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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
23
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pubmed:dateCreated |
1992-12-28
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pubmed:abstractText |
Depending on the selected synthetic pathway, structural variations of the neurotransmitter histamine led to mixtures of alpha,beta-dimethylhistamines as well as to the corresponding pure optical isomers. One of these isomers, namely (alpha R,beta S)-alpha,beta-dimethylhistamine, proved to be a highly potent H3 receptor agonist with exceptional receptor selectivity. The absolute configuration of the compound was determined by X-ray structure analysis of its dihydrobromide using the anomalous dispersion of bromine. The optical purity of both enantiomers of erythro-alpha,beta-dimethylhistamine was checked by 1HNMR investigations after acylation of the amines with (R)-2-methoxy-2-phenylacetyl chloride. As expected H3 receptors distinguish in a very strong way between the title compound and its alpha S,beta R-configured enantiomer. The agonistic potency of the latter is 2 orders of magnitude lower than the potency of (alpha R,beta S)-alpha,beta-dimethylhistamine.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:month |
Nov
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pubmed:issn |
0022-2623
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:day |
13
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pubmed:volume |
35
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
4434-41
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pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading |
pubmed-meshheading:1280301-Animals,
pubmed-meshheading:1280301-Brain,
pubmed-meshheading:1280301-Guinea Pigs,
pubmed-meshheading:1280301-Histamine,
pubmed-meshheading:1280301-Histamine Agonists,
pubmed-meshheading:1280301-Histamine Release,
pubmed-meshheading:1280301-Male,
pubmed-meshheading:1280301-Muscle, Smooth,
pubmed-meshheading:1280301-Rats,
pubmed-meshheading:1280301-Rats, Wistar,
pubmed-meshheading:1280301-Receptors, Histamine,
pubmed-meshheading:1280301-Receptors, Histamine H3,
pubmed-meshheading:1280301-Stereoisomerism,
pubmed-meshheading:1280301-Structure-Activity Relationship
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pubmed:year |
1992
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pubmed:articleTitle |
Synthesis, absolute configuration, stereoselectivity, and receptor selectivity of (alpha R, beta S)-alpha,beta-dimethylhistamine, a novel high potent histamine H3 receptor agonist.
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pubmed:affiliation |
Institute of Pharmacy, Freie Universität Berlin, Germany.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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