NAD-299 HCl

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

MedKoo CAT#: 562977

CAS#: 184674-99-5

Description: NAD-299 HCl is a high affinity 5-HT1A receptor antagonist.


Price and Availability

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NAD-299 HCl is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 562977
Name: NAD-299 HCl
CAS#: 184674-99-5
Chemical Formula: C18H24ClFN2O2
Exact Mass:
Molecular Weight: 354.85
Elemental Analysis: C, 60.93; H, 6.82; Cl, 9.99; F, 5.35; N, 7.89; O, 9.02


Synonym: NAD-299 HCl; NAD 299 HCl; NAD299 HCl; NAD-299 hydrochloride; NAD 299 Hydrochloride; NAD299 Hydrochloride;

IUPAC/Chemical Name: (R)-3-(dicyclobutylamino)-8-fluorochromane-5-carboxamide hydrochloride

InChi Key: GSZJANKLCPHEEX-BTQNPOSSSA-N

InChi Code: InChI=1S/C18H23FN2O2.ClH/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);1H/t13-;/m1./s1

SMILES Code: O=C(C1=C2C[C@@H](N(C3CCC3)C4CCC4)COC2=C(F)C=C1)N.[H]Cl


Technical Data

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).

Harmonized System Code:
293490


References

1: Kumar JR, Rajkumar R, Lee LC, Dawe GS. Nucleus incertus contributes to an anxiogenic effect of buspirone in rats: Involvement of 5-HT1A receptors. Neuropharmacology. 2016 Nov;110(Pt A):1-14. doi: 10.1016/j.neuropharm.2016.07.019. Epub 2016 Jul 18. PubMed PMID: 27436722.

2: 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.

3: Dill MJ, Shaw J, Cramer J, Sindelar DK. 5-HT1A receptor antagonists reduce food intake and body weight by reducing total meals with no conditioned taste aversion. Pharmacol Biochem Behav. 2013 Nov;112:1-8. doi: 10.1016/j.pbb.2013.09.003. Epub 2013 Sep 21. PubMed PMID: 24064183.

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5: Eriksson TM, Holst S, Stan TL, Hager T, Sjögren B, Ogren SÖ, Svenningsson P, Stiedl O. 5-HT1A and 5-HT7 receptor crosstalk in the regulation of emotional memory: implications for effects of selective serotonin reuptake inhibitors. Neuropharmacology. 2012 Nov;63(6):1150-60. doi: 10.1016/j.neuropharm.2012.06.061. Epub 2012 Jul 16. PubMed PMID: 22801295.

6: Wright JM, Dobosiewicz MR, Clarke PB. α- and β-Adrenergic receptors differentially modulate the emission of spontaneous and amphetamine-induced 50-kHz ultrasonic vocalizations in adult rats. Neuropsychopharmacology. 2012 Feb;37(3):808-21. doi: 10.1038/npp.2011.258. Epub 2011 Oct 26. PubMed PMID: 22030713; PubMed Central PMCID: PMC3260979.

7: 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.

8: 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.

9: 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.

10: 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.

11: 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.

12: Madjid N, Tottie EE, Lüttgen M, Meister B, Sandin J, Kuzmin A, Stiedl O, Ogren SO. 5-Hydroxytryptamine 1A receptor blockade facilitates aversive learning in mice: interactions with cholinergic and glutamatergic mechanisms. J Pharmacol Exp Ther. 2006 Feb;316(2):581-91. Epub 2005 Oct 13. PubMed PMID: 16223872.

13: 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.

14: 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.

15: Hajós M, Gartside SE, Varga V, Sharp T. In vivo inhibition of neuronal activity in the rat ventromedial prefrontal cortex by midbrain-raphe nuclei: role of 5-HT1A receptors. Neuropharmacology. 2003 Jul;45(1):72-81. PubMed PMID: 12814660.

16: 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.

17: 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.

18: 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.

19: 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.

20: 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.