ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /化合物

ヒスタミン

Histamine

HCID 774
ノートを作成反応を作成見積依頼を出す
印刷プレビュー
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
51-45-6
標準SMILES
NCCc1cnc[nH]1
InChIKey
NTYJJOPFIAHURM-UHFFFAOYSA-N
分子式
C5H9N3
平均分子量
111.15 g/mol
単同位体質量
111.07964729

概要

Histamine is a member of the class of imidazoles that is 1H-imidazole substituted at position C-4 by a 2-aminoethyl group. It has a role as a neurotransmitter, a mouse metabolite and a human metabolite. It is a member of imidazoles and an aralkylamino compound. It is a conjugate base of a histaminium.

名称と識別子

優先名称
Histamine
IUPAC
2-(1H-imidazol-5-yl)ethanamine
現地名
ヒスタミン
英語名
Histamine
分子式
C5H9N3
分子量
111.15

名称と別名

histamine51-45-62-(1H-imidazol-5-yl)ethanamineErgamineErgotidine1H-Imidazole-4-ethanamine2-(4-Imidazolyl)ethylamine5-ImidazoleethylamineEraminTheramineFree histaminebeta-Aminoethylglyoxaline
名称をさらに表示
2-(1H-イミダゾール-4-イル)エチルアミン1H-イミダゾール-4-エタンアミン1H-イミダゾール-4-(エタンアミン)1H-イミダゾール-5-(エタンアミン)1H-イミダゾール-5-エタンアミンエルガミンエラミン2-(1H-イミダゾール-4-イル)エタンアミン5-(2-アミノエチル)-1H-イミダゾール2-(1H-イミダゾール-4-イル)エタン-1-アミン4-(2-アミノエチル)-1H-イミダゾールテラミンβ-アミノエチルグリオキサリンエルゴチジンヒスタミン2-(1H-Imidazol-4-yl)ethan-1-amineHISTAMIN2-(1H-Imidazol-4-yl)ethanamine2-(1H-iMidazol-5-yl)ethan-1-aMineEramineistaminaHIS ELISA
beta-Aminoethylimidazole4-(2-Aminoethyl)-1H-imidazole4-ImidazoleethylamineImidazole-4-ethylaminebeta-Imidazolyl-4-ethylamineImidazole, 4-(2-aminoethyl)-DTXSID4023125CHEBI:18295

データベース識別子

CAS
51-45-6
PubChem CID
774
DTXSID
DTXSID4023125
ChEMBL
CHEMBL90
ChEBI
CHEBI:18295
UNII
820484N8I3
EC Number
200-100-6
Nikkaji
J4.117C

物性

構造計算による物性

XLogP
-0.7
極性表面積
54.7 Ų
水素結合供与体数
2
水素結合受容体数
2
回転可能結合数
2
重原子数
8
形式電荷
0
複雑度
64.7

実験および物理化学的性質

Drugs · 2 件

Pharmaceutical

Pharmaceuticals -> Listed in ZINC15

LogP · 2 件

-0.70

-0.7

Color/FormNEEDLES FROM CHLOROFORM
Solubility · 3 件

COLORLESS LONG PRISMATIC CRYSTALS; ODORLESS; 1 G SOL IN ABOUT 4 ML WATER; AQ SOLN IS ACID TO LITMUS; WHEN DRIED AT 105 °C FOR 2 HR, IT MELTS AT ABOUT 140 °C /PHOSPHATE/

FREELY SOL IN WATER, ALCOHOL, HOT CHLOROFORM; SPARINGLY SOL IN ETHER

14.1 [ug/mL] (The mean of the results at pH 7.4)

Boiling Point209-210 °C @ 18 MM HG
Melting Point · 2 件

83-84 °C

86 °C

Physical DescriptionSolid
Stability/Shelf LifeSTABLE IN AIR BUT IS AFFECTED BY LIGHT /PHOSPHATE/
Dissociation Constants · 2 件

9.756

PKA1= 9.68; PKA2= 5.88

Collision Cross Section · 3 件

安全と法規制

安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 6.7% (3 of 45) of reports.

