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MedKoo Cat#: 525271 | Name: Igmesine HCl
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Description:

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

Igmesine, also known as JO-1784 and CI1019, is a selective and potent σ1 receptor ligand (KD = 19.1 nM), with little or no activity at σ2 receptors (IC50 > 1000 nM). It inhibits the NMDA-induced increase in cGMP in a concentration-dependent manner (IC50 value is approximately 100 nM). Igmesine Hydrochloride is a weak inhibitor of brain 5-HT uptake in vitro. It exhibits neuroprotective and antidepressant effects.

Chemical Structure

Igmesine HCl
Igmesine HCl
CAS#130152-35-1 (HCl)

Theoretical Analysis

MedKoo Cat#: 525271

Name: Igmesine HCl

CAS#: 130152-35-1 (HCl)

Chemical Formula: C23H30ClN

Exact Mass: 0.0000

Molecular Weight: 355.94

Elemental Analysis: C, 77.61; H, 8.50; Cl, 9.96; N, 3.94

Price and Availability

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10mg USD 650.00 2 Weeks
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Related CAS #
140850-73-3 (free base) 130152-35-1 (HCl)
Synonym
Igmesine Hydrochloride; Igmesine HCl; CI 1019; CI-1019; JO-1784; JO 1784; JO1784.
IUPAC/Chemical Name
(+)-(E)-N-(Cyclopropylmethyl)-alpha-ethyl-N-methyl-alpha-(3-phenyl-2-propenyl)benzenemethanamine hydrochloride
InChi Key
SCHQQPAJNUHKSV-RSGUCCNWSA-N
InChi Code
InChI=1S/C23H29N.ClH/c1-3-23(22-14-8-5-9-15-22,24(2)19-21-16-17-21)18-10-13-20-11-6-4-7-12-20;/h4-15,21H,3,16-19H2,1-2H3;1H/b13-10+;
SMILES Code
CN(CC1CC1)C(C/C=C/C2=CC=CC=C2)(CC)C3=CC=CC=C3.[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# 130152-35-1 (Igmesine hydrochloride) 140850-73-3 (Igmesine free base)

Preparing Stock Solutions

The following data is based on the product molecular weight 355.94 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: Maurice T, Meunier J, Feng B, Ieni J, Monaghan DT. Interaction with sigma(1) protein, but not N-methyl-D-aspartate receptor, is involved in the pharmacological activity of donepezil. J Pharmacol Exp Ther. 2006 May;317(2):606-14. Epub 2006 Jan 5. PubMed PMID: 16397090. 2: Monnet FP, Morin-Surun MP, Leger J, Combettes L. Protein kinase C-dependent potentiation of intracellular calcium influx by sigma1 receptor agonists in rat hippocampal neurons. J Pharmacol Exp Ther. 2003 Nov;307(2):705-12. Epub 2003 Sep 15. PubMed PMID: 12975497. 3: Romieu P, Phan VL, Martin-Fardon R, Maurice T. Involvement of the sigma(1) receptor in cocaine-induced conditioned place preference: possible dependence on dopamine uptake blockade. Neuropsychopharmacology. 2002 Apr;26(4):444-55. PubMed PMID: 11927169. 4: Bermack JE, Debonnel G. Modulation of serotonergic neurotransmission by short- and long-term treatments with sigma ligands. Br J Pharmacol. 2001 Oct;134(3):691-9. PubMed PMID: 11588125; PubMed Central PMCID: PMC1572988. 5: Soriani O, Foll FL, Roman F, Monnet FP, Vaudry H, Cazin L. A-Current down-modulated by sigma receptor in frog pituitary melanotrope cells through a G protein-dependent pathway. J Pharmacol Exp Ther. 1999 Apr;289(1):321-8. PubMed PMID: 10087020. 6: Song C, Leonard BE. Comparison between the effects of sigma receptor ligand JO 1784 and neuropeptide Y on immune functions. Eur J Pharmacol. 1998 Mar 12;345(1):79-87. PubMed PMID: 9593598. 7: Matsuno K, Kobayashi T, Tanaka MK, Mita S. Sigma 1 receptor subtype is involved in the relief of behavioral despair in the mouse forced swimming test. Eur J Pharmacol. 1996 Oct 3;312(3):267-71. PubMed PMID: 8894608. 8: Debonnel G, Bergeron R, Monnet FP, De Montigny C. Differential effects of sigma ligands on the N-methyl-D-aspartate response in the CA1 and CA3 regions of the dorsal hippocampus: effect of mossy fiber lesioning. Neuroscience. 1996 Apr;71(4):977-87. PubMed PMID: 8684626. 9: O'Neill M, Caldwell M, Earley B, Canney M, O'Halloran A, Kelly J, Leonard BE, Junien JL. The sigma receptor ligand JO 1784 (igmesine hydrochloride) is neuroprotective in the gerbil model of global cerebral ischaemia. Eur J Pharmacol. 1995 Sep 5;283(1-3):217-25. PubMed PMID: 7498313. 10: Monnet FP, Debonnel G, Bergeron R, Gronier B, de Montigny C. The effects of sigma ligands and of neuropeptide Y on N-methyl-D-aspartate-induced neuronal activation of CA3 dorsal hippocampus neurones are differentially affected by pertussin toxin. Br J Pharmacol. 1994 Jun;112(2):709-15. PubMed PMID: 8075892; PubMed Central PMCID: PMC1910385. 11: Riviere PJ, Rao RK, Pascaud X, Junien JL, Porreca F. Effects of neuropeptide Y, peptide YY and sigma ligands on ion transport in mouse jejunum. J Pharmacol Exp Ther. 1993 Mar;264(3):1268-74. PubMed PMID: 8450462. 12: Pascaud XB, Chovet M, Soulard P, Chevalier E, Roze C, Junien JL. Effects of a new sigma ligand, JO 1784, on cysteamine ulcers and duodenal alkaline secretion in rats. Gastroenterology. 1993 Feb;104(2):427-34. PubMed PMID: 8425684. 13: Monnet FP, Debonnel G, Fournier A, de Montigny C. Neuropeptide Y potentiates the N-methyl-D-aspartate response in the CA3 dorsal hippocampus. II. Involvement of a subtype of sigma receptor. J Pharmacol Exp Ther. 1992 Dec;263(3):1219-25. PubMed PMID: 1469630. 14: Gué M, Yoneda M, Mönnikes H, Junien JL, Taché Y. Central neuropeptide Y and the sigma ligand, JO 1784, reverse corticotropin-releasing factor-induced inhibition of gastric acid secretion in rats. Br J Pharmacol. 1992 Nov;107(3):642-7. PubMed PMID: 1472962; PubMed Central PMCID: PMC1907747. 15: Monnet FP, Blier P, Debonnel G, de Montigny C. Modulation by sigma ligands of N-methyl-D-aspartate-induced [3H]noradrenaline release in the rat hippocampus: G-protein dependency. Naunyn Schmiedebergs Arch Pharmacol. 1992 Jul;346(1):32-9. PubMed PMID: 1407002. 16: Earley B, Burke M, Leonard BE, Gouret CJ, Junien JL. Evidence for an anti-amnesic effect of JO 1784 in the rat: a potent and selective ligand for the sigma receptor. Brain Res. 1991 Apr 19;546(2):282-6. PubMed PMID: 1676927.

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