MedKoo Cat#: 573853 | Name: Ipidacrine
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Description:

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

Ipidacrine is a ring-constricted derivative of tacrine (Cognex) and a reversible acetylcholinesterase inhibitor used in memory disorders. Ipidacrine directly stimulates impulse transmission in the central nervous system and neuromuscular synapses by blocking membrane potassium channels. Ipidacrine enhances not only choline, but also adrenaline, serotonin, histamine, and oxytocin effects on smooth muscle.

Chemical Structure

Ipidacrine
Ipidacrine
CAS#62732-44-9

Theoretical Analysis

MedKoo Cat#: 573853

Name: Ipidacrine

CAS#: 62732-44-9

Chemical Formula: C12H16N2

Exact Mass: 188.1313

Molecular Weight: 188.27

Elemental Analysis: C, 76.55; H, 8.57; N, 14.88

Price and Availability

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500mg USD 300.00 2 Weeks
1g USD 500.00 2 Weeks
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Related CAS #
No Data
Synonym
Amiridine, Ipidacrine
IUPAC/Chemical Name
1H-Cyclopenta(b)quinolin-9-amine, 2,3,5,6,7,8-hexahydro-
InChi Key
YLUSMKAJIQOXPV-UHFFFAOYSA-N
InChi Code
1S/C12H16N2/c13-12-8-4-1-2-6-10(8)14-11-7-3-5-9(11)12/h1-7H2,(H2,13,14)
SMILES Code
C1CCc2c(c(c3c(n2)CCC3)N)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
>3 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
Biological target:
2,3,5,6,7,8-Hexahydro-1H-cyclopenta[b]quinolin-9-amine is a pharmaceutically active compound which is a nootropic agent that acts as cholinesterase inhibitor and is used in treatment of Alzheimer disease.
In vitro activity:
NIK-247 (9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]-quinoline hydrochloride hydrate), an acetylcholinesterase inhibitor, is structurally related to 4-aminopyridine (AP). Its effects on ionic currents were examined in the artificial node of the crayfish axon under voltage-clamp. When applied externally, NIK-247 reversibly suppressed both inward and outward currents. NIK-247 suppressed the K current dose-dependently, but with an IC50 at of 10(-3) M. Furthermore, NIK-247 (and THA) suppressed the K current uniformly for the whole time course, whereas AP the AP's suppressed mainly the fast activating and inactivating K current with a voltage- and frequency-dependent recovery. Reference: Jpn J Pharmacol. 1991 Dec;57(4):545-52. https://pubmed.ncbi.nlm.nih.gov/1724992/
In vivo activity:
This is the first study to show that administration of ipidacrine, the reversible cholinesterase inhibitor, improved erectile function in diabetic rats and these results may be beneficial in further studies using ipidacrine for treatment of DMED, particularly in non-responders to PDE5 inhibitors. Reference: Sex Med. 2022 Feb;10(1):100477. https://pubmed.ncbi.nlm.nih.gov/35007992/
Solvent mg/mL mM
Solubility
DMF 25.0 132.79
DMSO 25.0 132.79
DMSO:PBS (pH 7.2) (1:3) 0.3 1.33
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 188.27 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
Formulation protocol:
1. Kojima J, Sugawara Y, Obara S. NIK-247 blocks voltage-dependent ionic currents in crayfish axon. Jpn J Pharmacol. 1991 Dec;57(4):545-52. doi: 10.1254/jjp.57.545. PMID: 1724992. 2. Bykov V, Gushchina E, Morozov S, Zhuravskaya N, Kryshen K, Makarov V, Matichin A, Zueva A. Ipidacrine (Axamon), A Reversible Cholinesterase Inhibitor, Improves Erectile Function in Male Rats With Diabetes Mellitus-Induced Erectile Dysfunction. Sex Med. 2022 Feb;10(1):100477. doi: 10.1016/j.esxm.2021.100477. Epub 2022 Jan 8. PMID: 35007992; PMCID: PMC8847829. 3. Uemura K, Yoshioka S, Surina-Baumgartner DM, Tamagawa T, Miura H, Ueda M, Tamaya N, Iguchi A, Hotta N. Central nervous system-mediated hyperglycemic effects of NIK-247, a cholinesterase inhibitor, and MKC-231, a choline uptake enhancer, in rats. Jpn J Pharmacol. 1999 Jan;79(1):113-5. doi: 10.1254/jjp.79.113. PMID: 10082325.
In vitro protocol:
1. Kojima J, Sugawara Y, Obara S. NIK-247 blocks voltage-dependent ionic currents in crayfish axon. Jpn J Pharmacol. 1991 Dec;57(4):545-52. doi: 10.1254/jjp.57.545. PMID: 1724992.
In vivo protocol:
1. Bykov V, Gushchina E, Morozov S, Zhuravskaya N, Kryshen K, Makarov V, Matichin A, Zueva A. Ipidacrine (Axamon), A Reversible Cholinesterase Inhibitor, Improves Erectile Function in Male Rats With Diabetes Mellitus-Induced Erectile Dysfunction. Sex Med. 2022 Feb;10(1):100477. doi: 10.1016/j.esxm.2021.100477. Epub 2022 Jan 8. PMID: 35007992; PMCID: PMC8847829. 2. Uemura K, Yoshioka S, Surina-Baumgartner DM, Tamagawa T, Miura H, Ueda M, Tamaya N, Iguchi A, Hotta N. Central nervous system-mediated hyperglycemic effects of NIK-247, a cholinesterase inhibitor, and MKC-231, a choline uptake enhancer, in rats. Jpn J Pharmacol. 1999 Jan;79(1):113-5. doi: 10.1254/jjp.79.113. PMID: 10082325.
1: Chernus VP, Vanchakova NP, Sivkova SK, Sivkov AS, Gorenkov RV. Ipidacrine in combination therapy regimens of functional constipation. Ter Arkh. 2018 Dec 30;90(12):48-55. doi: 10.26442/00403660.2018.12.000008. PubMed PMID: 30701833. 2: Ogura H, Kosasa T, Kuriya Y, Yamanishi Y. Comparison of inhibitory activities of donepezil and other cholinesterase inhibitors on acetylcholinesterase and butyrylcholinesterase in vitro. Methods Find Exp Clin Pharmacol. 2000 Oct;22(8):609-13. PubMed PMID: 11256231. 3: Onodera K, Kojima J, Wachi M. Ipidacrine (NIK-247), a novel antidementia, rapidly enters the brain and improves scopolamine-induced amnesia in rats during the Morris water maze task. Nihon Shinkei Seishin Yakurigaku Zasshi. 1998 Apr;18(2):33-7. PubMed PMID: 9656230.