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MedKoo Cat#: 562983 | Name: Robalzotan

Description:

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

Robalzotan is a elective antagonist at the 5-HT1A receptor.

Chemical Structure

Robalzotan
Robalzotan
CAS#169758-66-1

Theoretical Analysis

MedKoo Cat#: 562983

Name: Robalzotan

CAS#: 169758-66-1

Chemical Formula: C18H23FN2O2

Exact Mass: 318.1744

Molecular Weight: 318.39

Elemental Analysis: C, 67.90; H, 7.28; F, 5.97; N, 8.80; O, 10.05

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Robalzotan; AZD7371; AZD-7371; AZD 7371; NAD-299; NAD 299; NAD299;
IUPAC/Chemical Name
(3R)-3-[Di(cyclobutyl)amino]-8-fluoro-3,4-dihydro-2H-chromene-5-carboxamide
InChi Key
MQTUXRKNJYPMCG-CYBMUJFWSA-N
InChi Code
InChI=1S/C18H23FN2O2/c19-16-8-7-14(18(20)22)15-9-13(10-23-17(15)16)21(11-3-1-4-11)12-5-2-6-12/h7-8,11-13H,1-6,9-10H2,(H2,20,22)/t13-/m1/s1
SMILES Code
O=C(C1=CC=C(F)C2=C1C[C@@H](N(C3CCC3)C4CCC4)CO2)N
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

