Physostigmine (CAS 57-47-6)

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Alternate Names: Physostigmine is also known as Antilirium.

Application: Physostigmine is a reversible cholinesterase inhibitor and highly toxic parasympathomimetic alkaloid.

CAS Number: 57-47-6

Purity: ≥98%

Molecular Weight: 275.35

Molecular Formula: C₁₅H₂₁N₃O₂

Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

* Refer to Certificate of Analysis for lot specific data (including water content).

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Physostigmine is an alkaloid originally derived from the Calabar bean (Physostigma venenosum). Physostigmine is noted to act as a potent and reversible inhibitor of cholinesterase. Physostigmine is also reported to form a slowly degrading carbamylated enzyme complex with acetylcholinesterase (AChE). Physostigmine has been used as a positive control in a study investigating acetylcholinesterase inhibitors for potential antihelminthic drug targets. Additionally, as a parasympathomimetic compound, Physostigmine is reported to cross the blood-brain barrier.

References

1. Tamaddonfard, E. and Hamzeh-Gooshchi, N. 2010. Pharmacol Rep. 62: 858-863. PMID: 21098868

2. Valli, M., et al. 2011. Curr Med Chem. [Epub ahead of print]. PMID: 21728957

3. Kalogiannis, M., et al. 2011. PLoS ONE. 6: e18697. PMID: 21533254

Physical State :

Solid

Solubility :

Soluble in alcohol (1:10), chloroform (1:1), ether (1:30), and DMSO. Insoluble in water.

Storage :

Store at 4° C

Melting Point :

102-104° C (lit.)

Boiling Point :

~393.5° C at 760 mmHg (Predicted)

Density :

~1.2 g/cm³ (Predicted)

Refractive Index :

n²⁰_D 1.57 (Predicted)

Optical Activity :

α20_D -77±1, c = 1.7% in chloroform; α25_D -120 in benzene

IC50 :

AChE: IC₅₀ = 0.43 nM (human); AChE: IC₅₀ = 0.68 nM (rat); BChE: IC₅₀ = 7.6 nM (rat); BChE: IC₅₀ = 16 nM (human)

pK Values :

pK_a: 12.23 (Predicted), pK_b: 8.32 (Predicted)

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

WGK Germany :

RTECS :

TJ2100000

PubChem CID :

5983

Merck Index :

14: 7384

MDL Number :

MFCD00151090

EC Number :

200-332-8

Beilstein Registry :

91230

SMILES :

C[[email protected]@]12CCN([[email protected]@H]1N(C3=C2C=C(C=C3)OC(=O)NC)C)C

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Certificate of Analysis

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Physostigmine (CAS 57-47-6) Product Citations

See how others have used Physostigmine (CAS 57-47-6). Click on the entry to view the PubMed entry .

Citations 1 to 3 of 3 total

PMID: # 25269881 Lau, CG. et al. 2014. Mol. Reprod. Dev. 81: 994-1008.

PMID: # 31153601 J Chromatogr A. 458-466.

PMID: # 30557385 PLoS ONE. 13: e0209250.

Citations 1 to 3 of 3 total

Rated 5 out of 5 by SF from Kalogiannis et al Kalogiannis et al. (PubMed ID 21533254) found that the cholinesterase inhibitor physostigmine increased the number of spontaneous behavioral arrests without influencing circuits that determine arrest duration in double orexin receptor knockout mice. -SCBT Publication Review

Date published: 2015-05-31

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