Ephedrine

Summary sheet: Ephedrine

Ephedrine
Chemical Nomenclature
Common names	Ephedrine, Ephedra
Substitutive name	(1R,2S)-2-(methylamino)-1-phenylpropan-1-ol
Class Membership
Psychoactive class	Stimulant
Chemical class	Amphetamine
Routes of Administration
WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section. ⇣ Oral Dosage Threshold 5 mg Light 10 - 20 mg Common 20 - 30 mg Strong 30 - 50 mg Heavy 50 mg + Duration Total 2 - 5 hours Onset 20 - 90 minutes After effects 2 - 4 hours DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.
Interactions

Not to be confused with Ephedrone or Ephenidine.

Ephedrine is a naturally occurring central nervous system stimulant obtained from the plant Ephedra equisetina. Commonly used as a stimulant, concentration aid, decongestant, and appetite suppressant. It is often used to prevent low blood pressure during spinal anesthesia.

Ephedrine is closely related in structure to methamphetamine, and pseudoephedrine although its CNS actions are much less potent and also longer-acting than those of the amphetamines. Its peripheral stimulant actions are similar to but less powerful than those of epinephrine (adrenaline), a hormone produced in the body by the adrenal glands.

History and culture

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Ephedrine in its natural form, known as má huáng in traditional Chinese medicine, has been documented in China since the Han dynasty (206 BC – 220 AD) as an anti-asthmatic and stimulant. In 1885, the chemical synthesis of ephedrine was first accomplished by Japanese organic chemist Nagai Nagayoshi based on his research on traditional Japanese and Chinese herbal medicines. The industrial manufacture of ephedrine in China began in the 1920s, when Merck began marketing and selling the drug as ephetonin. Ephedrine exports from China to the West grew from 4 to 216 tonnes between 1926 and 1928. Ephedrine became a highly popular and effective treatment for asthma, particularly because, unlike adrenaline (until then the standard therapy), it can be given by mouth. Ephedrine as a treatment for asthma reached its zenith in the late 1950s, since when there has been a gradual and inevitable decline in its therapeutic use. From mainstream medicine, ephedrine moved into the twilight zone of street drugs and nutritional supplements. Ephedra and ephedrine products are now banned or heavily regulated in many countries, as they are a major source for the production of the addictive compound methamphetamine, and have been associated with severe adverse events such as heart attacks and strokes.

Chemistry

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Ephedrine is a substituted amphetamine and a structural methamphetamine analogue. It differs from methamphetamine only by the presence of a hydroxyl group (—OH).

Ephedrine is a sympathomimetic amine and substituted amphetamine. It is similar in molecular structure to phenylpropanolamine, methamphetamine, and epinephrine (adrenaline). 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 (noradrenaline) on adrenergic receptors. It is most usually marketed as the hydrochloride or sulfate salt.

Ephedrine exhibits optical isomerism and has two chiral centres, giving rise to four stereoisomers. By convention, the pair of enantiomers with the stereochemistry (1R,2S) and (1S,2R) is designated ephedrine, while the pair of enantiomers with the stereochemistry (1R,2R) and (1S,2S) is called pseudoephedrine. Ephedrine is a substituted amphetamine and a structural methamphetamine analogue. It differs from methamphetamine only by the presence of a hydroxyl group (—OH).

Pharmacology

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Ephedrine primary mechanism of action is through increasing catecholamine activity at alpha, beta-1, and beta-2 adrenergic receptors. It also acts as a NDRA (norepinephrine-dopamine releasing agent).

Ephedrine, a sympathomimetic amine, acts on part of the sympathetic nervous system (SNS). The principal mechanism of action relies on its indirect stimulation of the adrenergic receptor system by increasing the activity of norepinephrine at the postsynaptic α and β receptors. The presence of direct interactions with α receptors is unlikely, but still controversial. L-ephedrine, and particularly its stereoisomer norpseudoephedrine (which is also present in Catha edulis) has indirect sympathomimetic effects and due to its ability to cross the blood-brain barrier, it is a CNS stimulant similar to amphetamines, but less pronounced, as it releases noradrenaline and dopamine in the substantia nigra.

The presence of an N-methyl group decreases binding affinities at α receptors, compared with norephedrine. Ephedrine, though, binds better than N-methylephedrine, which has an additional methyl group at the nitrogen atom. Also the steric orientation of the hydroxyl group is important for receptor binding and functional activity.

Subjective effects

This subjective effects section is a stub. As such, it is still in progress and may contain incomplete or wrong information. You can help by expanding or correcting it.

Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.

It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.

