ISPRONICLINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H22N2O
Molecular Weight	234.3373
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=RPCVIAXDAUMJJP-PZBABLGHSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/67490152 | https://www.ncbi.nlm.nih.gov/pubmed/17192610 | https://scrip.pharmaintelligence.informa.com/SC030405/TargaceptAstraZeneca-Alzheimers-hope-fails-in-Phase-II

ISPRONICLINE is a partial agonist at the a4b2 subtype of nicotinic acetylcholine receptors (nAChRs) without interaction with other nAChRs or other receptor systems. It has antidepressant, nootropic, and neuroprotective effects. It progressed to phase II clinical trials for the treatment of dementia and Alzheimer's disease but is no longer under development.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Neuronal acetylcholine receptor; alpha4/beta2 76 Target ID: CHEMBL1907589 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15179444	Agonist 2678		11.0 nM [Ki]

PubMed

Title	Date	PubMed
TC-1734: an orally active neuronal nicotinic acetylcholine receptor modulator with antidepressant, neuroprotective and long-lasting cognitive effects.	2004 Summer	15179444
Ispronicline: a novel alpha4beta2 nicotinic acetylcholine receptor-selective agonist with cognition-enhancing and neuroprotective properties.	2006	17192610
Pharmacokinetics and safety profile of ispronicline (TC-1734), a new brain nicotinic receptor partial agonist, in young healthy male volunteers.	2006 Jul	16809797
Effect of ispronicline, a neuronal nicotinic acetylcholine receptor partial agonist, in subjects with age associated memory impairment (AAMI).	2007 Mar	17329297
Effects of TC-1734 (AZD3480), a selective neuronal nicotinic receptor agonist, on cognitive performance and the EEG of young healthy male volunteers.	2007 May	17225162
Pharmacological effects of nonselective and subtype-selective nicotinic acetylcholine receptor agonists in animal models of persistent pain.	2010 Apr	20167427

Patents

Name

Type

Language

ISPRONICLINE

Official Name

English

ispronicline [INN]

Common Name

English

(2S,4E)-N-Methyl-5-[5-(1-methylethoxy)pyridin-3-yl]pent-4-en-2-amine

Systematic Name

English

AZD3480

Code

English

TC-1734

Code

English

ISPRONICLINE [MI]

Common Name

English

4-PENTEN-2-AMINE, N-METHYL-5-(5-(1-METHYLETHOXY)-3-PYRIDINYL), (2S,4E)-

Common Name

English

TC-01734

Code

English

AZD-3480

Code

English

Ispronicline [WHO-DD]

Common Name

English

ISPRONICLINE [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C73579