reduction of firing rate of the postsynaptic neuron. In humans, the serotonin 1A receptor is encoded by the HTR1A gene.

5-HT<sub>1B</sub> receptor Mammalian protein found in Homo sapiens

5-hydroxytryptamine receptor 1B also known as the 5-HT1B receptor is a protein that in humans is encoded by the HTR1B gene. The 5-HT1B receptor is a 5-HT receptor subtype.

5-HT<sub>7</sub> receptor Protein-coding gene in the species Homo sapiens

The 5-HT7 receptor is a member of the GPCR superfamily of cell surface receptors and is activated by the neurotransmitter serotonin (5-hydroxytryptamine, 5-HT). The 5-HT7 receptor is coupled to Gs (stimulates the production of the intracellular signaling molecule cAMP) and is expressed in a variety of human tissues, particularly in the brain, the gastrointestinal tract, and in various blood vessels. This receptor has been a drug development target for the treatment of several clinical disorders. The 5-HT7 receptor is encoded by the HTR7 gene, which in humans is transcribed into 3 different splice variants.

<span class="mw-page-title-main">WAY-100635</span> Chemical compound

WAY-100635 is a piperazine drug and research chemical widely used in scientific studies. It was originally believed to act as a selective 5-HT1A receptor antagonist, but subsequent research showed that it also acts as potent full agonist at the D4 receptor. It is sometimes referred to as a silent antagonist at the former receptor. It is closely related to WAY-100135.

<span class="mw-page-title-main">Flesinoxan</span> Chemical compound

Flesinoxan (DU-29,373) is a potent and selective 5-HT1A receptor partial/near-full agonist of the phenylpiperazine class. Originally developed as a potential antihypertensive drug, flesinoxan was later found to possess antidepressant and anxiolytic effects in animal tests. As a result, it was investigated in several small human pilot studies for the treatment of major depressive disorder, and was found to have robust effectiveness and very good tolerability. However, due to "management decisions", the development of flesinoxan was stopped and it was not pursued any further.

<span class="mw-page-title-main">5-Carboxamidotryptamine</span> Chemical compound

5-Carboxamidotryptamine (5-CT) is a tryptamine derivative closely related to the neurotransmitter serotonin.

<span class="mw-page-title-main">Binospirone</span> Anxiolytic drug

Binospirone (MDL-73,005-EF) is a drug which acts as a partial agonist at 5-HT1A somatodendritic autoreceptors but as an antagonist at postsynaptic 5-HT1A receptors. It has anxiolytic effects.

<span class="mw-page-title-main">UH-301</span> Chemical compound

(S)-UH-301 is a drug and research chemical widely used in scientific studies. It acts as a selective 5-HT1A receptor silent antagonist. It is structurally related to 8-OH-DPAT. UH-301 was found to produce a head-twitch response in mice which is usually typical of 5-HT2A agonist drugs, and has subsequently been used to investigate how 5-HT1A receptor activity modulates 5-HT2A receptors downstream.

<span class="mw-page-title-main">7-OH-DPAT</span> Dopamine receptor agonist compound

7-OH-DPAT is a synthetic compound that acts as a dopamine receptor agonist with reasonable selectivity for the D3 receptor subtype, and low affinity for serotonin receptors, unlike its structural isomer 8-OH-DPAT. 7-OH-DPAT is self-administered in several animal models, and is used to study its addiction effects to cocaine.

<span class="mw-page-title-main">2-Aminotetralin</span> Chemical compound

2-Aminotetralin (2-AT), also known as 1,2,3,4-tetrahydronaphthalen-2-amine (THN), is a stimulant drug with a chemical structure consisting of a tetralin group combined with an amine.

<span class="mw-page-title-main">Osemozotan</span> Pharmaceutical drug

Osemozotan (MKC-242) is a selective 5-HT1A receptor agonist with some functional selectivity, acting as a full agonist at presynaptic and a partial agonist at postsynaptic 5-HT1A receptors. 5-HT1A receptor stimulation influences the release of various neurotransmitters including serotonin, dopamine, norepinephrine, and acetylcholine. 5-HT1A receptors are inhibitory G protein-coupled receptor.

<span class="mw-page-title-main">Sarizotan</span> Chemical compound

Sarizotan (EMD-128,130) is a selective 5-HT1A receptor agonist and D2 receptor antagonist, which has antipsychotic effects, and has also shown efficacy in reducing dyskinesias resulting from long-term anti-Parkinsonian treatment with levodopa.

<span class="mw-page-title-main">S-14671</span> Chemical compound

S-14671 is a naphthylpiperazine derivative which acts as a 5-HT1A receptor agonist (pKi = 9.3) with high efficacy and exceptional in vivo potency, and also as a 5-HT2A and 5-HT2C receptor antagonist (both are pKi = 7.8). It displays only low and non-significant affinity for 5-HT1B and 5-HT3 sites.

<span class="mw-page-title-main">5-OH-DPAT</span> Dopamine receptor agonist compound

5-OH-DPAT is a synthetic compound that acts as a dopamine receptor agonist with selectivity for the D2 receptor and D3 receptor subtypes. Only the (S)-enantiomer is active as an agonist, with the (R)-enantiomer being a weak antagonist at D2 receptors. Radiolabelled 11C-5-OH-DPAT is used as an agonist radioligand for mapping the distribution and function of D2 and D3 receptors in the brain, and the drug is also being studied in the treatment of Parkinson's disease.

<span class="mw-page-title-main">Bay R 1531</span> Chemical compound

Bay R 1531 is a tricyclic tryptamine derivative which acts as a selective serotonin receptor 5-HT1A agonist. It was researched unsuccessfully for the treatment of stroke but remains in use for scientific research.

<span class="mw-page-title-main">LY-215,840</span> Chemical compound

LY-215,840 is an ergoline derivative drug developed by Eli Lilly, which acts as a potent and selective antagonist at the serotonin 5-HT2 and 5-HT7 receptors. It has anti-hypertensive and muscle relaxant effects in animal studies.

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.



This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.