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M2824

Sigma-Aldrich

Meptazinol hydrochloride

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
EC Number:
261-683-0
MDL number:
MFCD00941476
UNSPSC Code:
12352200
PubChem Substance ID:
329817952
NACRES:
NA.77

Assay

≥98% (HPLC)

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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Biochem/physiol Actions

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

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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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