Talk:Ephedrine

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Summary sheet: Ephedrine
Ephedrine
(1R,2S)-Ephedrine.svg
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.

Not to be confused with Ephedrone or Ephenidine.

Ephedrine is a naturally occuring 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.[1]

Ephedrine is closely related in structure to methamphetamine, 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 antiasthmatic 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 in many countries, as they are a major source for the production of the addictive compound methamphetamine.[2]

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.[3] It also acts as a NDRA (norepinephrine-dopamine releasing agent).[4]

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.[5] The presence of direct interactions with α receptors is unlikely, but still controversial.[6] 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.[7]

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.[8]

Subjective effects

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Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), a research literature based on anecdotal reports and the personal experiences of PsychonautWiki contributors. As a result, they should be regarded with a healthy degree of skepticism. It is 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 much more likely with higher doses and may include addiction, serious injury, or death.


Physical effects
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Visual effects
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Cognitive effects
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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:

Toxicity and harm potential

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We also recommend that you conduct independent research and use harm reduction practices when using this substance.

It is strongly recommended that one use harm reduction practices when using this substance.

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.[9]

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

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Although many psychoactive substances are reasonably safe to use on their own, they can suddenly become dangerous or even life-threatening when combined with other substances. The following list includes some known dangerous combinations (although it is not guaranteed to include all of them). Independent research (e.g. Google, DuckDuckGo) should always be conducted 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.[10] 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

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  • Canada: Ephedrine can be sold for breathing purposes in 8 milligram doses OTC.
  • Sweden: Ephedrine is a prescription only medication.[11]
  • United states: Ephedrine is heavily regulated due to production of meth using ephedrine.

See also

External links

Literature

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References

  1. "Ephedrine". The American Society of Health-System Pharmacists. Archived from the original on 2017-09-09. Retrieved 8 September 2017.
  2. The history of Ephedra (ma-huang). (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/21365072
  3. Pharmacological Effects of Ephedrine | https://link.springer.com/referenceworkentry/10.1007/978-3-642-22144-6_41
  4. Dopamine-mediated actions of ephedrine in the rat substantia nigra. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/16386715
  5. Merck Manuals > EPHEDrine Archived 2011-03-24 at the Wayback Machine Last full review/revision January 2010
  6. Drew CD, Knight GT, Hughes DT, Bush M (September 1978). "Comparison of the effects of D-(-)-ephedrine and L-(+)-pseudoephedrine on the cardiovascular and respiratory systems in man". British Journal of Clinical Pharmacology. 6 (3): 221–5. doi:10.1111/j.1365-2125.1978.tb04588.x. PMC 1429447. PMID 687500.
  7. Munhall AC, Johnson SW (January 2006). "Dopamine-mediated actions of ephedrine in the rat substantia nigra". Brain Research. 1069 (1): 96–103. doi:10.1016/j.brainres.2005.11.044. PMID 16386715. S2CID 40626692.
  8. Guoyi Ma, et al. Pharmacological Effects of Ephedrine Alkaloids on Human {alpha}1- and {alpha}2-Adrenergic Receptor Subtypes Archived 2011-03-05 at the Wayback Machine J. Pharmacol. Exp. Ther. 322: pp. 214-221 (July 2007) PDF
  9. https://pubmed.ncbi.nlm.nih.gov/8988594/
  10. https://www.rxlist.com/consumer_ephedrine/drugs-condition.htm
  11. https://www.fass.se/LIF/substance?substanceId=IDE4POC8U9CKGVERT1