Ispronicline | AZD3480 | CAS#252870-53-4 | nicotinic receptor partial agonist

MedKoo Cat#: 329460 | Name: Ispronicline

Description:

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

Ispronicline, also known as AZD3480; TC 1734; TC-0173, and RJR 1734, is a alpha4beta2 nicotinic acetylcholine receptor-selective agonist with cognition-enhancing and neuroprotective properties. Ispronicline is potentially useful for the treatment of attention-deficit/hyperactivity disorder in adults.

Chemical Structure

Ispronicline

CAS#252870-53-4 (free base)

Theoretical Analysis

MedKoo Cat#: 329460

Name: Ispronicline

CAS#: 252870-53-4 (free base)

Chemical Formula: C14H22N2O

Exact Mass: 0.0000

Molecular Weight: 234.34

Elemental Analysis: C, 71.76; H, 9.46; N, 11.95; O, 6.83

Price and Availability

Size	Price	Availability
5mg	USD 90.00	Ready to ship
10mg	USD 150.00	Ready to ship
25mg	USD 320.00	Ready to ship
50mg	USD 550.00	Ready to ship
100mg	USD 950.00	Ready to ship
200mg	USD 1,650.00	Ready to ship
500mg	USD 3,650.00	Ready to ship

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Related CAS #

252870-53-4 (free base) 252870-54-5 (hemigalactarate) 957106-98-8 (phosphate) 957107-01-6 (citrate)

Synonym

Ispronicline; AZD3480; AZD-3480; AZD 3480; TC 1734; TC-01734; TC1734; TC01734; TC 1734; TC 01734; RJR 1734; RJR-1734; RJR1734.

IUPAC/Chemical Name

(S,E)-5-(5-isopropoxypyridin-3-yl)-N-methylpent-4-en-2-amine

InChi Key

RPCVIAXDAUMJJP-PZBABLGHSA-N

InChi Code

InChI=1S/C14H22N2O/c1-11(2)17-14-8-13(9-16-10-14)7-5-6-12(3)15-4/h5,7-12,15H,6H2,1-4H3/b7-5+/t12-/m0/s1

SMILES Code

C[C@H](NC)C/C=C/C1=CC(OC(C)C)=CN=C1

Appearance

Oily liquid

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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A21T11K04

View CoA: current batch, Lot#A22T01K26

QC Data

View QC data: current batch, Lot#A21T11K04

View QC data: current batch, Lot#A22T01K26

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Ispronicline (TC-1734) is a brain-selective α4β2 nicotine acetylcholine receptor (nAChR) partial agonist that binds to the α4β2 nAChR with high affinity (Ki=11 nM) and is highly selective to other nAChRs such as α7 nAChR and α3β4 nAChR.

In vitro activity:

TBD

In vivo activity:

Adult female Sprague-Dawley rats were trained to perform an operant visual signal detection task to a stable baseline of accuracy. The rats were then injected subcutaneously following a repeated measures, counter-balanced design with saline, AZD3480 (0.01, 0.1, and 1 mg/kg), dizocilpine (0.05 mg/kg), or their combinations 30 min before the test. Dizocilpine caused a significant (p < 0.0005) impairment in percent correct performance. This attentional impairment was significantly (p < 0.0005) reversed by 0.01 and 0.1 mg/kg of AZD3480. AZD3480 by itself did not alter the already high baseline control performance. AZD3480 also showed significant efficacy for counteracting the attentional impairment caused by the NMDA glutamate antagonist dizocilpine. Low doses of AZD3480 may provide therapeutic benefit for reversing attentional impairment in patients suffering from cognitive impairment due to glutamatergic dysregulation and likely other attentional disorders. Reference: Psychopharmacology (Berl). 2012 Oct;223(3):251-8. https://pubmed.ncbi.nlm.nih.gov/22526540/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	426.73

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 234.34 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.

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:

1. Rezvani AH, Cauley MC, Johnson EC, Gatto GJ, Levin ED. Effects of AZD3480, a neuronal nicotinic acetylcholine receptor agonist, and donepezil on dizocilpine-induced attentional impairment in rats. Psychopharmacology (Berl). 2012 Oct;223(3):251-8. doi: 10.1007/s00213-012-2712-2. Epub 2012 Apr 20. PMID: 22526540. 2. Jacobsen J, Hansen HH, Kiss A, Mikkelsen JD. The α4β2 nicotine acetylcholine receptor agonist ispronicline induces c-Fos expression in selective regions of the rat forebrain. Neurosci Lett. 2012 Apr 25;515(1):7-11. doi: 10.1016/j.neulet.2012.02.081. Epub 2012 Mar 3. PMID: 22414858.

In vitro protocol:

TBD

In vivo protocol:

