MedKoo Cat#: 596937 | Name: Levetimide

Description:

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

Levetimide is an inactive enantiomer of dexetimide.

Chemical Structure

Levetimide
CAS#21888-99-3

Theoretical Analysis

MedKoo Cat#: 596937

Name: Levetimide

CAS#: 21888-99-3

Chemical Formula: C23H26N2O2

Exact Mass: 362.1994

Molecular Weight: 362.47

Elemental Analysis: C, 76.21; H, 7.23; N, 7.73; O, 8.83

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Levetimide; l-Benzetimide; laevo-Benzetimide;
IUPAC/Chemical Name
(R)-1'-benzyl-3-phenyl-[3,4'-bipiperidine]-2,6-dione
InChi Key
LQQIVYSCPWCSSD-QHCPKHFHSA-N
InChi Code
InChI=1S/C23H26N2O2/c26-21-11-14-23(22(27)24-21,19-9-5-2-6-10-19)20-12-15-25(16-13-20)17-18-7-3-1-4-8-18/h1-10,20H,11-17H2,(H,24,26,27)/t23-/m0/s1
SMILES Code
O=C([C@](C1CCN(CC2=CC=CC=C2)CC1)(C3=CC=CC=C3)CC4)NC4=O
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

Preparing Stock Solutions

The following data is based on the product molecular weight 362.47 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: Sánchez-Roa PM, Wagner HN Jr, Villemagne VL, London ED, Lever JR. Effects of extracellular acetylcholine on muscarinic receptor binding assessed by [125I]dexetimide and a simple probe. Eur J Pharmacol. 1998 Oct 9;358(3):207-11. PubMed PMID: 9822886. 2: Waelbroeck M. Identification of drugs competing with d-tubocurarine for an allosteric site on cardiac muscarinic receptors. Mol Pharmacol. 1994 Oct;46(4):685-92. PubMed PMID: 7969047. 3: Adams EM, Lubrano TM, Gordon J, Fields JZ. Lack of [3H]quinuclidinyl benzylate binding to biologically relevant binding sites on mononuclear cells. Brain Behav Immun. 1992 Sep;6(3):307-13. PubMed PMID: 1392105. 4: Müller-Gärtner HW, Wilson AA, Dannals RF, Wagner HN Jr, Frost JJ. Imaging muscarinic cholinergic receptors in human brain in vivo with Spect, [123I]4-iododexetimide, and [123I]4-iodolevetimide. J Cereb Blood Flow Metab. 1992 Jul;12(4):562-70. PubMed PMID: 1618935. 5: Dickinson KE, Frizzell RA, Sekar MC. Activation of T84 cell chloride channels by carbachol involves a phosphoinositide-coupled muscarinic M3 receptor. Eur J Pharmacol. 1992 Apr 10;225(4):291-8. PubMed PMID: 1379932. 6: Leonard A, Cuq P, Magous R, Bali JP. M3-subtype muscarinic receptor that controls intracellular calcium release and inositol phosphate accumulation in gastric parietal cells. Biochem Pharmacol. 1991 Jul 25;42(4):839-45. PubMed PMID: 1651079. 7: Brunner F, Kukovetz WR. Radioligand binding to muscarinic receptors of bovine aortic endothelial cells. Br J Pharmacol. 1991 Feb;102(2):373-80. PubMed PMID: 2015420; PubMed Central PMCID: PMC1918019. 8: DeHaven-Hudkins DL, Hudkins RL. Binding of dexetimide and levetimide to [3H](+)pentazocine- and [3H]1,3-di(2-tolyl)guanidine-defined sigma recognition sites. Life Sci. 1991;49(18):PL135-9. PubMed PMID: 1656155. 9: Yamada S, Yamazawa T, Nakayama K. Direct binding and functional studies on muscarinic cholinoceptors in porcine coronary artery. J Pharmacol Exp Ther. 1990 Feb;252(2):765-9. PubMed PMID: 2313599. 10: Peterson JS, Hanson RC, Noronha-Blob L. In vivo cystometrogram studies in urethane-anesthetized and conscious guinea pigs. J Pharmacol Methods. 1989 May;21(3):231-41. PubMed PMID: 2724992. 11: van Megen YJ, Klaassen AB, Rodrigues de Miranda JF, Kuijpers W. Cholinergic muscarinic receptors in rat cochlea. Brain Res. 1988 Nov 22;474(1):185-8. PubMed PMID: 3214711. 12: Carmeliet P, Denef C. Immunocytochemical and pharmacological evidence for an intrinsic cholinomimetic system modulating prolactin and growth hormone release in rat pituitary. Endocrinology. 1988 Aug;123(2):1128-39. PubMed PMID: 3293981. 13: André C, Marullo S, Convents A, Lü BZ, Guillet JG, Hoebeke J, Strosberg DA. A human embryonic lung fibroblast with a high density of muscarinic acetylcholine receptors. Eur J Biochem. 1988 Jan 15;171(1-2):401-7. PubMed PMID: 2828056. 14: Dannals RF, Långström B, Ravert HT, Wilson AA, Wagner HN Jr. Synthesis of radiotracers for studying muscarinic cholinergic receptors in the living human brain using positron emission tomography: [11C]dexetimide and [11C]levetimide. Int J Rad Appl Instrum A. 1988;39(4):291-5. PubMed PMID: 2838435. 15: Laduron PM. Stereospecificity in binding studies. A useful criterion though insufficient to prove the presence of receptors. Biochem Pharmacol. 1988 Jan 1;37(1):37-40. Review. PubMed PMID: 2827683. 16: Wang JX, Roeske WR, Gulya K, Wang W, Yamamura HI. [3H]AF-DX 116 labels subsets of muscarinic cholinergic receptors in rat brain and heart. Life Sci. 1987 Oct 5;41(14):1751-60. PubMed PMID: 3657382. 17: Brunner F, Kukovetz WR. Muscarinic receptors of the vascular bed: radioligand binding studies on bovine splenic veins. J Cardiovasc Pharmacol. 1986 Jul-Aug;8(4):712-21. PubMed PMID: 2427809. 18: Akiyama K, Vickroy TW, Watson M, Roeske WR, Reisine TD, Smith TL, Yamamura HI. Muscarinic cholinergic ligand binding to intact mouse pituitary tumor cells (AtT-20/D16-16) coupling with two biochemical effectors: adenylate cyclase and phosphatidylinositol turnover. J Pharmacol Exp Ther. 1986 Mar;236(3):653-61. PubMed PMID: 3005550. 19: Murray TF, Mpitsos GJ, Siebenaller JF, Barker DL. Stereoselective L-[3H]quinuclidinyl benzilate-binding sites in nervous tissue of Aplysia californica: evidence for muscarinic receptors. J Neurosci. 1985 Dec;5(12):3184-8. PubMed PMID: 4078624. 20: Gray JA, Lüllmann H, Mitchelson F, Reil GH. Stereoselective binding in cardiac tissue of the enatiomers of benzetimide, and antimuscarinic drug. Br J Pharmacol. 1976 Apr;56(4):485-90. PubMed PMID: 1260229; PubMed Central PMCID: PMC1666893.