L-Hyoscyamine

L-Hyoscyamine Basic information
Product Name:L-Hyoscyamine
Synonyms:(-)-hyoscyamin;L-Hyoscyamine free base;[3(S)-ENDO]-8-METHYL-8-AZABICYCLO[3.2.1]OCT-3-YL ESTER, ALPHA-(HYDROXYMETHYL)-BENZENEACETIC ACID;L-Hyoscyamine (Daturine);L-HYOSCYAMINE FREE BASE CRYSTALLINE;Benzeneacetic acid, .alpha.-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo3.2.1oct-3-yl ester, (.alpha.S)-;HYOSCYAMINE,USP;L-(P)
CAS:101-31-5
MF:C17H23NO3
MW:289.37
EINECS:202-933-0
Product Categories:Inhibitors;LEVSIN;Alkaloids;Biochemistry;Tropane Alkaloids;Other APIs
Mol File:101-31-5.mol
L-Hyoscyamine Structure
L-Hyoscyamine Chemical Properties
Melting point 108,5°C
alpha D20 -21.0° (alc)
Boiling point 431.53°C (rough estimate)
density 1.0470 (rough estimate)
refractive index 1.5200 (estimate)
storage temp. 2-8°C
solubility DMSO:79.0(Max Conc. mg/mL);273.0(Max Conc. mM)
Ethanol:58.0(Max Conc. mg/mL);200.43(Max Conc. mM)
pkapKa (21°) 9.7
form powder
color white
Water Solubility 3.6g/L(20 ºC)
Merck 14,4858
InChIKeyRKUNBYITZUJHSG-FXUDXRNXSA-N
LogP1.380 (est)
CAS DataBase Reference101-31-5(CAS DataBase Reference)
NIST Chemistry ReferenceHyoscyamine(101-31-5)
EPA Substance Registry SystemBenzeneacetic acid, .alpha.-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (.alpha.S)- (101-31-5)
Safety Information
Hazard Codes T+
Risk Statements 26/28
Safety Statements 24-45
RIDADR UN 1544 6.1/PG 2
WGK Germany 3
RTECS NH0875000
HazardClass 6.1
PackingGroup I
HS Code 29339900
Hazardous Substances Data101-31-5(Hazardous Substances Data)
Toxicityman,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.
MSDS Information
ProviderLanguage
SigmaAldrich English
L-Hyoscyamine Usage And Synthesis
Chemical PropertiesWhite to Off-White Solid
UsesL-Hyoscyamine is a natural compound that has inhibitory activity against cholinesterases.
UsesL-Hyoscyamine can be used as anticholinergic and analgesic.
UsesSuggested starting dilutions are as follows: IHC-P: 1:100-1:1000, WB: 1:1000-1:10000. Not yet tested in other applications. Optimal working dilutions should be determined experimentally by the end user.
DefinitionChEBI: An atropine with a 2S-configuration.
General DescriptionHyoscyamine is a levorotatory alkaloidobtained from various solanaceous species. One ofthe commercial sources is Egyptian henbane (Hyoscyamusmuticus), in which it occurs to the extent of about 0.5%.Usually, it is prepared from the crude drug in a manner similarto that used for atropine and is purified as the oxalate.The free base is obtained easily from this salt.
It occurs as white needles that are sparingly soluble inwater (1:281), more soluble in ether (1:69) or benzene(1:150), very soluble in chloroform (1:1), and freely solublein alcohol. It is used as the sulfate and hydrobromide. Theprincipal reason for the popularity of the hydrobromide hasbeen its nondeliquescent nature. The salts have the advantageover the free base in being quite water soluble.
Biochem/physiol ActionsThe 21st amino acid, selenocysteine (sec), is distinct from other amino acids because it lacks its own tRNA synthetase and is the only amino acid synthesized on its cognate tRNA. Synthesis of sec begins with acylation of tRNA(sec) (TRSP; MIM 165060) by seryl-tRNA synthetase (SARS; MIM 607529) to give ser-tRNA(sec), which is subsequently phosphorylated by O-phosphoseryl-tRNA kinase (PSTK; MIM 611310) to give O-phosphoseryl-tRNA(sec). SEPSECS catalyzes the final step of sec synthesis by converting O-phosphoseryl-tRNA(sec) to selenocysteinyl-tRNA(sec) using selenophosphate as the selenium donor (Palioura et al., 2009 [PubMed 19608919]).[supplied by OMIM]
Clinical Use(L-Hyoscyamine)Hyoscyamine is used to treat disorders of the urinarytract more so than any other antispasmodic, although thereis no evidence that it has any advantages over the otherbelladonna preparations and the synthetic anticholinergics.It is used to treat spasms of the bladder and, in this manner,serves as a urinary stimulant. It is used together witha narcotic to counteract the spasm produced by the narcoticwhen the latter is used to relieve the pain of urethral colic.Hyoscyamine preparations are also used as antispasmodicsin the therapy of peptic ulcers.
targetAChR
L-Hyoscyamine Preparation Products And Raw materials
Preparation ProductsAtropine sulfate monohydrate
Methyl L(+)-Lactic acid 3-(4-Hydroxyphenyl)propionic acid Atropine HYOSCYAMINE N-OXIDE HYDROCHLORIDE Tribenuron methyl Kresoxim-methyl Atropine sulfate monohydrate Atropine sulfate Methyl salicylate Scopolamine butylbromide Methyl acetate Methyl bromide METSULFURON METHYL HYOSCYAMINE HYDROCHLORIDE ANISODAMINE HYOSCINE HYDROCHLORIDE Racanisodamine

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