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PHYSOSTIGMINE

Product Name:
PHYSOSTIGMINE
CAS No.
57-47-6
Chemical Name:
PHYSOSTIGMINE
CBNumber:
CB8770121
Molecular Formula:
C15H21N3O2
Formula Weight:
275.35
MOL File:
57-47-6.mol
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PHYSOSTIGMINE Property

Melting point:
102-104 °C(lit.)
alpha 
D17 -76° (c = 1.3 in chloroform); D25 -120° (benzene)
Boiling point:
418.29°C (rough estimate)
Density 
1.166±0.06 g/cm3 (20 ºC 760 Torr)
refractive index 
1.5600 (estimate)
Flash point:
>100℃
storage temp. 
2-8°C
pka
6.12, 12.24(at 25℃)
form 
Powder
color 
Off-white
Water Solubility 
Soluble in water (1:75), alcohol (1:10), chloroform (1:1), ether (1:30), and DMSO.
Sensitive 
Air & Light Sensitive
Merck 
7384
CAS DataBase Reference
57-47-6(CAS DataBase Reference)
EPA Substance Registry System
Physostigmine (57-47-6)
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Safety

Hazard Codes 
T+
Risk Statements 
26/28
Safety Statements 
23-45-25
RIDADR 
UN 1544 6.1/PG 1
WGK Germany 
3
RTECS 
TJ2100000
8-10
TSCA 
Yes
HazardClass 
6.1(a)
PackingGroup 
II
Toxicity
LD50 orally in mice: 4.5 mg/kg (Lynch, Coon)
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N-Bromosuccinimide Price More Price(5)

Alfa Aesar Gold
Product number:
J61477
Product name :
Eserine
Packaging:
100mg
Price:
$74.4
Updated:
2019/12/02
Buy:
Buy
Cayman Chemical Gold
Product number:
13027
Product name :
Physostigmine
Purity:
≥98%
Packaging:
100mg
Price:
$113
Updated:
2020/06/24
Buy:
Buy
Cayman Chemical Gold
Product number:
13027
Product name :
Physostigmine
Purity:
≥98%
Packaging:
50mg
Price:
$63
Updated:
2020/06/24
Buy:
Buy
Cayman Chemical Gold
Product number:
13027
Product name :
Physostigmine
Packaging:
10mg
Price:
$25
Updated:
2020/06/24
Buy:
Buy
Cayman Chemical Gold
Product number:
13027
Product name :
Physostigmine
Packaging:
25mg
Price:
$44
Updated:
2020/06/24
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PHYSOSTIGMINE Chemical Properties,Usage,Production

Chemical Properties

Physostigmine is a white crystalline solid. Odorless.

Uses

Physostigmine base (Eserine-Base) is used as bulk pharmaceuticals (parasympathomimetic, cholinergic, ophthalmic, anti-Alzheimer). Product Data Sheet

Uses

It is a parasympathomimetic, specifically, a reversible cholinesterase inhibitor obtained from the Calabar bean, used to treat glaucoma and delayed gastric emptying.

brand name

Eserine Sulfate (Ciba Vision, US Ophthalmics).

General Description

White, odorless, microcrystalline powder. Used as a cholinergic (anticholinesterase) agent and as a veterinary medication.

General Description

Physostigmine is an alkaloidobtained from the dried ripe seed of Physostigma venenosum.It occurs as a white, odorless, microcrystalline powderthat is slightly soluble in water and freely soluble inalcohol, chloroform, and the fixed oils. The alkaloid, asthe free base, is quite sensitive to heat, light, moisture,and bases, undergoing rapid decomposition. In solution,it is hydrolyzed to methyl carbamic acid and eseroline,neither of which inhibits AChE. Eseroline is oxidized toa red compound, rubreserine,and then further decomposedto eserine blue and eserine brown. Addition of sulfiteor ascorbic acid prevents oxidation of the phenol, eseroline,to rubreserine. Hydrolysis does take place,however, and the physostigmine is inactivated. Solutionsare most stable at pH 6 and should never be sterilizedby heat.
Physostigmine is a relatively poor carbamylating agentof AChE and is often considered a reversible inhibitor ofthe enzyme. Its cholinesterase-inhibiting properties varywith the pH of the medium . The conjugateacid of physostigmine has a pKa of about 8, and as the pHof the solution is lowered, more is present in the protonatedform. Inhibition of cholinesterase is greater in acidmedia, suggesting that the protonated form makes a contributionto the inhibitory activity well as its carbamylationof the enzyme.

Health Hazard

Super toxic. Probable oral lethal dose is less than 5 mg/kg for a 70 kg (150 lb.) person. Material is a cholinesterase inhibitor. Effects of exposure may involve the respiratory, gastrointestinal, cardiovascular and central nervous systems. Death occurs due to respiratory paralysis or impaired cardiac function. Time to death may vary from 5 minutes to 24 hours, in severely poisoned patients, depending on factors such as the dose and route. Persons with asthma and/or persons that require drugs containing choline esters are at risk.

