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57-47-6

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57-47-6 Usage

Description

The classic AChEI, physostigmine, is an alkaloid obtained from seeds of the Calabar bean (Physostigma venenosum). Its parasympathomimetic effects were recognized long before its structure was elucidated in 1923. In 1929, Stedman found that the mechanism of the parasympathomimetic effects of physostigmine was inhibition of AChE; it inhibits AChE by acting as a substrate and carbamylating the enzyme. Acetylcholinesterase is carbamylated at a slow rate, but physostigmine has exceptionally high affinity (Ki ~ 10-9 M) for the catalytic site of the enzyme. By comparison, the Ks for acetylcholine is on the order of 10-4 M. Thus, physostigmine is classified as a reversible AChEI that carbamylates the enzyme at a slow rate; the carbamylated AChE also is regenerated quite slowly. Because physostigmine is a tertiary amine with a pKa of 8.2 (+BH) rather than a quaternary ammonium salt, it is more lipophilic than many other AChEIs and can diffuse across the blood-brain barrier. The tertiary amine also imparts pH dependence to its ability to inhibit AChE, because its affinity for AChE is greater when the amine is protonated.

Chemical Properties

Physostigmine is a white crystalline solid. Odorless.

Physical properties

Appearance: flaky crystal. Solubility: slightly soluble in water; soluble in ethanol, benzene, and fatty oil. Melting point: 102–104 °C. Specific optical rotation: ?120° in benzene and ?76° in chloroform, respectively

History

Eserine was first discovered as a reversible AChE inhibitor, and it is also a tertiary amine and easily crosses the blood-brain barrier. In 1846, Robert Christison observed that the extract from Calabar bean caused cardiac arrest and death; he personally ate a certain amount of the extract and felt extremely feeble but luckily survived. In 1855, Christison reported that some kind of substances in the Calabar bean possessed strong biological activity.In 1864, chemists afforded crystal pure extract which was named as eserine. After that, Thomas Richard Fraser and Douglas Argyll Robertson cooperated to employ eserine in experimental ophthalmology, and the results showed that the antagonistic effect of eserine on mydriasis is induced by atropine. In 1875, Ludwig Laqueur declared that eserine could also be employed to depress intraocular pressure and first used as a treatment for glaucoma. In 1925, Edgar Stedman and George Barger determined the structure of eserine, which belongs to a natural product whose structure is characterized with hexahydropyrroloindole. In 1935, Percy Lavon Julian completed the chemical synthesis of its racemate for the first time .

Uses

Different sources of media describe the Uses of 57-47-6 differently. You can refer to the following data:
1. Physostigmine base (Eserine-Base) is used as bulk pharmaceuticals (parasympathomimetic, cholinergic, ophthalmic, anti-Alzheimer). Product Data Sheet
2. 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

Different sources of media describe the General Description of 57-47-6 differently. You can refer to the following data:
1. White, odorless, microcrystalline powder. Used as a cholinergic (anticholinesterase) agent and as a veterinary medication.
2. 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.

Pharmacology

Eserine was first discovered as one of AChE inhibitors. AChE inhibitor is the same as ACh, which can combine with cholinesterase, while AChE inhibitor will combine more tightly with cholinesterase, which leads to slow hydrolysis, inactive enzyme, cumulative ACh, and emergent biological activities . Although eserine does not directly activate M and N receptor, it can cross the central nervous system and strongly militate the central and peripheral nervous systems .When locally using eserine in the eyes, the effect is similar to pilocarpine but more powerful and durable. It can activate AChR of iridis sphincter, representing that the pupil is narrowed and the intraocular pressure is depressed, which is more obvious when being used to treat glaucoma patients. When being absorbed, the effect of eserine is similar to neostigmine, which is called as M- and N-like effects, representing that smooth muscle is activated strongly. After crossing the central nervous system, eserine can inhibit the activities induced by AChE, and it is presented as “activate previously, inhibit later.” It is noted that the effect of eserine is dependent on the status of the central nervous system .

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.

