Scopolamine
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Basic Info
| Common Name | Scopolamine(F04767) |
| 2D Structure | |
| Description | Scopolamine, also known as hyoscine, is a tropane alkaloid drug obtained from plants of the family Solanaceae (nightshades), such as henbane or jimson weed (Datura species). It is part of the secondary metabolites of plants. Scopolamine is used criminally as a date rape drug and as an aid to robbery, the most common act being the clandestine drugging of a victim's drink. It is preferred because it induces retrograde amnesia, or an inability to recall events prior to its administration. Victims of this crime are often admitted to a hospital in police custody, under the assumption that the patient is experiencing a psychotic episode. A telltale sign is a fever accompanied by a lack of sweat. An alkaloid from Solanaceae, especially Datura metel L. and Scopola carniolica. Scopolamine and its quaternary derivatives act as antimuscarinics like atropine, but may have more central nervous system effects. Among the many uses are as an anesthetic premedication, in urinary incontinence, in motion sickness, as an antispasmodic, and as a mydriatic and cycloplegic. |
| FRCD ID | F04767 |
| CAS Number | 51-34-3 |
| PubChem CID | 5184 |
| Formula | C17H21NO4 |
| IUPAC Name | None |
| InChI Key | STECJAGHUSJQJN-UHFFFAOYSA-N |
| InChI | InChI=1S/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 |
| Canonical SMILES | CN1C2CC(CC1C3C2O3)OC(=O)C(CO)C4=CC=CC=C4 |
| Isomeric SMILES | CN1C2CC(CC1C3C2O3)OC(=O)C(CO)C4=CC=CC=C4 |
| Wikipedia | Scopolamine |
| Synonyms |
l-Scopolamine
scopolamine
Hyosol
51-34-3
Skopolamin
Oscine
(-)-Scopolamine
Transcop
CHEMBL13030
Scopoderm-TTS
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Hydroxy acids and derivatives |
| Subclass | Beta hydroxy acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Beta hydroxy acids and derivatives |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Beta-hydroxy acid - Monocyclic benzene moiety - Morpholine - Oxazinane - Piperidine - N-alkylpyrrolidine - Benzenoid - Pyrrolidine - Amino acid or derivatives - Carboxylic acid ester - Tertiary amine - Tertiary aliphatic amine - Oxacycle - Organoheterocyclic compound - Azacycle - Carboxylic acid derivative - Dialkyl ether - Oxirane - Ether - Monocarboxylic acid or derivatives - Primary alcohol - Organopnictogen compound - Organonitrogen compound - Organooxygen compound - Amine - Organic oxide - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Alcohol - Hydrocarbon derivative - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 303.358 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 5 |
| Complexity | 418 |
| Monoisotopic Mass | 303.147 |
| Exact Mass | 303.147 |
| XLogP | 0.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 22 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 5 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8218 |
| Human Intestinal Absorption | HIA+ | 0.9615 |
| Caco-2 Permeability | Caco2+ | 0.8867 |
| P-glycoprotein Substrate | Non-substrate | 0.5174 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8700 |
| Non-inhibitor | 0.8623 | |
| Renal Organic Cation Transporter | Inhibitor | 0.5310 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5921 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7002 |
| CYP450 2D6 Substrate | Non-substrate | 0.7296 |
| CYP450 3A4 Substrate | Substrate | 0.5253 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9045 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9070 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9270 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9025 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8310 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8682 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9378 |
| Non-inhibitor | 0.9167 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.9581 |
| Fish Toxicity | High FHMT | 0.9317 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8790 |
| Honey Bee Toxicity | High HBT | 0.5122 |
| Biodegradation | Not ready biodegradable | 0.9073 |
| Acute Oral Toxicity | III | 0.7702 |
| Carcinogenicity (Three-class) | Non-required | 0.6988 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.5427 | LogS |
| Caco-2 Permeability | 0.9469 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0907 | LD50, mol/kg |
| Fish Toxicity | 0.6555 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4897 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Simultaneous quantification of atropine and scopolamine in infusions of herbal tea and Solanaceae plant material by matrix-assisted laser desorption/ionization time-of-flight (tandem) mass spectrometry. | Rapid Commun Mass Spectrom | 2018 Nov 30 | 30117208 |
| Monitoring the degradation of atropine and scopolamine in soil after spiking with naturally contaminated organic millet. | Sci Total Environ | 2018 Jun 1 | 29996405 |
| Atropa belladonna neurotoxicity: Implications to neurological disorders. | Food Chem Toxicol | 2018 Jun | 29653183 |
| "Bunanje": XX Century Abuse of Atropa Belladonna Halucinogenic Berries in Continental Croatia. | Psychiatr Danub | 2017 Sep | 28949320 |
| Assessment of environmental and health risks in former polymetallic ore miningand smelting area, Slovakia: Spatial distribution and accumulation of mercury in four different ecosystems. | Ecotoxicol Environ Saf | 2017 Oct | 28633101 |
