Eptapirone fumarate
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MedKoo CAT#: 329520

CAS#: 179756-85-5 (fumarate)

Description: Eptapirone, also known as F11440, is a potent 5HT(1A) receptor agonist with marked anxiolytic and antidepressant potential. The affinity of F 11440 for 5-HT1A binding sites (pKi, 8.33) was higher than that of buspirone (pKi, 7.50), and somewhat lower than that of flesinoxan (pKi, 8.91). In vivo, F 11440 was 4- to 20-fold more potent than flesinoxan, and 30- to 60-fold more potent than buspirone, in exerting 5-HT1A agonist activity at pre- and postsynaptic receptors in rats (measured by, for example, its ability to decrease hippocampal extracellular serotonin (5-HT) levels and to increase plasma corticosterone levels, respectively).

Chemical Structure

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Eptapirone fumarate
CAS# 179756-85-5 (fumarate)
Instruction

Theoretical Analysis

MedKoo Cat#: 329520
Name: Eptapirone fumarate
CAS#: 179756-85-5 (fumarate)
Chemical Formula: C20H27N7O6
Exact Mass: 345.19
Molecular Weight: 461.479
Elemental Analysis: C, 52.05; H, 5.90; N, 21.25; O, 20.80

Price and Availability

Size Price Availability Quantity
1g USD 3450 2 weeks
2g USD 5950 2 weeks
5g USD 8450 2 weeks
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Related CAS #: 179756-85-5 (fumarate)   179756-58-2 (free base)    

Synonym: Eptapirone; F11440; F-11440; F 11440.

IUPAC/Chemical Name: 4-Methyl-2-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]-1,2,4-triazine-3,5-dione fumarate

InChi Key: IRTCWPNSLGQHOR-WLHGVMLRSA-N

InChi Code: InChI=1S/C16H23N7O2.C4H4O4/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;5-3(6)1-2-4(7)8/h4-6,13H,2-3,7-12H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

SMILES Code: O=C(N1C)N(CCCCN2CCN(C3=NC=CC=N3)CC2)N=CC1=O.O=C(O)/C=C/C(O)=O

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 461.48 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.