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L-Hyoscyamine

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Name

L-Hyoscyamine

EINECS 202-933-0
CAS No. 101-31-5 Density 1.194 g/cm3
PSA 49.77000 LogP 1.86880
Solubility Easily soluble in ethanol and dilute acids; soluble in chloroform; can soluble in water, ether and benzene Melting Point 108.5 °C
Formula C17H23NO3 Boiling Point 429.804 °C at 760 mmHg
Molecular Weight 289.375 Flash Point 213.738 °C
Transport Information UN 1544 6.1/PG 2 Appearance White powder
Safety 24-45 Risk Codes 26/28
Molecular Structure Molecular Structure of 101-31-5 (L-Hyoscyamine) Hazard Symbols VeryT+
Synonyms

1aH,5aH-Tropan-3a-ol, (-)-tropate (ester) (8CI);Benzeneacetic acid, a-(hydroxymethyl)-,8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, [3(S)-endo]-;Tropic acid, 1aH,5aH-tropan-3a-yl ester, (-)- (8CI);(-)-Atropine;(-)-Hyoscyamine;(S)-(-)-Hyoscyamine;(S)-Atropine;1aH,5aH-Tropan-3a-yl (-)-tropate;Cystospaz;Daturine;Duboisine;(8-Methyl-8-azabicyclo[3.2.1]octan-3-yl) (2S)-3-hydroxy-2-phenylpropanoate;

Article Data 15

L-Hyoscyamine Synthetic route

114-49-8

hyoscine hydrobromide

A

55869-99-3

(3S,6S,2'S)-6β-hydroxyhyoscyamine

B

126371-43-5

(3R,6R,2'S)-6β-hydroxyhyoscyamine

C

101-31-5

Hyoscyamine

Conditions
ConditionsYield
With hydrogen; Nickel Raney W1A 41.7%
B 33.9%
C 19.7%
16202-15-6

(S)-tropic acid

120-29-6

3-tropanol

101-31-5

Hyoscyamine

Conditions
ConditionsYield
With hydrogenchloride und Darstellung;
3144-16-9

(1S)-10-camphorsulfonic acid

51-55-8

atropine

101-31-5

Hyoscyamine

Conditions
ConditionsYield
Man unterwirft das entstehende Salz einer fraktionierten Krystallisation aus alkoholhaltigem Essigester;
51-55-8

atropine

A

13269-35-7

(+)-Atropine

B

101-31-5

Hyoscyamine

Conditions
ConditionsYield
resolving agent: trans-cellulose tris(4-phenylazophenylcarbamate) ( CPAPC ) adsorbed on silica gel; optical resolution degree examined by HPLC on cis/trans-CPAPC;
Conditions
ConditionsYield
With hydrogen; nickel In water at 20℃; for 19h;A 150 mg
B 150 mg
C 290 mg

(-)-Littorine

101-31-5

Hyoscyamine

Conditions
ConditionsYield
With sodium (RS)-phenyl<2-(18)O,2-(2)H>acetate; Datura stramonium root cultures for 264h; Mechanism; different reaction times;
74-88-4

methyl iodide

nor-l-hyoscyamine

nor-l-hyoscyamine

101-31-5

Hyoscyamine

Conditions
ConditionsYield
With methanol
Conditions
ConditionsYield
With triethylamine In aq. phosphate buffer; acetonitrile at 10℃; pH=7.0; Thermodynamic data; pH-value; Reagent/catalyst; Solvent; Temperature; Resolution of racemate;
51-55-8

Atropine

A

13269-35-7

(+)-Atropine

B

101-31-5

Hyoscyamine

Conditions
ConditionsYield
With β‑cyclodextrin sulfonic acid In aq. phosphate buffer at 25℃; pH=3; pH-value; Reagent/catalyst; Resolution of racemate;
64-17-5

ethanol

101-31-5

Hyoscyamine

51-55-8

atropine

Conditions
ConditionsYield
bei langem Aufbewahren;
in Gegenwart von Natriumhydroxyd oder anderen Basen;

L-Hyoscyamine Consensus Reports

Reported in EPA TSCA Inventory.

L-Hyoscyamine Specification

The L-Hyoscyamine, with the CAS registry number 101-31-5, is also known as (8-Methyl-8-azabicyclo[3.2.1]octan-3-yl) (2S)-3-hydroxy-2-phenylpropanoate. It belongs to the product categories of Alkaloids; Biochemistry; Tropane Alkaloids. Its EINECS number is 202-933-0. This chemical's molecular formula is C17H23NO3 and molecular weight is 289.37. What's more, its systematic name is (3-endo)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl (2S)-3-hydroxy-2-phenylpropanoate. Its classification codes are: (1)Anticholinergic; (2)Human Data; (3)Natural Product. This chemical is an anticholinergic, specifically an antimuscarinic, working by blocking the action of acetylcholine at parasympathetic sites in smooth muscle, secretory glands and the CNS. It is used to provide symptomatic relief to various gastrointestinal disorders. It is also used in biochemical research. This chemical is extracted and refined from Belladonna extracts.

Physical properties of L-Hyoscyamine are: (1)ACD/LogP: 1.38; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.70; (4)ACD/LogD (pH 7.4): -1.09; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 49.77 Å2; (13)Index of Refraction: 1.581; (14)Molar Refractivity: 80.788 cm3; (15)Molar Volume: 242.421 cm3; (16)Polarizability: 32.027×10-24cm3; (17)Surface Tension: 50.46 dyne/cm; (18)Density: 1.194 g/cm3; (19)Flash Point: 213.738 °C; (20)Enthalpy of Vaporization: 72.224 kJ/mol; (21)Boiling Point: 429.804 °C at 760 mmHg; (22)Vapour Pressure: 0 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 and if swallowed. When using it, you must avoid contact with skin. In case of accident or if you feel unwell, you should seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: CN3[C@H]1CC[C@@H]3C[C@@H](C1)OC(=O)[C@H](CO)c2ccccc2
(2)Std. InChI: InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1
(3)Std. InChIKey: RKUNBYITZUJHSG-FXUDXRNXSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man LDLo unreported 1471ug/kg (1.471mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LD50 intravenous 95mg/kg (95mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
British Journal of Pharmacology and Chemotherapy. Vol. 24, Pg. 138, 1965.

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