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56-92-8

Basic Information
CAS No.: 56-92-8
Name: Histamine dihydrochloride
Article Data: 12
Molecular Structure:
Molecular Structure of 56-92-8 (Histamine dihydrochloride)
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: HarmfulXn, IrritantXi
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
Synthetic route
57090-90-1

1H-imidazole-4-carboxaldehyde oxime

56-92-8

histamine dichloride

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen; acetyl chloride In methanol at 0℃; for 17.5h; Inert atmosphere;98%
71-00-1

L-histidine

56-92-8

histamine dichloride

Conditions
ConditionsYield
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

C15H21N3

56-92-8

histamine dichloride

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol for 8h;90 mg
β--propionic acid hydrazide

β--propionic acid hydrazide

56-92-8

histamine dichloride

Conditions
ConditionsYield
With hydrogenchloride; n-Amyl nitrite Eindampfen des Gemisches und Kochen des Rueckstands mit konz. Salzsaeure;
872-82-2

2-(1H-imidazol-4-yl)ethanol

56-92-8

histamine dichloride

Conditions
ConditionsYield
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
55-36-7

histamine hydrochloride

56-92-8

histamine dichloride

Conditions
ConditionsYield
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
74294-60-3

NO-bis-p-tolylsulphonylhistaminol

56-92-8

histamine dichloride

Conditions
ConditionsYield
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

Conditions
ConditionsYield
With triethylamine In dichloromethane 1.) 0 deg C, 1 h, 2.) r.t., 20 h;100%
Raw Materials
55-36-7
872-82-2
Downstream Products
14509-66-1
51-45-6
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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: HarmfulXn, IrritantXi
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.