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MedKoo Cat#: 531371 | Name: A-85380 HCl

Description:

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

A-85380 is a nicotinic acetylcholine receptor agonist.

Chemical Structure

A-85380 HCl
A-85380 HCl
CAS#174740-86-4 (HCl)

Theoretical Analysis

MedKoo Cat#: 531371

Name: A-85380 HCl

CAS#: 174740-86-4 (HCl)

Chemical Formula: C9H14Cl2N2O

Exact Mass: 164.0950

Molecular Weight: 237.12

Elemental Analysis: C, 45.59; H, 5.95; Cl, 29.90; N, 11.81; O, 6.75

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 #
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
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 237.12 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: 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.

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