Check Digit Verification of cas no

The CAS Registry Mumber 57-47-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 7 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 57-47:
(4*5)+(3*7)+(2*4)+(1*7)=56
56 % 10 = 6
So 57-47-6 is a valid CAS Registry Number.
InChI:InChI=1/C15H21N3O2/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2/h5-6,9,13H,7-8H2,1-4H3,(H,16,19)/t13-,15+/m1/s1

57-47-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name physostigmine

1.2 Other means of identification

Product number -
Other names (3aS,8aR)-1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:57-47-6 SDS

57-47-6Synthetic route

formaldehyd
50-00-0

formaldehyd

(-)-N1-norphysostigmine fumarate
116181-32-9

(-)-N1-norphysostigmine fumarate

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
With sodium tetrahydroborate; triethylamine 1.) MeOH, room temperature, 2 h, 2.) room temperature, 0.5 h; Yield given. Multistep reaction;
methyl isocyanate
624-83-9

methyl isocyanate

eseroline
469-22-7

eseroline

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran
With sodium hydride In diethyl ether Yield given;
Stage #1: eseroline With sodium In diethyl ether at 20℃;
Stage #2: methyl isocyanate In diethyl ether at 20℃;
With sodium In diethyl ether at 20℃;
methyl isocyanate
624-83-9

methyl isocyanate

(-)-esermethole
65166-97-4

(-)-esermethole

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
With sodium; boron tribromide Yield given. Multistep reaction;
N8-norphysostigmine
19573-10-5

N8-norphysostigmine

methyl iodide
74-88-4

methyl iodide

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
With alkaline methanol
methyl isocyanate
624-83-9

methyl isocyanate

eserolin

eserolin

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
With diethyl ether; sodium; benzene
geneserin

geneserin

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
With ethanol; acetic acid; zinc
methyl isocyanate
624-83-9

methyl isocyanate

eseroline
469-22-7

eseroline

benzene
71-43-2

benzene

A

Physostigmin
57-47-6

Physostigmin

B

isoeserine

isoeserine

Conditions
ConditionsYield
at 100℃; im Rohr;
2-iodo-4-methoxy-N-methylaniline
139115-75-6

2-iodo-4-methoxy-N-methylaniline

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 55 percent / DCC, HOBT / tetrahydrofuran / Heating
2: 94 percent / Pd2(dba)3*CHCl3, (S)-BINAP, 1,2,2,6,6-pentamethylpiperidine / N,N-dimethyl-acetamide / 1.5 h / 100 °C
3: 80 percent / 3M aq. HCl / tetrahydrofuran / Ambient temperature
4: 1.) Et3N, MgSO4, 2.) LiAlH4 / 1.) THF, RT, overnight, 2.) THF, reflux, 1.5 h
5: BBr3 / CH2Cl2 / 23 °C
6: NaH / diethyl ether
View Scheme
(Z)-2-Methyl-4-triisopropylsilanyloxy-but-2-enoic acid
153109-50-3

(Z)-2-Methyl-4-triisopropylsilanyloxy-but-2-enoic acid

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 55 percent / DCC, HOBT / tetrahydrofuran / Heating
2: 94 percent / Pd2(dba)3*CHCl3, (S)-BINAP, 1,2,2,6,6-pentamethylpiperidine / N,N-dimethyl-acetamide / 1.5 h / 100 °C
3: 80 percent / 3M aq. HCl / tetrahydrofuran / Ambient temperature
4: 1.) Et3N, MgSO4, 2.) LiAlH4 / 1.) THF, RT, overnight, 2.) THF, reflux, 1.5 h
5: BBr3 / CH2Cl2 / 23 °C
6: NaH / diethyl ether
View Scheme
Multi-step reaction with 7 steps
1: 84 percent / Et3N / CH2Cl2 / 0.5 h / Ambient temperature
2: 80 percent / 4 h / 60 °C
3: 94 percent / Pd2(dba)3*CHCl3, (S)-BINAP, 1,2,2,6,6-pentamethylpiperidine / N,N-dimethyl-acetamide / 1.5 h / 100 °C
4: 80 percent / 3M aq. HCl / tetrahydrofuran / Ambient temperature
5: 1.) Et3N, MgSO4, 2.) LiAlH4 / 1.) THF, RT, overnight, 2.) THF, reflux, 1.5 h
6: BBr3 / CH2Cl2 / 23 °C
7: NaH / diethyl ether
View Scheme
Multi-step reaction with 5 steps
1: 1.) BOP, Et3N / 1.) CH2Cl2, 2.) 60 deg C
2: 1,2,2,6,6-pentamethylpiperidine / 20percent Pd-(S)-BINAP / N,N-dimethyl-acetamide / 100 °C
3: 3N aq. HCl / 23 °C
4: 1.) Et3N, MgSO4, 2.) LiAlH4 / 2.) THF, reflux
5: 1.) BBr3, 2.) Na
View Scheme
(Z)-2-Methyl-4-triisopropylsilanyloxy-but-2-enoic acid (2-iodo-4-methoxy-phenyl)-methyl-amide
153109-51-4

