1596-64-1

Basic information

• Product Name: L-(-)-Histidinol dihydrochloride
• Synonyms: L-HISTIDINOL 2 HCL;L-HISTIDINOL DIHYDROCHLORIDE;L-HISTIDINE DIHYDROCHLORIDE;L-BETA-AMINO-1H-IMIDAZOLE-4-PROPANOL DIHYDROCHLORIDE;(L)-2-AMINO-3-(4-IMIDAZOLYL)PROPANOL DIHYDROCHLORIDE;H-HIS-OL 2HCL;HISTIDINOL DIHYDROCHLORIDE, L-;(S)-2-AMINO-3-(4-IMIDAZOLYL)PROPANOL DIHYDROCHLORIDE
• CAS NO: 1596-64-1
• Molecular Formula: C₆H₁₁N₃O*2ClH
• Molecular Weight: 214.09
• EINECS: 216-482-2
• Product Categories: Amino hydrochloride;Chiral Reagents;Heterocycles;Metabolites & Impurities
• Mol File: 1596-64-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 198-201 °C (dec.)(lit.)
• Boiling Point: 455.5 °C at 760 mmHg
• Flash Point: 229.3 °C
• Appearance: White to slightly beige/Crystalline Powder
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Sparingly)
• BRN: 3914853
• CAS DataBase Reference: L-(-)-Histidinol dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: L-(-)-Histidinol dihydrochloride(1596-64-1)
• EPA Substance Registry System: L-(-)-Histidinol dihydrochloride(1596-64-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39-36/37-22
• WGK Germany: 3
• RTECS: NI8260000
• Hazardous Substances Data: 1596-64-1(Hazardous Substances Data)

Usage

Description

L-Histidinol is a natural amino alcohol that serves as an intermediate in the biosynthesis of the amino acid L-histidine in bacteria, archaebacteria, fungi, and plants. It is generated from its immediate precursor, L-histidinol phosphate, by a phosphatase. L-Histidinol is oxidized to L-histidinal, which in turn is oxidized to L-histidine, by a single enzyme, histidinol dehydrogenase.

Chemical Properties

white to slightly beige crystalline powder

Uses

A metabolite within Histidine metabolism.

in vitro

preliminary experiments were done to investigate the cytotoxic effect of l-histidinol on cultured eac cells. results showed that l-histidinol up to 4 mm had no cytotoxic effects on eac cells. doxorubicin alone showed concentration-dependent cytotoxic effects. l-histidinol combination with doxorubicin led to significant potentiation of doxorubicin cytotoxicity to eac cells compared to doxorubicin alone. the concentration that caused 50% growth inhibition in eac cells after 24 h incubation was about 0.2 μg/ml, whereas it was 0.1 μg/ml when l-histidinol was added to culture medium [1].

in vivo

l-histidinol at 250 mg/kg for five consecutive doses before doxorubicin single injection could enhance the antitumour activity of doxorubicin in eac-bearing mice as demonstrated by a significant increase in average life span and cure rate of mice. in normal mice, l-histidinol, in the same dose regimen, could not alter the acute cardiotoxicity and lethality of doxorubicin [1].

references

[1] al-shabanah oa, badary oa, al-gharably nm, al-sawaf ha. effects of l-histidinol on the antitumour activity and acute cardiotoxicity of doxorubicin in mice. pharmacol res. 1998 sep;38(3):225-30.

Upstream product

• 1596-64-1 (+/-)-2-amino-3-(1⁽³⁾H-imidazol-4-yl)-propan-1-ol; dihydrochloride 
• 4467-54-3 (R)-histidine methyl ester dihydrochloride 
• 223910-40-5 2-(R)-(triphenylmethylamino)-3-<1-(triphenylmethyl)imidazol-4(5)-yl>propanol ditrityl-D-histidinol 
• 223910-41-6 2-(S)-(triphenylmethylamino)-3-<1-(triphenylmethyl)imidazol-4(5)-yl>propanol ditrityl-L-histidinol 
• 71-00-1 L-histidine 
• 4467-54-3 l-histidine methyl ester dihydrochloride 
• 1499-46-3 histidine methyl ester 

Downstream Products

• 1001003-40-2 (S)-1-bromomethyl-2-(3H-imidazol-4-yl)-ethylamine 
• 25679-93-0 L-histidinol 1-phosphate 
• 1596-64-1 2-(R)-amino-3-(1H-imidazol-4⁽⁵⁾-yl)propanol dihydrochloride 
• 1333227-79-4 (Benzyl-{[(S)-2-hydroxy-1-(1H-imidazol-4-ylmethyl)-ethylcarbamoyl]-methyl}-amino)-acetic acid methyl ester 
• 1354692-93-5 (2R,3S,4R,5S)-3-(3-chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-1-methyl-pyrrolidine-2-carboxylic acid [(S)-2-hydroxy-1-(1H-imidazol-4-ylmethyl)-ethyl]-amide trifluoroacetate salt 
• 289506-26-9 S-O-(N-tert-butoxycarbonyl-L-phenylalanyl)-2-(N-methacryloylamino)-3-(5'-imidazolyl)propanol 

Relevant articles and documents

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

Synthesis and in vitro pharmacology of a series of new chiral histamine H3-receptor ligands: 2-(R and S)-amino-3-(1H-imidazol-4(5)-yl)propyl ether derivatives

To investigate stereospecificity and the mechanism of activation of the histamine H3-receptor, a series of 2-(R and S)-amino-3-(1H-imidazol-4(5)- yl)propyl ether derivatives were synthesized. In these compounds, the structures of the well-known antagonist iodoproxyfan and the full agonists R- or S-(α)-methylhistamine were combined in one molecule. The obtained 'hybrid' molecules were tested for H3-receptor affinity on rat cerebral cortex. Some selected compounds were further screened for H3-receptor functional activity with GTPγ[35S] autoradiography studies using rat brain tissue sections. The affinity of all the synthesized compounds (-log K(i) = 5.9-7.9) was lower than that found for iodoproxyfan or two of its analogues; however, the compounds showed stereospecificity. The S-configuration of the series of 2-amino-3-(1H-imidazol-4(5)-yl)propyl ether derivatives, which resembles the stereochemistry of R-(α)-methylhistamine, was more favorable. Incorporation of an amino group in the propyl chain of iodoproxyfan and analogues did not alter the antagonistic behavior for compounds with an aromatic side chain. However, when also the aromatic moiety was replaced by a cyclohexyl group, the compounds behaved as agonists. This indicates that an interaction between the side chain amino group and the H3-receptor protein is involved in H3-receptor activation. The 2-(S)-amino-3-(1H-imidazol-4(5)- yl)propyl cyclohexylmethyl ether (23) has H3-receptor agonistic properties with high affinity for the histamine H3-receptor (-log K(i) = 7.9 ± 0.2) and might serve as a useful tool for further studies concerning drug design and receptor-ligand interactions.