Ispronicline

Modify Date: 2024-01-12 17:47:04

Ispronicline Structure
Ispronicline structure
Common Name Ispronicline
CAS Number 252870-53-4 Molecular Weight 234.34
Density N/A Boiling Point N/A
Molecular Formula C14H22N2O Melting Point N/A
MSDS N/A Flash Point N/A

 Use of Ispronicline


Ispronicline (TC-1734), an orally active, brain-selective α4β2 nicotine acetylcholine receptor (nAChR) partial agonist, has shown memory-enhancing properties in rodents and a good tolerability profile. Ispronicline 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[1][2].

 Names

Name (E,2S)-N-methyl-5-(5-propan-2-yloxypyridin-3-yl)pent-4-en-2-amine
Synonym More Synonyms

 Ispronicline Biological Activity

Description Ispronicline (TC-1734), an orally active, brain-selective α4β2 nicotine acetylcholine receptor (nAChR) partial agonist, has shown memory-enhancing properties in rodents and a good tolerability profile. Ispronicline 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[1][2].
Related Catalog
In Vivo Ispronicline (10-20 mg/kg; s.c.) induces c-Fos expression in selective regions of the rat forebrain[1]. Ispronicline pharmacokinetics (half-life of 2 h in rats) contrasts with the long-lasting improvement of working memory (18 h to 2 d)[2]. Animal Model: Male Wistar rats weighting 180-200 g[1] Dosage: 10 and 30 mg/kg Administration: s.c. Result: Induced c-Fos in medial paraventricular nucleus of hypothalamus. Treatment with 30 mg/kg ispronicline, but not 10 mg/kg, increased the number of c-Fos immunoreactive cells significantly as compared to controls within the medial parvocellular part of paraventricular nucleus (PVN).
References

[1]. Julie Jacobsen, et al. 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.

 Chemical & Physical Properties

Molecular Formula C14H22N2O
Molecular Weight 234.34
Exact Mass 234.17300
PSA 34.15000
LogP 3.27090
Storage condition -20°C

 Synthetic Route

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Ispronicline Structure

Ispronicline

CAS#:252870-53-4

Literature: Targacept, Inc. Patent: US6979695 B2, 2005 ;

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Ispronicline Structure

Ispronicline

CAS#:252870-53-4

Literature: Targacept, Inc. Patent: US6218383 B1, 2001 ;

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Ispronicline Structure

Ispronicline

CAS#:252870-53-4

Literature: TARGACEPT INC.; DULL, Gary Maurice; GENUS, John; RATILAINEN, Tommi; RYBERG, Per Olof; HELLSTROeM, Janna; WAHLSTROeM, Niklas; WAeNNMAN, Thomas Patent: WO2011/146009 A1, 2011 ; Location in patent: Page/Page column 25 ;

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Ispronicline Structure

Ispronicline

CAS#:252870-53-4

Literature: TARGACEPT INC.; DULL, Gary Maurice; GENUS, John; RATILAINEN, Tommi; RYBERG, Per Olof; HELLSTROeM, Janna; WAHLSTROeM, Niklas; WAeNNMAN, Thomas Patent: WO2011/146009 A1, 2011 ;

~%

Ispronicline Structure

Ispronicline

CAS#:252870-53-4

Literature: TARGACEPT INC.; DULL, Gary Maurice; GENUS, John; RATILAINEN, Tommi; RYBERG, Per Olof; HELLSTROeM, Janna; WAHLSTROeM, Niklas; WAeNNMAN, Thomas Patent: WO2011/146009 A1, 2011 ;

~%

Ispronicline Structure

Ispronicline

CAS#:252870-53-4

Literature: TARGACEPT INC.; DULL, Gary Maurice; GENUS, John; RATILAINEN, Tommi; RYBERG, Per Olof; HELLSTROeM, Janna; WAHLSTROeM, Niklas; WAeNNMAN, Thomas Patent: WO2011/146009 A1, 2011 ;

 Synonyms

UNII-3E05NBH9V5
(2S)-(4E)-N-methyl-5-[5-isopropoxypyridin-3-yl]-4-penten-2-amine
(2S)-(4E)-N-methyl-5-(5-isopropoxy-3-pyridinyl)-4-penten-2-amine
(2S)-(4E)-N-methyl-5-[3-(5-isopropoxypyridin)yl]-4-penten-2-amine
(2S)-(4E)-N-methyl-5-(5-isopropoxy-3-pyridyl)-4-penten-2-amine
Ispronicline
AZD-3480
RJR-1734
Ispronicline (INN/USAN)
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