((1S,5R)-8-Methyl-8-Azabicyclo(3.2.1)Octan-3-Yl) (2R)-3-Hydroxy-2-Phenylpropanoate
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Basic information
- CAS
13269-35-7- Standard SMILES
CN1[C@@H]2CC[C@H]1CC(OC(=O)[C@@H](CO)c1ccccc1)C2- InChIKey
RKUNBYITZUJHSG-JJXSEGSLSA-N- Molecular formula
- C17H23NO3
- Average molar mass
- 289.4 g/mol
- Monoisotopic mass
- 289.1677936
Overview
(R)-atropine is an atropine with a 2R-configuration. It is functionally related to a (R)-tropic acid.
Names & identifiers
- Preferred name
- ((1S,5R)-8-Methyl-8-Azabicyclo(3.2.1)Octan-3-Yl) (2R)-3-Hydroxy-2-Phenylpropanoate
- IUPAC
- [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2R)-3-hydroxy-2-phenylpropanoate
- English name
- R-(+)-Hyoscyamine
- Molecular formula
- C17H23NO3
- Molecular weight
- 289.38
Names & synonyms
RefChem:1048825((1S,5R)-8-Methyl-8-Azabicyclo(3.2.1)Octan-3-Yl) (2R)-3-Hydroxy-2-Phenylpropanoated-hyoscyamine(+)-HYOSCYAMINE13269-35-7(+)-Atropine(R)-atropineR-(+)-HyoscyamineHyoscyamine, (+)-CHEMBL3084476V3203SI72Mhyoscyamine
Show more names
d-AtropineAtropine Impurity 42[(1α,5α)-8-Methyl-8-azabicyclo[3.2.1]octan-3β-yl]=(R)-α-(hydroxymethyl)phenylacetate(1R,5S)-8-Methyl-8-azabicyclo[3.2.1]octane-3α-ol (R)-α-(hydroxymethyl)benzeneacetateBenzeneacetic acid, α-(hydroxymethyl)-, 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, [3(R)-endo]-Benzeneacetic acid, α-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (αR)-
[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2R)-3-hydroxy-2-phenylpropanoatetropan-3alpha-yl (2R)-3-hydroxy-2-phenylpropanoate(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl (2R)-3-hydroxy-2-phenylpropanoateAtropine sulfateAtropine CRSHyoscyamine (D)-Atropine Impurity 27HYOSCYAMINE, D-
Properties
Computed structural propertiesFilling in
- XLogP
- 1.8
- Topological polar surface area
- 49.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 353
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Hallucinogens
Pharmaceuticals -> Listed in ZINC15
Color/FormNEEDLES FROM DIL ALCOHOL
SolubilitySLIGHTLY SOL IN WATER; VERY SOL IN ALCOHOL, ETHER, BENZENE, CHLOROFORM
Melting Point106 °C
Optical RotationSPECIFIC OPTICAL ROTATION (C= 4): +31.3 DEG/D
Physicochemical properties
- Melting point
- 106 °C · 106 °C
- Boiling point
- 429.8 · 429.8±45.0 °C(Predicted)
- Density
- 1.19 · 1.19±0.1 g/cm3(Predicted)
- pka
- 14.12 · 14.12±0.10(Predicted)
- FDA UNII
- 3203 SI72M · V3203SI72M
- Hazardous Substances Data
- 13269 · 13269-35-7(Hazardous Substances Data)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
InteractionsLOW CONCN OF (+)-HYOSCYAMINE, ACCELERATED THE ENZYMIC HYDROLYSIS OF TROPACOCAINE, WHEREAS HIGHER CONCN ABOVE 10-4 TO 10-3 MOLE/L OF THESE ALKALOIDS INHIBITED THE HYDROLYSIS. HYDROLYSIS OF NORTROPACOCAINE WAS INHIBITED AT ALL CONCN.
Health EffectsHyoscyamine affects the central nervous system. (L1255)
Exposure RoutesOral (ingestion) (L1817) ; dermal (L1817)
Toxicity SummaryHyoscyamine is an anticholinergic, specifically an antimuscarinic, and works by blocking the action of acetylcholine at parasympathetic sites in smooth muscle, secretory glands, and the central nervous system. (L1255)
Signs and Symptoms
Side effects of hyoscyamine include dry mouth and throat, eye pain, blurred vision, restlessness, dizziness, arrythmia, flushing, and faintness. An overdose will cause headache, nausea, vomiting, and central nervous system symptoms including disorientation, hallucinations, euphoria, sexual arousal, short-term memory loss, and possible coma in extreme cases. (L1255)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity Excerpts
AT THERAPEUTIC DOSAGES, THE ISOMERS DIFFER MARKEDLY IN POTENCY, BOTH PERIPHERALLY & CENTRALLY. AT TOXIC DOSES, THE ISOMERS ARE EQUALLY POTENT. IN MICE, THE LD50 IS 81 MG/KG FOR (+)-HYOSCYAMINE & 95 MG/KG FOR (-)-HYOSCYAMINE. THE ED50 (CONVULSIONS) IS THE SAME, 54 MG/KG, FOR BOTH ISOMERS IN THE MOUSE.
Safety data
- Hazardous Substances Data
Chemistry & industry
Uses & manufacturing
Uses
Hyoscyamine is a plant toxin found in certain plants of the Solanaceae family, including henbane (Hyoscyamus niger), mandrake (Mandragora officinarum), jimsonweed (Datura stramonium), and deadly nightshade (Atropa belladonna). It is used as a drug to provide symptomatic relief to various gastrointestinal disorders including spasms, peptic ulcers, irritable bowel syndrome, pancreatitis, colic and cystitis. It has also been used to relieve some heart problems, control some of the symptoms of Parkinson's disease, as well as for control of respiratory secretions in palliative care.(L1255)
General Manufacturing Information
THE DEXTRO & LEVO ISOMERS DIFFER MARKEDLY IN POTENCY AT THERAPEUTIC CONCENTRATIONS, BOTH CENTRALLY & PERIPHERALLY. BOTH ISOMERS APPEAR TO HAVE EQUAL POTENCY AT TOXIC CONCENTRATIONS, HOWEVER.
LIVER HOMOGENATES OF RABBITS CONTAINING HYOSCYAMINE ACYLHYDROLASE HYDROLYZED HYOSCYAMINE TO TROPINE AND (-)-TROPIC ACID BUT DID NOT CLEAVE (+)-HYOSCYAMINE. BECAUSE OF THE STEREOSPECIFICITY OF THIS ENZYME, THE HYOSCYAMINE COMPONENT OF (+)-HYOSCYAMINE PREPN OBTAINED CHEMICALLY COULD BE DETECTED AND THE DEXTROROTATORY OPTICAL ANTIPODE COULD BE PREPARED IN THE PURE FORM.
Applications
UsesD-Hyoscyamine is similar to L-Hyoscyamine (H674300), a natural compound that has inhibitory activity against cholinesterases. D-Hyoscyamine can be synthesized from Atropine (A794630).
Additional notes
DefinitionChEBI: An atropine with a 2R-configuration.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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