7-Hydroxytryptamine

7-Hydroxytryptamine
Clinical data
Other names7-HT; 7-OH-T; 7-HO-T; 7-Hydroxy-T
Drug classSerotonin receptor modulator; Monoamine reuptake inhibitor; Monoamine releasing agent
ATC code
  • None
Identifiers
  • 3-(2-aminoethyl)-1H-indol-7-ol
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC10H12N2O
Molar mass176.219 g·mol−1
3D model (JSmol)
  • C1=CC2=C(C(=C1)O)NC=C2CCN
  • InChI=1S/C10H12N2O/c11-5-4-7-6-12-10-8(7)2-1-3-9(10)13/h1-3,6,12-13H,4-5,11H2
  • Key:RETCYVKOCFWWTL-UHFFFAOYSA-N

7-Hydroxytryptamine (7-HT) is a serotonin receptor modulator of the tryptamine family.[1][2][3] It is the 7-hydroxy derivative of tryptamine and is a positional isomer of serotonin (5-hydroxytryptamine; 5-HT).[1][2]

The drug shows sympathomimetic effects similarly to serotonin.[1][4] On the other hand, similarly to 6-hydroxytryptamine but in contrast to serotonin, it showed little or no activity as a serotonin receptor agonist in the rabbit thoracic aorta, which expresses serotonin 5-HT2 receptors.[2] The drug is known to act as a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI), with greater potency on catecholamine reuptake than serotonin reuptake, whereas its possible effects in terms of monoamine release induction were not assessed.[5] However, in other studies, 7-HT was reported to increase serotonin and norepinephrine release.[6][7][4][8] It did not show the long-lasting monoaminergic neurotoxicity of certain related compounds like 5,7-dihydroxytryptamine (5,7-DHT) in rodents.[5][9]

7-HT was first described in the scientific literature by Irvine Page by 1952.[1]

See also

References

  1. ^ a b c d Page IH (May 1952). "The vascular action of natural serotonin, 5- and 7-hydroxytryptamine and tryptamine". The Journal of Pharmacology and Experimental Therapeutics. 105 (1): 58–73. doi:10.1016/S0022-3565(25)05007-4. PMID 14939154.
  2. ^ a b c Clancy BM, Maayani S (June 1985). "5-Hydroxytryptamine receptor in isolated rabbit aorta: characterization with tryptamine analogs". The Journal of Pharmacology and Experimental Therapeutics. 233 (3): 761–769. doi:10.1016/S0022-3565(25)22895-6. PMID 4009488.
  3. ^ Branchek T, Kates M, Gershon MD (December 1984). "Enteric receptors for 5-hydroxytryptamine". Brain Research. 324 (1): 107–118. doi:10.1016/0006-8993(84)90627-9. PMID 6518379.
  4. ^ a b Göthert M, Dührsen U (July 1979). "Effects of 5-hydroxytryptamine and related compounds on the sympathetic nerves of the rabbit heart". Naunyn-Schmiedeberg's Archives of Pharmacology. 308 (1): 9–18. doi:10.1007/BF00499713. PMID 492358.
  5. ^ a b Horn AS, Baumgarten HG, Schlosserberger HG (July 1973). "Inhibition of the uptake of 5-hydroxytryptamine, noradrenaline and dopamine into rat brain homogenates by various hydroxylated tryptamines". Journal of Neurochemistry. 21 (1): 233–236. doi:10.1111/j.1471-4159.1973.tb04242.x. PMID 4720899.
  6. ^ Göthert M, Schlicker E (March 1983). "Autoreceptor-mediated inhibition of 3H-5-hydroxytryptamine release from rat brain cortex slices by analogues of 5-hydroxytryptamine". Life Sciences. 32 (11): 1183–1191. doi:10.1016/0024-3205(83)90186-8. PMID 6572776.
  7. ^ Paton DM (November 1973). "Letter: Effect of substituted tryptamines on the efflux of noradrenaline from adrenergic nerves in rabbit atria". The Journal of Pharmacy and Pharmacology. 25 (11): 905–907. doi:10.1111/j.2042-7158.1973.tb09971.x. PMID 4149655.
  8. ^ Daly JW, Creveling CR, Witkop B (May 1966). "The chemorelease of norepinephrine from mouse hearts. Structure-activity relationships. I. Sympathomimetic and related amines". Journal of Medicinal Chemistry. 9 (3): 273–280. doi:10.1021/jm00321a001. PMID 5960887.
  9. ^ Lachenmayer L, Groth HP (July 1973). "Degeneration and regeneration of the adrenergic nerves in the rat iris induced by dihydroxytryptamines". Virchows Archiv. B, Cell Pathology. 13 (3) 197: 197–213. doi:10.1007/BF02889308. PMID 4201204.

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