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Identification
Name Ephedrine
Accession Number DB01364
Type small molecule
Groups approved
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]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories
  • Vasoconstrictor Agents
  • Adrenergic Agents
  • Central Nervous System Stimulants
  • Sympathomimetics
CAS number 299-42-3
Weight Average: 165.2322
Monoisotopic: 165.115364107
Chemical Formula C10H15NO
InChI Key InChIKey=KWGRBVOPPLSCSI-WPRPVWTQSA-N
InChI
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
Plain Text
IUPAC Name
(1R,2S)-2-(methylamino)-1-phenylpropan-1-ol
SMILES
CN[C@@H](C)[C@H](O)C1=CC=CC=C1
Plain Text
Mass Spec show (7.84 KB)
Taxonomy
Kingdom Organic
Classes
  • Phenethylamines
  • Amphetamines
Substructures
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Amino Alcohols
  • Phenethylamines
  • Aromatic compounds
  • Alcohols and Polyols
  • Amphetamines
Pharmacology
Indication Ephedrine commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia.
Pharmacodynamics Ephedrine is similar in structure to the derivatives amphetamine and methamphetamine. Chemically, it is an alkaloid derived from various plants in the genus Ephedra (family Ephedraceae). It works mainly by increasing the activity of noradrenaline on adrenergic receptors.
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 α-receptors and β-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.
Absorption 85%
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination mainly renal
Half life 3-6 hours
Clearance Not Available
Toxicity Cardiovascular: tachycardia, cardiac arrhythmias, angina pectoris, vasoconstriction with hypertension
Affected organisms Not Available
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms
Form Route Strength
Capsule Oral
Liquid Intramuscular
Liquid Intravenous
Powder Oral
Solution Intramuscular
Tablet Oral
Prices
Unit description Cost Unit
Ephedrine sulfate 250 mg/5 ml 7.82 USD ml
Ephedrine-ns 50 mg/5 ml syr 2.91 USD ml
Ephedrine-ns 100 mg/10 ml syr 2.07 USD ml
Ephedrine su 50 mg/ml vial 1.75 USD ml
Ephedrine 50 mg/ml ampul 0.76 USD ml
Ephedrine powder 0.47 USD g
Ephedrine sulfate powder 0.46 USD g
Ephedrine su 25 mg capsule 0.3 USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 34 °C PhysProp
boiling point 255 °C PhysProp
water solubility 6.36E+004 mg/L (at 30 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP 1.13 AVDEEF,A (1997)
pKa 10.3 (at 0 °C) PERRIN,DD (1965)
Predicted Properties
Property Value Source
water solubility 8.26e+00 g/l ALOGPS
logP 1 ALOGPS
logP 1.32 ChemAxon
logS -1.3 ALOGPS
pKa (strongest acidic) 13.89 ChemAxon
pKa (strongest basic) 9.52 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 32.26 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 49.69 ChemAxon
polarizability 18.8 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00124 Link_out
KEGG Compound C01575 Link_out
PubChem Compound 9294 Link_out
PubChem Substance 46507538 Link_out
ChemSpider 8935 Link_out
ChEBI 15407 Link_out
ChEMBL 15407 Link_out
Therapeutic Targets Database DAP000228 Link_out
PharmGKB PA449466 Link_out
IUPHAR 556 Link_out
Guide to Pharmacology 556 Link_out
Drug Product Database 38121 Link_out
RxList http://www.rxlist.com/cgi/generic/ephedrine.htm Link_out
Drugs.com http://www.drugs.com/ephedrine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Ephedrine Link_out
ATC Codes
  • C01CA26
  • S01FB02
  • R03CA02
  • R01AB05
  • R01AA03
AHFS Codes
  • 12:12.12
  • 92:01.00*
  • 12:12.00
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Amitriptyline The tricyclic antidepressant, amitriptyline, increases the sympathomimetic effect of ephedrine.
Amoxapine The tricyclic antidepressant, amoxapine, increases the sympathomimetic effect of ephedrine.
Clomipramine The tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of ephedrine.
Desipramine The tricyclic antidepressant, desipramine, increases the sympathomimetic effect of ephedrine.
Desvenlafaxine Desvenlafaxine may increase the tachycardic and vasopressor effects of ephedrine. Consider alternate therapy or monitor for increased sympathomimetic effects, such as increased blood pressure, chest pain and headache.
Doxepin The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of ephedrine.
Guanethidine Ephedrine may decrease the effect of guanethidine.
Imipramine The tricyclic antidepressant, imipramine, increases the sympathomimetic effect of ephedrine.
Iobenguane Sympathomimetic that increase chances of producing a false negative imaging result
Isocarboxazid Increased arterial pressure
Linezolid Possible increase of arterial pressure
Methyldopa Increased arterial pressure
Midodrine Increased arterial pressure
Moclobemide Moclobemide increases the sympathomimetic effect of ephedrine.
Nortriptyline The tricyclic antidepressant, nortriptyline, increases the sympathomimetic effect of ephedrine.
Phenelzine Increased arterial pressure
Rasagiline Increased arterial pressure
Reserpine Increased arterial pressure
Tranylcypromine The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of Ephedrine. Concomitant therapy should be avoided.
Venlafaxine Venlafaxine may increase the tachycardic and vasopressor effects of ephedrine. Consider alternate therapy or monitor for increased sympathomimetic effects, such as increased blood pressure, chest pain and headache.
Food Interactions Not Available
Targets