Physical effects

• If applicable, a brief paragraph summary of the substance's physical effects may be included here. You may select physical effects to add below here.
  • Stimulation
  • Bronchodilation
  • Appetite suppression
  • Stamina enhancement - Ephedrine is commonly used as a performance enhancer by athletes and bodybuilders
  • Physical euphoria
  • Nausea - At high doses
  • Dry mouth
  • Vasoconstriction
  • Increased heart rate - Ephedrine is often reported to increase heart rate to a greater extent than other amphetamines.
  • Spontaneous bodily sensations
  • Increased perspiration
  • Abnormal heartbeat - Heart palpitations are more frequently reported with ephedrine than with other amphetamines.
  • Increased bodily temperature
  • Pupil dilation - This effect is milder and less frequent than with other amphetamines.
  • Teeth grinding

Visual effects

• Ephedrine is rarely reported to cause any noticeable visual effects in comparison to other amphetamines, likely due to having only mild effects on dopamine relative to epinephrine. However, mild enhancements and distortions may occur.

  Enhancements

  • Visual acuity enhancement

  Distortions

  • Double vision

Cognitive effects

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  • Cognitive euphoria - The euphoria produced by ephedrine is reported to be similar to, but more intense than the euphoria produced by amphetamine, but less intense than the euphoria produced by methamphetamine or MDMA.
  • Empathy, affection and sociability enhancement
  • Anxiety
  • Irritability
  • Focus enhancement
  • Memory enhancement
  • Thought acceleration
  • Increased music appreciation
  • Ego inflation
  • Time compression - This effect is more intense with ephedrine than with most other stimulants
  • Increased libido or Decreased libido - Some users report that ephedrine enhances libido, while others experience a suppression of libido. Overall, the effects of ephedrine on libido are milder than that of other amphetamines
  • Increased music appreciation
  • Motivation enhancement
  • Emotion suppression
  • Wakefulness

Experience reports

There are currently no anecdotal reports which describe the effects of this compound within our experience index. Additional experience reports can be found here:

• Erowid Experience Vaults: Ephedrine

Toxicity and harm potential

This toxicity and harm potential section is a stub. As a result, it may contain incomplete or even dangerously wrong information! You can help by expanding upon or correcting it. Note: Always conduct independent research and use harm reduction practices if using this substance.

It is strongly recommended that one use harm reduction practices when using this substance. In comparison to other stimulants, ephedrine has particularly strong effects on the cardiovascular system, and its use has been associated with heart attacks, strokes, and arrythmia.

Lethal dosage

A 28-year-old white female with a history of two prior suicide attempts was found dead in her home by her common law husband. Autopsy findings were unremarkable except for partially dissolved ephedrine tablets in the stomach contents. Significant toxicological finding included ephedrine concentrations in the blood of 11 mg/L, liver of 24 mg/kg, kidney of 14 mg/kg, and brain of 8.9 mg/kg.

Tolerance and addiction potential

As with other stimulants, the chronic use of ephedrine can be considered moderately addictive and is capable of causing psychological dependence among certain users.

Tolerance to the effects of ephedrine are quickly built after repeated and frequent usage. Ephedrinepresents cross-tolerance with other dopaminergic stimulants, meaning that after the consumption of ephedrine, most other stimulant compounds will have a reduced effect.

Dangerous interactions

This dangerous interactions section is a stub. As such, it may contain incomplete or invalid information. You can help by expanding upon or correcting it.

Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).

Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.

Severe Interactions of ephedrine include: iobenguane I 123, isocarboxazid, linezolid, phenelzine, procarbazine, rasagiline, selegiline, and tranylcypromine. Check with your health care professional or doctor for additional medical advice, or if you have health questions, concerns or for more information about this medicine.

Legal status

This legality section is a stub. As such, it may contain incomplete or wrong information. You can help by expanding it.

• Canada: Ephedrine can be sold for breathing purposes in 8 milligram doses OTC.
• Germany: Ephedrine is a prescription only medication.
• Sweden: Ephedrine is a prescription only medication.
• United states: Ephedrine is controlled under the Combat Methamphetamine Epidemic Act of 2005 and can be purchased behind the counter in all U.S. states. All pseudoephedrine, ephedrine, and phenylpropanolamine purchases are kept and maintained in state databases to ensure that no individual may exceed daily and monthly thresholds. The daily limit is 3.6 g of any of these substances and 9 g per 30 day period. Pseudoephedrine products can also be bought in larger quantities with a valid prescription.

See also

• Responsible use

External links

• Ephedrine (Wikipedia)
• Ephedrine (Erowid Vault)
• Ephedrine (Isomer Design)
• Ephedrine (DrugBank)

Literature

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