Danger

H301 (93.3%): Toxic if swallowed [Danger Acute toxicity, oral]

P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 3 (93.3%)

毒性情報

Interactions · 2 件

INHIBITORY EFFECT OF METHAMIDE (POTENT H2 ANTAGONIST) ON GASTRIC ACID SECRETION ELICITED BY CONTINUOUS HISTAMINE IV INFUSION IN MAX EFFECTIVE DOSE (20 UMOLE/HR) IN DOGS IS SHOWN TO BE APPROX 20%/10 UMOLE/KG AFTER 1.5 HR. COMPARABLE EFFECTS WERE OBSERVED IN NORMAL HUMANS IN SAME STUDY. /H2-RECEPTOR ANTAGONISTS, FROM TABLE/

IN GUINEA PIGS, DEATH BY ASPHYXIA FOLLOWS QUITE SMALL DOSES OF HISTAMINE, YET ANIMAL MAY SURVIVE A HUNDRED LETHAL DOSES OF HISTAMINE IF GIVEN AN H1-BLOCKING DRUG. IN SAME SPECIES, H1 ANTAGONISTS OFFER STRIKING PROTECTION AGAINST ANAPHYLACTIC BRONCHOSPASM, BUT THIS IS NOT SO IN MAN... /H1-RECEPTOR ANTAGONISTS/

Natural Pollution Sources · 3 件

OCCURS WIDELY IN NATURE AS A RESULT OF PUTREFACTIVE PROCESSES.

.../HISTAMINE/ IS A NATURAL CONSTITUENT OF BODY. ... LIBERATED FROM CELLS OF SKIN BY INJURIOUS STIMULI.../&/ INVOLVED IN MANY... DIVERSE PHYSIOLOGICAL PROCESSES...HISTAMINE RECEPTORS...FALL INTO 2 BROAD CLASSES: H1 & H2...

HISTAMINE IS WIDELY, IF UNEVENLY, DISTRIBUTED THROUGHOUT ANIMAL KINGDOM & IS PRESENT IN MANY VENOMS, NOXIOUS SECRETIONS, BACTERIA & PLANTS.

化学と産業

薬理情報

Bionecessity...ENDOGENOUS HISTAMINE IS FINAL COMMON MEDIATOR OF GASTRIC SECRETORY RESPONSES.../IT IS SUPPOSED/ TO BE INVOLVED IN TISSUE GROWTH & REPAIR, IN REGULATION OF MICROCIRCULATION, & IN FUNCTIONING OF CNS...
PharmacodynamicsHistamine stimulates gastric gland secretion, causing an increased secretion of gastric juice of high acidity. This action is probably due mainly to a direct action on parietal and chief gland cells.
Mechanism of Action · 6 件

Histamine acts directly on the blood vessels to dilate arteries and capillaries; this action is mediated by both H 1- and H 2-receptors. Capillary dilatation may produce flushing of the face, a decrease in systemic blood pressure, and gastric gland secretion, causing an increased secretion of gastric juice of high acidity. Increased capillary permeability accompanies capillary dilatation, producing an outward passage of plasma protein and fluid into the extracellular spaces, an increase in lymph flow and protein content, and the formation of edema. In addition, histamine has a direct stimulant action on smooth muscle, producing contraction if H 1-receptors are activated, or mostly relaxation if H 2-receptors are activated. Also in humans, the stimulant effect of histamine may cause contraction of the intestinal muscle. However, little effect is noticed on the uterus, bladder, or gallbladder. Histamine has some stimulant effect on duodenal, salivary, pancreatic, bronchial, and lacrimal glands. Histamine also can bind to H3 and H4 receptors which are involved in the CNS/PNS neurotransmitter release and immune system chemotaxis, respectively.