(Z)-2-Methyl-4-triisopropylsilanyloxy-but-2-enoic acid (2-iodo-4-methoxy-phenyl)-methyl-amide

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 94 percent / Pd2(dba)3*CHCl3, (S)-BINAP, 1,2,2,6,6-pentamethylpiperidine / N,N-dimethyl-acetamide / 1.5 h / 100 °C
2: 80 percent / 3M aq. HCl / tetrahydrofuran / Ambient temperature
3: 1.) Et3N, MgSO4, 2.) LiAlH4 / 1.) THF, RT, overnight, 2.) THF, reflux, 1.5 h
4: BBr3 / CH2Cl2 / 23 °C
5: NaH / diethyl ether
View Scheme
Multi-step reaction with 4 steps
1: 1,2,2,6,6-pentamethylpiperidine / 20percent Pd-(S)-BINAP / N,N-dimethyl-acetamide / 100 °C
2: 3N aq. HCl / 23 °C
3: 1.) Et3N, MgSO4, 2.) LiAlH4 / 2.) THF, reflux
4: 1.) BBr3, 2.) Na
View Scheme
(3S)-(5-methoxy-1,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-3-yl)acetaldehyde
153109-52-5

(3S)-(5-methoxy-1,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-3-yl)acetaldehyde

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) Et3N, MgSO4, 2.) LiAlH4 / 1.) THF, RT, overnight, 2.) THF, reflux, 1.5 h
2: BBr3 / CH2Cl2 / 23 °C
3: NaH / diethyl ether
View Scheme
Multi-step reaction with 2 steps
1: 1.) Et3N, MgSO4, 2.) LiAlH4 / 2.) THF, reflux
2: 1.) BBr3, 2.) Na
View Scheme
(S)-5-Methoxy-1,3-dimethyl-3-((E)-2-triisopropylsilanyloxy-vinyl)-1,3-dihydro-indol-2-one
153109-54-7

(S)-5-Methoxy-1,3-dimethyl-3-((E)-2-triisopropylsilanyloxy-vinyl)-1,3-dihydro-indol-2-one

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 80 percent / 3M aq. HCl / tetrahydrofuran / Ambient temperature
2: 1.) Et3N, MgSO4, 2.) LiAlH4 / 1.) THF, RT, overnight, 2.) THF, reflux, 1.5 h
3: BBr3 / CH2Cl2 / 23 °C
4: NaH / diethyl ether
View Scheme
Multi-step reaction with 3 steps
1: 3N aq. HCl / 23 °C
2: 1.) Et3N, MgSO4, 2.) LiAlH4 / 2.) THF, reflux
3: 1.) BBr3, 2.) Na
View Scheme
(Z)-1-Benzotriazol-1-yl-2-methyl-4-triisopropylsilanyloxy-but-2-en-1-one

(Z)-1-Benzotriazol-1-yl-2-methyl-4-triisopropylsilanyloxy-but-2-en-1-one

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 80 percent / 4 h / 60 °C
2: 94 percent / Pd2(dba)3*CHCl3, (S)-BINAP, 1,2,2,6,6-pentamethylpiperidine / N,N-dimethyl-acetamide / 1.5 h / 100 °C
3: 80 percent / 3M aq. HCl / tetrahydrofuran / Ambient temperature
4: 1.) Et3N, MgSO4, 2.) LiAlH4 / 1.) THF, RT, overnight, 2.) THF, reflux, 1.5 h
5: BBr3 / CH2Cl2 / 23 °C
6: NaH / diethyl ether
View Scheme
(-)-esermethole
65166-97-4

