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M2824

Meptazinol hydrochloride

Name: Meptazinol hydrochloride
Brand: SIGMA

Synonym(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

Empirical Formula (Hill Notation):

C₁₅H₂₃NO· HCl

CAS Number:

59263-76-2

Molecular Weight:

269.81

NACRES:

NA.77

PubChem Substance ID:

329817952

UNSPSC Code:

12352200

EC Number:

261-683-0

MDL number:

MFCD00941476

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

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assay

≥98% (HPLC)

Quality Level

100

form

powder

color

white to off-white

solubility

H₂O: >10 mg/mL

originator

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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Related Categories

Bioactive Small Molecule Inhibitors

Biochem/physiol Actions

Meptazinol entered the human pharmaceutical market as a racemic mixture in the 1980s for use as an analgesic.

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.

Features and Benefits

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.

pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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The crystal structure of a complex of acetylcholinesterase with a bis-(-)-nor-meptazinol derivative reveals disruption of the catalytic triad.

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

[New opiates in anesthesiology-resuscitation].

L Aguilera et al.

Revista espanola de anestesiologia y reanimacion, 40(2), 94-98 (1993-03-01)

Enhancement of systemic and CNS delivery of meptazinol hydrochloride by intranasal administration to rats.

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

Determination of Bis(9)-(-)-Meptazinol, a bis-ligand for Alzheimer's disease, in rat plasma by liquid chromatography-tandem mass spectrometry: application to pharmacokinetics study.

Xin-xing Ge et al.

Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 881-882, 126-130 (2011-12-30)

A rapid, simple and sensitive LC-MS/MS method was developed and validated for the determination of Bis(9)-(-)-Meptazinol (B9M) in rat plasma. Protein precipitation method was used for sample preparation, using five volumes of methanol as the precipitation agent. The analytes were

Meptazinol and ethanol: a fatal intoxication.

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

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Global Trade Item Number

SKU	GTIN
M2824-10MG	04061832557120
M2824-50MG	04061832557137

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