Product Name

  • Name

    (-)-Scopolamine

  • EINECS 228-065-2
  • CAS No. 138-12-5
  • Article Data21
  • CAS DataBase
  • Density 1.31 g/cm3
  • Solubility
  • Melting Point ?15?°C(lit.)
  • Formula C17H21NO4
  • Boiling Point 460.3 °C at 760 mmHg
  • Molecular Weight 303.358
  • Flash Point 232.2 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes R36/37/38
  • Molecular Structure Molecular Structure of 138-12-5 ((-)-Scopolamine)
  • Hazard Symbols
  • Synonyms Atroscine;
  • PSA 62.30000
  • LogP 0.85600

Synthetic route

glutaric anhydride,
108-55-4

glutaric anhydride,

scopalamine
138-12-5

scopalamine

O-glutaryl-(-)-scopolamine

O-glutaryl-(-)-scopolamine

Conditions
ConditionsYield
In benzene for 24h; Ambient temperature;50%
scopalamine
138-12-5

scopalamine

A

nor-(-)-scopolamine
3292-20-4

nor-(-)-scopolamine

B

3-Hydroxy-2-phenyl-propionic acid (1R,2R,4S,5S,7S)-9-formyl-3-oxa-9-aza-tricyclo[3.3.1.02,4]non-7-yl ester
25650-58-2

3-Hydroxy-2-phenyl-propionic acid (1R,2R,4S,5S,7S)-9-formyl-3-oxa-9-aza-tricyclo[3.3.1.02,4]non-7-yl ester

Conditions
ConditionsYield
With oxygen; lithium perchlorate; 9,10-Dicyanoanthracene In acetonitrile at 20℃; Irradiation;A 82 % Spectr.
B 18 % Spectr.
With oxygen; 9,10-Dicyanoanthracene In acetonitrile at 20℃; Irradiation;A 50 % Spectr.
B 50 % Spectr.
scopalamine
138-12-5

scopalamine

(1R,3S,5S)-3'-hydroxy-2'-phenylpropionic acid 8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl ester
22150-33-0

(1R,3S,5S)-3'-hydroxy-2'-phenylpropionic acid 8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl ester

Conditions
ConditionsYield
With copper; zinc In ethanol Heating; Yield given;
scopalamine
138-12-5

scopalamine

(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol
20513-09-1

(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Zn-Cu / ethanol / Heating
2: 77 percent / OH(1-)/H2O / Heating
View Scheme
scopalamine
138-12-5

scopalamine

tert-butyl-((3Z,5Z)-cyclohepta-3,5-dienyloxy)dimethylsilane
119146-80-4

tert-butyl-((3Z,5Z)-cyclohepta-3,5-dienyloxy)dimethylsilane

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Zn-Cu / ethanol / Heating
2: 77 percent / OH(1-)/H2O / Heating
3: 88 percent
4: 35percent H2O2 / ethanol / 48 h
5: various solvent(s) / 3 h / Heating
View Scheme
scopalamine
138-12-5

scopalamine

(1S,3R,5S)-8-Methyl-8-aza-bicyclo[3.2.1]octane-1,3-diol

(1S,3R,5S)-8-Methyl-8-aza-bicyclo[3.2.1]octane-1,3-diol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: Zn-Cu / ethanol / Heating
2: 77 percent / OH(1-)/H2O / Heating
3: 88 percent
4: 35percent H2O2 / ethanol / 48 h
5: 15 percent / various solvent(s) / 3 h / Heating
6: 92 percent / Zn/AcOH
7: H2 / Pd/C
8: PCC
9: 3percent aq. HCl
View Scheme
scopalamine
138-12-5

scopalamine

(1S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methylamino-cycloheptanol

(1S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methylamino-cycloheptanol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: Zn-Cu / ethanol / Heating
2: 77 percent / OH(1-)/H2O / Heating
3: 88 percent
4: 35percent H2O2 / ethanol / 48 h
5: 15 percent / various solvent(s) / 3 h / Heating
6: 92 percent / Zn/AcOH
7: H2 / Pd/C
View Scheme
scopalamine
138-12-5

scopalamine

(1S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-8-aza-bicyclo[3.2.1]oct-6-ene
173425-93-9