(-)-esermethole

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: BBr3 / CH2Cl2 / 23 °C
2: NaH / diethyl ether
View Scheme
Multi-step reaction with 2 steps
1: BBr3 / CH2Cl2 / 0 deg C -> r.t.
2: NaH / tetrahydrofuran
View Scheme
(S)-3-(5-Methoxy-2-methylamino-phenyl)-1,3-dimethyl-pyrrolidin-2-one

(S)-3-(5-Methoxy-2-methylamino-phenyl)-1,3-dimethyl-pyrrolidin-2-one

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: LAH / tetrahydrofuran / Heating
2: BBr3 / CH2Cl2 / 0 deg C -> r.t.
3: NaH / tetrahydrofuran
View Scheme
N-[2-((S)-2-Hydroxy-3-methyl-tetrahydro-furan-3-yl)-4-methoxy-phenyl]-N-methyl-acetamide
136569-51-2

N-[2-((S)-2-Hydroxy-3-methyl-tetrahydro-furan-3-yl)-4-methoxy-phenyl]-N-methyl-acetamide

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 88 percent / Ag2CO3 on Celite / benzene / Heating
2: 76 percent / H2O / 180 °C / sealed tube
3: iBu2AlH / CH2Cl2 / -78 °C
4: NH4OH
5: LAH / tetrahydrofuran / Heating
6: BBr3 / CH2Cl2 / 0 deg C -> r.t.
7: NaH / tetrahydrofuran
View Scheme
(S)-3-{2-[(1-Hydroxy-ethyl)-methyl-amino]-5-methoxy-phenyl}-1,3-dimethyl-pyrrolidin-2-one

(S)-3-{2-[(1-Hydroxy-ethyl)-methyl-amino]-5-methoxy-phenyl}-1,3-dimethyl-pyrrolidin-2-one

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NH4OH
2: LAH / tetrahydrofuran / Heating
3: BBr3 / CH2Cl2 / 0 deg C -> r.t.
4: NaH / tetrahydrofuran
View Scheme
N-[4-Methoxy-2-((S)-3-methyl-2-oxo-tetrahydro-furan-3-yl)-phenyl]-N-methyl-acetamide
136569-52-3

N-[4-Methoxy-2-((S)-3-methyl-2-oxo-tetrahydro-furan-3-yl)-phenyl]-N-methyl-acetamide

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 76 percent / H2O / 180 °C / sealed tube
2: iBu2AlH / CH2Cl2 / -78 °C
3: NH4OH
4: LAH / tetrahydrofuran / Heating
5: BBr3 / CH2Cl2 / 0 deg C -> r.t.
6: NaH / tetrahydrofuran
View Scheme
N-{2-[(S)-2,3-Dihydroxy-1-(2-hydroxy-ethyl)-1-methyl-propyl]-4-methoxy-phenyl}-N-methyl-acetamide

N-{2-[(S)-2,3-Dihydroxy-1-(2-hydroxy-ethyl)-1-methyl-propyl]-4-methoxy-phenyl}-N-methyl-acetamide

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 1) 10percent HCl, 2) NaIO4
2: 88 percent / Ag2CO3 on Celite / benzene / Heating
3: 76 percent / H2O / 180 °C / sealed tube
4: iBu2AlH / CH2Cl2 / -78 °C
5: NH4OH
6: LAH / tetrahydrofuran / Heating
7: BBr3 / CH2Cl2 / 0 deg C -> r.t.
8: NaH / tetrahydrofuran
View Scheme
N-[2-((S)-1,3-Dimethyl-2-oxo-pyrrolidin-3-yl)-4-methoxy-phenyl]-N-methyl-acetamide
136569-53-4

N-[2-((S)-1,3-Dimethyl-2-oxo-pyrrolidin-3-yl)-4-methoxy-phenyl]-N-methyl-acetamide

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: iBu2AlH / CH2Cl2 / -78 °C
2: NH4OH
3: LAH / tetrahydrofuran / Heating
4: BBr3 / CH2Cl2 / 0 deg C -> r.t.
5: NaH / tetrahydrofuran
View Scheme
N-[4-Methoxy-2-((S)-3-methyl-2-oxo-6,7,8-trioxa-bicyclo[3.2.1]oct-3-yl)-phenyl]-N-methyl-acetamide

N-[4-Methoxy-2-((S)-3-methyl-2-oxo-6,7,8-trioxa-bicyclo[3.2.1]oct-3-yl)-phenyl]-N-methyl-acetamide

