A-85380 HCl

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

MedKoo CAT#: 531371

CAS#: 174740-86-4 (HCl)

Description: A-85380 is a nicotinic acetylcholine receptor agonist.


Price and Availability

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A-85380 dihydrochloride 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#: 531371
Name: A-85380 HCl
CAS#: 174740-86-4 (HCl)
Chemical Formula: C9H14Cl2N2O
Exact Mass: 164.095
Molecular Weight: 237.124
Elemental Analysis: C, 45.59; H, 5.95; Cl, 29.90; N, 11.81; O, 6.75


Related CAS #: 174740-86-4 (HCl)   161416-98-4 (free base).  

Synonym: A-85380; A 85380; A85380; A-85380 dihydrochloride

IUPAC/Chemical Name: 3-[(2S)-azetidin-2-ylmethoxy]pyridine dihydrochloride

InChi Key: GVEVDINKRFDXFP-JZGIKJSDSA-N

InChi Code: InChI=1S/C9H12N2O.2ClH/c1-2-9(6-10-4-1)12-7-8-3-5-11-8;;/h1-2,4,6,8,11H,3,5,7H2;2*1H/t8-;;/m0../s1

SMILES Code: [H]Cl.[H]Cl.C1(OC[C@H]2NCC2)=CC=CN=C1


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: Lagarde J, Sarazin M, Chauviré V, Stankoff B, Kas A, Lacomblez L, Peyronneau MA, Bottlaender M. Cholinergic Changes in Aging and Alzheimer Disease: An [18F]-F-A-85380 Exploratory PET Study. Alzheimer Dis Assoc Disord. 2016 Sep 27. [Epub ahead of print] PubMed PMID: 27680780.

2: Le Foll B, Chefer SI, Kimes AS, Stein EA, Goldberg SR, Mukhin AG. Impact of short access nicotine self-administration on expression of α4β2* nicotinic acetylcholine receptors in non-human primates. Psychopharmacology (Berl). 2016 May;233(10):1829-35. doi: 10.1007/s00213-016-4250-9. PubMed PMID: 26911381; PubMed Central PMCID: PMC4846528.

3: Miyauchi M, Neugebauer NM, Oyamada Y, Meltzer HY. Nicotinic receptors and lurasidone-mediated reversal of phencyclidine-induced deficit in novel object recognition. Behav Brain Res. 2016 Mar 15;301:204-12. doi: 10.1016/j.bbr.2015.10.044. PubMed PMID: 26519556.

4: Ogunjirin AE, Fortunak JM, Brown LL, Xiao Y, Dávila-García MI. Competition, Selectivity and Efficacy of Analogs of A-84543 for Nicotinic Acetylcholine Receptors with Repositioning of Pyridine Nitrogen. Neurochem Res. 2015 Oct;40(10):2131-42. doi: 10.1007/s11064-015-1705-z. PubMed PMID: 26508288; PubMed Central PMCID: PMC4741274.

5: Freitas K, Carroll FI, Negus SS. Comparison of effects produced by nicotine and the α4β2-selective agonist 5-I-A-85380 on intracranial self-stimulation in rats. Exp Clin Psychopharmacol. 2016 Feb;24(1):65-75. doi: 10.1037/pha0000055. PubMed PMID: 26461167; PubMed Central PMCID: PMC4821675.

6: Freitas KC, Carroll FI, Negus SS. Effects of nicotinic acetylcholine receptor agonists in assays of acute pain-stimulated and pain-depressed behaviors in rats. J Pharmacol Exp Ther. 2015 Nov;355(2):341-50. doi: 10.1124/jpet.115.226803. PubMed PMID: 26359313; PubMed Central PMCID: PMC4613961.

7: Holt JC, Kewin K, Jordan PM, Cameron P, Klapczynski M, McIntosh JM, Crooks PA, Dwoskin LP, Lysakowski A. Pharmacologically distinct nicotinic acetylcholine receptors drive efferent-mediated excitation in calyx-bearing vestibular afferents. J Neurosci. 2015 Feb 25;35(8):3625-43. doi: 10.1523/JNEUROSCI.3388-14.2015. PubMed PMID: 25716861; PubMed Central PMCID: PMC4339364.

8: Yu LF, Zhang HK, Caldarone BJ, Eaton JB, Lukas RJ, Kozikowski AP. Recent developments in novel antidepressants targeting α4β2-nicotinic acetylcholine receptors. J Med Chem. 2014 Oct 23;57(20):8204-23. doi: 10.1021/jm401937a. Review. PubMed PMID: 24901260; PubMed Central PMCID: PMC4207546.

9: Lorenz R, Samnick S, Dillmann U, Schiller M, Ong MF, Faßbender K, Buck A, Spiegel J. Nicotinic α4β2 acetylcholine receptors and cognitive function in Parkinson's disease. Acta Neurol Scand. 2014 Sep;130(3):164-71. doi: 10.1111/ane.12259. PubMed PMID: 24762290.