(1S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-8-aza-bicyclo[3.2.1]oct-6-ene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Zn-Cu / ethanol / Heating
2: 77 percent / OH(1-)/H2O / Heating
3: 88 percent
View Scheme
scopalamine
138-12-5

scopalamine

(3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methylamino-cycloheptanone

(3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methylamino-cycloheptanone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: Zn-Cu / ethanol / Heating
2: 77 percent / OH(1-)/H2O / Heating
3: 88 percent
4: 35percent H2O2 / ethanol / 48 h
5: 15 percent / various solvent(s) / 3 h / Heating
6: 92 percent / Zn/AcOH
7: H2 / Pd/C
8: PCC
View Scheme
scopalamine
138-12-5

scopalamine

(1R,4S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-methylamino-cyclohept-2-enol

(1R,4S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-methylamino-cyclohept-2-enol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Zn-Cu / ethanol / Heating
2: 77 percent / OH(1-)/H2O / Heating
3: 88 percent
4: 35percent H2O2 / ethanol / 48 h
5: 15 percent / various solvent(s) / 3 h / Heating
6: 92 percent / Zn/AcOH
View Scheme
scopalamine
138-12-5

scopalamine

(1R*,3S*,5S*)-3α-tert-butyldimethylsiloxy-9-methyl-8-oxa-9-azabicyclo<3.2.2>non-6-ene

(1R*,3S*,5S*)-3α-tert-butyldimethylsiloxy-9-methyl-8-oxa-9-azabicyclo<3.2.2>non-6-ene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Zn-Cu / ethanol / Heating
2: 77 percent / OH(1-)/H2O / Heating
3: 88 percent
4: 35percent H2O2 / ethanol / 48 h
5: 15 percent / various solvent(s) / 3 h / Heating
View Scheme
scopalamine
138-12-5

scopalamine

(1S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-8-aza-bicyclo[3.2.1]oct-6-ene 8-oxide

(1S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-8-aza-bicyclo[3.2.1]oct-6-ene 8-oxide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Zn-Cu / ethanol / Heating
2: 77 percent / OH(1-)/H2O / Heating
3: 88 percent
4: 35percent H2O2 / ethanol / 48 h
View Scheme
N-(hepta-3,5-diyn-1-yl)-N-(penta-1,3-diyn-1-yl)methanesulfonamide

N-(hepta-3,5-diyn-1-yl)-N-(penta-1,3-diyn-1-yl)methanesulfonamide

scopalamine
138-12-5

scopalamine

C30H34N2O6S

C30H34N2O6S

C30H34N2O6S

C30H34N2O6S

Conditions
ConditionsYield
In benzene at 85℃; for 16h; Diels-Alder Cycloaddition; Sealed tube; Overall yield = 48 %; regioselective reaction;
...Expand

(-)-Scopolamine Specification

The (-)-Scopolamine, with the CAS registry number of 138-12-5, is also known as Atroscine. This chemical's molecular formula is C17H21NO4 and molecular weight is 303.35. What's more, its systematic name is (1R,2R,4S,5S)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl 3-hydroxy-2-phenylpropanoate.

Physical properties about the (-)-Scopolamine are: (1)ACD/LogP: 0.76; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.65; (4)ACD/LogD (pH 7.4): 0.05; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 12.15; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 51.3 Å2; (13)Index of Refraction: 1.613; (14)Molar Refractivity: 80.44 cm3; (15)Molar Volume: 230.9 cm3; (16)Surface Tension: 56.3 dyne/cm; (17)Density: 1.31 g/cm3; (18)Flash Point: 232.2 °C; (19)Enthalpy of Vaporization: 75.97 kJ/mol; (20)Boiling Point: 460.3 °C at 760 mmHg; (21)Vapour Pressure: 2.87E-09 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(OC1C[C@@H]2N([C@H](C1)[C@H]3O[C@@H]23)C)C(c4ccccc4)CO
(2) InChI: InChI=1/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11?,12?,13-,14+,15-,16+
(3) InChIKey: STECJAGHUSJQJN-QBMZJCKTBI

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