Physostigmin
57-47-6

Physostigmin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: NaBH4 / -78 deg C -> r.t.
2: 1) 10percent HCl, 2) NaIO4
3: 88 percent / Ag2CO3 on Celite / benzene / Heating
4: 76 percent / H2O / 180 °C / sealed tube
5: iBu2AlH / CH2Cl2 / -78 °C
6: NH4OH
7: LAH / tetrahydrofuran / Heating
8: BBr3 / CH2Cl2 / 0 deg C -> r.t.
9: NaH / tetrahydrofuran
View Scheme
Physostigmin
57-47-6

Physostigmin

eseroline
469-22-7

eseroline

Conditions
ConditionsYield
With sodium In butan-1-ol at 20℃;95%
With hydrogenchloride
With sulfuric acid
(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

Physostigmin
57-47-6

Physostigmin

(-)-eseroline fumarate salt

(-)-eseroline fumarate salt

Conditions
ConditionsYield
Stage #1: Physostigmin With sodium In butan-1-ol Heating;
Stage #2: (2E)-but-2-enedioic acid In butan-1-ol
95%
methyl bromide
74-83-9

methyl bromide

Physostigmin
57-47-6

Physostigmin

Br(1-)*C16H24N3O2(1+)
1239457-13-6

Br(1-)*C16H24N3O2(1+)

Conditions
ConditionsYield
In diethyl ether; acetonitrile at 20℃; Inert atmosphere;80%
glacial HOAc

glacial HOAc

m-chlorophenyl isocyanate
2909-38-8

m-chlorophenyl isocyanate

Physostigmin
57-47-6

Physostigmin

eseroline
469-22-7

eseroline

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran71.3%
With potassium tert-butylate In tetrahydrofuran
Physostigmin
57-47-6

Physostigmin

geneserine hydrochloride

geneserine hydrochloride

Conditions
ConditionsYield
With dihydrogen peroxide In various solvent(s) for 16h; Ambient temperature;71%
Physostigmin
57-47-6

Physostigmin

Methyl-carbamic acid (3aS,8aR)-8-formyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester
128562-54-9

Methyl-carbamic acid (3aS,8aR)-8-formyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester

Conditions
ConditionsYield
With dipyridinium dichromate In dichloromethane for 24h; Ambient temperature;28%
With dipyridinium dichromate In dichloromethane25%
Physostigmin
57-47-6

Physostigmin

aq.-ethanolic Ba(OH)2

aq.-ethanolic Ba(OH)2

(3aS)-1,3a,6b,9,10,14-hexamethyl-(3ar,6bt,9at,14ac)-1,2,3,3a,6b,7,8,9,9a,10,14,14a-dodecahydro-12-oxa-1,5,9,10,14-pentaaza-dipentaleno-<1,2-b;2',1'-i>anthracen-4-one

(3aS)-1,3a,6b,9,10,14-hexamethyl-(3ar,6bt,9at,14ac)-1,2,3,3a,6b,7,8,9,9a,10,14,14a-dodecahydro-12-oxa-1,5,9,10,14-pentaaza-dipentaleno-<1,2-b;2',1'-i>anthracen-4-one

Conditions
ConditionsYield
unter Luftzutritt;
Physostigmin
57-47-6

Physostigmin

aqueous ammonium salt

aqueous ammonium salt

(3aS)-1,3a,6b,9,10,14-hexamethyl-(3ar,6bt,9at,14ac)-1,2,3,3a,6b,7,8,9,9a,10,14,14a-dodecahydro-12-oxa-1,5,9,10,14-pentaaza-dipentaleno-<1,2-b;2',1'-i>anthracen-4-one

(3aS)-1,3a,6b,9,10,14-hexamethyl-(3ar,6bt,9at,14ac)-1,2,3,3a,6b,7,8,9,9a,10,14,14a-dodecahydro-12-oxa-1,5,9,10,14-pentaaza-dipentaleno-<1,2-b;2',1'-i>anthracen-4-one

Physostigmin
57-47-6

Physostigmin

(3aS)-6-hydroxy-1,3a,8-trimethyl-5-oxo-(3ar,8ac)-1,2,3,3a,5,8a-hexahydro-pyrrolo<2,3-b>indolium betaine