| The protective effect of fermented Curcuma longa L. on memory dysfunction in oxidative stress-induced C6 gliomal cells, proinflammatory-activated BV2 microglial cells, and scopolamine-induced amnesia model in mice. | BMC Complement Altern Med | 2017 Jul 17 | 28716085 |
| Isolation of atropine and scopolamine from plant material using liquid-liquid extraction and EXtrelut<sup>®</sup> columns. | J Chromatogr B Analyt Technol Biomed Life Sci | 2017 Feb 1 | 27616063 |
| Effect of petroleum-derived substances on life history traits of black bean aphid(Aphis fabae Scop.) and on the growth and chemical composition of broad bean. | Ecotoxicology | 2017 Apr | 28144803 |
| Poisoned after Dinner: Dolma with Datura Stramonium. | Turk J Emerg Med | 2015 Mar | 27437523 |
| Developmental toxicity assessment of the new turf herbicide, methiozolin([5-(2,6-difluorobenzyl)oxymethyl-5-methyl-3,3(3-methylthiophen-2-yl)-1,2-isoxazoline]), in rabbits. | Regul Toxicol Pharmacol | 2015 Aug | 26003517 |
| A case of pediatric age anticholinergic intoxication due to accidental Datura stramonium ingestion admitting with visual hallucination. | Turk J Pediatr | 2014 May-Jun | 25341608 |
| Intra- and inter-laboratory validation of a dipstick immunoassay for the detection of tropane alkaloids hyoscyamine and scopolamine in animal feed. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2014 | 24823431 |
| Determination of antimicrobial effect, antioxidant activity and phenolic contentsof desert truffle in Turkey. | Afr J Tradit Complement Altern Med | 2013 May 16 | 24146501 |
| Colonization of the biomass energy crop miscanthus by the three aphid species,Aphis fabae, Myzus persicae, and Rhopalosiphum padi. | J Econ Entomol | 2013 Apr | 23786055 |
| Risk assessment of buckwheat flour contaminated by thorn-apple (Datura stramonium L.) alkaloids: a case study from Slovenia. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2013 | 23244511 |
| Fermentation kinetics of sainfoin hay with and without PEG. | J Anim Physiol Anim Nutr (Berl) | 2012 Oct | 22168179 |
| Accidental poisoning after ingestion of "aphrodisiac" berries: diagnosis by analytical toxicology. | J Emerg Med | 2012 Jun | 21571482 |
| Mass intoxication with Datura innoxia--case series and confirmation by analytical toxicology. | Clin Toxicol (Phila) | 2010 Feb | 20136480 |
| [Datura intoxication--report of three cases]. | Przegl Lek | 2010 | 20684356 |
| Urinary excretion of dietary contaminants in horses. | Equine Vet J Suppl | 2006 Aug | 17402502 |
Targets
- General Function:
- Phosphatidylinositol phospholipase c activity
- Specific Function:
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
- Gene Name:
- CHRM5
- Uniprot ID:
- P08912
- Molecular Weight:
- 60073.205 Da
References
- Reitz AB, Gupta SK, Huang Y, Parker MH, Ryan RR: The preparation and human muscarinic receptor profiling of oxybutynin and N-desethyloxybutynin enantiomers. Med Chem. 2007 Nov;3(6):543-5. [18045203 ]
- General Function:
- Sucrose alpha-glucosidase activity
- Specific Function:
- Plays an important role in the final stage of carbohydrate digestion. Isomaltase activity is specific for both alpha-1,4- and alpha-1,6-oligosaccharides.
- Gene Name:
- SI
- Uniprot ID:
- P14410
- Molecular Weight:
- 209451.49 Da
References
- Minai-Tehrani D, Fooladi N, Minoui S, Sobhani-Damavandifar Z, Aavani T, Heydarzadeh S, Attar F, Ghaffari M, Nazem H: Structural changes and inhibition of sucrase after binding of scopolamine. Eur J Pharmacol. 2010 Jun 10;635(1-3):23-6. doi: 10.1016/j.ejphar.2010.02.040. Epub 2010 Mar 15. [20230815 ]
- General Function:
- Phosphatidylinositol phospholipase c activity
- Specific Function:
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
- Gene Name:
- CHRM1
- Uniprot ID:
- P11229
- Molecular Weight:
- 51420.375 Da
- Mechanism of Action:
- Scopolamine acts by interfering with the transmission of nerve impulses by acetylcholine in the parasympathetic nervous system (specifically the vomiting center).
References
- Murasaki O, Kaibara M, Nagase Y, Mitarai S, Doi Y, Sumikawa K, Taniyama K: Site of action of the general anesthetic propofol in muscarinic M1 receptor-mediated signal transduction. J Pharmacol Exp Ther. 2003 Dec;307(3):995-1000. Epub 2003 Oct 8. [14534362 ]
- General Function:
- Receptor activity
- Specific Function:
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
- Gene Name:
- CHRM3
- Uniprot ID:
- P20309
- Molecular Weight:
- 66127.445 Da
References
- Reitz AB, Gupta SK, Huang Y, Parker MH, Ryan RR: The preparation and human muscarinic receptor profiling of oxybutynin and N-desethyloxybutynin enantiomers. Med Chem. 2007 Nov;3(6):543-5. [18045203 ]
- General Function:
- Guanyl-nucleotide exchange factor activity
- Specific Function:
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase.
- Gene Name:
- CHRM4
- Uniprot ID:
- P08173
- Molecular Weight:
- 53048.65 Da
References
- Reitz AB, Gupta SK, Huang Y, Parker MH, Ryan RR: The preparation and human muscarinic receptor profiling of oxybutynin and N-desethyloxybutynin enantiomers. Med Chem. 2007 Nov;3(6):543-5. [18045203 ]
- General Function:
- G-protein coupled acetylcholine receptor activity
- Specific Function:
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then triggers calcium ion release into the cytosol.
- Gene Name:
- CHRM2
- Uniprot ID:
- P08172
- Molecular Weight:
- 51714.605 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]