Identification

Name
Ephedra
Accession Number
DB01363
Type
Small Molecule
Groups
Approved, Nutraceutical, Withdrawn
Description

Ephedra is an alkaloid chemical compound traditionally obtained from the plant Ephedra sinica. The sale of ephedra-containing supplements was banned in the United States in 2004. The drug is still sold in Canada in OTC formulations.

Synonyms
  • Chinese jointfir
  • Indian jointfir
  • Ma huang
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Congest-easeCapsule8 mgOralPuresource Inc.Not applicableNot applicableCanada
H.O. Formula With M/hTablet8 mgOralAbundance Naturally LtdNot applicableNot applicableCanada
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Chi FormulaCapsule4.2 mgOralNatures Sunshine Products, Inc.1995-12-312006-07-10Canada
CitrivateCapsule84 mgOralGreat Canadian Lifestyles Co.2001-07-132002-09-03Canada
Decongestionnant - Cap OrlCapsule250 mgOralLaboratoire Lalco Inc.1997-01-202002-09-05Canada
Dp FormulaTablet107 mgOralPep Products Inc.2000-03-012003-01-13Canada
Dp Formula - 133mg TabTablet133 mgOralPep Products Inc.1994-12-312003-01-13Canada
EphedraCapsule8 mgOralNatural Balance2002-01-142009-08-17Canada
EphedraCapsule300 mgOralKaizen Inc.1997-04-221999-03-15Canada
EphedraCapsule8 mgOralChampion's Choice Advanced Nutrition Inc.1997-06-111999-08-28Canada
Ephedra - Cap 300mgCapsule300 mgOralNutrion Health & Fitness Inc.1996-12-311999-08-28Canada
Ephedra -tab 100mgTablet100 mgOralVita Health Products Inc1997-09-082002-07-31Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Dr. Miller's Formula No. 1Ephedra (280 mg) + Willow bark (280 mg)TabletOralLite & Rite Inc.1994-12-311998-06-09Canada
Herbal Cold and Flu Formula - TabEphedra (8 mg) + Salix alba bark (3 g)TabletOralQuest Vitamins A Div Of Purity Life Health Products1995-12-311999-08-08Canada
International/Other Brands
Ephedra vulgaris / Sinueaze
Categories
UNII
D0P20CT40D
CAS number
Not Available
Weight
Not Available
Chemical Formula
Not Available
InChI Key
Not Available
InChI
Not Available
IUPAC Name
Not Available
SMILES
Not Available

Pharmacology

Indication

Ephedra is widely used by athletes, despite a lack of evidence that it enhances athletic performance. Ephedra has also been used for weight loss.

Pharmacodynamics
Not Available
Mechanism of action

The alkaloids ephedrine and pseudoephedrine are the active constituents of Ephedra. Pseudoephedrine is used in over-the-counter decongestants. Derivatives of ephedrine are used to treat low blood pressure, but alternatives with reduced cardiovascular risk have replaced it for treating asthma. Ephedrine is also considered a performance-enhancing drug and is prohibited in most competitive sports. 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.

TargetActionsOrganism
ASodium-dependent dopamine transporter
negative modulator
Human
ASodium-dependent noradrenaline transporter
negative modulator
Human
AAlpha-2A adrenergic receptor
agonist
Human
AAlpha-2B adrenergic receptor
agonist
Human
AAlpha-2C adrenergic receptor
agonist
Human
AAmine oxidase [flavin-containing] A
inhibitor
Human
AAmine oxidase [flavin-containing] B
inhibitor
Human
ABeta-1 adrenergic receptor
agonist
Human
ABeta-2 adrenergic receptor
agonist
Human
ABeta-3 adrenergic receptor
agonist
Human
ASodium-dependent serotonin transporter
negative modulator
Human
ASynaptic vesicular amine transporter
inhibitor
Human
AChromaffin granule amine transporter
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Ephedra.
AcebutololThe therapeutic efficacy of Ephedra can be decreased when used in combination with Acebutolol.
AcepromazineAcepromazine may decrease the vasoconstricting activities of Ephedra.
AlclometasoneThe risk or severity of hypokalemia can be increased when Alclometasone is combined with Ephedra.
AlfuzosinThe therapeutic efficacy of Ephedra can be decreased when used in combination with Alfuzosin.
AlprenololAlprenolol may decrease the bronchodilatory activities of Ephedra.
AmcinonideThe risk or severity of hypokalemia can be increased when Amcinonide is combined with Ephedra.
AmineptineAmineptine may decrease the antihypertensive activities of Ephedra.
AmitriptylineThe therapeutic efficacy of Ephedra can be decreased when used in combination with Amitriptyline.
AmitriptylinoxideAmitriptylinoxide may decrease the antihypertensive activities of Ephedra.
Food Interactions
Not Available