(3aS)-6-hydroxy-1,3a,8-trimethyl-5-oxo-(3ar,8ac)-1,2,3,3a,5,8a-hexahydro-pyrrolo<2,3-b>indolium betaine

Conditions
ConditionsYield
Luftoxidation;
Physostigmin
57-47-6

Physostigmin

colloid/al palladium

colloid/al palladium

acid

acid

dihydroeserine

dihydroeserine

Conditions
ConditionsYield
Hydrogenation;
Physostigmin
57-47-6

Physostigmin

sodium amalgam

sodium amalgam

diluted hydrochloric acid

diluted hydrochloric acid

dihydroeserine

dihydroeserine

Physostigmin
57-47-6

Physostigmin

zinc dust

zinc dust

hydrochloric acid

hydrochloric acid

dihydroeserine

dihydroeserine

sodium ethanolate
141-52-6

sodium ethanolate

ethyl ester of p-toluenesulfonic acid
80-40-0

ethyl ester of p-toluenesulfonic acid

Physostigmin
57-47-6

Physostigmin

eseraethole

eseraethole

Physostigmin
57-47-6

Physostigmin

air oxygen

air oxygen

Eserine Blue

Eserine Blue

Physostigmin
57-47-6

Physostigmin

eserolin

eserolin

Conditions
ConditionsYield
at 150 - 160℃; im Hochvakuum;
Physostigmin
57-47-6

Physostigmin

concentrated hydrochloric acid

concentrated hydrochloric acid

eserolin

eserolin

57-47-6Relevant articles and documents

Physostigmine and N8-norphysostigmine, insecticidal compounds, and Streptomyces sp.

Murao,Hayashi

, p. 523 - 524 (1986)

-

A novel and efficient total synthesis of (±)-physostigmine

Kulkarni, Mukund G.,Dhondge, Attrimuni P.,Borhade, Ajit S.,Gaikwad, Dnyaneshwar D.,Chavhan, Sanjay W.,Shaikh, Yunnus B.,Ningdale, Vijay B.,Desai, Mayur P.,Birhade, Deekshaputra R.,Shinde, Mahadev P.

supporting information; experimental part, p. 2411 - 2413 (2009/07/26)

Application of the Wittig olefination-Claisen rearrangement protocol for the total synthesis of (±)-physostigmine.

Inhibition of human acetyl- and butyrylcholinesterase by novel carbamates of (-)- and (+)-tetrahydrofurobenzofuran and methanobenzodioxepine

Luo, Weiming,Yu, Qian-Sheng,Kulkarni, Santosh S.,Parrish, Damon A.,Holloway, Harold W.,Tweedie, David,Shafferman, Avigdor,Lahiri, Debomoy K.,Brossi, Arnold,Greig, Nigel H.

, p. 2174 - 2185 (2007/10/03)

A new enantiomeric synthesis utilizing classical resolution provided two novel series of optically active inhibitors of cholinesterase: (-)- and (+)-O-carbamoyl phenols of tetrahydrofurobenzofuran and methanobenzodioxepine. An additional two series of (-)- and (+)-O-carbamoyl phenols of pyrroloindole and furoindole were obtained by known procedures, and their anticholinesterase actions were similarly quantified against freshly prepared human acetyl- (AChE) and butyrylcholinesterase (BChE). Both enantiomeric forms of each series demonstrated potent cholinesterase inhibitory activity (with IC50 values as low as 10 nM for AChE and 3 nM for BChE), with the exception of the (+)-O-carbamoyl phenols of pyrroloindole, which lacked activity (IC50 values > 1 μM). Based on the biological data of these four series, a structure-activity relationship (SAR) analysis was provided by molecular volume calculations. In addition, a probable transition-state model was established according to the known X-ray structure of a transition-state complex of Torpedo californica AChE-m-(N,N,N-trimethylammonio)-2,2,2-trifluoroacetophenone (TcAChE-TMTFA). This model proved valuable in explaining the enantioselectivity and enzyme subtype selectivity of each series. These carbamates are more potent than, or similarly potent to, anticholinesterases in current clinical use, providing not only inhibitors of potential clinical relevance but also pharmacological tools to define drug-enzyme binding interactions within an enzyme crucial in the maintenance of cognition and numerous systemic physiological functions in health, aging, and disease.

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