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M2824

Sigma-Aldrich

Meptazinol hydrochloride

Sinônimo(s):

3-(3-ethylhexahydro-1-methyl-1H-azepin-3-yl)-phenol hydrochloride, IL-22811 hydrochloride, WY-22811 hydrochloride

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About This Item

Fórmula empírica (Notação de Hill):
C15H23NO· HCl
Número CAS:
59263-76-2
Peso molecular:
269.81
Número CE:
261-683-0
Número MDL:
MFCD00941476
Código UNSPSC:
12352200
ID de substância PubChem:
329817952
NACRES:
NA.77

Ensaio

≥98% (HPLC)

forma

powder

cor

white to off-white

solubilidade

H2O: >10 mg/mL

originador

Wyeth

cadeia de caracteres SMILES

Cl.CCC1(CCCCN(C)C1)c2cccc(O)c2

InChI

1S/C15H23NO.ClH/c1-3-15(9-4-5-10-16(2)12-15)13-7-6-8-14(17)11-13;/h6-8,11,17H,3-5,9-10,12H2,1-2H3;1H

chave InChI

MPJUSISYVXABBH-UHFFFAOYSA-N

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Ações bioquímicas/fisiológicas

Meptazinol 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.

Características e benefícios

This compound is featured on the Opioid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Wyeth. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H302

Declarações de precaução

P264 - P270 - P301 + P312 - P501

Classificações de perigo

Acute Tox. 4 Oral

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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A Galli et al.
The Journal of pharmacy and pharmacology, 43(5), 366-369 (1991-05-01)
The protective action of meptazinol against acute di-isopropyl fluorophosphate (DFP) intoxication has been evaluated in mice by measuring the effects on the DFP LD50 of the pretreatment of the animals with increasing doses of the drug. Meptazinol at the doses
Zhen-qi Shi et al.
Yao xue xue bao = Acta pharmaceutica Sinica, 40(8), 754-757 (2005-11-05)
To investigate the extent of systemic absorption and uptake of meptazinol (MEP) hydrochloride in cerebrospinal fluid (CSF) after intranasal administration on rats and compare with oral administration. CSF samples were collected by a serial sampling method. The concentration of MEP
Jian Qiao et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 877(30), 3787-3791 (2009-10-13)
A robust and validated liquid chromatography-tandem mass spectrometry (LC-MS/MS) method with positive electrospray ionization (ESI) was developed for the determination of hydrochloride meptazinol in human plasma. After liquid-liquid extraction of 200mul of human plasma, HPLC separation was achieved on a
Aviv Paz et al.
Journal of medicinal chemistry, 52(8), 2543-2549 (2009-03-31)
A bis-(-)-nor-meptazinol derivative in which the two meptazinol rings are linked by a nonamethylene spacer is a novel acetylcholinesterase inhibitor that inhibits both catalytic activity and Abeta peptide aggregation. The crystal structure of its complex with Torpedo californica acetylcholinesterase was
Wei Li et al.
Acta pharmacologica Sinica, 26(3), 334-338 (2005-02-18)
To investigate the mechanism of action of a potent analgesic, (+/-)-meptazinol. The structures of meptazinol enantiomers were compared with opioid pharmacophore and tramadol. Neither enantiomer of meptazinol fitted any patterns among the opioid pharmacophore and tramadol, although they did share
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