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57-47-6

Basic Information
CAS No.: 57-47-6
Name: PHYSOSTIGMINE
Article Data: 19
Molecular Structure:
Molecular Structure of 57-47-6 (PHYSOSTIGMINE)
Formula: C15H21 N3 O2
Molecular Weight: 275.351
Synonyms: Physostigmine(8CI); Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-,methylcarbamate (ester), (3aS,8aR)- (9CI); Pyrrolo[2,3-b]indol-5-ol,1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)-;(-)-Eserine; (-)-Physostigmine; Cogmine; Eserine; Esromiotin; MCV 4484; NIH10421; NSC 30782; Physostol
Density: 1.166g/cm3
Melting Point: 102-104 °C(lit.)
Boiling Point: 393.5°Cat760mmHg
Flash Point: 191.8°C
Solubility: Soluble in water (1:75), alcohol (1:10), chloroform (1:1), ether (1:30), and DMSO.
Appearance: solid
Hazard Symbols: Toxic by ingestion.
Risk Codes: 26/28
Safety: 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 within 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.
PSA: 44.81000
LogP: 2.16770
Synthetic route
50-00-0

formaldehyd

116181-32-9

(-)-N1-norphysostigmine fumarate

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;
624-83-9

methyl isocyanate

469-22-7

eseroline

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℃;
624-83-9

methyl isocyanate

65166-97-4

(-)-esermethole

57-47-6

Physostigmin

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

N8-norphysostigmine

74-88-4

methyl iodide

57-47-6

Physostigmin

Conditions
ConditionsYield
With alkaline methanol
624-83-9

methyl isocyanate

eserolin

eserolin

57-47-6

Physostigmin

Conditions
ConditionsYield
With diethyl ether; sodium; benzene
geneserin

geneserin

57-47-6

Physostigmin

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

methyl isocyanate

469-22-7

eseroline

71-43-2

benzene

A

57-47-6

Physostigmin

B

isoeserine

isoeserine

Conditions
ConditionsYield
at 100℃; im Rohr;
139115-75-6

2-iodo-4-methoxy-N-methylaniline

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
153109-50-3

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

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
153109-51-4

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

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
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Chemistry

IUPAC Name: (3,4,8B-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl) N-methylcarbamate
Synonyms: (3as-cis)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-olmeth ; (3aS-cis)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-olmethylcarbamate (ester) ; 1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo-[2,3-b]indol-5-yl methylcarbamate ; 1,2,3,3abeta,8abeta-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]-indol-5-yl methylcarbamate ; 1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate ; (2,3-b)Indol-5-ol,1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo(methylcarb) ; Antilirium ; Calabarine
Product Categories: Alkaloids;Biochemistry;Indole Alkaloids
CAS NO: 57-47-6
Molecular Formula: C15H21N3O2
Molecular Weight:275.35
Molecular Structure:
EINECS: 200-332-8
Merck: 7384
Mol File: 57-47-6.mol
Index of Refraction: 1.567
Surface Tension: 42.3 dyne/cm
Density: 1.166 g/cm3
Flash Point: 191.8 °C
Enthalpy of Vaporization: 64.34 kJ/mol
Boiling Point: 393.5 °C at 760 mmHg
Vapour Pressure: 2.12E-06 mmHg at 25°C
Melting point: 102-104 °C(lit.)
Storage temp: 2-8°C
Appearance: Physostigmine (CAS NO.57-47-6) is colorless flaky crysta.
Solubility: Physostigmine (CAS NO.57-47-6) is soluble in dichloromethane, soluble in chloroform (1:1), ethanol (1:10), ether (1:30) and water (1:75).

Uses

 Physostigmine (CAS NO.57-47-6) is used in biochemical research, also used as intermediates in drug synthesis and anti-cholinesterase drugs.

Production

 Physostigmine (CAS NO.57-47-6) is derived from dry mature seeds of Legumes physostigmine (physostigma venenosum Balfour) by extraction and refining using ethanol, ether and other solvent , Physostigmine (CAS NO.57-47-6) can be also synthetic.

Toxicity Data With Reference

1.    

orl-man TDLo:12 mg/kg/60D-I

    NEURAI    Neurology. 37 (1987),345.
2.    

unr-man LDLo:882 µg/kg

    85DCAI    Poisoning; Toxicology, Symptoms, Treatments. 2 (1970),73.
3.    

orl-wmn TDLo:40 µg/kg/5D-I:BPR

    AJPSAO    American Journal of Psychiatry. 143 (1985),910.
4.    

orl-wmn TDLo:3920 µg/kg/2W-I

    NEURAI    Neurology. 37 (1987),345.
5.    

orl-hmn TDLo:20 mg/kg:CNS,GIT,PUL

    34ZIAG    Toxicology of Drugs and Chemicals ,Deichmann, W.B.,New York, NY.: Academic Press, Inc.,1969,475.
6.    

ipr-mus LD50:644 µg/kg

    FATOAO    Farmakologiya i Toksikologiya (Moscow). 43 (1980),717.
7.    

scu-mus LD50:740 µg/kg:PNS

    JPETAB    Journal of Pharmacology and Experimental Therapeutics. 123 (1958),121.
8.    

ivn-mus LD50:400 µg/kg

    JPETAB    Journal of Pharmacology and Experimental Therapeutics. 58 (1936),337.
9.    

scu-dog LDLo:1138 µg/kg

    FEPRA7    Federation Proceedings, Federation of American Societies for Experimental Biology. 5 (1946),184.
10.    

orl-rbt LD50:11,200 µg/kg

    DCTODJ

Consensus Reports

EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory.

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 within 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.
Hazard Codes VeryT+
Risk Statements 26/28
R26/28:Very toxic by inhalation and if swallowed.
Safety Statements 23-45-25
S23:Do not breathe vapour. 
S25:Avoid contact with eyes. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR UN 1544 6.1/PG 1
WGK Germany 3
RTECS TJ2100000
F 8-10
HazardClass 6.1(a)
PackingGroup II

Specification

1.General Description :White, odorless, microcrystalline powder. Used as a cholinergic (anticholinesterase) agent and as a veterinary medication.
2.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.
3.Fire Hazard : Physostigmine (CAS NO.57-47-6) is a slight fire hazard. When heated to decomposition Physostigmine emits toxic fumes of nitrogen oxides. Keep from light and heat.