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Showing toxin card for Ephedrine (T3D3040)

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Version 1.0
Creation Date 2009-07-21 20:28:47
Update Date 2010-05-18 21:01:50
Accession Number T3D3040
Name Ephedrine
Compound Type
  • Adrenergic Agent
  • Central Nervous System Stimulant
  • Drug
  • Sympathomimetic
  • Vasoconstrictor Agent
Description 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]
Synonyms
  1. (-)-(1R,2S)-Ephedrine
  2. (-)-a-(1-Methylaminoethyl)benzyl alcohol
  3. (-)-alpha-(1-Methylaminoethyl)benzyl alcohol
  4. (-)-ephedrine
  5. (-)-ephedrine hemisulfate
  6. (-)-erythro-ephedrine
  7. (1R,2S)-(-)-2-Methylamino-1-phenyl-1-propanol
  8. (1R,2S)-(-)-Ephedrine
  9. (1R,2S)-(-)-alpha-(1-Methylaminoethyl)benzenemethanol
  10. (1R,2S)-(-)-alpha-(1-Methylaminoethyl)benzyl alcohol
  11. (1R,2S)-1-phenyl-1-hydroxy-2-methylaminopropane
  12. (1R,2S)-2-(methylamino)-1-phenylpropan-1-ol
  13. (1R,2S)-2-Methylamino-1-phenyl-1-propanol
  14. (1R,2S)-2-methylamino-1-phenylpropan-1-ol
  15. (l)-ephedrine
  16. 1(R),2(S)-erythro-(-)-Ephedrine
  17. 1-2-Methylamino-1-phenylpropanol
  18. 1-Hydroxy-2-methylamino-1-phenylpropane
  19. 1-Phenyl-1-hydroxy-2-methylaminopropane
  20. 1-Phenyl-2-methylaminopropanol
  21. 1-Sedrin
  22. 1-alpha-(1-Methylaminoethyl)benzyl alcohol
  23. 2-(Methylamino)-1-phenyl-1-propanol
  24. 2-Methylamino-1-phenyl-1-propanol
  25. Abundance Ephedrine Hydrochloride
  26. Alpha-hydroxy-beta-methyl amine propylbenzene
  27. Alpha-hydroxy-beta-methylaminopropylbenzene
  28. Biophedrin
  29. Eciphin
  30. Efedrin
  31. Ephedra
  32. Ephedral
  33. Ephedrate
  34. Ephedremal
  35. Ephedrin
  36. Ephedrine (TN)
  37. Ephedrine (usp)
  38. Ephedrine 8mg
  39. Ephedrine HCL
  40. Ephedrine Hydrochloride Tablets
  41. Ephedrine III
  42. Ephedrine [(-)-ephedrine]
  43. Ephedrine [usan:ban]
  44. Ephedrine hydrochloride
  45. Ephedrine l form
  46. Ephedrine sulfate injection
  47. Ephedrine sulfate injection usp
  48. Ephedrital
  49. Ephedrol
  50. Ephedrosan
  51. Ephedrotal
  52. Ephedsol
  53. Ephendronal
  54. Ephoxamin
  55. Fedrin
  56. I-sedrin
  57. Isoephedrine
  58. Isofedrol
  59. Kratedyn
  60. L(-)-ephedrine
  61. L-(-)-ephedrine
  62. L-ephedrine
  63. Lexofedrin
  64. Manadrin
  65. Mandrin
  66. Nasol
  67. Pseudoephedrine
  68. Sanedrine
  69. Vencipon
  70. Zephrol
  71. a-Hydroxy-a-(1-Methylaminoethyl)benzyl alcohol
  72. a-hydroxy-b-methyl amino propylbenzene
  73. alpha-(1-(Methylamino)ethyl)benzenemethanol
  74. l-2-Methylamino-1-phenylpropanol
  75. l-Erythro-2-(methylamino)-1-phenylpropan-1-ol
  76. l-a-(1-Methylaminoethyl)benzyl alcohol
  77. l-a-[1-(Methylamino)ethyl]benzenemethanol
  78. l-alpha-(1-Methylaminoethyl)benzyl alcohol
Chemical IUPAC Name 2-(methylamino)-1-phenylpropan-1-ol
Chemical Formula C10H15NO
Chemical Structure Structure
CAS Registry Number 299-42-3
InChI Identifier InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3
InChI Key InChIKey=KWGRBVOPPLSCSI-UHFFFAOYSA-N
PubChem Compound ID 9294 Link Image
KEGG ID C01575 Link Image
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID 15407 Link Image
BioCyc ID --EPHEDRINE Link Image
SuperToxic ID Not Available
CTD ID Not Available
Stitch ID Ephedrine Link Image
DrugBank ID DB01364 Link Image
PDB ID Not Available
ACToR ID Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Ephedrine Link Image
Monoisotopic Mass 165.115364
MOL File Show
PDB File Show
SDF File Show
SMILES CNC(C)C(O)C1=CC=CC=C1
Appearance Not Available
Melting Point 34 oC
Solubility 63.6 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
Predicted LogP 1.3178
Route of Exposure Oral ; parenteral (intramuscular or intravenous injection).
