File:Histamine.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ61233· pop 66· linked from 1,846 articles

هیستامین

Sign in to save

Also known as 2-(1H-imidazol-5-yl)ethanamine, 2-(1H-imidazol-5-yl)ethylamine, 4-Imidazoleethylamine, 2-(1H-imidazol-4-yl)ethan-1-amine, 4-(2-Aminoethyl)imidazole, 2-Imidazol-4-yl-Ethylamine, Eramin, HSM

یکی از بهترین آنتی بیوتیک ها است

OverviewAI-generated

Histamine is a chemical compound with the formula C₅H₉N₃ and a molecular weight of 111.15. Its IUPAC name is 2-(1H-imidazol-5-yl)ethanamine, and its canonical SMILES representation is C1=C(NC=N1)CCN. The substance has a melting point of 182.3 and a boiling point of 409.1. It possesses a calculated xlogP value of -0.7 and a topological polar surface area of 54.7.

The molecule contains two hydrogen bond donors and two hydrogen bond acceptors, with a net charge of 0. In academic literature, a search for histamine yields 96,190 results. The subject is referenced by 1,846 other encyclopedia articles.

Synthesized by Vinony from 20 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula: C5H9N3
Molecular weight: 111.15 g/mol
IUPAC name: 2-(1H-imidazol-5-yl)ethanamine
SMILES: C1=C(NC=N1)CCN
InChIKey: NTYJJOPFIAHURM-UHFFFAOYSA-N
XLogP: -0.7
Polar surface area: 54.7 Å²
H-bond donors: 2
H-bond acceptors: 2
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1939
Admin. routes: parenteral
Indications: pterygium, seasonal allergic rhinitis, osteoarthritis, knee, allergic rhinitis

via ChEMBL · EBI

Research

96,190 papers

The basics of histamine biology.ReviewAnnals of allergy, asthma & immunology : official publication of the American College of Allergy, Asthma, & Immunology · 2011Lieberman PDOI: 10.1016/j.anai.2010.08.005
Histamine and Scombrotoxins.ReviewToxicon : official journal of the International Society on Toxinology · 2021Hungerford JMDOI: 10.1016/j.toxicon.2021.08.013
Mechanisms and implications of histamine-induced reactions and complications.ReviewAllergologia et immunopathologia · 2025Al-Maamari A, Sultan M, Ding S et al.DOI: 10.15586/aei.v53i3.1272
A Closer Look at Histamine in Drosophila.ReviewInternational journal of molecular sciences · 2024Volonté C, Liguori F, Amadio SDOI: 10.3390/ijms25084449
Histamine--a major role in allergy?ReviewClinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology · 1998Bachert CDOI: 10.1046/j.1365-2222.1998.0280s6015.x
Sex Differences in Histamine Regulation of Striatal Dopamine.The Journal of neuroscience : the official journal of the Society for Neuroscience · 2025Van Zandt M, Pittenger CDOI: 10.1523/JNEUROSCI.2182-24.2025
Historical Anecdotes and Breakthroughs of Histamine: From Discovery to Date.ReviewEndocrine, metabolic & immune disorders drug targets · 2021Charitos IA, Castellaneta F, Santacroce L et al.DOI: 10.2174/1871530320666200729150124
Histamine and its congener derivatives as immune modulators.ReviewAgents and actions. Supplements · 1991Khan MM, Melmon KLDOI: 10.1007/978-3-0348-7309-3_26

Wikidata facts

Has part: carbon
Mass: 111.08

Show 9 more facts

Commons category: Histamine
chemical formula: C₅H₉N₃
topic's main category: Category:Histamine
canonical SMILES: C1=C(NC=N1)CCN
melting point: 182.3
boiling point: 409.1
physically interacts with: Histamine receptor H4
discoverer or inventor: Henry Hallett Dale
legal status (medicine): boxed warning

Sources (6)

via Wikidata · CC0

Gallery (12)

Available in 66 languages

Show 47 more

via Wikidata sitelinks · CC0