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MedKoo Cat#: 326954 | Name: Phenserine
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Description:

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

Phenserine is an acetylcholinesterase (AChE) inhibitor potentially for the treatment of Alzheimer Disease (AD). Phenserine produces rapid, potent, and long-lasting AChE inhibition, in vivo. It is significantly less toxic than (-)-physostigmine. Phenserine improves cognitive performance in both young learning-impaired and elderly rats.

Chemical Structure

Phenserine
Phenserine
CAS#101246-66-6 (free base)

Theoretical Analysis

MedKoo Cat#: 326954

Name: Phenserine

CAS#: 101246-66-6 (free base)

Chemical Formula: C20H23N3O2

Exact Mass: 337.1790

Molecular Weight: 337.42

Elemental Analysis: C, 71.19; H, 6.87; N, 12.45; O, 9.48

Price and Availability

Size Price Availability Quantity
10mg USD 450.00 2 Weeks
25mg USD 850.00 2 Weeks
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Related CAS #
101246-66-6 (free base) 156910-61-1 (tartrate) 159652-53-6 (racemic) 865795-23-9 (tartrate)
Synonym
Phenserine; (-)-Eseroline phenylcarbamate; (-)-N-Phenylcarbamoyleseroline; (-)-Phenserine,
IUPAC/Chemical Name
(3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl phenylcarbamate
InChi Key
PBHFNBQPZCRWQP-QUCCMNQESA-N
InChi Code
InChI=1S/C20H23N3O2/c1-20-11-12-22(2)18(20)23(3)17-10-9-15(13-16(17)20)25-19(24)21-14-7-5-4-6-8-14/h4-10,13,18H,11-12H2,1-3H3,(H,21,24)/t18-,20+/m1/s1
SMILES Code
CN1[C@](N(C)CC2)([H])[C@]2(C)C3=C1C=CC(OC(NC4=CC=CC=C4)=O)=C3
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
More Info
Related CAS# CAS#101246-66-6 (Phenserine free base) CAS#156910-61-1 (Phenserine tartrate)
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Phenserine is an acetylcholinesterase (AChE) inhibitor.
In vitro activity:
The addition of (−)-phenserine to SH-SY5Y neuronal cultures proved well tolerated at concentrations up to 30 μM, as appraised by measuring cell viability by MTT assay under normoxic conditions. At a concentration of 100 μM, however, (−)-phenserine induced substantial cell death (Fig. 1a). A concentration-dependent evaluation of (−)-phenserine (0 to 100 μM) to mitigate SH-SY5Y cell death-induced by OGD-Hypoxia 4 h exposure is illustrated in Figure 1C. An inverted U-shaped dose-response relationship between (−)-phenserine concentration and improved cellular survival was evident, with 10 μM providing optimal protection. Reference: Brain Res. 2017 Dec 15;1677:118-128. https://pubmed.ncbi.nlm.nih.gov/28963051/
In vivo activity:
Phen (phenserine) mitigated mTBI-induced cognitive impairment, assessed by Novel Object Recognition and Y-maze behavioral paradigms, in WT mice. Phen fully abated mTBI-induced neurodegeneration, evaluated by counting Fluoro-Jade C-positive (FJC+) cells, in hippocampus and cortex of WT mice. Phen decreased IBA1-IR throughout hippocampi and cortices of WT mice, and in cortices of AD mice. Phen, likewise, reduced levels of IBA1/TNF-α-IR colocalization volume across all areas in WT animals, with a similar trend in APP/PSEN1 mice. Reference: Neurobiol Dis. 2019 Oct;130:104528. https://pubmed.ncbi.nlm.nih.gov/31295555/