Mechanism of Action Ephedrine is a sympathomimetic amine - that is, its principal mechanism of action relies on its direct and indirect actions on the adrenergic receptor system, which is part of the sympathetic nervous system. Ephedrine increases post-synaptic noradrenergic receptor activity by (weakly) directly activating post-synaptic Œ±-receptors and Œ?-receptors, but the bulk of its effect comes from the pre-synaptic neuron being unable to distinguish between real adrenaline or noradrenaline from ephedrine. The ephedrine, mixed with noradrenaline, is transported through the noradrenaline reuptake complex and packaged (along with real noradrenaline) into vesicles that reside at the terminal button of a nerve cell. Ephedrine's action as an agonist at most major noradrenaline receptors and its ability to increase the release of both dopamine and to a lesser extent, serotonin by the same mechanism is presumed to have a major role in its mechanism of action.
Metabolism Not Available
Toxicity Values Not Available
Lethal Dose Not Available
Carcinogenicity (IARC Classification) Not Available
Uses/Sources Not Available
Minimum Risk Level Not Available
Health Effects Using large amounts of these drugs can result in a condition known as amphetamine psychosis -- which can result in auditory, visual and tactile hallucinations, intense paranoia, irrational thoughts and beliefs, delusions, and mental confusion.
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.
Treatment If respirations are shallow or cyanosis is present, artificial respiration should be administered. Vasopressors are contraindicated. In cardiovascular collapse blood pressure should be maintained. (V650)
General References
  • S405 - DrugBank: a knowledgebase for drugs, drug actions and drug targets. Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. [PubMed Link Image]
Targets
  1. Acetylcholinesterase
Target 1 [top]
Target 1 ID 312
Target 1 Name Acetylcholinesterase
Target 1 Mechanism of Action Ephedrine is a sympathomimetic amine - that is, its principal mechanism of action relies on its direct and indirect actions on the adrenergic receptor system, which is part of the sympathetic nervous system. Ephedrine increases post-synaptic noradrenergic receptor activity by (weakly) directly activating post-synaptic ?-receptors and ?-receptors, but the bulk of its effect comes from the pre-synaptic neuron being unable to distinguish between real adrenaline or noradrenaline from ephedrine. The ephedrine, mixed with noradrenaline, is transported through the noradrenaline reuptake complex and packaged (along with real noradrenaline) into vesicles that reside at the terminal button of a nerve cell. Ephedrine's action as an agonist at most major noradrenaline receptors and its ability to increase the release of both dopamine and to a lesser extent, serotonin by the same mechanism is presumed to have a major role in its mechanism of action.
Target 1 Description Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis
Target 1 Synonyms
  1. AChE
Target 1 Gene Name ACHE
Target 1 Protein Sequence >Acetylcholinesterase 
MRPPQCLLHTPSLASPLLLLLLWLLGGGVGAEGREDAELLVTVRGGRLRGIRLKTPGGPV
SAFLGIPFAEPPMGPRRFLPPEPKQPWSGVVDATTFQSVCYQYVDTLYPGFEGTEMWNPN
RELSEDCLYLNVWTPYPRPTSPTPVLVWIYGGGFYSGASSLDVYDGRFLVQAERTVLVSM
NYRVGAFGFLALPGSREAPGNVGLLDQRLALQWVQENVAAFGGDPTSVTLFGESAGAASV
GMHLLSPPSRGLFHRAVLQSGAPNGPWATVGMGEARRRATQLAHLVGCPPGGTGGNDTEL
VACLRTRPAQVLVNHEWHVLPQESVFRFSFVPVVDGDFLSDTPEALINAGDFHGLQVLVG
