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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:41:58 UTC
NP-MRD IDNP0001365
Secondary Accession NumbersNone
Natural Product Identification
Common NameHistamine
DescriptionHistamine is an amine derived by enzymatic decarboxylation of histidine. It is a powerful stimulant of gastric secretion, a constrictor of bronchial smooth muscle, a vasodilator, and also a centrally acting neurotransmitter. Histamine can be found in Photobacterium phosphoreum and Lactobacillus (PMID: 17066936 ). Histamine belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group. High amounts of histamine have been found in spinach, oats and ryes. Another foods such as green beans, broccoli, and beetroots also contain histamine but in lower concentrations. Histamine has also been detected but not quantified in several different foods, such as groundcherries, carobs, bok choy, biscuits, and longans.
Structure
Thumb
Synonyms
ValueSource
1H-Imidazole-4-ethanamineChEBI
2-(4-Imidazolyl)ethylamineChEBI
2-(1H-Imidazol-4-yl)ethanamineHMDB
2-(1H-Imidazol-4-yl)ethylamineHMDB
2-(1H-Imidazol-5-yl)ethanamineHMDB
2-(1H-Imidazol-5-yl)ethylamineHMDB
2-(4-Imidazolyl)ethanamineHMDB
2-Imidazol-4-yl-ethylamineHMDB
2-Imidazol-4-ylethylamineHMDB
4-(2-Aminoethyl)-1H-imidazoleHMDB
4-(2-Aminoethyl)imidazoleHMDB
4-ImidazoleethylamineHMDB
5-ImidazoleethylamineHMDB
b-Imidazolyl-4-ethylamineHMDB
beta-AminoethylglyoxalineHMDB
beta-AminoethylimidazoleHMDB
beta-AminothethylglyoxalineHMDB
beta-Imidazolyl-4-ethylamineHMDB
EraminHMDB
ErgamineHMDB
ErgotidineHMDB
HSMHMDB
2-(3H-Imidazol-4-yl)ethylamineHMDB
Imidazole-4-ethylamineHMDB
Β-imidazolyl-4-ethylamineHMDB
HistamineHMDB
Chemical FormulaC5H9N3
Average Mass111.1451 Da
Monoisotopic Mass111.07965 Da
IUPAC Name2-(1H-imidazol-4-yl)ethan-1-amine
Traditional Namehistamine
CAS Registry Number51-45-6
SMILES
NCCC1=CNC=N1
InChI Identifier
InChI=1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)
InChI KeyNTYJJOPFIAHURM-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-08-03View Spectrum
Species
Species of Origin
Species NameSourceReference
Capsella bursa-pastorisKNApSAcK Database
Casimiroa edulisKNApSAcK Database
Drosera spp.KNApSAcK Database
Echinocereus blanckiiKNApSAcK Database
Echinocereus triglochidiatusKNApSAcK Database
Glochidion philippicumKNApSAcK Database
Lolium perenneKNApSAcK Database
Musa sapientumKNApSAcK Database
Nepenthes spp.KNApSAcK Database
Sarracenia spp.KNApSAcK Database
Spinacia oleraceaKNApSAcK Database
Urtica dioicaKNApSAcK Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct Parent2-arylethylamines
Alternative Parents
Substituents
  • 2-arylethylamine
  • Aralkylamine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point86 °CNot Available
Boiling Point380.29 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.70Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
PropertyValueSource
Water Solubility169 g/LALOGPS
logP-0.69ALOGPS
logP-0.7ChemAxon
logS0.18ALOGPS
pKa (Strongest Acidic)14.46ChemAxon
pKa (Strongest Basic)9.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.7 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity31.66 m³·mol⁻¹ChemAxon
Polarizability12.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000870
DrugBank IDDB05381
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012596
KNApSAcK IDC00001414
Chemspider ID753
KEGG Compound IDC00388
BioCyc IDHISTAMINE
BiGG ID1810403
Wikipedia LinkHistamine
METLIN ID68
PubChem Compound774
PDB IDNot Available
ChEBI ID18295
Good Scents IDrw1250321
References
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Dvorak AM: New aspects of mast cell biology. Int Arch Allergy Immunol. 1997 Sep;114(1):1-9. [PubMed:9303324 ]
  3. Ito C: The role of the central histaminergic system on schizophrenia. Drug News Perspect. 2004 Jul-Aug;17(6):383-7. [PubMed:15334189 ]
  4. Bordignon V, Burastero SE: Age, gender and reactivity to allergens independently influence skin reactivity to histamine. J Investig Allergol Clin Immunol. 2006;16(2):129-35. [PubMed:16689187 ]
  5. Yosipovitch G, Fast K, Bernhard JD: Noxious heat and scratching decrease histamine-induced itch and skin blood flow. J Invest Dermatol. 2005 Dec;125(6):1268-72. [PubMed:16354198 ]