Solvent mg/mL mM
Solubility
DMF 25.0 74.09
DMSO 115.0 340.82
DMSO:PBS (pH 7.2) (1:5) 0.2 0.47
Ethanol 25.0 74.09
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 337.42 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. Chang CF, Lai JH, Wu JC, Greig NH, Becker RE, Luo Y, Chen YH, Kang SJ, Chiang YH, Chen KY. (-)-Phenserine inhibits neuronal apoptosis following ischemia/reperfusion injury. Brain Res. 2017 Dec 15;1677:118-128. doi: 10.1016/j.brainres.2017.09.015. Epub 2017 Sep 27. PMID: 28963051; PMCID: PMC6703552. 2. Lahiri DK, Chen D, Maloney B, Holloway HW, Yu QS, Utsuki T, Giordano T, Sambamurti K, Greig NH. The experimental Alzheimer's disease drug posiphen [(+)-phenserine] lowers amyloid-beta peptide levels in cell culture and mice. J Pharmacol Exp Ther. 2007 Jan;320(1):386-96. doi: 10.1124/jpet.106.112102. Epub 2006 Sep 26. PMID: 17003227. 3. Lecca D, Bader M, Tweedie D, Hoffman AF, Jung YJ, Hsueh SC, Hoffer BJ, Becker RE, Pick CG, Lupica CR, Greig NH. (-)-Phenserine and the prevention of pre-programmed cell death and neuroinflammation in mild traumatic brain injury and Alzheimer's disease challenged mice. Neurobiol Dis. 2019 Oct;130:104528. doi: 10.1016/j.nbd.2019.104528. Epub 2019 Jul 8. PMID: 31295555; PMCID: PMC6716152. 4. Hsueh SC, Lecca D, Greig NH, Wang JY, Selman W, Hoffer BJ, Miller JP, Chiang YH. (-)-Phenserine Ameliorates Contusion Volume, Neuroinflammation, and Behavioral Impairments Induced by Traumatic Brain Injury in Mice. Cell Transplant. 2019 Sep-Oct;28(9-10):1183-1196. doi: 10.1177/0963689719854693. Epub 2019 Jun 10. PMID: 31177840; PMCID: PMC6767878.
In vitro protocol:
1. Chang CF, Lai JH, Wu JC, Greig NH, Becker RE, Luo Y, Chen YH, Kang SJ, Chiang YH, Chen KY. (-)-Phenserine inhibits neuronal apoptosis following ischemia/reperfusion injury. Brain Res. 2017 Dec 15;1677:118-128. doi: 10.1016/j.brainres.2017.09.015. Epub 2017 Sep 27. PMID: 28963051; PMCID: PMC6703552. 2. Lahiri DK, Chen D, Maloney B, Holloway HW, Yu QS, Utsuki T, Giordano T, Sambamurti K, Greig NH. The experimental Alzheimer's disease drug posiphen [(+)-phenserine] lowers amyloid-beta peptide levels in cell culture and mice. J Pharmacol Exp Ther. 2007 Jan;320(1):386-96. doi: 10.1124/jpet.106.112102. Epub 2006 Sep 26. PMID: 17003227.
In vivo protocol:
1. Lecca D, Bader M, Tweedie D, Hoffman AF, Jung YJ, Hsueh SC, Hoffer BJ, Becker RE, Pick CG, Lupica CR, Greig NH. (-)-Phenserine and the prevention of pre-programmed cell death and neuroinflammation in mild traumatic brain injury and Alzheimer's disease challenged mice. Neurobiol Dis. 2019 Oct;130:104528. doi: 10.1016/j.nbd.2019.104528. Epub 2019 Jul 8. PMID: 31295555; PMCID: PMC6716152. 2. Hsueh SC, Lecca D, Greig NH, Wang JY, Selman W, Hoffer BJ, Miller JP, Chiang YH. (-)-Phenserine Ameliorates Contusion Volume, Neuroinflammation, and Behavioral Impairments Induced by Traumatic Brain Injury in Mice. Cell Transplant. 2019 Sep-Oct;28(9-10):1183-1196. doi: 10.1177/0963689719854693. Epub 2019 Jun 10. PMID: 31177840; PMCID: PMC6767878.
