Record Information |
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Version | 2.0 |
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Creation Date | 2009-07-21 20:28:47 UTC |
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Update Date | 2014-12-24 20:25:56 UTC |
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Accession Number | T3D3040 |
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Identification |
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Common Name | Ephedrine |
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Class | Small Molecule |
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Description | Ephedrine is only found in individuals who have consumed this drug. Ephedrine is an alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used in the treatment of several disorders including asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists. [PubChem] Ephedrine is similar in molecular structure to the well-known drugs phenylpropanolamine and methamphetamine, as well as to the important neurotransmitter epinephrine (adrenalin). Chemically, it is an alkaloid with a phenethylamine skeleton found in various plants in the genus Ephedra (family Ephedraceae). It works mainly by increasing the activity of norepinephrine (noradrenalin) on adrenergic receptors. It is most usually marketed as the hydrochloride or sulfate salt. |
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Compound Type | - Adrenergic Agent
- Amine
- Central Nervous System Stimulant
- Drug
- Metabolite
- Organic Compound
- Sympathomimetic
- Synthetic Compound
- Vasoconstrictor Agent
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Chemical Structure | |
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Synonyms | Synonym | (-)-Ephedrine | (1R,2S)-1-Phenyl-1-hydroxy-2-methylaminopropane | L(-)-Ephedrine | L-Ephedrine | L-erythro-2-(Methylamino)-1-phenylpropan-1-ol |
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Chemical Formula | C10H15NO |
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Average Molecular Mass | 165.232 g/mol |
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Monoisotopic Mass | 165.115 g/mol |
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CAS Registry Number | 299-42-3 |
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IUPAC Name | (1R,2S)-2-(methylamino)-1-phenylpropan-1-ol |
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Traditional Name | ephedrine |
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SMILES | [H][C@@](C)(NC)[C@]([H])(O)C1=CC=CC=C1 |
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InChI Identifier | InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1 |
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InChI Key | InChIKey=KWGRBVOPPLSCSI-WPRPVWTQSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Phenylpropanes |
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Direct Parent | Phenylpropanes |
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Alternative Parents | |
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Substituents | - Phenylpropane
- Aralkylamine
- 1,2-aminoalcohol
- Secondary alcohol
- Secondary aliphatic amine
- Secondary amine
- Alcohol
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Amine
- Aromatic alcohol
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | |
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Biological Roles | |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 34°C | Boiling Point | 255°C | Solubility | 6.36E+004 mg/L (at 30°C) | LogP | 1.13 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-9300000000-5bdf33e08e94f0c0bd26 | 2017-09-01 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-05di-9610000000-8f364065f58e7dd69444 | 2017-10-06 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0002-0900000000-33d551e262321705ae8a | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-014j-0900000000-32a84e7b7e5332fe2026 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0002-0900000000-82640acc94773485568a | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0002-0900000000-bdfb6079227a418eb706 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0002-0900000000-c04df5fb623578be67ea | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-00l2-1900000000-3a68bc210684b52a9fd8 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0159-2900000000-e12bf9df640426404f1c | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-014j-0900000000-0218a677989aab76b176 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0002-0900000000-3dd538034653edb47df1 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0002-0900000000-553c930e0970a8c1a866 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0002-0900000000-0499cdf7955d013fca29 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-015a-1900000000-f6b6229ef8c2d7fd24ab | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0159-2900000000-7c8549f8cd727886d67d | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0002-0900000000-bcbf5073df33d11415cc | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 60V, Positive | splash10-0002-0900000000-8df1676350e720b21d8c | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 75V, Positive | splash10-015a-1900000000-8d8e8c6689866070b7de | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 90V, Positive | splash10-0159-2900000000-573a202622c26aee5f4e | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0002-0900000000-a2c5df7e718fb237fcb4 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0002-0900000000-33d551e262321705ae8a | 2021-09-20 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kb-0900000000-677d622716b4c2545f16 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00kb-2900000000-416def0e527ddf116a39 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0aou-9500000000-155625a572f19610e138 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-ea7e1b550b5dc0d6d41d | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03dj-2900000000-f4de25860574bb60daf1 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a6r-9600000000-62e375458e5f83795e90 | 2016-08-03 | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0a4i-9000000000-bcc578719d003732d7f8 | 2014-09-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Oral ; parenteral (intramuscular or intravenous injection). 85%. |
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Mechanism of Toxicity | Ephedrine is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen. |
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Metabolism |
Route of Elimination: mainly renal
Half Life: 3-6 hours |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | Ephedrine commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia. |
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Minimum Risk Level | Not Available |
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Health Effects | Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides. |
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Symptoms | Side-effects can include sweating, dry mouth, blurred vision, insomnia, loss of appetite, and dizziness. In addition users can feel restless, anxious and moody, become excitable and have a false sense of power and security. Amphetamine overdose can also cause cardiac arrhythmias, headaches, convulsions, hypertension, rapid heart rate, coma and death. Amphetamines are psychologically and physically addictive. |
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Treatment | If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally. |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB01364 |
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HMDB ID | HMDB15451 |
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PubChem Compound ID | 9294 |
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ChEMBL ID | CHEMBL211456 |
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ChemSpider ID | 8935 |
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KEGG ID | C01575 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 15407 |
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BioCyc ID | --EPHEDRINE |
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CTD ID | Not Available |
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Stitch ID | Ephedrine |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Ephedrine |
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References |
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Synthesis Reference | Thomas Moest, Uwe Loeffler, Hans Waiblinger, “Production of pellets composed of an ephedrine derivative.” U.S. Patent US5453280, issued March, 1994. |
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MSDS | T3D3040.pdf |
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General References | - Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [18048412 ]
- RxList: The Internet Drug Index (2009). [Link]
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Gene Regulation |
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Up-Regulated Genes | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
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Down-Regulated Genes | Not Available |
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