Preparing Stock Solutions

The following data is based on the product molecular weight 318.39 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
1: Pittalà V, Siracusa MA, Salerno L, Romeo G, Modica MN, Madjid N, Ogren SO. Analysis of mechanisms for memory enhancement using novel and potent 5-HT1A receptor ligands. Eur Neuropsychopharmacol. 2015 Aug;25(8):1314-23. doi: 10.1016/j.euroneuro.2015.04.017. Epub 2015 Apr 29. PubMed PMID: 25963581. 2: Brenna E, Gatti FG, Malpezzi L, Monti D, Parmeggiani F, Sacchetti A. Synthesis of robalzotan, ebalzotan, and rotigotine precursors via the stereoselective multienzymatic cascade reduction of α,β-unsaturated aldehydes. J Org Chem. 2013 May 17;78(10):4811-22. doi: 10.1021/jo4003097. Epub 2013 May 8. PubMed PMID: 23611252. 3: Eriksson TM, Delagrange P, Spedding M, Popoli M, Mathé AA, Ögren SO, Svenningsson P. Emotional memory impairments in a genetic rat model of depression: involvement of 5-HT/MEK/Arc signaling in restoration. Mol Psychiatry. 2012 Feb;17(2):173-84. doi: 10.1038/mp.2010.131. Epub 2011 Jan 18. PubMed PMID: 21242991; PubMed Central PMCID: PMC3265836. 4: Kehr J, Hu XJ, Yoshitake T, Wang FH, Osborne P, Stenfors C, Ogren SO. The selective 5-HT(1A) receptor antagonist NAD-299 increases acetylcholine release but not extracellular glutamate levels in the frontal cortex and hippocampus of awake rat. Eur Neuropsychopharmacol. 2010 Jul;20(7):487-500. doi: 10.1016/j.euroneuro.2010.03.003. Epub 2010 Apr 21. PubMed PMID: 20413275. 5: Youn J, Misane I, Eriksson TM, Millan MJ, Ogren SO, Verhage M, Stiedl O. Bidirectional modulation of classical fear conditioning in mice by 5-HT(1A) receptor ligands with contrasting intrinsic activities. Neuropharmacology. 2009 Oct-Nov;57(5-6):567-76. doi: 10.1016/j.neuropharm.2009.07.011. Epub 2009 Jul 15. PubMed PMID: 19607850. 6: Lindström E, Ravnefjord A, Brusberg M, Hjorth S, Larsson H, Martinez V. The selective 5-hydroxytryptamine 1A antagonist, AZD7371 [3(R)-(N,N-dicyclobutylamino)-8-fluoro-3,4-dihydro-2H-1-benzopyran-5-carboxamide (R,R)-tartrate monohydrate] (robalzotan tartrate monohydrate), inhibits visceral pain-related visceromotor, but not autonomic cardiovascular, responses to colorectal distension in rats. J Pharmacol Exp Ther. 2009 Jun;329(3):1048-55. doi: 10.1124/jpet.109.152330. Epub 2009 Mar 26. PubMed PMID: 19325032. 7: Drossman DA, Danilewitz M, Naesdal J, Hwang C, Adler J, Silberg DG. Randomized, double-blind, placebo-controlled trial of the 5-HT1A receptor antagonist AZD7371 tartrate monohydrate (robalzotan tartrate monohydrate) in patients with irritable bowel syndrome. Am J Gastroenterol. 2008 Oct;103(10):2562-9. doi: 10.1111/j.1572-0241.2008.02115.x. Epub 2008 Sep 4. PubMed PMID: 18775020. 8: Eriksson MA, Gabrielsson J, Nilsson LB. Studies of drug binding to plasma proteins using a variant of equilibrium dialysis. J Pharm Biomed Anal. 2005 Jul 1;38(3):381-9. Epub 2005 Feb 24. PubMed PMID: 15925237. 9: Lüttgen M, Elvander E, Madjid N, Ogren SO. Analysis of the role of 5-HT1A receptors in spatial and aversive learning in the rat. Neuropharmacology. 2005 May;48(6):830-52. PubMed PMID: 15829255. 10: Tordera R, Pei Q, Newson M, Gray K, Sprakes M, Sharp T. Effect of different 5-HT1A receptor antagonists in combination with paroxetine on expression of the immediate-early gene Arc in rat brain. Neuropharmacology. 2003 Jun;44(7):893-902. PubMed PMID: 12726821. 11: Andrée B, Hedman A, Thorberg SO, Nilsson D, Halldin C, Farde L. Positron emission tomographic analysis of dose-dependent NAD-299 binding to 5-hydroxytryptamine-1A receptors in the human brain. Psychopharmacology (Berl). 2003 Apr;167(1):37-45. Epub 2003 Mar 11. PubMed PMID: 12632244. 12: Misane I, Ogren SO. Selective 5-HT1A antagonists WAY 100635 and NAD-299 attenuate the impairment of passive avoidance caused by scopolamine in the rat. Neuropsychopharmacology. 2003 Feb;28(2):253-64. PubMed PMID: 12589378. 13: Jerning E, Rosqvist S, Mohell N. Nad-299 antagonises 5-HT-stimulated and spiperone-inhibited [35S]GTPgammaS binding in cloned 5-HT1A receptors. J Recept Signal Transduct Res. 2002 Feb-Nov;22(1-4):483-95. PubMed PMID: 12503636. 14: Pehrson R, Ojteg G, Ishizuka O, Andersson KE. Effects of NAD-299, a new, highly selective 5-HT1A receptor antagonist, on bladder function in rats. Naunyn Schmiedebergs Arch Pharmacol. 2002 Dec;366(6):528-36. Epub 2002 Oct 17. PubMed PMID: 12444493. 15: Sandell J, Halldin C, Chou YH, Swahn CG, Thorberg SO, Farde L. PET-examination and metabolite evaluation in monkey of [(11)C]NAD-299, a radioligand for visualisation of the 5-HT(1A) receptor. Nucl Med Biol. 2002 Jan;29(1):39-45. PubMed PMID: 11786274. 16: Stenfors C, Ross SB. Hypothermia reduces the rate of dissociation of specific ligands from dopamine-D2 and 5-hydroxytryptamine1A receptors in the mouse brain in vivo. Naunyn Schmiedebergs Arch Pharmacol. 2001 Nov;364(5):479-86. PubMed PMID: 11692232. 17: Mucke HA. Robalzotan AstraZeneca. Curr Opin Investig Drugs. 2000 Oct;1(2):236-40. PubMed PMID: 11249580. 18: Passchier J, van Waarde A. Visualisation of serotonin-1A (5-HT1A) receptors in the central nervous system. Eur J Nucl Med. 2001 Jan;28(1):113-29. Review. PubMed PMID: 11202445. 19: Andrée B, Halldin C, Thorberg SO, Sandell J, Farde L. Use of PET and the radioligand [carbonyl-(11)C]WAY-100635 in psychotropic drug development. Nucl Med Biol. 2000 Jul;27(5):515-21. PubMed PMID: 10962260. 20: Malmberg A, Strange PG. Site-directed mutations in the third intracellular loop of the serotonin 5-HT(1A) receptor alter G protein coupling from G(i) to G(s) in a ligand-dependent manner. J Neurochem. 2000 Sep;75(3):1283-93. PubMed PMID: 10936212.