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M2824

Sigma-Aldrich

Meptazinol hydrochloride

Synonyme(s) :

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

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10 MG
82.50 CHF

82.50 CHF

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82.50 CHF

About This Item

Formule empirique (notation de Hill) :
C15H23NO· HCl
Numéro CAS:
59263-76-2
Poids moléculaire :
269.81
Numéro CE :
261-683-0
Numéro MDL:
MFCD00941476
Code UNSPSC :
12352200
ID de substance PubChem :
329817952
Nomenclature NACRES :
NA.77

82.50 CHF

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Essai

≥98% (HPLC)

Forme

powder

Couleur

white to off-white

Solubilité

H2O: >10 mg/mL

Auteur

Wyeth

Chaîne 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

Clé InChI

MPJUSISYVXABBH-UHFFFAOYSA-N

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Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000417554
0000417554
070M4700V
0000135872
0000135871

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[New opiates in anesthesiology-resuscitation].
L Aguilera et al.
Revista espanola de anestesiologia y reanimacion, 40(2), 94-98 (1993-03-01)
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
J B Madsen et al.
Acta anaesthesiologica Scandinavica, 37(3), 307-313 (1993-04-01)
A technique of epidural catheterization in rabbits is described. Twelve albino rabbits received a totally implanted epidural catheter system. The system was implanted surgically, and the functioning of the system tested for a period of 3 months. X-ray examinations following
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
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
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