1: Batool S, Furqan T, Hasan Mahmood MS, Tweedie D, Kamal MA, Greig NH. In Silico and Ex Vivo Analyses of the Inhibitory Action of the Alzheimer Drug Posiphen and Primary Metabolites with Human Acetyl- and Butyrylcholinesterase Enzymes. ACS Pharmacol Transl Sci. 2022 Jan 12;5(2):70-79. doi: 10.1021/acsptsci.1c00200. PMID: 35178511; PMCID: PMC8845043. 2: Winand L, Schneider P, Kruth S, Greven NJ, Hiller W, Kaiser M, Pietruszka J, Nett M. Mutasynthesis of Physostigmines in Myxococcus xanthus. Org Lett. 2021 Aug 20;23(16):6563-6567. doi: 10.1021/acs.orglett.1c02374. Epub 2021 Aug 6. PMID: 34355569. 3: Ghiam MK, Patel SD, Hoffer A, Selman WR, Hoffer BJ, Hoffer ME. Drug Repurposing in the Treatment of Traumatic Brain Injury. Front Neurosci. 2021 Mar 23;15:635483. doi: 10.3389/fnins.2021.635483. PMID: 33833663; PMCID: PMC8021906. 4: Košak U, Gobec S. A Simple and Effective Synthesis of 3- and 4-((Phenylcarbamoyl)oxy)benzoic Acids. Acta Chim Slov. 2020 Sep;67(3):940-948. PMID: 33533422. 5: Chen XQ, Salehi A, Pearn ML, Overk C, Nguyen PD, Kleschevnikov AM, Maccecchini M, Mobley WC. Targeting increased levels of APP in Down syndrome: Posiphen-mediated reductions in APP and its products reverse endosomal phenotypes in the Ts65Dn mouse model. Alzheimers Dement. 2021 Feb;17(2):271-292. doi: 10.1002/alz.12185. Epub 2020 Sep 25. PMID: 32975365; PMCID: PMC7984396. 6: Yu SJ, Wu KJ, Bae E, Wang YS, Chiang CW, Kuo LW, Harvey BK, Greig NH, Wang Y. Post-treatment with Posiphen Reduces Endoplasmic Reticulum Stress and Neurodegeneration in Stroke Brain. iScience. 2020 Feb 21;23(2):100866. doi: 10.1016/j.isci.2020.100866. Epub 2020 Jan 28. PMID: 32058974; PMCID: PMC7013187. 7: Greig NH, Lecca D, Hsueh SC, Nogueras-Ortiz C, Kapogiannis D, Tweedie D, Glotfelty EJ, Becker RE, Chiang YH, Hoffer BJ. (-)-Phenserine tartrate (PhenT) as a treatment for traumatic brain injury. CNS Neurosci Ther. 2020 Jun;26(6):636-649. doi: 10.1111/cns.13274. Epub 2019 Dec 11. PMID: 31828969; PMCID: PMC7248544. 8: Kisby B, Jarrell JT, Agar ME, Cohen DS, Rosin ER, Cahill CM, Rogers JT, Huang X. Alzheimer's Disease and Its Potential Alternative Therapeutics. J Alzheimers Dis Parkinsonism. 2019;9(5):477. doi: 10.4172/2161-0460.1000477. Epub 2019 Sep 13. PMID: 31588368; PMCID: PMC6777730. 9: Lecca D, Bader M, Tweedie D, Hoffman AF, Jung YJ, Hsueh SC, Hoffer BJ, Becker RE, Pick CG, Lupica CR, Greig NH. (-)-Phenserine and the prevention of pre- programmed cell death and neuroinflammation in mild traumatic brain injury and Alzheimer's disease challenged mice. Neurobiol Dis. 2019 Oct;130:104528. doi: 10.1016/j.nbd.2019.104528. Epub 2019 Jul 8. PMID: 31295555; PMCID: PMC6716152. 10: Tabrez S, Damanhouri GA. Computational and Kinetic Studies of Acetylcholine Esterase Inhibition by Phenserine. Curr Pharm Des. 2019;25(18):2108-2112. doi: 10.2174/1381612825666190618141015. PMID: 31258059. 