1. Sodium-dependent noradrenaline transporter

Pharmacological action: unknown
Actions: inverse agonist

Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals

Organism class: human
UniProt ID: P23975 Link_out
Gene: SLC6A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Kobayashi S, Endou M, Sakuraya F, Matsuda N, Zhang XH, Azuma M, Echigo N, Kemmotsu O, Hattori Y, Gando S: The sympathomimetic actions of l-ephedrine and d-pseudoephedrine: direct receptor activation or norepinephrine release? Anesth Analg. 2003 Nov;97(5):1239-45. Pubmed
  2. McMahon LR, Cunningham KA: Discriminative stimulus effects of (-)-ephedrine in rats: analysis with catecholamine transporter and receptor ligands. Drug Alcohol Depend. 2003 Jun 5;70(3):255-64. Pubmed
  3. Fleckenstein AE, Volz TJ, Riddle EL, Gibb JW, Hanson GR: New insights into the mechanism of action of amphetamines. Annu Rev Pharmacol Toxicol. 2007;47:681-98. Pubmed
  4. Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. Pubmed

2. Alpha-1A adrenergic receptor

Pharmacological action: unknown

This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins

Organism class: human
UniProt ID: P35348 Link_out
Gene: ADRA1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ma G, Bavadekar SA, Davis YM, Lalchandani SG, Nagmani R, Schaneberg BT, Khan IA, Feller DR: Pharmacological effects of ephedrine alkaloids on human alpha(1)- and alpha(2)-adrenergic receptor subtypes. J Pharmacol Exp Ther. 2007 Jul;322(1):214-21. Epub 2007 Apr 3. Pubmed
  2. Wellman PJ, Miller DK, Ho DH: Noradrenergic modulation of ephedrine-induced hypophagia. Synapse. 2003 Apr;48(1):18-24. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

3. Synaptic vesicular amine transporter

Pharmacological action: unknown
Actions: inhibitor

Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles. Requisite for vesicular amine storage prior to secretion via exocytosis

Organism class: human
UniProt ID: Q05940 Link_out
Gene: SLC18A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ellis JD, German CL, Birdsall E, Hanson JE, Crosby MA, Rowley SD, Sawada NA, West JN, Hanson GR, Fleckenstein AE: Ephedrine decreases vesicular monoamine transporter-2 function. Synapse. 2010 Dec 15. Pubmed
  2. Horton DB, Siripurapu KB, Norrholm SD, Culver JP, Hojahmat M, Beckmann JS, Harrod SB, Deaciuc AG, Bardo MT, Crooks PA, Dwoskin LP: meso-Transdiene Analogs Inhibit Vesicular Monoamine Transporter-2 Function and Methamphetamine-evoked Dopamine Release. J Pharmacol Exp Ther. 2010 Dec 21. Pubmed
  3. Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. Pubmed
  4. Sulzer D, Chen TK, Lau YY, Kristensen H, Rayport S, Ewing A: Amphetamine redistributes dopamine from synaptic vesicles to the cytosol and promotes reverse transport. J Neurosci. 1995 May;15(5 Pt 2):4102-8. Pubmed
  5. Yasumoto S, Tamura K, Karasawa J, Hasegawa R, Ikeda K, Yamamoto T, Yamamoto H: Inhibitory effect of selective serotonin reuptake inhibitors on the vesicular monoamine transporter 2. Neurosci Lett. 2009 May 1;454(3):229-32. Epub 2009 Mar 18. Pubmed
  6. Fleckenstein AE, Volz TJ, Riddle EL, Gibb JW, Hanson GR: New insights into the mechanism of action of amphetamines. Annu Rev Pharmacol Toxicol. 2007;47:681-98. Pubmed

4. Acetylcholinesterase

Pharmacological action: unknown

Rapidly hydrolyzes choline released into the synapse

Organism class: human
UniProt ID: P22303 Link_out
Gene: ACHE Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Singh AK, Spassova D: Effects of hexamethonium, phenothiazines, propranolol and ephedrine on acetylcholinesterase carbamylation by physostigmine, aldicarb and carbaryl: interaction between the active site and the functionally distinct peripheral sites in acetylcholinesterase. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1998 Jan;119(1):97-105. Pubmed
Enzymes

1. Cholinesterase

Actions: substrate

An acylcholine + H(2)O = choline + a carboxylate

UniProt ID: P06276 Link_out
Gene: BCHE Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Maizel’ EB, Rozengart EV, Khakimov IuP, Abduvakhabov AA, Aslanov KhA: [Ephedrine, salsoline and cytisine derivatives as substrates and inhibitirs of cholinesterases]. Biokhimiia. 1978 Jul;43(7):1150-6. Pubmed
Comments
Drug created on July 06, 2007 13:56 / Updated on February 08, 2013 16:20