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(+)-Pilocarpine hydrochloride
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Name

(+)-Pilocarpine hydrochloride

 EINECS 200-212-5
CAS No. 54-71-7 Density 1.22 g/cm3
PSA 44.12000 LogP 1.96380
Solubility 100 mg/mL in water Melting Point 199-204 °C
Formula C11H16N2O2.HCl Boiling Point 431.8 °C at 760 mmHg
Molecular Weight 244.721 Flash Point 215 °C
Transport Information UN 1544 6.1/PG 3 Appearance white crystalline solid
Safety 25-45 Risk Codes 26/28
Molecular Structure Molecular Structure of 54-71-7 ((+)-Pilocarpine hydrochloride) Hazard Symbols VeryT+
Synonyms

2(3H)-Furanone,3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, monohydrochloride,(3S,4R)- (9CI);2(3H)-Furanone,3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, monohydrochloride,(3S-cis)-;Pilocarpine, monohydrochloride (8CI);(+)-Pilocarpine hydrochloride;Adsorbocarpine;Almocarpine;Isopto Carpine;NSC 5746;Pilocar;Pilocar SMP;Pilocarpal;Pilocarpine chloride;Pilocarpine hydrochloride;Pilocarpinemuriate;Pilocarpinium chloride;Pilocel;Pilovisc;Salagen;Sanpilo;Vistacarpin N;

Article Data 5

(+)-Pilocarpine hydrochloride Synthetic route

(2S,3RS)-2-ethyl-3-(1-methyl-1H-imidazol-5-yl)butane-1,4-dioic acid 4-methyl ester

54-71-7

pilocarpine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; sodium tetrahydroborate 1a.) iPrOH, -5 deg C, 1 h, 1b.) RT, 21 h, 2.) MeOH, water, 2 h; Yield given. Multistep reaction;

(3S,4RS,5RS)-3-ethyl-4-(methoxycarbonyl)-5-(1-methyl-1H-imidazol-5-yl)dihydro-2(3H)-furanone

54-71-7

pilocarpine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / H2 / Pd/C (5percent) / methanol / 60 h / 3102.9 Torr
2: 1.) NaBH4, 2.) conc. aq. HCl / 1a.) iPrOH, -5 deg C, 1 h, 1b.) RT, 21 h, 2.) MeOH, water, 2 h
View Scheme

(2S,3R)-2-ethyl-3-(methoxycarbonyl)4-(1-methylimidazol-5-yl)-butyricacid

54-71-7

pilocarpine hydrochloride

Conditions
ConditionsYield
With lithium borohydride; sodium hydrogencarbonate In hydrogenchloride; methanol; water; isopropyl alcohol
1192231-13-2

(R)-3-ethylidene-4-[(1-methylimidazol-5-yl)methyl]tetrahydrofuran-2-one

54-71-7

pilocarpine hydrochloride

Conditions
ConditionsYield
Stage #1: (R)-3-ethylidene-4-[(1-methylimidazol-5-yl)methyl]tetrahydrofuran-2-one With platinum(IV) oxide; hydrogen In methanol at 20℃; for 24h;
Stage #2: With hydrogenchloride In ethanol; water at 0℃; Cooling;

cobalt(II) chloride hexahydrate

54-71-7

pilocarpine hydrochloride

dichloro-bis(κN-(+)-pilocarpine)cobalt(II)

Conditions
ConditionsYield
With Na2CO3 In ethanol; water; ethyl acetate organic ligand in water alkalinized with Na2CO3 to pH=9; extracted with ethyl acetate; overlayered with 0.5 equivalent CoCl2*6H2O in EtOH; allowed to evaporate slowly at room temp. for 2 days; elem. anal.;97%
10417-94-4

all cis-5,8,11,14,17-eicosapentaenoic acid

54-71-7

pilocarpine hydrochloride

5-(((3R,4S)-4-ethyl-5-oxotetrahydrofuran-3-yl)methyl)-1-methyl-1H-imidazol-1-ium (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate

Conditions
ConditionsYield
Stage #1: pilocarpine hydrochloride With sodium hydrogencarbonate In methanol for 0.0833333h;
Stage #2: all cis-5,8,11,14,17-eicosapentaenoic acid In methanol at 20℃; for 16h;		96.8%
54-71-7

pilocarpine hydrochloride

1200-22-2

(R)-1,2-dithiolane-3-pentanoic acid

5-(((3R,4S)-4-ethyl-5-oxotetrahydrofuran-3-yl)methyl)-1-methyl-1H-imidazol-1-ium (R)-5-(1,2-dithiolan-3-yl)pentanoate

Conditions
ConditionsYield
Stage #1: pilocarpine hydrochloride With sodium hydrogencarbonate In acetone at 20℃; for 0.0833333h;
Stage #2: (R)-1,2-dithiolane-3-pentanoic acid In acetone at 20℃; for 16h;		91.58%
54-71-7

pilocarpine hydrochloride

copper dichloride

dichloro-bis(κN-(+)-pilocarpine)copper(II)