Fire Hazard

PHYSOSTIGMINE is a slight fire hazard. When heated to decomposition PHYSOSTIGMINE emits toxic fumes of nitrogen oxides. Keep from light and heat.

Clinical Use

Physostigmine was used first as a topical application inthe treatment of glaucoma. Its lipid solubility properties permitadequate absorption from ointment bases. It is used systemicallyas an antidote for atropine poisoning and otheranticholinergic drugs by increasing the duration of actionof ACh at cholinergic sites through inhibition of AChE.Physostigmine, along with other cholinomimetic drugs actingin the CNS, has been studied for use in the treatment ofAlzheimer disease. Cholinomimetics that are currentlyused or which have been recently evaluated in the treatmentof Alzheimer disease include donepezil, galantamine, metrifonate,rivastigmine, and tacrine. It is anticipated that thislist will continue to grow as the etiology of this disease becomesbetter understood.

Safety Profile

A human poison by an unspecified route. Poison experimentally by ingestion, subcutaneous, intramuscular, intravenous, and intraperitoneal routes. Human systemic effects by ingestion: nausea, dyspnea, coma, blood pressure elevation, flaccid paralysis without anesthesia, muscle weakness. Normally administered by injection. Poisoning can occur as a result of a mistake in dosage or due to hypersensitivity of the patient withm 5 to 25 minutes after administration. Death usually results from respiratory paralysis. Experimental reproductive effects. Combustible when exposed to heat or flame. When heated to decomposition it emits toxic fumes of NOx. See also CARBAMATES.

Potential Exposure

Physostigmine, an alkaloid, originally derived from the calabar bean (Physostigma venenosum) isa potent and reversible inhibitor of cholinesterase. Material is used as a cholinergic (anticholinesterase) agent and as a veterinary medication. Although listed as a carbamate pesticide, physostigmine is not registered for use as an agricultural chemical in the United States.

Veterinary Drugs and Treatments

Physostigmine has been used for the adjunctive treatment of ivermectin toxicity in dogs, as a provocative agent for the diagnosis of narcolepsy in dogs and horses, and as a treatment for anticholinergic toxicity. Because of the potential for serious adverse effects, use of physostigmine as an antidote is generally reserved for very serious toxicity affecting the CNS. Otherwise, safer alternatives such as neostigmine or pyridostigmine are preferred.
While physostigmine has been used to antagonize the CNS depressant effects of benzodiazepines in humans, it should not be used for this purpose because of the potential toxicity and nonspecific action of physostigmine.

Metabolism

Physostigmine is the tertiary amine that are rapidly absorbed from the gastrointestinal tract, as are tacrine, donepezil, and galanthamine, whereas quaternary ammonium compounds are poorly absorbed after oral administration. Nevertheless, quaternary ammonium compounds like neostigmine and pyridostigmine are orally active if larger doses are employed. Only the quaternary ammonium inhibitors do not readily enter the CNS. Because of their high lipid solubility and low molecular weight, most of the organophosphates are absorbed by all routes of administration; even percutaneous exposure can result in the absorption of sufficient drug to permit the accumulation of toxic levels of these compounds.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN1544 Alkaloids, solid, n.o.s. or Alkaloid salts, solid, n.o.s. poisonous, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Eserine crystallises from Et2O or *C6H6 and forms an unstable low melting form m 86-87o [Harley-Mason & Jackson J Chem Soc 3651 1954, Wijnberg & Speckamp Tetrahedron 34 2399 1978]. [Beilstein 23/11 V 401.]

Incompatibilities

Light and heat.

Waste Disposal

It is not appropriate to dispose of expired or waste drugs or waste product such as lab chemicals by flushing them down the toilet or discarding them to the trash. Larger quantities shall carefully take into consideration applicable EPA, and FDA regulations. If possible return the lab chemicals to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste lab chemicals shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

PHYSOSTIGMINE Preparation Products And Raw materials Raw materials

Raw materials

Preparation Products

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PHYSOSTIGMINE Suppliers

Global(94)Suppliers
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57-47-6, PHYSOSTIGMINERelated Search:

physostigmine methiodide Physostigmine-D3 PHYSOSTIGMINE-D3 (N-METHYL-D3-CARBAMOYL) physostigmine heptyl PHYSOSTIGMINE HEMISULFATE,PHYSOSTIGMINE SULFATE,PHYSOSTIGMINE HEMISULFATE SALT Physostigmine salicylate (Eserine salicylate),physostigmine,[salicylate(1:1) PHYSOSTIGMINE (-)-N-METHYLPHYSOSTIGMINE PHYSOSTIGMINE HYDROCHLORIDE PHENSERINE PHYSOSTIGMINE HYDROBROMIDE
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  • Acetylcholinesterase inhibitor that crosses the blood-brain barrier and forms a carbamylated enzyme complex with acetyl cholinesterase that degrades slowly.
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