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MedKoo Cat#: 329462 | Name: Meptazinol HCl

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Meptazinol, also known as IL 22811 and WY 22811, is an opioid analgesic developed by Wyeth in the 1970s. Indications for use in moderate to severe pain, most commonly used to treat pain in obstetrics (childbirth). Meptazinol is a 3-phenylazpane derivative, whereas the other phenazepanes like ethoheptazine and proheptazine are 4-phenylazepanes. A partial µ-opioid receptor agonist, its mixed agonist/antagonist activity affords it a lower risk of dependence and abuse than full µ agonists like morphine. Meptazinol exhibits not only a short onset of action, but also a shorter duration of action relative to other opioids such as morphine, pentazocine, or buprenorphine.

Chemical Structure

Meptazinol HCl
Meptazinol HCl
CAS#59263-76-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 329462

Name: Meptazinol HCl

CAS#: 59263-76-2 (HCl)

Chemical Formula: C15H24ClNO

Exact Mass: 0.0000

Molecular Weight: 269.81

Elemental Analysis: C, 66.77; H, 8.97; Cl, 13.14; N, 5.19; O, 5.93

Price and Availability

This product was removed for the commercial reasons.
Related CAS #
54340-58-8 (free base) 59263-76-2 (HCl)
Synonym
Meptazinol Hydrochloride, IL 22811 HCl; IL-22811; IL22811; WY 22811; WY-22811; WY22811. trade name Meptid.
IUPAC/Chemical Name
3-(3-Ethylhexahydro-1-methyl-1H-azepin-3-yl)phenol hydrochloride
InChi Key
MPJUSISYVXABBH-UHFFFAOYSA-N
InChi Code
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
SMILES Code
OC1=CC=CC(C2(CC)CN(C)CCCC2)=C1.[H]Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Related CAS# 59263-76-2 (Meptazinol HCl) 54340-58-8 (Meptazinol free base).

