S 20499

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

MedKoo CAT#: 461634

CAS#: 143413-69-8

Description: S 20499 is a potential anxiolytic drug that acts by stimulation of 5-HT1A receptors.

Chemical Structure

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S 20499
CAS# 143413-69-8
Instruction

Theoretical Analysis

MedKoo Cat#: 461634
Name: S 20499
CAS#: 143413-69-8
Chemical Formula: C26H39ClN2O4
Exact Mass: 478.26
Molecular Weight: 479.050
Elemental Analysis: C, 65.19; H, 8.21; Cl, 7.40; N, 5.85; O, 13.36

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: S 20499; S-20499; S20499; Alnespiron;

IUPAC/Chemical Name: 8-(4-((5-methoxychroman-3-yl)(propyl)amino)butyl)-8-azaspiro[4.5]decane-7,9-dione hydrochloride

InChi Key: QYFHCFNBYQZGKW-UHFFFAOYSA-N

InChi Code: InChI=1S/C26H38N2O4.ClH/c1-3-13-27(20-16-21-22(31-2)9-8-10-23(21)32-19-20)14-6-7-15-28-24(29)17-26(18-25(28)30)11-4-5-12-26;/h8-10,20H,3-7,11-19H2,1-2H3;1H

SMILES Code: O=C(N(CCCCN(C1COC2=CC=CC(OC)=C2C1)CCC)C(C3)=O)CC43CCCC4.[H]Cl

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: >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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 479.05 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: Protais P, Lesourd M, Comoy E. Similar pharmacological properties of 8-OH-DPAT and alnespirone (S 20499) at dopamine receptors: comparison with buspirone. Eur J Pharmacol. 1998 Jul 10;352(2-3):179-87. PubMed PMID: 9716353.

2: Van de Kar LD, Levy AD, Li Q, Brownfield MS. A comparison of the oxytocin and vasopressin responses to the 5-HT1A agonist and potential anxiolytic drug alnespirone (S-20499). Pharmacol Biochem Behav. 1998 Jul;60(3):677-83. PubMed PMID: 9678651.

3: Dugast C, Soulière F, Schmitt P, Casanovas JM, Fattaccini CM, Mocaër E, Lesourd M, Renaud B, Artigas F, Hamon M, Chouvet G. Is the potent 5-HT1A receptor agonist, alnespirone (S-20499), affecting dopaminergic systems in the rat brain? Eur J Pharmacol. 1998 Jun 5;350(2-3):171-80. PubMed PMID: 9696405.

4: Mac Sweeney CP, Lesourd M, Gandon JM. Antidepressant-like effects of alnespirone (S 20499) in the learned helplessness test in rats. Eur J Pharmacol. 1998 Mar 19;345(2):133-7. PubMed PMID: 9600628.

5: Astier B, Lambás Señas L, Soulière F, Schmitt P, Urbain N, Rentero N, Bert L, Denoroy L, Renaud B, Lesourd M, Muñoz C, Chouvet G. In vivo comparison of two 5-HT1A receptors agonists alnespirone (S-20499) and buspirone on locus coeruleus neuronal activity. Eur J Pharmacol. 2003 Jan 10;459(1):17-26. PubMed PMID: 12505530.

6: Muñoz C, Papp M. Alnespirone (S 20499), an agonist of 5-HT1A receptors, and imipramine have similar activity in a chronic mild stress model of depression. Pharmacol Biochem Behav. 1999 Aug;63(4):647-53. PubMed PMID: 10462194.

7: Kidd EJ, Haj-Dahmane S, Jolas T, Lanfumey L, Fattaccini CM, Guardiola-Lemaitre B, Gozlan H, Hamon M. New methoxy-chroman derivatives, 4[N-(5-methoxy-chroman-3-yl)N- propylamino]butyl-8-azaspiro-(4,5)-decane-7,9-dione [(+/-)-S 20244] and its enantiomers, (+)-S 20499 and (-)-S 20500, with potent agonist properties at central 5-hydroxytryptamine1A receptors. J Pharmacol Exp Ther. 1993 Feb;264(2):863-72. PubMed PMID: 8094756.

8: McGrath C, Norman TR. (+)-S-20499 -- a potential antidepressant? A behavioural and neurochemical investigation in the olfactory bulbectomised rat. Eur Neuropsychopharmacol. 1999 Jan;9(1-2):21-7. PubMed PMID: 10082224.

