An alkaloid and cholinergic agent
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(−)-Physostigmine (salicylate)

Item No. 33106

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-hydroxybenzoic acid with (3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate
CAS Number
57-64-7
Synonyms
  • Physostigmine
Molecular Formula
C15H21N3O2 • C7H6O3
Formula Weight
413.5
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 10 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
240 nm
SMILES
CNC(OC1=CC([C@@](CCN2C)(C)[C@@]2([H])N3C)=C3C=C1)=O.OC(C4=C(O)C=CC=C4)=O
InChi Code
InChI=1S/C15H21N3O2.C7H6O3/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2;8-6-4-2-1-3-5(6)7(9)10/h5-6,9,13H,7-8H2,1-4H3,(H,16,19);1-4,8H,(H,9,10)/t13-,15+;/m1./s1
InChi Key
HZOTZTANVBDFOF-PBCQUBLHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 mg

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    Product Description

    (–)-Physostigmine is an alkaloid that has been found in Calabar beans and a cholinergic agent.1,2 It inhibits acetylcholinesterase (AChE; IC50 = 0.67 nM).2 (–)-Physostigmine (10 µM) inhibits ChE and increases vagal stimulation-induced ACh output in isolated chicken heart.3 In vivo, (–)-physostigmine (200 and 400 µg/kg) induces decentralized lower eyelid contractions and increases blood pressure in anesthetized rats.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Proudfoot, A. The early toxicology of physostigmine: a tale of beans, great men and egos. Toxicol. Rev. 25(2), 99-138 (2006).

    2. Ogura, H., Kosasa, T., Kuriya, Y., et al. Comparison of inhibitory activities of donepezil and other cholinesterase inhibitors on acetylcholinesterase and butyrylcholinesterase in vitro. Methods Find. Exp. Clin. Pharmacol. 22(8), 609-613 (2000).

    3. Dieterich, H.A., Kaffel, H., Kilbinger, H., et al. The effects of physostigmine on cholinesterase activity, storage and release of acetylcholine in the isolated chicken heart. J. Pharmacol. Exp. Ther. 199(1), 236-246 (1976).

    4. Szeberényi, J., Varga, A., Pongrácz, M.F., et al. Centrally mediated contraction of the lower eyelid elicited by anticholinesterases in anaesthetized rats. J. Pharm. Pharmacol. 24(1), 85-86 (1972).