  6. Koizumi H, Ohkawara A: H2 histamine receptor-mediated increase in intracellular Ca2+ in cultured human keratinocytes. J Dermatol Sci. 1999 Sep;21(2):127-32. [PubMed:10511481 ]
  7. Brew OB, Sullivan MH: Localisation of mRNAs for diamine oxidase and histamine receptors H1 and H2, at the feto-maternal interface of human pregnancy. Inflamm Res. 2001 Sep;50(9):449-52. [PubMed:11603849 ]
  8. Narasimha SK, Srinivas CR, Mathew AC: Effect of topical corticosteroid application frequency on histamine-induced wheals. Int J Dermatol. 2005 May;44(5):425-7. [PubMed:15869544 ]
  9. Musio S, Gallo B, Scabeni S, Lapilla M, Poliani PL, Matarese G, Ohtsu H, Galli SJ, Mantegazza R, Steinman L, Pedotti R: A key regulatory role for histamine in experimental autoimmune encephalomyelitis: disease exacerbation in histidine decarboxylase-deficient mice. J Immunol. 2006 Jan 1;176(1):17-26. [PubMed:16365391 ]
  10. Kidon MI, See Y, Bun CY, Goh A, Chay OM, Balakrishnan A: Bimodal skin reactivity to histamine in atopic children in Singapore: influence of specific sensitizations. Pediatr Allergy Immunol. 2004 Dec;15(6):545-50. [PubMed:15610369 ]
  11. Masaki T, Yoshimatsu H, Chiba S, Watanabe T, Sakata T: Central infusion of histamine reduces fat accumulation and upregulates UCP family in leptin-resistant obese mice. Diabetes. 2001 Feb;50(2):376-84. [PubMed:11272150 ]
  12. Khandelwal JK, Hough LB, Morrishow AM, Green JP: Measurement of tele-methylhistamine and histamine in human cerebrospinal fluid, urine, and plasma. Agents Actions. 1982 Dec;12(5-6):583-90. [PubMed:7164933 ]
  13. Morgan TK, Montgomery K, Mason V, West RB, Wang L, van de Rijn M, Higgins JP: Upregulation of histidine decarboxylase expression in superficial cortical nephrons during pregnancy in mice and women. Kidney Int. 2006 Jul;70(2):306-14. Epub 2006 Jun 7. [PubMed:16760908 ]
  14. Xie H, He SH, Cheng MH, Fu YL: [Effect of tryptase inhibitors on histamine release from human colon mast cells]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi. 2004 Nov;20(6):678-81. [PubMed:15555433 ]
  15. Gill DS, Fonseca VA, Barradas MA, Balliod R, Moorhead JF, Dandona P: Plasma histamine in patients with chronic renal failure and nephrotic syndrome. J Clin Pathol. 1991 Mar;44(3):243-5. [PubMed:2013627 ]
  16. Tedeschi A, Lorini M, Asero R: No evidence of increased serum substance P levels in chronic urticaria patients with and without demonstrable circulating vasoactive factors. Clin Exp Dermatol. 2005 Mar;30(2):171-5. [PubMed:15725248 ]
  17. Bruysters M, Jongejan A, Gillard M, van de Manakker F, Bakker RA, Chatelain P, Leurs R: Pharmacological differences between human and guinea pig histamine H1 receptors: Asn84 (2.61) as key residue within an additional binding pocket in the H1 receptor. Mol Pharmacol. 2005 Apr;67(4):1045-52. Epub 2004 Dec 30. [PubMed:15626750 ]
  18. Ronchetti R, Villa MP, Rennerova Z, Haluszka J, Dawi EB, Di Felice G, Al-Bousafy A, Zakrzewski J, Barletta B, Barreto M: Allergen skin weal/radioallergosorbent test relationship in childhood populations that differ in histamine skin reactivity: a multi-national survey. Clin Exp Allergy. 2005 Jan;35(1):70-4. [PubMed:15649269 ]
  19. Yamamoto T, Katayama I, Nishioka K: Possible contribution of stem cell factor in psoriasis vulgaris. J Dermatol Sci. 2000 Dec;24(3):171-6. [PubMed:11084298 ]
  20. Fahmy NR, Sunder N, Soter NA: Role of histamine in the hemodynamic and plasma catecholamine responses to morphine. Clin Pharmacol Ther. 1983 May;33(5):615-20. [PubMed:6839633 ]
  21. Kyllonen H, Malmberg P, Remitz A, Rytila P, Metso T, Helenius I, Haahtela T, Reitamo S: Respiratory symptoms, bronchial hyper-responsiveness, and eosinophilic airway inflammation in patients with moderate-to-severe atopic dermatitis. Clin Exp Allergy. 2006 Feb;36(2):192-7. [PubMed:16433856 ]
  22. de las Rivas B, Marcobal A, Carrascosa AV, Munoz R: PCR detection of foodborne bacteria producing the biogenic amines histamine, tyramine, putrescine, and cadaverine. J Food Prot. 2006 Oct;69(10):2509-14. doi: 10.4315/0362-028x-69.10.2509. [PubMed:17066936 ]