References

General References
  1. Gurley BJ, Wang P, Gardner SF: Ephedrine-type alkaloid content of nutritional supplements containing Ephedra sinica (Ma-huang) as determined by high performance liquid chromatography. J Pharm Sci. 1998 Dec;87(12):1547-53. [PubMed:10189265]
  2. Abourashed EA, El-Alfy AT, Khan IA, Walker L: Ephedra in perspective--a current review. Phytother Res. 2003 Aug;17(7):703-12. [PubMed:12916063]
  3. Haller CA, Benowitz NL: Adverse cardiovascular and central nervous system events associated with dietary supplements containing ephedra alkaloids. N Engl J Med. 2000 Dec 21;343(25):1833-8. [PubMed:11117974]
  4. Bent S, Tiedt TN, Odden MC, Shlipak MG: The relative safety of ephedra compared with other herbal products. Ann Intern Med. 2003 Mar 18;138(6):468-71. [PubMed:12639079]
External Links
PubChem Substance
46504840
PharmGKB
PA164777031
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Ephedra
AHFS Codes
  • 12:12.12 — Alpha-and Beta-adrenergic Agonists
  • 92:01.00* — Herbs and Natural Products
  • 12:12.00 — Sympathomimetic (Adrenergic) Agents

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CapsuleOral4.2 mg
CapsuleOral84 mg
TabletOral107 mg
TabletOral133 mg
CapsuleOral300 mg
TabletOral100 mg
CapsuleOral250 mg
CapsuleOral133.4 mg
CapsuleOral8 mg
TabletOral8 mg
CapsuleOral10 mg
Kit; liquidOral10 mg
TabletOral
CapsuleOral100 mg
CapsuleOral680 mg
CapsuleOral125 mg
CapsuleOral167.5 mg
CapsuleOral4 mg
CapsuleOral7.5 mg
CapsuleOral10.8 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
Not Available
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Negative modulator
General Function
Monoamine transmembrane transporter activity
Specific Function
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A3
Uniprot ID
Q01959
Uniprot Name
Sodium-dependent dopamine transporter
Molecular Weight
68494.255 Da
References
  1. 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:15955613]
  2. Wee S, Ordway GA, Woolverton WL: Reinforcing effect of pseudoephedrine isomers and the mechanism of action. Eur J Pharmacol. 2004 Jun 16;493(1-3):117-25. [PubMed:15189772]
  3. Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA: In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates. J Pharmacol Exp Ther. 2003 Oct;307(1):138-45. Epub 2003 Sep 3. [PubMed:12954796]
  4. 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:17209801]
  5. Haughey HM, Brown JM, Wilkins DG, Hanson GR, Fleckenstein AE: Differential effects of methamphetamine on Na(+)/Cl(-)-dependent transporters. Brain Res. 2000 Apr 28;863(1-2):59-65. [PubMed:10773193]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Negative modulator
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
  1. Wee S, Ordway GA, Woolverton WL: Reinforcing effect of pseudoephedrine isomers and the mechanism of action. Eur J Pharmacol. 2004 Jun 16;493(1-3):117-25. [PubMed:15189772]
  2. 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:15955613]
  3. Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA: In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates. J Pharmacol Exp Ther. 2003 Oct;307(1):138-45. Epub 2003 Sep 3. [PubMed:12954796]
  4. 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:17209801]
  5. Haughey HM, Brown JM, Wilkins DG, Hanson GR, Fleckenstein AE: Differential effects of methamphetamine on Na(+)/Cl(-)-dependent transporters. Brain Res. 2000 Apr 28;863(1-2):59-65. [PubMed:10773193]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
Molecular Weight
48956.275 Da
References
  1. 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:15955613]
  2. 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:14570629]
  3. Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA: In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates. J Pharmacol Exp Ther. 2003 Oct;307(1):138-45. Epub 2003 Sep 3. [PubMed:12954796]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Epinephrine binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...
Gene Name
ADRA2B
Uniprot ID
P18089
Uniprot Name
Alpha-2B adrenergic receptor
Molecular Weight
49565.8 Da
References
  1. 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:15955613]
  2. 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:14570629]