9: Casanovas JM, Vilaró MT, Mengod G, Artigas F. Differential regulation of somatodendritic serotonin 5-HT1A receptors by 2-week treatments with the selective agonists alnespirone (S-20499) and 8-hydroxy-2-(Di-n-propylamino)tetralin: microdialysis and autoradiographic studies in rat brain. J Neurochem. 1999 Jan;72(1):262-72. PubMed PMID: 9886078.

10: Barrett JE, Gamble EH, Zhang L, Guardiola-Lemaitre B. Anticonflict and discriminative stimulus effects in the pigeon of a new methoxy-chroman 5-HT1A agonist, (+)S 20244 and its enantiomers (+)S 20499 and (-)S 20500. Psychopharmacology (Berl). 1994 Sep;116(1):73-8. PubMed PMID: 7862933.

11: Levy AD, Li Q, Gustafson M, Van de Kar LD. Neuroendocrine profile of the potential anxiolytic drug S-20499. Eur J Pharmacol. 1995 Feb 14;274(1-3):141-9. PubMed PMID: 7768266.

12: Got P, Raimbaud E, Bussey C, Caron G, Carrupt PA, Walther B, Bensussan A, Scherrmann JM. Production and characterization of 22 monoclonal antibodies directed against S 20499, a new potent 5-HT1A chiral agonist: influence of the hapten structure on specificity and stereorecognition. Pharm Res. 1999 May;16(5):725-35. PubMed PMID: 10350017.

13: Got PA, Guillaumet G, Boursier-Neyret C, Scherrmann JM. Production and characterization of polyclonal anti-S 20499 antibodies: influence of the hapten structure on stereospecificity. J Pharm Sci. 1997 Jun;86(6):654-9. PubMed PMID: 9188046.

14: Casanovas JM, Lésourd M, Artigas F. The effect of the selective 5-HT1A agonists alnespirone (S-20499) and 8-OH-DPAT on extracellular 5-hydroxytryptamine in different regions of rat brain. Br J Pharmacol. 1997 Oct;122(4):733-41. PubMed PMID: 9375971; PubMed Central PMCID: PMC1564978.

15: Simon P, Guardiola B, Bizot-Espiard J, Schiavi P, Costentin J. 5-HT1A receptor agonists prevent in rats the yawning and penile erections induced by direct dopamine agonists. Psychopharmacology (Berl). 1992;108(1-2):47-50. PubMed PMID: 1357709.

16: Blanchard RJ, Griebel G, Guardiola-Lemaître B, Brush MM, Lee J, Blanchard DC. An ethopharmacological analysis of selective activation of 5-HT1A receptors: the mouse 5-HT1A syndrome. Pharmacol Biochem Behav. 1997 Aug;57(4):897-908. PubMed PMID: 9259022.

17: Scott PA, Chou JM, Tang H, Frazer A. Differential induction of 5-HT1A-mediated responses in vivo by three chemically dissimilar 5-HT1A agonists. J Pharmacol Exp Ther. 1994 Jul;270(1):198-208. PubMed PMID: 8035316.

18: de Boer SF, Lesourd M, Mocaër E, Koolhaas JM. Somatodendritic 5-HT(1A) autoreceptors mediate the anti-aggressive actions of 5-HT(1A) receptor agonists in rats: an ethopharmacological study with S-15535, alnespirone, and WAY-100635. Neuropsychopharmacology. 2000 Jul;23(1):20-33. PubMed PMID: 10869883.

19: Fabre V, Boni C, Mocaër E, Lesourd M, Hamon M, Laporte AM. [3H]Alnespirone: a novel specific radioligand of 5-HT1A receptors in the rat brain. Eur J Pharmacol. 1997 Oct 22;337(2-3):297-308. PubMed PMID: 9430429.

20: de Boer SF, Lesourd M, Mocaer E, Koolhaas JM. Selective antiaggressive effects of alnespirone in resident-intruder test are mediated via 5-hydroxytryptamine1A receptors: A comparative pharmacological study with 8-hydroxy-2-dipropylaminotetralin, ipsapirone, buspirone, eltoprazine, and WAY-100635. J Pharmacol Exp Ther. 1999 Mar;288(3):1125-33. PubMed PMID: 10027850.