Preparing Stock Solutions

The following data is based on the product molecular weight 269.81 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Singer J, Jank A, Amara S, Stepan PD, Kaisers U, Hoehne C. Efficacy and Effects of Parenteral Pethidine or Meptazinol and Regional Analgesia for Pain Relief during Delivery. A Comparative Observational Study. Geburtshilfe Frauenheilkd. 2016 Sep;76(9):964-971. PubMed PMID: 27681521; PubMed Central PMCID: PMC5033648. 2: Bajda M, Panek D, Hebda M, Więckowska A, Guzior N, Malawska B. SEARCH FOR POTENTIAL CHOLINESTERASE INHIBITORS FROM THE ZINC DATABASE BY VIRTUAL SCREENING METHOD. Acta Pol Pharm. 2015 Jul-Aug;72(4):737-45. PubMed PMID: 26647631. 3: Cheng S, Zheng W, Gong P, Zhou Q, Xie Q, Yu L, Zhang P, Chen L, Li J, Chen J, Chen H, Chen H. (-)-Meptazinol-melatonin hybrids as novel dual inhibitors of cholinesterases and amyloid-β aggregation with high antioxidant potency for Alzheimer's therapy. Bioorg Med Chem. 2015 Jul 1;23(13):3110-8. doi: 10.1016/j.bmc.2015.04.084. PubMed PMID: 26025073. 4: Brown R, Howard R, Candy B, Sampson EL. Opioids for agitation in dementia. Cochrane Database Syst Rev. 2015 May 14;(5):CD009705. doi: 10.1002/14651858.CD009705.pub2. Review. PubMed PMID: 25972091. 5: Yu J, Zhao Y, Song J, Guo X. Enantioseparation of meptazinol and its three intermediate enantiomers by capillary electrophoresis using a new cationic β-cyclodextrin derivative in single and dual cyclodextrin systems. Biomed Chromatogr. 2014 Jun;28(6):868-74. doi: 10.1002/bmc.3187. PubMed PMID: 24861756. 6: Zheng Z, Tang Y, Lv H, Xu J, Zhao H, Xie Q, Qiu Z, Chen H, Wang H. Determination of Meserine, a new candidate for Alzheimer's disease in mice brain by liquid chromatography-tandem mass spectrometry and its application to a pharmacokinetic and tissue distribution study. Anal Bioanal Chem. 2014 May;406(14):3451-8. doi: 10.1007/s00216-014-7779-7. PubMed PMID: 24756818. 7: Xie Y, Jiang P, Ge X, Wang H, Shao B, Xie Q, Qiu Z, Chen H. Determination of a novel carbamate AChE inhibitor meserine in mouse plasma, brain and rat plasma by LC-MS/MS: application to pharmacokinetic study after intravenous and subcutaneous administration. J Pharm Biomed Anal. 2014 Aug 5;96:156-61. doi: 10.1016/j.jpba.2014.03.025. PubMed PMID: 24747147. 8: Shao BY, Xia Z, Xie Q, Ge XX, Zhang WW, Sun J, Jiang P, Wang H, Le WD, Qiu ZB, Lu Y, Chen HZ. Meserine, a novel carbamate AChE inhibitor, ameliorates scopolamine-induced dementia and alleviates amyloidogenesis of APP/PS1 transgenic mice. CNS Neurosci Ther. 2014 Feb;20(2):165-71. doi: 10.1111/cns.12183. PubMed PMID: 24279603. 9: Yu J, Jiang Z, Sun T, Ji F, Xu S, Wei L, Guo X. Enantiomeric separation of meptazinol and its three intermediate enantiomers by capillary electrophoresis: quantitative analysis of meptazinol in pharmaceutical formulations. Biomed Chromatogr. 2014 Jan;28(1):135-41. doi: 10.1002/bmc.2997. PubMed PMID: 23893795. 10: Kranke P, Girard T, Lavand'homme P, Melber A, Jokinen J, Muellenbach RM, Wirbelauer J, Hönig A. Must we press on until a young mother dies? Remifentanil patient controlled analgesia in labour may not be suited as a "poor man's epidural". BMC Pregnancy Childbirth. 2013 Jul 2;13:139. doi: 10.1186/1471-2393-13-139. Review. PubMed PMID: 23815762; PubMed Central PMCID: PMC3700797. 11: Liu T, Xia Z, Zhang WW, Xu JR, Ge XX, Li J, Cui Y, Qiu ZB, Xu J, Xie Q, Wang H, Chen HZ. Bis(9)-(-)-nor-meptazinol as a novel dual-binding AChEI potently ameliorates scopolamine-induced cognitive deficits in mice. Pharmacol Biochem Behav. 2013 Mar;104:138-43. doi: 10.1016/j.pbb.2012.11.009. PubMed PMID: 23262302. 12: Zheng W, Li J, Qiu Z, Xia Z, Li W, Yu L, Chen H, Chen J, Chen Y, Hu Z, Zhou W, Shao B, Cui Y, Xie Q, Chen H. Novel bis-(-)-nor-meptazinol derivatives act as dual binding site AChE inhibitors with metal-complexing property. Toxicol Appl Pharmacol. 2012 Oct 1;264(1):65-72. doi: 10.1016/j.taap.2012.07.018. PubMed PMID: 22842334. 13: Maskell PD, De Paoli G, Seetohul LN, Pounder DJ. Meptazinol and ethanol: a fatal intoxication. J Anal Toxicol. 2012 Jan-Feb;36(1):69-73. doi: 10.1093/jat/bkr005. PubMed PMID: 22290756. 14: Ge XX, Wang XL, Jiang P, Xie Y, Jiang T, Rong ZX, Zhang QZ, Xie Q, Qiu ZB, Wang H, Chen HZ. 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. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Jan 15;881-882:126-30. doi: 10.1016/j.jchromb.2011.12.010. PubMed PMID: 22204875. 15: Schnabel A, Hahn N, Muellenbach R, Frambach T, Hoenig A, Roewer N, Kranke P. [Obstetric analgesia in German clinics. Remifentanil as alternative to regional analgesia]. Anaesthesist. 2011 Nov;60(11):995-1001. doi: 10.1007/s00101-011-1933-9. German. PubMed PMID: 21918824. 16: Frambach T, Wirbelauer J, Schelling P, Rieger L, Muellenbach RM, Roewer N, Kranke P. [Patient-controlled intravenous analgesia with remifentanil as an alternative to epidural analgesia during labor: case series and discussion of medicolegal aspects]. Z Geburtshilfe Neonatol. 2010 Aug;214(4):145-50. doi: 10.1055/s-0030-1255025. German. PubMed PMID: 20806149. 17: Sun J, Xie Q, Qiu ZB. 3-[(3S)-3-Ethyl-1-methyl-azepan-3-yl]phenyl N-(4-fluoro-phen-yl)carbamate. Acta Crystallogr Sect E Struct Rep Online. 2010 Jun 26;66(Pt 7):o1822. doi: 10.1107/S1600536810024396. PubMed PMID: 21588029; PubMed Central PMCID: PMC3007005. 18: Qiao J, Tan Z, Li W, Huang L, Ge M. Liquid chromatography/positive ion electrospray tandem mass spectrometry method for the quantification of hydrochloride meptazinol in human plasma: application to a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Nov 15;877(30):3787-91. doi: 10.1016/j.jchromb.2009.08.051. PubMed PMID: 19819764. 19: Paz A, Xie Q, Greenblatt HM, Fu W, Tang Y, Silman I, Qiu Z, Sussman JL. The crystal structure of a complex of acetylcholinesterase with a bis-(-)-nor-meptazinol derivative reveals disruption of the catalytic triad. J Med Chem. 2009 Apr 23;52(8):2543-9. doi: 10.1021/jm801657v. PubMed PMID: 19326912. 20: Xie Q, Wang H, Xia Z, Lu M, Zhang W, Wang X, Fu W, Tang Y, Sheng W, Li W, Zhou W, Zhu X, Qiu Z, Chen H. Bis-(-)-nor-meptazinols as novel nanomolar cholinesterase inhibitors with high inhibitory potency on amyloid-beta aggregation. J Med Chem. 2008 Apr 10;51(7):2027-36. doi: 10.1021/jm070154q. PubMed PMID: 18333606.