Eptapirone free base | F11440 | CAS#179756-85-5 | 5HT(1A) receptor agonist

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

MedKoo CAT#: 326691

CAS#: 179756-58-2 (free base)

Description: Eptapirone, also known as F11440 and L0068, is a potent, selective, high efficacy 5-HT1A 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.

Chemical Structure

Eptapirone free base

CAS# 179756-58-2 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326691
Name: Eptapirone free base
CAS#: 179756-58-2 (free base)
Chemical Formula: C16H23N7O2
Exact Mass: 345.19
Molecular Weight: 345.407
Elemental Analysis: C, 55.64; H, 6.71; N, 28.39; O, 9.26

Price and Availability

Size	Price	Availability
50mg	USD 450	2 weeks
100mg	USD 850	2 weeks
200mg	USD 1250	2 weeks
500mg	USD 1950	2 weeks
1g	USD 2950	2 weeks
2g	USD 4650	2 weeks
5g	USD 6950	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 179756-85-5 (fumarate) 179756-58-2 (free base)

Synonym: F11440; F-11440; F 11440; Eptapirone; L0068; L-0068; L 0068; 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

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, 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

More Info:

Product Data:

Product Data

Instruction:

View handling instruction

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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	10.0	28.95

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.

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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.

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Eptapirone free base featured