Synonym
F11440; F-11440; F 11440; Eptapirone; Eptapirone free base;
IUPAC/Chemical Name
4-Methyl-2-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)-as-triazine-3,5(2H,4H)-dione
InChi Key
NMYAHEULKSYAPP-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H23N7O2/c1-20-14(24)13-19-23(16(20)25)8-3-2-7-21-9-11-22(12-10-21)15-17-5-4-6-18-15/h4-6,13H,2-3,7-12H2,1H3
SMILES Code
O=C(N1C)N(CCCCN2CCN(C3=NC=CC=N3)CC2)N=CC1=O
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, not in water
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
Biological target:
Eptapirone (F11440) is a potent, selective, high efficacy 5-HT1A receptor agonist with marked anxiolytic and antidepressant potential.
In vitro activity:
In cells transfected with human 5-HT1Areceptors, F 11440 inhibited forskolin-induced stimulation of cAMP with a pEC50 value of 6.80 ± 0.11 (mean ± S.E.M.) (fig. 3, top).
Reference: J Pharmacol Exp Ther. 1998 Oct;287(1):266-83. https://pubmed.ncbi.nlm.nih.gov/9765347/
In vivo activity:
F 11440 dose-dependently inhibited methylphenidate-induced gnawing (data not shown) (ED50: 0.12 mg/kg; maximal effect: 1.0 ± 1.0). Pretreatment with WAY-100635 (0.63 mg/kg, s.c.) attenuated the effects of F 11440 on methylphenidate-induced gnawing (ED50: 55 mg/kg; maximal effect: 0.40 ± 0.25). F 11440 was unable to normalize the behavior of methylphenidate-treated rats, either in the absence or in the presence of WAY-100635 (maximum percentage of rats normalized: 0% and 40%, respectively).
Reference: J Pharmacol Exp Ther. 1998 Oct;287(1):266-83. https://pubmed.ncbi.nlm.nih.gov/9765347/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
10.0 |
28.95 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
345.41
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:
1. Thomas GH, Babbs AJ, Chatfield RE, Krülle TM, Widdowson PS, Provost D, McCormack JG. 5-HT(1A) activation counteracts cardiovascular but not hypophagic effects of sibutramine in rats. Obesity (Silver Spring). 2009 Mar;17(3):467-73. doi: 10.1038/oby.2008.550. Epub 2008 Dec 11. PMID: 19219064.
2. Koek W, Patoiseau JF, Assié MB, Cosi C, Kleven MS, Dupont-Passelaigue E, Carilla-Durand E, Palmier C, Valentin JP, John G, Pauwels PJ, Tarayre JP, Colpaert FC. F 11440, a potent, selective, high efficacy 5-HT1A receptor agonist with marked anxiolytic and antidepressant potential. J Pharmacol Exp Ther. 1998 Oct;287(1):266-83. PMID: 9765347.
In vitro protocol:
1. Koek W, Patoiseau JF, Assié MB, Cosi C, Kleven MS, Dupont-Passelaigue E, Carilla-Durand E, Palmier C, Valentin JP, John G, Pauwels PJ, Tarayre JP, Colpaert FC. F 11440, a potent, selective, high efficacy 5-HT1A receptor agonist with marked anxiolytic and antidepressant potential. J Pharmacol Exp Ther. 1998 Oct;287(1):266-83. PMID: 9765347.
In vivo protocol:
1. Thomas GH, Babbs AJ, Chatfield RE, Krülle TM, Widdowson PS, Provost D, McCormack JG. 5-HT(1A) activation counteracts cardiovascular but not hypophagic effects of sibutramine in rats. Obesity (Silver Spring). 2009 Mar;17(3):467-73. doi: 10.1038/oby.2008.550. Epub 2008 Dec 11. PMID: 19219064.
2. Koek W, Patoiseau JF, Assié MB, Cosi C, Kleven MS, Dupont-Passelaigue E, Carilla-Durand E, Palmier C, Valentin JP, John G, Pauwels PJ, Tarayre JP, Colpaert FC. F 11440, a potent, selective, high efficacy 5-HT1A receptor agonist with marked anxiolytic and antidepressant potential. J Pharmacol Exp Ther. 1998 Oct;287(1):266-83. PMID: 9765347.
1: Wilson SJ, Bailey JE, Nutt DJ. Dizziness produced by a potent 5HT(1A) receptor agonist (eptapirone) is not due to postural hypotension. Psychopharmacology (Berl). 2005 Jun;179(4):895-6. doi: 10.1007/s00213-004-2111-4. Epub 2004 Dec 24. PMID: 15619110.
2: Wilson SJ, Bailey JE, Rich AS, Nash J, Adrover M, Tournoux A, Nutt DJ. The use of sleep measures to compare a new 5HT1A agonist with buspirone in humans. J Psychopharmacol. 2005 Nov;19(6):609-13. doi: 10.1177/0269881105058775. PMID: 16272182.
3: Pauwels PJ, Colpaert FC. Ca2+ responses in Chinese hamster ovary-K1 cells demonstrate an atypical pattern of ligand-induced 5-HT1A receptor activation. J Pharmacol Exp Ther. 2003 Nov;307(2):608-14. doi: 10.1124/jpet.103.055871. Epub 2003 Sep 11. PMID: 12970382.
4: Li CJ, Zhang LG, Liu LB, An MQ, Dong LG, Gu HY, Dai YP, Wang F, Mao CJ, Liu CF. Inhibition of Spinal 5-HT3 Receptor and Spinal Dorsal Horn Neuronal Excitability Alleviates Hyperalgesia in a Rat Model of Parkinson's Disease. Mol Neurobiol. 2022 Dec;59(12):7253-7264. doi: 10.1007/s12035-022-03034-8. Epub 2022 Sep 27. PMID: 36168076.
5: Prinssen EP, Colpaert FC, Koek W. 5-HT1A receptor activation and anti- cataleptic effects: high-efficacy agonists maximally inhibit haloperidol-induced catalepsy. Eur J Pharmacol. 2002 Oct 25;453(2-3):217-21. doi: 10.1016/s0014-2999(02)02430-5. PMID: 12398907.
6: Thomas GH, Babbs AJ, Chatfield RE, Krülle TM, Widdowson PS, Provost D, McCormack JG. 5-HT(1A) activation counteracts cardiovascular but not hypophagic effects of sibutramine in rats. Obesity (Silver Spring). 2009 Mar;17(3):467-73. doi: 10.1038/oby.2008.550. Epub 2008 Dec 11. PMID: 19219064.
7: Koek W, Patoiseau JF, Assié MB, Cosi C, Kleven MS, Dupont-Passelaigue E, Carilla-Durand E, Palmier C, Valentin JP, John G, Pauwels PJ, Tarayre JP, Colpaert FC. F 11440, a potent, selective, high efficacy 5-HT1A receptor agonist with marked anxiolytic and antidepressant potential. J Pharmacol Exp Ther. 1998 Oct;287(1):266-83. PMID: 9765347.