...CONTRACTS MANY SMOOTH MUSCLES, SUCH AS...BRONCHI & GUT, BUT...RELAXES OTHERS...OF FINE BLOOD VESSELS. IT IS...POTENT STIMULUS TO GASTRIC ACID PRODUCTION & ELICITS...OTHER EXOCRINE SECRETIONS. ...BRONCHOCONSTRICTION & CONTRACTION OF GUT...INVOLVE H1 RECEPTORS...GASTRIC SECRETION...INVOLVE ACTIVATION OF H2 RECEPTORS...

...AT CELLULAR LEVEL, MANY RESPONSES TO HISTAMINE ARE CLEARLY ATTRIBUTABLE TO INCR IN MEMBRANE PERMEABILITY THAT ALLOWS COMMON INORG IONS (MAINLY CATIONS) TO FLOW DOWN ELECTROCHEM GRADIENTS & ALTER TRANSMEMBRANE POTENTIAL. IT DOUBTLESS EXPLAINS STIMULANT ACTIONS...OF HISTAMINE ON NERVE ENDINGS OR GANGLION CELLS...

...ESSENTIALLY SIMILAR ACTION /TO THAT AT CELLULAR LEVEL/ APPEARS TO ACCOUNT FOR SECRETION, AT LEAST AS IT OCCURS IN CHROMAFFIN CELLS OF ADRENAL MEDULLA. HERE HISTAMINE...MIMIC PHYSIOLOGICAL SECRETAGOGUE ACH IN DEPOLARIZING THE PLASMALEMMA.

関連反応

24 件
反応記録を作成
HRID 57260 の反応式
HRID 57260反応物としてuspto-grants-2016_09
HRID 407319 の反応式
HRID 407319反応物としてuspto-grants-2014_06
HRID 723117 の反応式
HRID 723117反応物としてuspto-grants-2006_11
HRID 726239 の反応式
HRID 726239反応物としてuspto-grants-1998_01
HRID 726240 の反応式
HRID 726240反応物としてuspto-grants-1998_01
HRID 726241 の反応式
HRID 726241反応物としてuspto-grants-1998_01
HRID 744047 の反応式
HRID 744047反応物としてuspto-grants-1996_09
HRID 744048 の反応式
HRID 744048反応物としてuspto-grants-1996_09
1 / 3 ページ

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す

120.4 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

120 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

120.4 Ų [M+H]+

Other Experimental Properties · 2 件

DELIQUESCENT

PRISMS FROM ETHANOL; MP: 244-246 °C; FREELY SOL IN WATER, METHANOL /DIHYDROCHLORIDE/

物理化学的性質

融点
83 · 83-84 °C (lit.)
沸点
167 °C/0.8 · 167 °C/0.8 mmHg (lit.)
比重(密度)
0.9902 · 0.9902 (rough estimate)
屈折率
1.469 · 1.4690 (estimate)
貯蔵温度
-20 °C · -20°C
溶解性
20 mg/ml; · DMSO: 20 mg/ml; Ethanol: 10 mg/ml; PBS (pH 7.2): 10 mg/ml
外見
個体
酸解離定数(Pka)
6.04 · 6.04(at 25℃)
色
白色～淡黄色
水溶解度
水、アルコール、熱クロロホルムに溶ける。
Merck
13 · 13,4739
BRN
2012 · 2012
安定性
Hygroscopic
InChI
1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)
InChIKey
NTYJJOPFIAHURM-UHFFFAOYSA-N
SMILES
NCCc1c[nH]cn1
LogP
-0.7 · -0.700
CAS データベース
51 · 51-45-6(CAS DataBase Reference)
NISTの化学物質情報
Histamine(51-45-6)
EPAの化学物質情報
Histamine (51-45-6)

化学的性質

化学的特性White to slightly yellow powder

Human Toxicity Excerpts · 4 件

OVERDOSAGE WITH HISTAMINE IS RARE, & SYMPTOMS ARE GENERALLY NOT DANGEROUS. HOWEVER, MASSIVE DOSES CAUSE INTENSE HEADACHE, FLUSHING, PROFOUND FALL OF BLOOD PRESSURE, BRONCHOSPASM, DYSPNEA, A METALLIC TASTE, VOMITING & DIARRHEA.