11: Hsueh SC, Lecca D, Greig NH, Wang JY, Selman W, Hoffer BJ, Miller JP, Chiang YH. (-)-Phenserine Ameliorates Contusion Volume, Neuroinflammation, and Behavioral Impairments Induced by Traumatic Brain Injury in Mice. Cell Transplant. 2019 Sep-Oct;28(9-10):1183-1196. doi: 10.1177/0963689719854693. Epub 2019 Jun 10. PMID: 31177840; PMCID: PMC6767878. 12: Rogers JT, Xia N, Wong A, Bakshi R, Cahill CM. Targeting the Iron-Response Elements of the mRNAs for the Alzheimer's Amyloid Precursor Protein and Ferritin to Treat Acute Lead and Manganese Neurotoxicity. Int J Mol Sci. 2019 Feb 25;20(4):994. doi: 10.3390/ijms20040994. PMID: 30823541; PMCID: PMC6412244. 13: Turcato F, Kim P, Barnett A, Jin Y, Scerba M, Casey A, Selman W, Greig NH, Luo Y. Sequential combined Treatment of Pifithrin-α and Posiphen Enhances Neurogenesis and Functional Recovery After Stroke. Cell Transplant. 2018 Apr;27(4):607-621. doi: 10.1177/0963689718766328. Epub 2018 Jun 5. PMID: 29871513; PMCID: PMC6041885. 14: Becker RE, Greig NH, Lahiri DK, Bledsoe J, Majercik S, Ballard C, Aarsland D, Schneider LS, Flanagan D, Govindarajan R, Sano M, Ferrucci L, Kapogiannis D. (-)-Phenserine and Inhibiting Pre-Programmed Cell Death: In Pursuit of a Novel Intervention for Alzheimer's Disease. Curr Alzheimer Res. 2018;15(9):883-891. doi: 10.2174/1567205015666180110120026. PMID: 29318971; PMCID: PMC6039273. 15: Sahoo AK, Dandapat J, Dash UC, Kanhar S. Features and outcomes of drugs for combination therapy as multi-targets strategy to combat Alzheimer's disease. J Ethnopharmacol. 2018 Apr 6;215:42-73. doi: 10.1016/j.jep.2017.12.015. Epub 2017 Dec 14. PMID: 29248451. 16: Becker RE, Kapogiannis D, Greig NH. Does traumatic brain injury hold the key to the Alzheimer's disease puzzle? Alzheimers Dement. 2018 Apr;14(4):431-443. doi: 10.1016/j.jalz.2017.11.007. Epub 2017 Dec 12. PMID: 29245000; PMCID: PMC5958613. 17: Chang CF, Lai JH, Wu JC, Greig NH, Becker RE, Luo Y, Chen YH, Kang SJ, Chiang YH, Chen KY. (-)-Phenserine inhibits neuronal apoptosis following ischemia/reperfusion injury. Brain Res. 2017 Dec 15;1677:118-128. doi: 10.1016/j.brainres.2017.09.015. Epub 2017 Sep 27. PMID: 28963051; PMCID: PMC6703552. 18: Hoffer BJ, Pick CG, Hoffer ME, Becker RE, Chiang YH, Greig NH. Repositioning drugs for traumatic brain injury - N-acetyl cysteine and Phenserine. J Biomed Sci. 2017 Sep 9;24(1):71. doi: 10.1186/s12929-017-0377-1. PMID: 28886718; PMCID: PMC5591517. 19: Kinthada LK, Medisetty SR, Parida A, Babu KN, Bisai A. FeCl3-Catalyzed Allylation Reactions onto 3-Hydroxy-2-oxindoles: Formal Total Syntheses of Bis-cyclotryptamine Alkaloids, (±)-Chimonanthine, and (±)-Folicanthine. J Org Chem. 2017 Aug 18;82(16):8548-8567. doi: 10.1021/acs.joc.7b01232. Epub 2017 Aug 7. PMID: 28718647. 20: Xie Q, Zheng Z, Shao B, Fu W, Xia Z, Li W, Sun J, Zheng W, Zhang W, Sheng W, Zhang Q, Chen H, Wang H, Qiu Z. Pharmacophore-based design and discovery of (-)-meptazinol carbamates as dual modulators of cholinesterase and amyloidogenesis. J Enzyme Inhib Med Chem. 2017 Dec;32(1):659-671. doi: 10.1080/14756366.2016.1265521. PMID: 28274151; PMCID: PMC6009976.