Conditions
ConditionsYield
With Na2CO3 In chloroform; water; butan-1-ol organic ligand in water alkalinized with Na2CO3 to pH=9; extracted with CHCl3; removed in vacuo; dissolved in butanol; 0.5 equivalent of CuCl2 in butanol added; heated for a few minutes; sepd. by filtration; crystals grown from acetone; elem. anal.;14%
54-71-7

pilocarpine hydrochloride

117639-12-0

3-ethyl-4,5-dihydro-4-<(1-methyl-1H-imidazol-5-yl)methyl>-2(3H)-thiophenethione

Conditions
ConditionsYield
With Lawessons reagent In xylene at 135℃; for 7h;4.63 g
54-71-7

pilocarpine hydrochloride

A

101769-87-3

sodium isopilocarpate

B

92598-79-3

sodium pilocarpate

Conditions
ConditionsYield
With sodium hydroxide In water at 0 - 4℃; for 1h; Yield given;

(+)-Pilocarpine hydrochloride Chemical Properties

The Molecular formula of  PILOCARPINE MONOHYDROCHLORIDE(54-71-7):C11H17ClN2O2
The Molecular Weight of  PILOCARPINE MONOHYDROCHLORIDE(54-71-7):244.72 
The Molecular Structure of  PILOCARPINE MONOHYDROCHLORIDE(54-71-7) is:
Melting point:202-205 °C(lit.) 
Boiling point:431.8 °C at 760 mmHg
Flash point:215 °C    
Solubility in water:100 mg/mL
Sensitive:Hygroscopic
Merck:14,7424
Enthalpy of Vaporization:68.75 kJ/mol  
Vapour Pressure:1.16E-07 mmHg at 25°C 
Appearance:crystalline Solid  
IUPAC Name:(3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one hydrochloride
Synonyms:ALMOCARPINE HYDROCHLORIDE;3-ETHYL-4-[(1-METHYL-5-IMIDAZOLYL)METHYL]TETRAHYDROFURAN-2-ONE HYDROCHLORIDE;(3S,4R)-4,5-DIHYDRO-3-ETHYL-4-(1-METHYL-1H-IMIDAZOL-5-YLMETHYL)-2(3H)-FURANONE HYDROCHLORIDE;(3S-CIS)-3-ETHYLDIHYDRO-4-[(1-METHYL-1H-IMIDAZOL-5-YL)METHYL]-2(3H)-FURANONE HYDROCHLORIDE;PILOCARPINE HCL;(+)-PILOCARPINE HYDROCHLORIDE;PILOCARPINE HYDROCHLORIDE;(3s-cis)-ochlorid

(+)-Pilocarpine hydrochloride Uses

Antiglaucoma agent; miotic; sialogogue.

(+)-Pilocarpine hydrochloride Toxicity Data With Reference

1.   

ocu-man TDLo:200 µg/kg/7H-I:CVS

   AIMDAP    Archives of Internal Medicine. 147 (1987),586.
2.   

orl-mus LD50:200 mg/kg

   NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),646.
3.   

ipr-mus LD50:155 mg/kg

   ATXKA8    Archiv fuer Toxikologie. 29 (1972),39.
4.   

ivn-pgn LDLo:353 mg/kg

   HBAMAK    “Abdernalden’s Handbuch der Biologischen Arbeitsmethoden.“ 4 (1935),1289.

(+)-Pilocarpine hydrochloride Consensus Reports

Reported in EPA TSCA Inventory.

(+)-Pilocarpine hydrochloride Safety Profile

Poison by ingestion, intraperitoneal, and intravenous routes. Experimental teratogenic and reproductive effects. Human systemic effects: cardiac changes. When heated to decomposition it emits very toxic fumes of HCl and NOx. See also PILOCARPINE
Hazard Codes:T+
T+ :Very Toxic
Risk Statements
R26/28:Very Toxic by inhalation and if swallowed .
Safety Statements
S25:Avoid contact with eyes .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
RIDADR:UN 1544 6.1/PG 3
WGK Germany:3
RTECS:TK1450000
F:3-8-10
F3:Hygroscopic.
F8:Photosensitive.
F10:Keep under argon.
HazardClass:6.1
PackingGroup:III


 

(+)-Pilocarpine hydrochloride Specification

Chemical Stability: Stable. 
Incompatibilities with Other Materials Strong oxidizing agents. 
Conditions to Avoid: Incompatible materials, light, exposure to moist air or water, heat
Hazardous Decomposition Products Hydrogen chloride, nitrogen oxides, carbon monoxide, carbon dioxide, oxides of chlorine. 
Hazardous Polymerization Will not occur.  
   
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