  3. Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA: In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates. J Pharmacol Exp Ther. 2003 Oct;307(1):138-45. Epub 2003 Sep 3. [PubMed:12954796]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Protein homodimerization activity
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
Gene Name
ADRA2C
Uniprot ID
P18825
Uniprot Name
Alpha-2C adrenergic receptor
Molecular Weight
49521.585 Da
References
  1. 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:15955613]
  2. 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:14570629]
  3. Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA: In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates. J Pharmacol Exp Ther. 2003 Oct;307(1):138-45. Epub 2003 Sep 3. [PubMed:12954796]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serotonin binding
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
References
  1. 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:15955613]
  2. Ulus IH, Maher TJ, Wurtman RJ: Characterization of phentermine and related compounds as monoamine oxidase (MAO) inhibitors. Biochem Pharmacol. 2000 Jun 15;59(12):1611-21. [PubMed:10799660]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Primary amine oxidase activity
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. 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:15955613]
  2. Ulus IH, Maher TJ, Wurtman RJ: Characterization of phentermine and related compounds as monoamine oxidase (MAO) inhibitors. Biochem Pharmacol. 2000 Jun 15;59(12):1611-21. [PubMed:10799660]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. Vansal SS, Feller DR: Direct effects of ephedrine isomers on human beta-adrenergic receptor subtypes. Biochem Pharmacol. 1999 Sep 1;58(5):807-10. [PubMed:10449190]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
References
  1. Vansal SS, Feller DR: Direct effects of ephedrine isomers on human beta-adrenergic receptor subtypes. Biochem Pharmacol. 1999 Sep 1;58(5):807-10. [PubMed:10449190]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis.
Gene Name
ADRB3
Uniprot ID
P13945
Uniprot Name
Beta-3 adrenergic receptor
Molecular Weight
43518.615 Da
References
  1. Vansal SS, Feller DR: Direct effects of ephedrine isomers on human beta-adrenergic receptor subtypes. Biochem Pharmacol. 1999 Sep 1;58(5):807-10. [PubMed:10449190]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Negative modulator
General Function
Serotonin:sodium symporter activity
Specific Function
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. Wee S, Ordway GA, Woolverton WL: Reinforcing effect of pseudoephedrine isomers and the mechanism of action. Eur J Pharmacol. 2004 Jun 16;493(1-3):117-25. [PubMed:15189772]
  2. 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:17209801]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Monoamine transmembrane transporter activity
Specific Function
Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles...
Gene Name
SLC18A2
Uniprot ID
Q05940
Uniprot Name
Synaptic vesicular amine transporter
Molecular Weight
55712.075 Da
References
  1. 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:15955613]
  2. Henry JP, Sagne C, Bedet C, Gasnier B: The vesicular monoamine transporter: from chromaffin granule to brain. Neurochem Int. 1998 Mar;32(3):227-46. [PubMed:9587917]
  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:17209801]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serotonin transmembrane transporter activity
Specific Function
Involved in the transport of biogenic monoamines, such as serotonin, from the cytoplasm into the secretory vesicles of neuroendocrine and endocrine cells.
Gene Name
SLC18A1
Uniprot ID
P54219
Uniprot Name
Chromaffin granule amine transporter
Molecular Weight
56256.71 Da
References
  1. 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:15955613]
  2. Henry JP, Sagne C, Bedet C, Gasnier B: The vesicular monoamine transporter: from chromaffin granule to brain. Neurochem Int. 1998 Mar;32(3):227-46. [PubMed:9587917]
  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:17209801]

Drug created on July 06, 2007 13:55 / Updated on October 16, 2018 08:36