View source for Ephedrine


{{SummarySheet}}
{{SubstanceBox/Ephedrine}}
{{Distinguish|Ephedrone|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.<ref>"Ephedrine". The American Society of Health-System Pharmacists. Archived from the original on 2017-09-09. Retrieved 8 September 2017.</ref>

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==
{{historyStub}}
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]],<ref>The history of Ephedra (ma-huang). (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/21365072</ref> and have been associated with severe adverse events such as heart attacks and strokes.<ref>der Hooft CS & Stricker BH (2002) "Ephedrine and ephedra in weight loss products and other preparations" https://europepmc.org/article/med/12148223</ref>

==Chemistry==
{{chemistry}}
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==
{{pharmacology}}
Ephedrine primary mechanism of action is through increasing catecholamine activity at alpha, beta-1, and beta-2 [[adrenergic]] [[receptor]]s.<ref>Pharmacological Effects of Ephedrine | https://link.springer.com/referenceworkentry/10.1007/978-3-642-22144-6_41</ref> It also acts as a NDRA ([[norepinephrine]]-[[dopamine]] [[releasing agent]]).<ref>Dopamine-mediated actions of ephedrine in the rat substantia nigra. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/16386715</ref>

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.<ref>Merck Manuals > EPHEDrine Archived 2011-03-24 at the Wayback Machine Last full review/revision January 2010</ref> The presence of direct interactions with α receptors is unlikely, but still controversial.<ref>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.</ref> 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.<ref>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.</ref>

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.<ref>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</ref>

==Subjective effects==
{{EffectStub}}
{{Preamble/SubjectiveEffects}}

{{effects/base

|{{effects/physical|
If applicable, a brief paragraph summary of the substance's physical effects may be included here. 

You may select physical effects to add below [[Subjective effect index#Physical effects|here]].

*'''[[Effect::Stimulation]]''' 
*'''[[Effect::Bronchodilation]]'''
*'''[[Effect::Appetite suppression]]'''
*'''[[Effect::Stamina enhancement]]''' - Ephedrine is commonly used as a performance enhancer by athletes and bodybuilders
*'''[[Effect::Physical euphoria]]'''
*'''[[Effect::Nausea]]''' - At high doses
*'''[[Effect::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]]'''

}}
{{effects/visual|
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====
*'''[[Effect::Visual acuity enhancement]]'''

====Distortions====
*'''[[Effect::Double vision]]'''

}}

|{{effects/cognitive|
If applicable, a brief paragraph summary of the substance's cognitive effects may be included here. 

You may select from a list of cognitive effects to add below [[Subjective effect index#Cognitive effects|here]].

*'''[[Effect::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]].
*'''[[Effect::Empathy, affection and sociability enhancement]]'''
*'''[[Effect::Anxiety]]''' 
*'''[[Irritability]]'''
*'''[[Effect::Focus enhancement]]'''
*'''[[Effect::Memory enhancement]]''' 
*'''[[Effect::Thought acceleration]]''' 
*'''[[Effect::Increased music appreciation]]''' 
*'''[[Effect::Ego inflation]]'''
*'''[[Effect::Time distortion|Time compression]]''' - This effect is more intense with ephedrine than with most other stimulants
*'''[[Effect::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:

*[https://www.erowid.org/experiences/subs/exp_Ephedrine.shtml Erowid Experience Vaults: Ephedrine]

==Toxicity and harm potential==
{{toxicity}}
It is strongly recommended that one use [[responsible 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<ref>der Hooft CS & Stricker BH (2002) "Ephedrine and ephedra in weight loss products and other preparations" https://europepmc.org/article/med/12148223</ref>. 
===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.<ref>https://pubmed.ncbi.nlm.nih.gov/8988594/</ref>

===Tolerance and addiction potential===
As with other [[stimulant]]s, 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===
{{DangerousInteractions}}
{{DangerousInteractions/Intro}}

Severe Interactions of ephedrine include: iobenguane I 123, isocarboxazid, linezolid, phenelzine, procarbazine, rasagiline, selegiline, and tranylcypromine.<ref>https://www.rxlist.com/consumer_ephedrine/drugs-condition.htm</ref> 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==
{{LegalStub}}

*'''Canada''': Ephedrine can be sold for breathing purposes in 8 milligram doses OTC.
*'''Germany''': Ephedrine is a prescription only medication.<ref>http://www.buzer.de/gesetz/7048/index.htm</ref>
*'''Sweden''': Ephedrine is a prescription only medication.<ref>https://www.fass.se/LIF/substance?substanceId=IDE4POC8U9CKGVERT1</ref>
*'''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.<ref>Combat Methamphetamine Epidemic Act of 2005<nowiki/>https://www.deadiversion.usdoj.gov/meth/cma2005.htm</ref> [[Pseudoephedrine]] products can also be bought in larger quantities with a valid prescription.

==See also==

*[[Responsible use]]

==External links==

*[https://en.wikipedia.org/wiki/Ephedrine Ephedrine (Wikipedia)]
*[https://www.erowid.org/chemicals/ephedrine/ Ephedrine (Erowid Vault)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=2000 Ephedrine (Isomer Design)]
*[https://go.drugbank.com/drugs/DB01364 Ephedrine (DrugBank)]

==Literature==

*APA formatted reference

Please see the [[citation formatting guide]] if you need assistance properly formatting citations.

==References==
<references />

[[Category:Psychoactive substance]]
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[[Category:Approval]]