1: Buoli M, Serati M, Cahn W. Alternative pharmacological strategies for adult ADHD treatment: a systematic review. Expert Rev Neurother. 2016;16(2):131-44. doi: 10.1586/14737175.2016.1135735. Review. PubMed PMID: 26693882. 2: Gabrielsson J, Peletier LA. Dose-response-time data analysis involving nonlinear dynamics, feedback and delay. Eur J Pharm Sci. 2014 Aug 1;59:36-48. doi: 10.1016/j.ejps.2014.04.007. PubMed PMID: 24751673. 3: Levin ED. Nicotinic attention-deficit/hyperactivity disorder treatment. Biol Psychiatry. 2014 Feb 1;75(3):174. doi: 10.1016/j.biopsych.2013.11.024. PubMed PMID: 24370349. 4: Potter AS, Dunbar G, Mazzulla E, Hosford D, Newhouse PA. AZD3480, a novel nicotinic receptor agonist, for the treatment of attention-deficit/hyperactivity disorder in adults. Biol Psychiatry. 2014 Feb 1;75(3):207-14. doi: 10.1016/j.biopsych.2013.06.002. PubMed PMID: 23856296. 5: Rezvani AH, Cauley MC, Johnson EC, Gatto GJ, Levin ED. Effects of AZD3480, a neuronal nicotinic acetylcholine receptor agonist, and donepezil on dizocilpine-induced attentional impairment in rats. Psychopharmacology (Berl). 2012 Oct;223(3):251-8. doi: 10.1007/s00213-012-2712-2. PubMed PMID: 22526540. 6: Jacobsen J, Hansen HH, Kiss A, Mikkelsen JD. The α4β2 nicotine acetylcholine receptor agonist ispronicline induces c-Fos expression in selective regions of the rat forebrain. Neurosci Lett. 2012 Apr 25;515(1):7-11. doi: 10.1016/j.neulet.2012.02.081. PubMed PMID: 22414858. 7: Velligan D, Brenner R, Sicuro F, Walling D, Riesenberg R, Sfera A, Merideth C, Sweitzer D, Jaeger J. Assessment of the effects of AZD3480 on cognitive function in patients with schizophrenia. Schizophr Res. 2012 Jan;134(1):59-64. doi: 10.1016/j.schres.2011.10.004. PubMed PMID: 22088556. 8: Frölich L, Ashwood T, Nilsson J, Eckerwall G; Sirocco Investigators.. Effects of AZD3480 on cognition in patients with mild-to-moderate Alzheimer's disease: a phase IIb dose-finding study. J Alzheimers Dis. 2011;24(2):363-74. doi: 10.3233/JAD-2011-101554. PubMed PMID: 21258153. 9: Dalén P, Vik T, Alverlind S, Jostell KG, Hårdemark HG. Evaluation of the effects of AZD3480 on cardiac repolarization: a thorough QT/QTc study using moxifloxacin as a positive control. Clin Pharmacol Ther. 2010 Oct;88(4):532-9. doi: 10.1038/clpt.2010.131. PubMed PMID: 20811348. 10: Dunbar GC, Kuchibhatla RV, Lee G; TC-1734 (AZD3480) AAMI Clinical Study Group (USA).. A randomized double-blind study comparing 25 and 50 mg TC-1734 (AZD3480) with placebo, in older subjects with age-associated memory impairment. J Psychopharmacol. 2011 Aug;25(8):1020-9. doi: 10.1177/0269881110367727. PubMed PMID: 20542923. 11: Gao B, Hierl M, Clarkin K, Juan T, Nguyen H, Valk Mv, Deng H, Guo W, Lehto SG, Matson D, McDermott JS, Knop J, Gaida K, Cao L, Waldon D, Albrecht BK, Boezio AA, Copeland KW, Harmange JC, Springer SK, Malmberg AB, McDonough SI. Pharmacological effects of nonselective and subtype-selective nicotinic acetylcholine receptor agonists in animal models of persistent pain. Pain. 2010 Apr;149(1):33-49. doi: 10.1016/j.pain.2010.01.007. PubMed PMID: 20167427. 12: Bayés M, Rabasseda X. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 Jan-Feb;30(1):67-99. PubMed PMID: 18389098. 13: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Jul-Aug;29(6):427-37. PubMed PMID: 17922073. 14: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Jan-Feb;29(1):53-71. PubMed PMID: 17344945. 15: Dunbar GC, Inglis F, Kuchibhatla R, Sharma T, Tomlinson M, Wamsley J. Effect of ispronicline, a neuronal nicotinic acetylcholine receptor partial agonist, in subjects with age associated memory impairment (AAMI). J Psychopharmacol. 2007 Mar;21(2):171-8. Erratum in: J Psychopharmacol. 2008 Aug;22(6):698. PubMed PMID: 17329297. 16: Dunbar G, Boeijinga PH, Demazières A, Cisterni C, Kuchibhatla R, Wesnes K, Luthringer R. Effects of TC-1734 (AZD3480), a selective neuronal nicotinic receptor agonist, on cognitive performance and the EEG of young healthy male volunteers. Psychopharmacology (Berl). 2007 May;191(4):919-29. PubMed PMID: 17225162. 17: Dunbar GC, Kuchibhatla R. Cognitive enhancement in man with ispronicline, a nicotinic partial agonist. J Mol Neurosci. 2006;30(1-2):169-72. PubMed PMID: 17192668. 18: Lippiello P, Letchworth SR, Gatto GJ, Traina VM, Bencherif M. Ispronicline: a novel alpha4beta2 nicotinic acetylcholine receptor-selective agonist with cognition-enhancing and neuroprotective properties. J Mol Neurosci. 2006;30(1-2):19-20. PubMed PMID: 17192610. 19: Dunbar G, Demazières A, Monreal A, Cisterni C, Metzger D, Kuchibhatla R, Luthringer R. Pharmacokinetics and safety profile of ispronicline (TC-1734), a new brain nicotinic receptor partial agonist, in young healthy male volunteers. J Clin Pharmacol. 2006 Jul;46(7):715-26. PubMed PMID: 16809797. 20: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2006 Mar;28(2):121-42. PubMed PMID: 16636723.

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Description:

Chemical Structure

Theoretical Analysis

Price and Availability

Preparing Stock Solutions

View History

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