VVKDEGSYFLVYGAPGFSKDNESLISRAEFLAGVRVGVPQVSDLAAEAVVLHYTDWLHPE
DPARLREALSDVVGDHNVVCPVAQLAGRLAAQGARVYAYVFEHRASTLSWPLWMGVPHGY
EIEFIFGIPLDPSRNYTAEEKIFAQRLMRYWANFARTGDPNEPRDPKAPQWPPYTAGAQQ
YVSLDLRPLEVRRGLRAQACAFWNRFLPKLLSATDTLDEAERQWKAEFHRWSSYMVHWKN
QFDHYSKQDRCSDL
Target 1 Number of Residues 614
Target 1 Molecular Weight 67795.5
Target 1 Theoretical pI 6.24
Target 1 GO Classification
Function
catalytic activity
hydrolase activity
hydrolase activity, acting on ester bonds
carboxylic ester hydrolase activity
cholinesterase activity
Process
Not Available
Component
Not Available
Target 1 General Function Lipid transport and metabolism
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Signals
  • 1-31
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non Essential
Target 1 Domain Function PF08674:AChE_tetra PF00135:COesterase
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB ID P22303 Link Image
Target 1 Cellular Location Isoform H:Cell membrane
Target 1 Gene Sequence >1845 bp 
ATGAGGCCCCCGCAGTGTCTGCTGCACACGCCTTCCCTGGCTTCCCCACTCCTTCTCCTC
CTCCTCTGGCTCCTGGGTGGAGGAGTGGGGGCTGAGGGCCGGGAGGATGCAGAGCTGCTG
GTGACGGTGCGTGGGGGCCGGCTGCGGGGCATTCGCCTGAAGACCCCCGGGGGCCCTGTC
TCTGCTTTCCTGGGCATCCCCTTTGCGGAGCCACCCATGGGACCCCGTCGCTTTCTGCCA
CCGGAGCCCAAGCAGCCTTGGTCAGGGGTGGTAGACGCTACAACCTTCCAGAGTGTCTGC
TACCAATATGTGGACACCCTATACCCAGGTTTTGAGGGCACCGAGATGTGGAACCCCAAC
CGTGAGCTGAGCGAGGACTGCCTGTACCTCAACGTGTGGACACCATACCCCCGGCCTACA
TCCCCCACCCCTGTCCTCGTCTGGATCTATGGGGGTGGCTTCTACAGTGGGGCCTCCTCC
TTGGACGTGTACGATGGCCGCTTCTTGGTACAGGCCGAGAGGACTGTGCTGGTGTCCATG
AACTACCGGGTGGGAGCCTTTGGCTTCCTGGCCCTGCCGGGGAGCCGAGAGGCCCCGGGC
AATGTGGGTCTCCTGGATCAGAGGCTGGCCCTGCAGTGGGTGCAGGAGAACGTGGCAGCC
TTCGGGGGTGACCCGACATCAGTGACGCTGTTTGGGGAGAGCGCGGGAGCCGCCTCGGTG
GGCATGCACCTGCTGTCCCCGCCCAGCCGGGGCCTGTTCCACAGGGCCGTGCTGCAGAGC
GGTGCCCCCAATGGACCCTGGGCCACGGTGGGCATGGGAGAGGCCCGTCGCAGGGCCACG
CAGCTGGCCCACCTTGTGGGCTGTCCTCCAGGCGGCACTGGTGGGAATGACACAGAGCTG
GTAGCCTGCCTTCGGACACGACCAGCGCAGGTCCTGGTGAACCACGAATGGCACGTGCTG
CCTCAAGAAAGCGTCTTCCGGTTCTCCTTCGTGCCTGTGGTAGATGGAGACTTCCTCAGT
GACACCCCAGAGGCCCTCATCAACGCGGGAGACTTCCACGGCCTGCAGGTGCTGGTGGGT
GTGGTGAAGGATGAGGGCTCGTATTTTCTGGTTTACGGGGCCCCAGGCTTCAGCAAAGAC
AACGAGTCTCTCATCAGCCGGGCCGAGTTCCTGGCCGGGGTGCGGGTCGGGGTTCCCCAG
GTAAGTGACCTGGCAGCCGAGGCTGTGGTCCTGCATTACACAGACTGGCTGCATCCCGAG
GACCCGGCACGCCTGAGGGAGGCCCTGAGCGATGTGGTGGGCGACCACAATGTCGTGTGC
CCCGTGGCCCAGCTGGCTGGGCGACTGGCTGCCCAGGGTGCCCGGGTCTACGCCTACGTC
TTTGAACACCGTGCTTCCACGCTCTCCTGGCCCCTGTGGATGGGGGTGCCCCACGGCTAC
GAGATCGAGTTCATCTTTGGGATCCCCCTGGACCCCTCTCGAAACTACACGGCAGAGGAG
AAAATCTTCGCCCAGCGACTGATGCGATACTGGGCCAACTTTGCCCGCACAGGGGATCCC
AATGAGCCCCGAGACCCCAAGGCCCCACAATGGCCCCCGTACACGGCGGGGGCTCAGCAG
TACGTTAGTCTGGACCTGCGGCCGCTGGAGGTGCGGCGGGGGCTGCGCGCCCAGGCCTGC
GCCTTCTGGAACCGCTTCCTCCCCAAATTGCTCAGCGCCACCGACACGCTCGACGAGGCG
GAGCGCCAGTGGAAGGCCGAGTTCCACCGCTGGAGCTCCTACATGGTGCACTGGAAGAAC
CAGTTCGACCACTACAGCAAGCAGGATCGCTGCTCAGACCTGTGA
Target 1 GenBank Gene ID Not Available
Target 1 GeneCard ID ACHE Link Image
Target 1 GenAtlas ID ACHE Link Image
Target 1 HGNC ID HGNC:108 Link Image
Target 1 Chromosome Location Not Available
Target 1 Locus 7q22
Target 1 SNPs SNPJam Report Link Image
Target 1 Toxin References
  • S405 - DrugBank: a knowledgebase for drugs, drug actions and drug targets. Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. [PubMed Link Image]
Target 1 General References 2263619; 8299725; 14702039; 12853948; 15489334; 11239002

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