Histamine

For the use as an immunostimulant drug, see Histamine dihydrochloride.
Histamine
Names
IUPAC name
2-(1H-Imidazol-4-yl)ethanamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.092 Edit this at Wikidata
KEGG
MeSH Histamine
UNII
  • InChI=1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8) checkY
    Key: NTYJJOPFIAHURM-UHFFFAOYSA-N checkY
  • InChI=1/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)
    Key: NTYJJOPFIAHURM-UHFFFAOYAP
  • NCCc1c[nH]cn1
Properties
C5H9N3
Molar mass 111.148 g·mol−1
Melting point 83.5 °C (182.3 °F; 356.6 K)
Boiling point 209.5 °C (409.1 °F; 482.6 K)
Easily soluble in cold water, hot water[1]
Solubility in other solvents Easily soluble in methanol. Very slightly soluble in diethyl ether.[1] Easily soluble in ethanol.
log P −0.7[2]
Acidity (pKa) Imidazole: 6.04
Terminal NH2: 9.75[2]
Pharmacology
L03AX14 (WHO) V04CG03 (WHO) (phosphate)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Histamine is an organic nitrogenous compound involved in local immune responses communication, as well as regulating physiological functions in the gut and acting as a neurotransmitter for the brain, spinal cord, and uterus.[3][4] Discovered in 1910, histamine has been considered a local hormone (autocoid) because it's produced without involvement of the classic endocrine glands; however, in recent years, histamine has been recognized as a central neurotransmitter.[5] Histamine is involved in the inflammatory response and has a central role as a mediator of itching.[6] As part of an immune response to foreign pathogens, histamine is produced by basophils and by mast cells found in nearby connective tissues. Histamine increases the permeability of the capillaries to white blood cells and some proteins, to allow them to engage pathogens in the infected tissues.[7] It consists of an imidazole ring attached to an ethylamine chain; under physiological conditions, the amino group of the side-chain is protonated.

  1. ^ a b Histamine Material Safety Data Sheet (Technical report). sciencelab.com. 2013-05-21. Archived from the original on 2012-03-24.
  2. ^ a b Vuckovic D, Pawliszyn J (March 2011). "Systematic evaluation of solid-phase microextraction coatings for untargeted metabolomic profiling of biological fluids by liquid chromatography-mass spectrometry". Analytical Chemistry. 83 (6): 1944–54. doi:10.1021/ac102614v. PMID 21332182.
  3. ^ Marieb E (2001). Human anatomy & physiology. San Francisco: Benjamin Cummings. pp. 414. ISBN 0-8053-4989-8.
  4. ^ Nieto-Alamilla G, Márquez-Gómez R, García-Gálvez AM, Morales-Figueroa GE, Arias-Montaño JA (November 2016). "The Histamine H3 Receptor: Structure, Pharmacology, and Function". Molecular Pharmacology. 90 (5): 649–673. doi:10.1124/mol.116.104752. PMID 27563055.
  5. ^ Keppel Hesselink JM (December 2015). "The terms 'autacoid', 'hormone' and 'chalone' and how they have shifted with time". Autonomic & Autacoid Pharmacology. 35 (4): 51–8. doi:10.1111/aap.12037. PMID 27028114.
  6. ^ Andersen HH, Elberling J, Arendt-Nielsen L (September 2015). "Human surrogate models of histaminergic and non-histaminergic itch" (PDF). Acta Dermato-Venereologica. 95 (7): 771–7. doi:10.2340/00015555-2146. PMID 26015312. Archived (PDF) from the original on 2019-03-30. Retrieved 2024-02-20.
  7. ^ Di Giuseppe M, Fraser D (2003). Nelson Biology 12. Toronto: Thomson Canada. p. 473. ISBN 0-17-625987-2.