An AChE inhibitor
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Phenserine

Item No. 21060

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3aS,8aR)-5-(N-phenylcarbamate)1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo[2,3-b]indol-5-ol
CAS Number
101246-66-6
Synonyms
  • (-)-Eseroline phenylcarbamate
  • (-)-N-Phenylcarbamoyleseroline
  • (-)-Phenserine
Molecular Formula
C20H23N3O2
Formula Weight
337.4
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:5): 0.16 mg/mlEthanol: 25 mg/ml
λmax
238, 252, 310 nm
SMILES
O=C(OC1=CC([C@@](CCN2C)(C)[C@@]2([H])N3C)=C3C=C1)NC4=CC=CC=C4
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
InChi Key
PBHFNBQPZCRWQP-QUCCMNQESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $42

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    10 mg

    $80

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    25 mg

    $158

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    50 mg

    $272

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    Product Description

    Phenserine is an analog of physostigmine that inhibits acetylcholinesterase with an IC50 value of 24 nM.1,2 It is reported to prevent amyloid-β production by diminishing the expression of amyloid-β precursor protein.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yu, Q.S., Zhu, X., Holloway, H.W., et al. Anticholinesterase activity of compounds related to geneserine tautomers. N-oxides and 1,2-oxazines. J. Med. Chem. 45(17), 3684-3691 (2002).

    2. Luo, W., Yu, Q.S., Kulkarni, S.S., et al. Inhibition of human acetyl- and butyrylcholinesterase by novel carbamates of (−)- and (+)-tetrahydrofurobenzofuran and methanobenzodioxepine. J. Med. Chem. 49(7), 2174-2185 (2006).

    3. Utsuki, T., Yu, Q.-s., Davidson, D., et al. Identification of novel small molecule inhibitors of amyloid precursor protein synthesis as a route to lower Alzheimer’s disease amyloid-β peptide. J. Pharmacol. Exp. Ther. 318(2), 855-862 (2006).