Product Name

  • Name

    (+)-Pilocarpine hydrochloride

  • EINECS 200-212-5
  • CAS No. 54-71-7
  • Article Data5
  • CAS DataBase
  • Density 1.22 g/cm3
  • 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;
  • PSA 44.12000
  • LogP 1.96380

Synthetic route

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

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

pilocarpine hydrochloride
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

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

pilocarpine hydrochloride
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

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

pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

Conditions
ConditionsYield
With lithium borohydride; sodium hydrogencarbonate In hydrogenchloride; methanol; water; isopropyl alcohol
(R)-3-ethylidene-4-[(1-methylimidazol-5-yl)methyl]tetrahydrofuran-2-one
1192231-13-2

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

pilocarpine hydrochloride
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

cobalt(II) chloride hexahydrate

pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

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

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%
all cis-5,8,11,14,17-eicosapentaenoic acid
10417-94-4

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

pilocarpine hydrochloride
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

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%
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

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

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%
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

copper dichloride

copper dichloride

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

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%
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

3-ethyl-4,5-dihydro-4-<(1-methyl-1H-imidazol-5-yl)methyl>-2(3H)-thiophenethione
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
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

A

sodium isopilocarpate
101769-87-3

sodium isopilocarpate

B

sodium pilocarpate
92598-79-3

sodium pilocarpate

Conditions
ConditionsYield
With sodium hydroxide In water at 0 - 4℃; for 1h; Yield given;
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

A

isopilocarpine
531-35-1

isopilocarpine

B

Pilocarpinsaeure
28406-15-7

Pilocarpinsaeure

C

Isopilocarpinsaeure
34350-99-7

Isopilocarpinsaeure

Conditions
ConditionsYield
With potassium chloride In water for 1h; Kinetics; Thermodynamic data; Mechanism; Heating; var. pH-value, temp., times; epimerisation;
...Expand
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

methanolic hydrochloric acid

methanolic hydrochloric acid

chloropilocarpinic acid methyl ester

chloropilocarpinic acid methyl ester

Conditions
ConditionsYield
Erhitzen auf Siedetemperatur;
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

aniline
62-53-3

aniline

(+-)-isopilocarpine
92-13-7, 531-35-1, 4354-74-9, 35594-23-1, 48148-73-8, 54163-69-8, 102282-25-7

(+-)-isopilocarpine

B

isopilocarpinanil

isopilocarpinanil

Conditions
ConditionsYield
at 205 - 210℃;
...Expand
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

benzylamine
100-46-9

benzylamine

A

cis-N-benzylpilolactam

cis-N-benzylpilolactam

B

trans-N-benzylpilolactam

trans-N-benzylpilolactam

Conditions
ConditionsYield
for 40h; Benzylation; Heating;
...Expand
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

isopilocarpine
531-35-1

isopilocarpine

Conditions
ConditionsYield
Stage #1: pilocarpine hydrochloride With sodium hydroxide
Stage #2: With hydrogenchloride
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

Pilocarpinsaeure
28406-15-7

Pilocarpinsaeure

Conditions
ConditionsYield
With ammonium hydroxide at 90℃; for 2h;
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

Isopilocarpinsaeure
34350-99-7

Isopilocarpinsaeure

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: aq. NaOH
1.2: aq. HCl
2.1: aq. NH3 / 2 h / 90 °C
View Scheme
Multi-step reaction with 2 steps
1.1: aq. NH3 / 2 h / 90 °C
2.1: aq. NaOH
2.2: aq. HCl
View Scheme
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

(3R,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)-methyl]-2-pyrrolidinone
137034-76-5

(3R,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)-methyl]-2-pyrrolidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 40 h / Heating
2: Li; PrNH2; H2NCH2CH2NH2 / 2-methyl-propan-2-ol / 4 h / 0 °C
View Scheme
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid ethyl ester
96914-10-2

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / H2O / 1 h / 0 - 4 °C
2: 27 percent / dimethylformamide / Ambient temperature
View Scheme
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid hexyl ester
96914-11-3

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid hexyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / H2O / 1 h / 0 - 4 °C
2: 36 percent / dimethylformamide / Ambient temperature
View Scheme
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid butyl ester
92598-80-6

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / H2O / 1 h / 0 - 4 °C
2: 30 percent / dimethylformamide / Ambient temperature
View Scheme
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid benzyl ester
92598-82-8

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid benzyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / H2O / 1 h / 0 - 4 °C
2: 35 percent / dimethylformamide / Ambient temperature
View Scheme
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid phenethyl ester
92598-86-2

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid phenethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / H2O / 1 h / 0 - 4 °C
2: 22 percent / dimethylformamide / Ambient temperature
View Scheme
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

pilocarpic acid 4-methylbenzyl ester
92598-93-1

pilocarpic acid 4-methylbenzyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / H2O / 1 h / 0 - 4 °C
2: 40 percent / dimethylformamide / Ambient temperature
View Scheme
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid 1-phenyl-ethyl ester
92598-81-7

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid 1-phenyl-ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / H2O / 1 h / 0 - 4 °C
2: 35 percent / dimethylformamide / Ambient temperature
View Scheme
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid 2-methyl-benzyl ester
92598-92-0

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid 2-methyl-benzyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / H2O / 1 h / 0 - 4 °C
2: 35 percent / dimethylformamide / Ambient temperature
View Scheme
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid 4-chloro-benzyl ester
92598-89-5

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid 4-chloro-benzyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / H2O / 1 h / 0 - 4 °C
2: 43 percent / dimethylformamide / Ambient temperature
View Scheme
pilocarpine hydrochloride
54-71-7

pilocarpine hydrochloride

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid 4-tert-butyl-benzyl ester
92598-99-7

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid 4-tert-butyl-benzyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / H2O / 1 h / 0 - 4 °C
2: 18 percent / dimethylformamide / Ambient temperature
View Scheme

(+)-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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