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75614-87-8

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75614-87-8 Usage

Chemical Properties

White to off-white solid

Uses

R(-)-alpha-Methylhistamine is a potent agonist of the histamine H3-receptor.

Definition

ChEBI: An aralkylamino compound that is histamine bearing a methyl substituent at the alpha-position (the R-enantiomer).

Biological Activity

Very potent, high affinity H 3?agonist (K D = 50.3 nM) that displays > 200-fold selectivity over H 4 receptors. Inhibits H 3 -mediated histamine synthesis and release in the CNS and stimulates H 4 -mediated eosinophil shape change (EC 50 = 66 nM). Also available as part of the Histamine H 3 Receptor Tocriset? .

Check Digit Verification of cas no

The CAS Registry Mumber 75614-87-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,5,6,1 and 4 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 75614-87:
(7*7)+(6*5)+(5*6)+(4*1)+(3*4)+(2*8)+(1*7)=148
148 % 10 = 8
So 75614-87-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H11N3/c1-5(7)2-6-3-8-4-9-6/h3-5H,2,7H2,1H3,(H,8,9)/t5-/m1/s1

75614-87-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name (R)-(-)-α-Methylhistamine dihydrobromide,(R)-(-)-α-Methyl-1H-imidazole-4-ethanaminedihydrobromide

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:75614-87-8 SDS

75614-87-8Downstream Products

75614-87-8Relevant articles and documents

Enzyme-catalyzed prodrug approaches for the histamine H3-receptor agonist (R)-α-methylhistamine

Stark, Holger,Krause, Michael,Rouleau, Agnes,Garbarg, Monique,Schwartz, Jean-Charles,Schunack, Walter

, p. 191 - 198 (2007/10/03)

Five novel prodrug types of the potent and selective histamine H3-receptor agonist (R)-α-methylhistamine (1) were prepared and pharmacologically tested in vitro as well as in vivo. In particular, an amide of fatty acid, mono- and dicarbamates, an (acyloxy)alkylcarbamate, and a diphthalidyl derivative were synthesized, all of which require initial prodrug activation through an enzyme-catalyzed reaction in contrast to formerly developed azomethine prodrugs which are cleaved by chemical hydrolysis only. Further drug liberation may ensue spontaneously in a cascade to give 1. Since they have diverse stabilities the prodrugs were investigated for drug liberation in vitro under neutral, acidic, and basic conditions at different temperatures as well as with liver homogenates. In vivo investigation of prodrugs after oral administration to mice proved that the fatty amide 2, the Nα-methylcarbamate 4a, and the Nα-(1-(acetyloxy)ethylcarbamate) 5 showed moderate to high plasma levels of 1. Compound 5 displayed even more than 2.5 times the AUC for 1 than that of the reference azomethine prodrug BP2.94 in the periphery and also displayed a detectable drug level in the central nervous system. It was shown that prodrug approaches based on an initial enzyme-catalyzed liberation step are successfully applicable to different pro-moieties for improved bioavailability and prolonged half-live. These approaches may also be used for other aminergic compounds of this class to optimize pharmacokinetic behavior.

New potent azomethine prodrugs of the histamine H3-receptor agonist (R)-α-methylhistamine1 containing a heteroarylphenyl partial structure

Krause, Michael,Rouleau, Agnes,Stark, Holger,Luger, Peter,Garbarg, Monique,Schwartz, Jean-Charles,Schunack, Walter

, p. 209 - 215 (2007/10/03)

The therapeutic value of histamine H3-receptor ligands is under current investigation. On the basis of recently described diaryl imine prodrugs of the histamine H3-receptor agonist (R)-α-methylhistamine (1) a series of new azomethine prodrugs containing five-and six-membered heterocycles were synthesized and tested for their in vitro hydrolysis rates and in vivo activity after oral application. It was found that electron-deficient six-membered heterocycles drastically destabilized the imine double bond so that these prodrugs decomposed unsuitably fast. On the contrary, prodrugs containing five-membered heterocycles appeared to be highly effective for the CNS delivery of 1, and a remarkable correlation between chemical structure and pharmacokinetic profile was observed. Particularly (R)-4-fluoro-2-[[N-[1-(1H-imidazol-4-yl)-2-propyl]imino](1H-pyrrol-2-yl)methyl] phenol (8c), the 2-furanyl analogue 8d, and its 3-furanyl isomer 8e proved to be equipotent to the most potent of recently described halogenated diaryl imine prodrugs of 1. However, in contrast to any other azomethine prodrug, 8c exhibited an incomparably long lasting delivery of 1 in the CNS and can thus be regarded as a 'retard' prodrug. Assuming that a therapeutic indication of histamine H3-receptor agonists will soon be established, these highly potent heteroarylphenyl azomethine prodrugs, which already serve as valuable pharmacological tools, may also become potential drugs in clinical use.

Structure-activity relationships of histamine analogues, XX: absolute configuration and histamine-like activity of the enantiomeric alpha-methylhistamines

Gerhard,Schunack

, p. 709 - 714 (2007/10/02)

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