Meptazinol hydrochloride

Meptazinol hydrochloride Basic information
Product Name:Meptazinol hydrochloride
Synonyms:1-Methyl-3-ethyl-3-(m-hydroxy-phenyl)hexahydro-1H-azepine;Meptazinol-d3 hydrochloride;Meptazinol hcl;Phenol,3-(3-ethylhexahydro-1-Methyl-1H-azepin-3-yl)-, hydrochloride (1:1);1-Methyl-3-ethyl-3-(3-hydroxyphenyl)hexahydro-1H-azepine hydrochloride;IL-22811 hydrochloride;WY-22811 hydrochloride;MEPTAZINOL HYDROCHLORIDE
CAS:59263-76-2
MF:C15H24ClNO
MW:269.81
EINECS:261-683-0
Product Categories:API;Intermediates & Fine Chemicals;Pharmaceuticals;59263-76-2
Mol File:59263-76-2.mol
Meptazinol hydrochloride Structure
Meptazinol hydrochloride Chemical Properties
Melting point 250-252°C
storage temp. Inert atmosphere,2-8°C
solubility H2O: >10mg/mL
form powder
color white to off-white
Stability:Hygroscopic
InChIKeyMPJUSISYVXABBH-UHFFFAOYSA-N
Safety Information
Hazard Codes Xn
Risk Statements 22
WGK Germany 1
RTECS SL4250000
MSDS Information
Meptazinol hydrochloride Usage And Synthesis
DescriptionMeptazinol hydrochloride is an injectable narcotic analgesic with antagonist properties; it is similar in potency to meperidine. Meptazinol appears to have a low propensity toward respiratory depression and other opiate-like side effects, possibly due to selective interaction with the mu-1 receptor. Also somewhat unique for an analgesic, it interacts with central cholinergic receptors. An oral form of meptazinol is under development.
Chemical PropertiesWhite Solid
OriginatorWyeth (United Kingdom)
UsesAnalgesic;Opiate receptor agonist
UsesMixed opioid agonist-antagonist. Analgesic (narcotic).
Brand nameMEPTID
Biological ActivityCentrally active opioid analgesic. Partial agonist at the μ 1 opioid receptor. Also shown to inhibit acetylcholinesterase.
Biochem/physiol ActionsMeptazinol entered the human pharmaceutical market as a racemic mixture in the 1980s for use as an analgesic. Its pharmacology is not completely understood; however, its analgesic properties are mostly due to its partial agonism at the mu1 opioid receptor. Due to its partial agonism, Meptazinol antagonizes morphine dependence in vivo. Its advantage over other opiates is its reduced capacity to cause addition and respiratory depression, also due to its intrinsic activity as a partial agonist. Meptazinol has been found to have additional activity as an acetylcholinesterase (AChE) inhibitor, particularly in its (-) enantiomeric form, which may partially explain its analgesic properties. AChE inhibitors are used to treat Alzheimer′s disease, providing additional interest in this compound.
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