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| CAS No.: | 56-92-8 |
|---|---|
| Name: | Histamine dihydrochloride |
| Molecular Structure: | |
|
|
|
| Formula: | C5H11Cl2N3 |
| Molecular Weight: | 184.068 |
| Synonyms: | 1H-Imidazole-4-ethanamine,dihydrochloride (9CI);Histamine, dihydrochloride (8CI);2-(1H-Imidazol-4-yl)ethanamine dihydrochloride;4-(2-Aminoethyl)imidazole dihydrochloride;Ceplene;Histaminechloride;Histamine dichloride;1H-Imidazole-5-ethanamine,hydrochloride (1:2); |
| EINECS: | 200-298-4 |
| Density: | 1.14 g/cm3 |
| Melting Point: | 249-252 °C(lit.) |
| Boiling Point: | 331 °C at 760 mmHg |
| Flash Point: | 180.3 °C |
| Solubility: | 0.1 g/mL in water |
| Appearance: | white powder |
| Hazard Symbols: |
 Xn,  Xi
|
| Risk Codes: | 36/37/38-42/43-42-22 |
| Safety: | 22-26-36/37/39-45-37-36/37 |
| Transport Information: | UN 3335 |
| PSA: | 54.70000 |
| LogP: | 2.21520 |
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- 56-92-8
histamine dichloride
| Conditions | Yield |
|---|---|
| With 5%-palladium/activated carbon; hydrogen; acetyl chloride In methanol at 0℃; for 17.5h; Inert atmosphere; | 98% |
| Conditions | Yield |
|---|---|
| Stage #1: L-histidine With (R)-Carvone In propan-1-ol at 190℃; under 11251.1 Torr; for 0.2h; Sealed tube; Stage #2: With hydrogenchloride In propan-1-ol; water at 190℃; for 0.0833333h; | 92% |
| Multi-step reaction with 2 steps 1: propan-1-ol / 20 - 190 °C / Green chemistry 2: hydrogenchloride / propan-1-ol / 0.2 h / 190 °C / Green chemistry View Scheme | |
| Multi-step reaction with 3 steps 1: copper(I) bromide / 10 h / 100 - 110 °C / Inert atmosphere; Darkness 2: hydrogenchloride / 30 °C 3: hydrogenchloride / methanol / 30 °C View Scheme |
- 56-92-8
histamine dichloride
| Conditions | Yield |
|---|---|
| With hydrogenchloride In propan-1-ol at 190℃; for 0.2h; Temperature; Green chemistry; | 92% |
- 58995-29-2
Nα-Trityl-L-histidin
- 56-92-8
histamine dichloride
| Conditions | Yield |
|---|---|
| Stage #1: Nα-Trityl-L-histidin With (R)-Carvone In propan-1-ol at 0 - 190℃; Green chemistry; Stage #2: With hydrogenchloride In propan-1-ol; water at 190℃; for 0.0833333h; Microwave irradiation; Green chemistry; | 86% |
- 74294-62-5
4-(2-Azido-ethyl)-1-(toluene-4-sulfonyl)-1H-imidazole
- 56-92-8
histamine dichloride
| Conditions | Yield |
|---|---|
| With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol for 8h; | 90 mg |
- 56-92-8
histamine dichloride
| Conditions | Yield |
|---|---|
| With hydrogenchloride; n-Amyl nitrite Eindampfen des Gemisches und Kochen des Rueckstands mit konz. Salzsaeure; |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: 336 mg / pyridine / 2 h / -23 °C 2: 180 mg / lithium azide / dimethylformamide / 18 h / 21 °C 3: 90 mg / aq. hydrochloric acid, hydrogen / palladium-charcoal / ethanol / 8 h View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: 34 mg / ethanol, NAD+, liver alcohol dehydrogenase, catalase, diamine oxidase from pea seedling / 48 h / 37 °C / phosphate buffer (pH 7) 2: 336 mg / pyridine / 2 h / -23 °C 3: 180 mg / lithium azide / dimethylformamide / 18 h / 21 °C 4: 90 mg / aq. hydrochloric acid, hydrogen / palladium-charcoal / ethanol / 8 h View Scheme | |
| With hydrogenchloride In methanol at 30℃; | 4.11 g |
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- 56-92-8
histamine dichloride
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 180 mg / lithium azide / dimethylformamide / 18 h / 21 °C 2: 90 mg / aq. hydrochloric acid, hydrogen / palladium-charcoal / ethanol / 8 h View Scheme |
- 605-65-2
5-(dimethylamino)naphth-1-ylsulfonyl chloride
- 56-92-8
histamine dichloride
- 13285-08-0
N,Nim-Didansylhistamine
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|---|---|
| With triethylamine In dichloromethane 1.) 0 deg C, 1 h, 2.) r.t., 20 h; | 100% |
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Chemistry
Molecule structure of Histamine dihydrochloride (CAS NO.56-92-8):
IUPAC: 2-(1H-Imidazol-5-yl)ethanamine
Molecular formula: C5H11Cl2N3
Molecular Weight: 184.07 g/mol
EINECS: 200-298-4
Density: 1.14g/cm3
Melting Point: 249-252 °C
Boiling Point: 331 °C at 760 mmHg
Flash Point: 180.3 °C
Water Solubility: 0.1g/mL, clear, colorless
Stability: Stable. Incompatible with strong oxidizing agents.
