M2824

Sigma-Aldrich

Meptazinol hydrochloride

Sinónimos:
WY-22811 hydrochloride, IL-22811 hydrochloride, 3-(3-ethylhexahydro-1-methyl-1H-azepin-3-yl)-phenol hydrochloride
Empirical Formula (Hill Notation):
C15H23NO· HCl
Número de CAS:
Peso molecular:
269.81
Número de EC:
Número MDL:
ID de la sustancia en PubChem:
NACRES:
NA.77

Nivel de calidad

100

ensayo

≥98% (HPLC)

formulario

powder

color

white to off-white

solubilidad

H2O: >10 mg/mL

emisor

Wyeth

SMILES string

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

InChI key

MPJUSISYVXABBH-UHFFFAOYSA-N

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Envase

10, 50 mg in glass bottle

Acciones bioquímicas o 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.

pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

RIDADR

NONH for all modes of transport

WGK Alemania

WGK 1

Punto de inflamabilidad F

Not applicable

Punto de inflamabilidad C

Not applicable

Qiong Xie et al.
Bioorganic & medicinal chemistry letters, 15(22), 4953-4956 (2005-09-13)
Based on the known coumarin-based prodrug system, a new meptazinol (Z)-3-[2-(propionyloxy) phenyl]-2-propenoic ester (3) was designed and synthesized as prodrug to minimize the first-pass effect of meptazinol (1) and improve the oral bioavailability. The prodrug (3) showed a 4-fold increase...
Wei Zheng et al.
Toxicology and applied pharmacology, 264(1), 65-72 (2012-07-31)
The strategy of dual binding site acetylcholinesterase (AChE) inhibition along with metal chelation may represent a promising direction for multi-targeted interventions in the pathophysiological processes of Alzheimer's disease (AD). In the present study, two derivatives (ZLA and ZLB) of a...
Peter D Maskell et al.
Journal of analytical toxicology, 36(1), 69-73 (2012-02-01)
Meptazinol (Meptid(®)) is an analgesic drug that is used to treat mild to moderate pain including postoperative pain, obstetrical pain, and the pain of renal colic. This case reports a death due to the combined effects of meptazinol and alcohol...
E Freye et al.
European journal of anaesthesiology, 24(1), 53-58 (2006-07-13)
To evaluate the different potencies of several opioids in obtunding reflex mechanisms of laryngoscopy and intubation. Three groups of patients (each n = 25, ASA 1-2) undergoing elective plastic surgery were randomly given meptazinol (2.5 mg kg-1), nalbuphine (0.3 mg...
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...
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