.../EYE EFFECT/ OF AN 8% SOLN OF HISTAMINE HYDROCHLORIDE HAS BEEN DESCRIBED IN CASE OF GIRL WHO SPILLED SOME...ON HER HANDKERCHIEF & CONTAMINATED HER RIGHT EYE... IN 10 MIN CONJUNCTIVAE BECAME HYPEREMIC & LIDS EDEMATOUS, WITHOUT DISCOMFORT. REACTION HAD NEARLY DISAPPEARED IN 5 HR & COMPLETELY GONE NEXT DAY... /HCL SALT/

IN SOME HUMAN GLAUCOMATOUS EYES, APPLICATION OF 3% HISTAMINE HYDROCHLORIDE EYEDROPS HAS BEEN KNOWN TO CAUSE RISE IN OCULAR PRESSURE, PARTICULAR IN CASES OF ACUTE GLAUCOMA. /HCL SALT/

...INJECTED INTRADERMALLY...TRIPLE RESPONSE /FOLLOWS/...RED SPOT...BRIGHTER RED...FLARE...DEVELOPING...MORE SLOWLY, &...LOCALIZED EDEMA...DUE TO LOCAL DILATATION OF MINUTE BLOOD VESSELS /&/...DILATATION OF NEIGHBORING ARTERIOLES.../& EDEMA/ DUE TO DIRECT ACTION...ON WALLS OF...VESSELS TO INCR THEIR PERMEABILITY.

Non-Human Toxicity Excerpts · 2 件

IN MOST EXPTL SUSCEPTIBLE SPECIES (CALVES, SWINE, DUCKS, GUINEA PIGS, CATS, DOGS), IM INJECTIONS OF HISTAMINE IN BEESWAX AT RATE OF 1-4 MG/KG/DAY PRODUCES GASTRIC ULCERS WITHIN 1-6 WK.

EXPT ON EXCISED BEEF CORNEAS HAVE DEMONSTRATED THAT HISTAMINE AT CONCN AS LOW AS 0.000005 MOLAR HAS AN UNUSUAL CAPACITY FOR LOOSENING SUPERFICIAL EPITHELIAL CELLS FROM BASAL CELLS OF CORNEA AFTER SEVERAL HR OF INCUBATION.

安全データ

F
3-10-23
wgk
3
tsca
TSCA listed
rtecs
MS1050000
ridadr
UN 2811 6.1/PG 3
毒性
LD50 i.p. in mice: 2020 mg/kg (Nagai)
hs_code
29332900
risk_code
22-36/37/38-42/43
hazard_code
Xn
safety_code
22-26-36/37
hazard_class
6.1(b)
packing_group
III
Hazard Classifications
Acute Tox. 3 OralEye Irrit. 2Resp. Sens. 1Skin Irrit. 2Skin Sens. 1STOT SE 3
ストレージクラス
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
有毒物質データの
51-45-6(Hazardous Substances Data)
毒性と防護 · 1 件

毒性ヒスタミンが細菌によって合成された食品が原因で、食中毒が起きます。血小板輸血後には、敗血性ショック症状も知られています。熟成チーズ、シイタケ、発酵食品、魚醤、ワイン、魚などの食品中に蓄積され、赤身魚や青身魚などはとくに食中毒の原因になりやすいです。 高濃度のヒスタミンを含む食品を食べた場合には、アレルギー様症状を呈すこともあり、口のまわりや耳たぶの紅潮のほか、頭痛やじんましんなどの症状が出ます。ただし通常、症状は1日以内に回復します。 ヒスタミンは調理による加熱では分解しません。蓄積によって味や臭いが変わらないため、汚染の有無の判断は困難です。予防策として、保存時に温度の管理や鮮度の確認などが重要です。

MODE OF ACTION OF HISTAMINE...TO PRODUCE SMOOTH MUSCLE RELAXATION, INCL VASODILATION, HAS NOT BEEN DEFINED.