Storage Temp.: 2-8 °C
H-Bond Donor: 4
H-Bond Acceptor: 2
Rotatable Bond Count: 2
Tautomer Count: 2
Exact Mass: 183.033003
MonoIsotopic Mass: 183.033003
Topological Polar Surface Area: 54.7
Heavy Atom Count: 10
Canonical SMILES: C1=C(NC=N1)CCN.Cl.Cl
InChI: InChI=1S/C5H9N3.2ClH/c6-2-1-5-3-7-4-8-5;;/h3-4H,1-2,6H2,(H,7,8);2*1H
InChIKey: PPZMYIBUHIPZOS-UHFFFAOYSA-N
Product Categories:Imidazoles & Benzimidazoles;Heterocyclic Compounds;Histidine [His, H];Amino acid salt;Imidazoles & Benzimidazoles
Uses
Histamine dihydrochloride (CAS NO.56-92-8) can be used in biochemical research because it can impact on local immune responses, regulating physiological function in the gut and as a neurotransmitter. It has also been used as substrate in determinating histamine enzyme.
Production
Histamine dihydrochloride can be extracted from Claviceps purpurea, many plants and animals.
Toxicity Data With Reference
| 1. | orl-mus LD50:2534 mg/kg | ARTODN Archives of Toxicology. 2 (1979),371. | ||
| 2. | ipr-mus LD50:184 mg/kg | YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. 97 (1977),1117. | ||
| 3. | scu-mus LDLo:1300 mg/kg | AEPPAE Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 166 (1932),437. | ||
| 4. | ivn-mus LD50:370 mg/kg | ATSUDG Archives of Toxicology, Supplement. 2 (1979),371. | ||
| 5. | ipr-rbt LDLo:200 mg/kg | JIDIAQ Journal of Infectious Diseases. 42 (1928),473. | ||
| 6. | ipr-gpg LD50:4602 µg/kg | JPETAB Journal of Pharmacology and Experimental Therapeutics. 77 (1943),54. | ||
| 7. | scu-gpg LD50:1250 µg/kg | TXAPA9 Toxicology and Applied Pharmacology. 8 (1966),339. | ||
| 8. | ivn-gpg LD50:294 µg/kg | JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. 33 (1944),80. | ||
| 9. | par-gpg LDLo:570 µg/kg | AEPPAE Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 211 (1950),328. |
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
Poison by subcutaneous, intravenous, intraperitoneal, and parenteral routes. Moderately toxic by ingestion. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of Cl− and NOx. See also HISTAMINE.
Hazard Codes: 
Xn, 
Xi
Risk Statements:36/37/38-42/43-42-22
22:(Harmful if swallowed)
36/37/38: (Irritating to the eyes piratory system and skin)
42/43:(May cause sensitization by inhalation and skin contact)
42:(May cause sensitization by inhalation)
Safety Statements:22-26-36/37/39-45-37-36/37
22:(Do not breathe dust)
26: (In case of contact with eyes,rinse immediately with plenty of water and seek medical advice)
36/37/39:(Wear suitable protective clothing, gloves and eye/face protection)
45:(In case of accident or if you feel unwell, seek medical advice immediately (show label where possible))
37:(Wear suitable gloves)
36/37:(Wear suitable protective clothing and gloves)
WGK Germany:2
RTECS:MS1575000
F:1-8-9
Hazard Note:Irritant
Specification
Histamine dihydrochloride (CAS NO.56-92-8) is also named as 2-(1H-Imidazol-4-yl)ethanamine dihydrochloride ; 2-(1H-Imidazol-4-yl)ethylamine dihydrochloride ; 4-(2-Aminoethyl)imidazole dihydrochloride ; AI3-24394 ; Bichlorhydrate d'histamine ; Bichlorhydrate d'histamine [French] ; Ceplene ; Histamine HCl ; Histamine chloride ; Histamine dichloride ; Histamine dihydrochloride ; NSC 257873 ; Peremin ; UNII-3POA0Q644U . Histamine dihydrochloride (CAS NO.56-92-8) is white powder.