Synonym
AZ-66; AZ 66; AZ66
IUPAC/Chemical Name
3-(4-(4-cyclohexylpiperazin-1-yl)pentyl)-6-fluorobenzo[d]thiazol-2(3H)-one
InChi Key
AXVCFARJNXIHLD-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H32FN3OS/c1-17(24-12-14-25(15-13-24)19-7-3-2-4-8-19)6-5-11-26-20-10-9-18(23)16-21(20)28-22(26)27/h9-10,16-17,19H,2-8,11-15H2,1H3
SMILES Code
O=C1SC2=CC(F)=CC=C2N1CCCC(N3CCN(C4CCCCC4)CC3)C
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
>3 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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
405.58
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: Robson MJ, Seminerio MJ, McCurdy CR, Coop A, Matsumoto RR. σ Receptor antagonist attenuation of methamphetamine-induced neurotoxicity is correlated to body temperature modulation. Pharmacol Rep. 2013;65(2):343-9. PubMed PMID: 23744418.
2: Jamalapuram S, Vuppala PK, Abdelazeem AH, McCurdy CR, Avery BA. Ultra-performance liquid chromatography tandem mass spectrometry method for the determination of AZ66, a sigma receptor ligand, in rat plasma and its application to in vivo pharmacokinetics. Biomed Chromatogr. 2013 Aug;27(8):1034-40. doi: 10.1002/bmc.2901. Epub 2013 Apr 5. PubMed PMID: 23558564; PubMed Central PMCID: PMC4122523.
3: Seminerio MJ, Hansen R, Kaushal N, Zhang HT, McCurdy CR, Matsumoto RR. The evaluation of AZ66, an optimized sigma receptor antagonist, against methamphetamine-induced dopaminergic neurotoxicity and memory impairment in mice. Int J Neuropsychopharmacol. 2013 Jun;16(5):1033-44. doi: 10.1017/S1461145712000831. Epub 2012 Aug 29. PubMed PMID: 22932447.
4: Seminerio MJ, Robson MJ, McCurdy CR, Matsumoto RR. Sigma receptor antagonists attenuate acute methamphetamine-induced hyperthermia by a mechanism independent of IL-1β mRNA expression in the hypothalamus. Eur J Pharmacol. 2012 Sep 15;691(1-3):103-9. doi: 10.1016/j.ejphar.2012.07.029. Epub 2012 Jul 20. PubMed PMID: 22820108; PubMed Central PMCID: PMC3726051.
5: Seminerio MJ, Robson MJ, Abdelazeem AH, Mesangeau C, Jamalapuram S, Avery BA, McCurdy CR, Matsumoto RR. Synthesis and pharmacological characterization of a novel sigma receptor ligand with improved metabolic stability and antagonistic effects against methamphetamine. AAPS J. 2012 Mar;14(1):43-51. doi: 10.1208/s12248-011-9311-8. Epub 2011 Dec 20. PubMed PMID: 22183188; PubMed Central PMCID: PMC3291180.