10: Hernández-Vivanco A, Hone AJ, Scadden ML, Carmona-Hidalgo B, McIntosh JM, Albillos A. Monkey adrenal chromaffin cells express α6β4* nicotinic acetylcholine receptors. PLoS One. 2014 Apr 11;9(4):e94142. doi: 10.1371/journal.pone.0094142. PubMed PMID: 24727685; PubMed Central PMCID: PMC3984115.

11: Eaton JB, Lucero LM, Stratton H, Chang Y, Cooper JF, Lindstrom JM, Lukas RJ, Whiteaker P. The unique α4+/-α4 agonist binding site in (α4)3(β2)2 subtype nicotinic acetylcholine receptors permits differential agonist desensitization pharmacology versus the (α4)2(β2)3 subtype. J Pharmacol Exp Ther. 2014 Jan;348(1):46-58. doi: 10.1124/jpet.113.208389. PubMed PMID: 24190916; PubMed Central PMCID: PMC3868879.

12: Piao MH, Liu Y, Wang YS, Qiu JP, Feng CS. Volatile anesthetic isoflurane inhibits LTP induction of hippocampal CA1 neurons through α4β2 nAChR subtype-mediated mechanisms. Ann Fr Anesth Reanim. 2013 Oct;32(10):e135-41. doi: 10.1016/j.annfar.2013.05.012. PubMed PMID: 24011619.

13: Liu X. Positive allosteric modulation of α4β2 nicotinic acetylcholine receptors as a new approach to smoking reduction: evidence from a rat model of nicotine self-administration. Psychopharmacology (Berl). 2013 Nov;230(2):203-13. doi: 10.1007/s00213-013-3145-2. PubMed PMID: 23712602; PubMed Central PMCID: PMC3797181.

14: Leung K. 3-(2-(S)-3,4-Dehydropyrrolinyl methoxy)-5-(3'-[(18)F]fluoropropyl)pyridine. 2013 Mar 18 [updated 2013 May 23]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK138310/ PubMed PMID: 23700644.

15: Picard F, Sadaghiani S, Leroy C, Courvoisier DS, Maroy R, Bottlaender M. High density of nicotinic receptors in the cingulo-insular network. Neuroimage. 2013 Oct 1;79:42-51. doi: 10.1016/j.neuroimage.2013.04.074. PubMed PMID: 23631995.

16: Esterlis I, Hannestad JO, Perkins E, Bois F, D'Souza DC, Tyndale RF, Seibyl JP, Hatsukami DM, Cosgrove KP, O'Malley SS. Effect of a nicotine vaccine on nicotine binding to β2*-nicotinic acetylcholine receptors in vivo in human tobacco smokers. Am J Psychiatry. 2013 Apr;170(4):399-407. doi: 10.1176/appi.ajp.2012.12060793. PubMed PMID: 23429725; PubMed Central PMCID: PMC3738000.

17: Brody AL, Mukhin AG, La Charite J, Ta K, Farahi J, Sugar CA, Mamoun MS, Vellios E, Archie M, Kozman M, Phuong J, Arlorio F, Mandelkern MA. Up-regulation of nicotinic acetylcholine receptors in menthol cigarette smokers. Int J Neuropsychopharmacol. 2013 Jun;16(5):957-66. doi: 10.1017/S1461145712001022. PubMed PMID: 23171716; PubMed Central PMCID: PMC3758251.

18: Zappettini S, Grilli M, Olivero G, Mura E, Preda S, Govoni S, Salamone A, Marchi M. Beta Amyloid Differently Modulate Nicotinic and Muscarinic Receptor Subtypes which Stimulate in vitro and in vivo the Release of Glycine in the Rat Hippocampus. Front Pharmacol. 2012 Jul 27;3:146. doi: 10.3389/fphar.2012.00146. PubMed PMID: 22866037; PubMed Central PMCID: PMC3406330.

19: Saricicek A, Esterlis I, Maloney KH, Mineur YS, Ruf BM, Muralidharan A, Chen JI, Cosgrove KP, Kerestes R, Ghose S, Tamminga CA, Pittman B, Bois F, Tamagnan G, Seibyl J, Picciotto MR, Staley JK, Bhagwagar Z. Persistent β2*-nicotinic acetylcholinergic receptor dysfunction in major depressive disorder. Am J Psychiatry. 2012 Aug;169(8):851-9. doi: 10.1176/appi.ajp.2012.11101546. PubMed PMID: 22772158; PubMed Central PMCID: PMC3494404.

20: Kennett A, Heal DJ, Wonnacott S. Pharmacological differences between rat frontal cortex and hippocampus in the nicotinic modulation of noradrenaline release implicate distinct receptor subtypes. Nicotine Tob Res. 2012 Nov;14(11):1339-45. doi: 10.1093/ntr/nts128. PubMed PMID: 22614547.