Histamine

Histamine
Names
	IUPAC name 2-(1H-Imidazol-4-yl)ethanamine
Identifiers
CAS Number	51-45-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18295 ;
ChEMBL	ChEMBL90 ;
ChemSpider	753 ;
DrugBank	DB05381;
ECHA InfoCard	100.000.092
IUPHAR/BPS	1204;
KEGG	D08040 ;
MeSH	Histamine
PubChem CID	774;
UNII	820484N8I3 ;
CompTox Dashboard (EPA)	DTXSID4023125 ;
	InChI InChI=1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8) Key: NTYJJOPFIAHURM-UHFFFAOYSA-N ; InChI=1/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8) Key: NTYJJOPFIAHURM-UHFFFAOYAP;
	SMILES NCCc1c[nH]cn1;
Properties
Chemical formula	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)
Solubility in water	Easily soluble in cold water, hot water
Solubility in other solvents	Easily soluble in methanol. Very slightly soluble in diethyl ether. Easily soluble in ethanol.
log P	−0.7
Acidity (pKa)	Imidazole: 6.04 ; Terminal NH2: 9.75
Pharmacology
ATC code	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). verify (what is ?) Infobox references

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] Since histamine was discovered in 1910, it has been considered a local hormone (autocoid) because it lacks the classic endocrine glands to secrete it; 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.

^ ^a ^b Histamine Material Safety Data Sheet (Technical report). sciencelab.com. 2013-05-21. Archived from the original on 2012-03-24.
^ ^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.
^ Marieb E (2001). Human anatomy & physiology. San Francisco: Benjamin Cummings. pp. 414. ISBN 0-8053-4989-8.
^ 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.
^ 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.
^ 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.
^ Di Giuseppe M, Fraser D (2003). Nelson Biology 12. Toronto: Thomson Canada. p. 473. ISBN 0-17-625987-2.