CLASSICAL...ANTIHISTAMINES ARE...CAPABLE OF BLOCKING...H1 RECEPTORS ONLY... H2 RECEPTORS...ARE INHIBITED PREFERENTIALLY BY H2-RECEPTORS ANTAGONISTS.

Metabolism/Metabolites · 4 件

Primarily hepatic. Histamine is rapidly metabolized by methylation and oxidation. Methylation involves ring methylation and catalyzation by the enzyme histamine-N-methyltransferase, producing N-methylhistamine, which is mostly converted to N-methyl imidazole acetic acid. 2 to 3% excreted as free histamine, 4 to 8% as N-methylhistamine, 42 to 47% as N-methyl imidazole acetic acid, 9 to 11% as imidazole acetic acid, and 16 to 23% as imidazole acetic acid riboside.

IN MAN THERE ARE 2 MAJOR PATHS OF HISTAMINE METAB. MORE IMPORTANT ONE INVOLVES RING METHYLATION & IS CATALYZED BY...HISTAMINE-N-METHYLTRANSFERASE (IMIDAZOLE-N-METHYLTRANSFERASE, INMT). MOST OF PRODUCT, METHYLHISTAMINE, IS CONVERTED BY MONOAMINE OXIDASE TO METHYL IMIDAZOLE ACETIC ACID (METHYL IMAA).

IN OTHER PATH, HISTAMINE UNDERGOES OXIDATIVE DEAMINATION CATALYZED MAINLY BY DIAMINOXIDASE (DAO), ALSO CALLED "HISTAMINASE"... THE PRODUCTS ARE IMIDAZOLE ACETIC ACID (IMAA) &, EVENTUALLY, ITS RIBOSIDE.

.../MUCH OF VERY LARGE AMT OF HISTAMINE GIVEN ORALLY/ IS CONVERTED BY INTESTINAL BACTERIA TO N-ACETYLHISTAMINE.

MeSH Pharmacological ClassificationDrugs that bind to and activate histamine receptors. Although they have been suggested for a variety of clinical applications histamine agonists have so far been more widely used in research than therapeutically.
Absorption, Distribution and Excretion · 4 件

Readily absorbed after parenteral administration.

HISTAMINE IS READILY ABSORBED AFTER PARENTERAL INJECTION...

THE VARIOUS METAB, WHICH HAVE LITTLE OR NO PHARMACOLOGICAL ACTIVITY, ARE EXCRETED IN URINE.

HISTAMINE & N-METHYLHISTAMINE ACCUM IN TISSUE DEPOTS.

Tissue LocationsAdipose Tissue
Cellular LocationsExtracellular
Metabolite PathwaysAcrivastine H1-Antihistamine Action

用途と製造

UsesMEDICATION
Methods of ManufacturingPRODUCED FROM HISTIDINE BY PNEUMOCOCCI OR B COLI: LEVY-BRUHL, UNGAR, ANN INST PASTEUR 61, 828 (1938).
Formulations/Preparations · 1 件

HISTAMINE PHOSPHATE, USP, & HISTAMINE DIHYDROCHLORIDE... HISTAMINE PHOSPHATE INJECTION, USP, CONTAINS 1 MG OF SALT (0.36 MG OF HISTAMINE BASE) IN 1 ML. OTHER AVAIL PREPN CONTAIN 0.275 & 2.75 MG OF HISTAMINE PHOSPHATE IN 1 ML (0.1 & 1 MG OF HISTAMINE BASE IN 1 ML), & ARE PACKAGED IN 1- OR 5-ML AMPULES.

