WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H414749
CAS#: 139225-22-2
Description: 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.
Hodoodo Cat#: H414749
Name: Panamesine
CAS#: 139225-22-2
Chemical Formula: C23H26N2O6
Exact Mass: 426.18
Molecular Weight: 426.470
Elemental Analysis: C, 64.78; H, 6.15; N, 6.57; O, 22.51
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:
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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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: 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.
2: 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.
3: 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.
4: 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.
5: 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.
6: 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.
7: 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.
8: 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.
9: 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.
10: 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.
