Panamesine | CAS# 139225-22-2 | sigma receptor antagonist

MedKoo Cat#: 414749 | Name: Panamesine

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Description:

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

Panamesine is a sigma receptor antagonist that was under development by Merck as a potential antipsychotic for the treatment of schizophrenia in the 1990s but was never marketed. It is a selective antagonist of both sigma receptor subtypes, the σ₁ and σ₂ receptors. In a 1999 study, it was shown that PAN in doses up to 90 mg/day improved psychometric variables in patients with an acute episode of schizophrenia.

Chemical Structure

Panamesine

CAS#139225-22-2

Theoretical Analysis

MedKoo Cat#: 414749

Name: Panamesine

CAS#: 139225-22-2

Chemical Formula: C23H26N2O6

Exact Mass: 426.1791

Molecular Weight: 426.47

Elemental Analysis: C, 64.78; H, 6.15; N, 6.57; O, 22.51

Price and Availability

Size	Price	Availability
5mg	USD 660.00	2 Weeks
10mg	USD 1,090.00	2 Weeks
25mg	USD 2,150.00	2 Weeks
50mg	USD 3,450.00	2 Weeks
100mg	USD 5,250.00	2 Weeks

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Related CAS #

No Data

Synonym

Panamesine

IUPAC/Chemical Name

(5S)-5-((4-Hydroxy-4-(3,4-(methylenedioxy)phenyl)piperidino)methyl)-3-(p-methoxyphenyl)-2-oxazolidinone.

InChi Key

NINYZUDVKTUKIA-IBGZPJMESA-N

InChi Code

InChI=1S/C23H26N2O6/c1-28-18-5-3-17(4-6-18)25-14-19(31-22(25)26)13-24-10-8-23(27,9-11-24)16-2-7-20-21(12-16)30-15-29-20/h2-7,12,19,27H,8-11,13-15H2,1H3/t19-/m0/s1

SMILES Code

O=C1O[C@@H](CN2CCC(C3=CC(OCO4)=C4C=C3)(O)CC2)CN1C5=CC=C(OC)C=C5

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 426.47 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.

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: Skuza G, Rogóz Z. Effect of BD 1047, a sigma1 receptor antagonist, in the animal models predictive of antipsychotic activity. Pharmacol Rep. 2006 Sep- Oct;58(5):626-35. PMID: 17085854. 2: Skuza G. Effect of sigma ligands on the cocaine-induced convulsions in mice. Pol J Pharmacol. 1999 Nov-Dec;51(6):477-83. PMID: 10817525. 3: Müller MJ, Gründer G, Wetzel H, Müller-Siecheneder F, Marx-Dannigkeit P, Benkert O. Antipsychotic effects and tolerability of the sigma ligand EMD 57445 (panamesine) and its metabolites in acute schizophrenia: an open clinical trial. Psychiatry Res. 1999 Dec 27;89(3):275-80. doi: 10.1016/s0165-1781(99)00100-6. PMID: 10708274. 4: Okuyama S. [Atypical antipsychotic profiles of sigma receptor ligands]. Nihon Yakurigaku Zasshi. 1999 Jul;114(1):13-23. Japanese. doi: 10.1254/fpj.114.13. PMID: 10562961. 5: Gründer G, Müller MJ, Andreas J, Heydari N, Wetzel H, Schlösser R, Schlegel S, Nickel O, Eissner D, Benkert O. Occupancy of striatal D(2)-like dopamine receptors after treatment with the sigma ligand EMD 57445, a putative atypical antipsychotic. Psychopharmacology (Berl). 1999 Sep 1;146(1):81-6. doi: 10.1007/s002130051091. PMID: 10485968. 6: Skuza G, Kolasiewicz W, Dziedzicka-Wasylewska M, Margas W. Effect of local intracerebral administration of EMD 57445, a selective sigma receptor ligand, on the locomotor activity of the rat. Pol J Pharmacol. 1998 Nov-Dec;50(6):399-406. PMID: 10385922. 7: Huber MT, Gotthardt U, Schreiber W, Krieg JC. Efficacy and safety of the sigma receptor ligand EMD 57445 (panamesine) in patients with schizophrenia: an open clinical trial. Pharmacopsychiatry. 1999 Mar;32(2):68-72. doi: 10.1055/s-2007-979194. PMID: 10333165. 8: Frieboes RM, Murck H, Antonijevic I, Kraus T, Hinze-Selch D, Pollmächer T, Steiger A. Characterization of the sigma ligand panamesine, a potential antipsychotic, by immune response in patients with schizophrenia and by sleep- EEG changes in normal controls. Psychopharmacology (Berl). 1999 Jan;141(1):107-10. doi: 10.1007/s002130050813. PMID: 9952072. 9: Skuza G, Gołembiowska K, Wedzony K. Effect of EMD 57445, the selective sigma receptor ligand, on the turnover and release of dopamine. Pol J Pharmacol. 1998 Jan-Feb;50(1):61-4. PMID: 9662740. 10: Skuza G, Rogóz Z, Gołembiowska K. EMD 57445, the selective sigma receptor ligand, has no effect on the 5-hydroxytryptamine system. Pol J Pharmacol. 1997 Nov-Dec;49(6):489-93. PMID: 9566054. 11: Skuza G, Rogóz Z. Effect of 1,3-di-o-tolylguanidine (DTG), rimcazole and EMD 57445, the sigma receptor ligands, in the forced swimming test. Pol J Pharmacol. 1997 Sep-Oct;49(5):329-35. PMID: 9566032. 12: Frieboes RM, Murck H, Wiedemann K, Holsboer F, Steiger A. Open clinical trial on the sigma ligand panamesine in patients with schizophrenia. Psychopharmacology (Berl). 1997 Jul;132(1):82-8. doi: 10.1007/s002130050323. PMID: 9272763. 13: Maj J, Rogóz Z, Skuza G, Mazela H. Neuropharmacological profile of EMD 57445, a sigma receptor ligand with potential antipsychotic activity. Eur J Pharmacol. 1996 Nov 21;315(3):235-43. doi: 10.1016/s0014-2999(96)00602-4. PMID: 8982660. 14: Dahmen N, Fischer V, Hödl P, Rujescu D, Reuss S, Bartoszyk GD, Hiemke C. Induction of c-fos gene expression by the selective sigma receptor ligand EMD 57445 in rat brain. Eur Neuropsychopharmacol. 1996 Aug;6(3):237-43. doi: 10.1016/0924-977x(96)00026-0. PMID: 8880084.