General Manufacturing Information1H-Imidazole-5-ethanamine: ACTIVE
応用分野 · 6 件

解説ヒスタミン，針状結晶．融点83～84 ℃，沸点209～210 ℃．水，エタノールに可溶，エーテルに難溶．中枢神経にも局在し，神経伝達に関与している．毛細血管を拡張する．組織内で多量に生成するとアレルギーやアナフィラキシー症状を起こす．胃液分泌促進剤．森北出版「化学辞典（第2版）

用途血圧降下、血管透過性亢進、平滑筋収縮、血管拡張、腺分泌促進などの薬理作用があり、アレルギー反応や炎症の発現に介在物質として働く。ヒスタミンが過剰に分泌されると、ヒスタミン1型受容体(H1受容体)というタンパク質と結合して、アレルギー疾患の原因となる。 神経組織では神経伝達物質として働き、音や光などの外部刺激および情動、空腹、体温上昇といった内部刺激などによっても放出が促進され、オキシトシン分泌や覚醒状態の維持、食行動の抑制、記憶学習能の修飾などの生理機能を促進することで知られている。

来歴Histamine is an important protein involved in many allergic reactions. Allergies are caused by an immune response to a normally innocuous substance (i.e. pollen, dust) that comes in contact with lymphocytes specific for that substance, or antigen. The history of histamine and the development of antihistamines have been reviewed in [Drugs of Today (1986) and the Journal of Allergy & Clinical Immunology]. Histamine was the first to be characterized of a series of biogenic amines that are released in the inflammatory process. As early as 1910, it was shown that histamine caused constriction of isolated guinea pig ileum and, subsequently, it was found that histamine induced a shock-like syndrome. In 1927 the presence of histamine in normal tissues was demonstrated. Attempts to reduce histamine manifestations led to the report, in 1933, that certain phenolic ethers inhibited histamine action. Toxicity precluded clinical use. In 1942 phenbenzamine (Antergan), C17H22N2, was the first antihistamine to be successfully used in humans. In 1966, the name H1 was proposed for receptors blocked by the at that time known antihistamines. It was also speculated that the other actions of histamine were likely to be mediated by other histamine receptors. The existence of the H2 receptor was accepted in 1972 and the H3 receptor was recognized in rat brain in 1983. H3 receptors in the brain appear to be involved in the feedback control of both histamine synthesis and release, whereas release of various other neurotransmitters, eg, serotinin (5-HT), dopamine, noradrenaline, and acetylcholine, is also modulated. H3 receptor effects have also been demonstrated in various peripheral tissues and H3 agonists and antagonists are undergoing intensive study for therapeutic applications.

使用Histamine inhibits the synthesis of IL-2 and γ-IFN in peripheral blood mononuclear cells and lipopolysaccharide-induced synthesis of TNF-α in monocytes via H2receptor activation. It is a powerful stimulant of gastric secretion, a constrictor of bronchial smooth muscle, a vasodilator, and also a centrally acting neurotransmitter.

一般的な説明Histamine is a neurotransmitter produced by neurons of the posterior hypothalamus. In the brain, histamine is predominantly present in the gray matter.

使用用途ヒスタミンは、胃液分泌機能の検査やクロム親和細胞腫の検査に利用可能です。ただし、薬理作用としてヒスタミンは、平滑筋の収縮、細動脈の拡張による急激な血圧降下、炎症時の発赤、毛細血管透過性亢進による浮腫の発生、分泌腺の機能亢進などを生じる場合があります。

調製方法

純化方法It crystallises from *benzene or chloroform. [Beilstein 25 I 628, 25 II 302, 25 III/IV 2049.]

上流・下流製品情報

上流原料

L-ヒスチジンベンゾイルクロリド硫酸水素

下流製品

DL-ヒスチジンL-ヒスチジン4-ピリジン-2-イル-4,5,6,7-テトラヒドロ-3H-イミダゾ[4,5-C]ピリジン

補足説明

定義ChEBI: A member of the class of imidazoles that is 1H-imidazole substituted at position C-4 by a 2-aminoethyl group.