Ispronicline
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MedKoo CAT#: 329460

CAS#: 252870-53-4

Description: 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

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Ispronicline
CAS# 252870-53-4

Theoretical Analysis

MedKoo Cat#: 329460
Name: Ispronicline
CAS#: 252870-53-4
Chemical Formula: C14H22N2O
Exact Mass: 234.1732
Molecular Weight: 234.343
Elemental Analysis: C, 71.76; H, 9.46; N, 11.95; O, 6.83

Price and Availability

Size Price Availability Quantity
500.0mg USD 2450.0 2 Weeks
1.0g USD 3950.0 2 Weeks
2.0g USD 6950.0 2 Weeks
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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: 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

Preparing Stock Solutions

The following data is based on the product molecular weight 234.343 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

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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.