ヒスタミン
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
識別子と物理属性
| CAS No. | 51-45-6 |
|---|---|
| 分子式 | C5H9N3 |
| 平均分子量 | 111.15 g/mol |
| 単同位体質量 | 111.07964729 g/mol |
| SMILES | NCCc1cnc[nH]1 |
| InChIKey | NTYJJOPFIAHURM-UHFFFAOYSA-N |
| PubChem CID | 774 |
| ChEMBL | CHEMBL90 |
| ChEBI | CHEBI:18295 |
| EC No. | 200-100-6 |
| DTXSID | DTXSID4023125 |
| 現地名 | ヒスタミン |
化学・物理的性質
| XLogP | -0.7 |
|---|---|
| 極性表面積 | 54.7 |
| 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 |
| 医薬品 | PharmaceuticalPharmaceuticals -> Listed in ZINC15 |
| LogP（分配係数） | -0.70 |
| Color/Form | NEEDLES FROM CHLOROFORM |
| 溶解度 | COLORLESS LONG PRISMATIC CRYSTALSODORLESS1 G SOL IN ABOUT 4 ML WATERAQ SOLN IS ACID TO LITMUSWHEN DRIED AT 105 °C FOR 2 HR, IT MELTS AT ABOUT 140 °C /PHOSPHATE/FREELY SOL IN WATER, ALCOHOL, HOT CHLOROFORMSPARINGLY SOL IN ETHER14.1 [ug/mL] (The mean of the results at pH 7.4)DMSO: 20 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 10 mg/ml水、アルコール、熱クロロホルムに溶ける。 |
| 沸点 | 209-210 °C @ 18 MM HG167 °C/0.8 mmHg (lit.) |
| 融点 | 83-84 °C86 °C83-84 °C (lit.) |
| Physical Description | Solid |
| Stability/Shelf Life | STABLE IN AIR BUT IS AFFECTED BY LIGHT /PHOSPHATE/ |
| Dissociation Constants | 9.756PKA1= 9.68PKA2= 5.88 |
| Collision Cross Section | 120.4 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]120 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)] |
| Other Experimental Properties | DELIQUESCENTPRISMS FROM ETHANOLMP: 244-246 °CFREELY SOL IN WATER, METHANOL /DIHYDROCHLORIDE/ |
| 密度 | 0.9902 (rough estimate) |
| 屈折率 | 1.4690 (estimate) |
| 貯蔵条件 | -20°C |
| 外観・状態 | 個体 |
| pKa（酸解離定数） | 6.04(at 25℃) |
| 色 | 白色～淡黄色 |
| Merck | 13,4739 |
| BRN | 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（分配係数） | -0.700 |
| CAS データベース | 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) |
化学的特性
White to slightly yellow powder
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 6.7% (3 of 45) of reports.DangerH301 (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. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 3 (93.3%) |
| 相互作用 | 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 | 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. |
| Human Toxicity Excerpts | 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/ |
用途
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.
製法・合成法
純化方法
It crystallises from *benzene or chloroform. [Beilstein 25 I 628, 25 II 302, 25 III/IV 2049.]