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(-)-Scopolamine hydrochloride

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Name

(-)-Scopolamine hydrochloride

EINECS 200-225-6
CAS No. 55-16-3 Density N/A
PSA 62.30000 LogP 1.65800
Solubility H2O: 50 mg/mL Melting Point 200°
Formula C17H21NO4.HCl Boiling Point 460.3 °C at 760 mmHg
Molecular Weight 339.819 Flash Point 232.2 °C
Transport Information UN 1544 6.1/PG 3 Appearance white powder
Safety 25-45 Risk Codes 26/27/28
Molecular Structure Molecular Structure of 55-16-3 (HYOSCINE HYDROCHLORIDE) Hazard Symbols VeryT+
Synonyms

1aH,5aH-Tropan-3a-ol, 6b,7b-epoxy-, (-)-tropate (ester), hydrochloride (8CI);Benzeneacetic acid, a-(hydroxymethyl)-, (1a,2b,4b,5a,7b)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-ylester, hydrochloride, (aS)- (9CI);Benzeneacetic acid, a-(hydroxymethyl)-, 9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-ylester, hydrochloride, [7(S)-(1a,2b,4b,5a,7b)]-;(-)-Scopolamine hydrochloride;Hyoscine hydrochloride;Scopolaminehydrochloride;

Article Data 1

(-)-Scopolamine hydrochloride Synthetic route

(2S,3S)-<1-14C,3-3H>phenylalanine

A

C16(14)CH22(3)HNO3*ClH

B

<1-14C,3-3H>hyoscyamine hydrochloride

C

<1-14C,3-3H>scopolamine hydrochloride

D

C16(14)CH20(3)HNO4*ClH

E

5934-50-9

(-)-Atropine hydrochloride

F

55-16-3

(-)-Scopolamine hydrochloride

Conditions
ConditionsYield
Mechanism; Product distribution; Datura innoxia plants; (feeding experiments to study the stereochemistry of the migration of the carboxyl group);
55-16-3

(-)-Scopolamine hydrochloride

16202-15-6

(S)-tropic acid

Conditions
ConditionsYield
Acid hydrolysis;

(-)-Scopolamine hydrochloride Specification

The CAS register number of (-)-Scopolamine hydrochloride is 55-16-3. It also can be called as Hyoscine hydrochloride and the systematic name about this chemical is (1S,2R,4S,5S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl 3-hydroxy-2-phenylpropanoate hydrochloride (1:1). The molecular formula about this chemical is C17H21NO4.HCl and the molecular weight is 339.81. Classification code about this chemical is Drug / Therapeutic Agent. This chemical is an alkaloid from solanaceae, especially datura and scopolia. Scopolamine and its quaternary derivatives act as antimuscarinics like atropine, but may have more central nervous system effects. Among the many uses, this chemical can be used as an anesthetic premedication in urinary incontinence. In motion sickness, this chemical can be used as an antispasmodic, and also it can be used as a mydriatic and cycloplegic.

Physical properties about (-)-Scopolamine hydrochloride are: (1)ACD/LogP: 0.76; (2)ACD/LogD (pH 5.5): -1.65; (3)ACD/LogD (pH 7.4): 0.05; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 12.15; (8)#H bond acceptors: 5; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 6; (11)Polar Surface Area: 51.3Å2; (12)Flash Point: 232.2 °C; (13)Enthalpy of Vaporization: 75.97 kJ/mol; (14)Boiling Point: 460.3 °C at 760 mmHg; (15)Vapour Pressure: 2.87E-09 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is very toxic by inhalation, in contact with skin and if swallowed. When you are using it, please avoid contact with eyes. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

You can still convert the following datas into molecular structure:
(1)SMILES: Cl.O=C(OC1C[C@@H]2N([C@@H](C1)[C@H]3O[C@@H]23)C)C(c4ccccc4)CO
(2)InChI: InChI=1/C17H21NO4.ClH/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;1H/t11?,12?,13-,14-,15-,16+;/m0./s1
(3)InChIKey: KXPXJGYSEPEXMF-JHCWSWNABK
(4)Std. InChI: InChI=1S/C17H21NO4.ClH/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;1H/t11?,12?,13-,14-,15-,16+;/m0./s1
(5)Std. InChIKey: KXPXJGYSEPEXMF-JHCWSWNASA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 104mg/kg (104mg/kg) AUTONOMIC NERVOUS SYSTEM: PARASYMPATHOLYTIC Archiv fuer Toxikologie. Vol. 29, Pg. 39, 1972.
mouse LD50 oral 1275mg/kg (1275mg/kg)   Schweizerische Medizinische Wochenschrift. Vol. 88, Pg. 713, 1958.

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