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Revision as of 18:19, 13 January 2013

Other Names

Aphetonin, efedrina, ephedrin, ephedrine,

ephedrinum, ephetonin, erythro-2-methylaminoI-

hydroxyl-l-phenylpropane, (IR,2S)-2-methylamino-

l-phenyl-l-propanol

Empirical formula: ClQH1SNO

Substance type: ephedra alkaloid

Ephedrine was first isolated in 1887 by Nagai from

Ephedra distachya (cf. Ephedra spp.) and was first

introduced into ophthalmology as Mydriaticum

(cf. atropine). Since around 1925, the alkaloid also

been an important asthma medication (Schneider

1974,2:54*).

Ephedrine occurs in almost all species of

ephedra (cf. Ephedra gerardiana, Ephedra sinensis,

Ephedra spp.). Two Malvaceae, Sida acuta Burm.

and Sida rhombifolia 1. (Sida spp.), which are

smoked along the Mexican Gulf Coast as a lTlarijuana

substitute (cf. Cannabis indica), also

contain ephedrine (Schultes and Hoffmann 1992,

56*). Ephedrine is probably present in other

species of Sida as well. Ephedrine has also been

found in Aconitum spp., yew (Taxus bacata L.; cf.

witches' ointments), and khat (Catha edulis)

(Rompp 1995, 1191*; Roth et al. 1994,695*).

Ephedrine has sympathomimetic effects and

causes an increased excretion of the endogenous

neurotransmitter noradrenaline, which is responsible

for the stimulant effects (Kalix 1991). Ephedrine

hydrochloride has potent stimulant effects;

it improves the general mood and may even

induce euphoria. These effects can last up to eight

hours. It is known that "therapeutic overdoses of

ephedrine (Aphetonin) can also cause pronounced

states of excitation combined with sexual arousal"

(Fiihner 1943, 199*). In men, however, ephedrine

induces a temporary state of impotence. Ephedrine

is a popular doping agent for athletes but is

prohibited for this purpose (Korner 1994, 1483*).

There have been reports of "ephedrine addiction"

(Prokop 1968).

Because ephedrine helps reduce swelling of the

mucous membranes, it is a component of rnany

cough syrups (see codeine). Ephedrine suppresses

the effects of alcohol and is administered subcutaneously

to prevent hypotension during anesthesia

(Morton 1977,35*). Between 55 and 75% of ephedrine

is excreted in the urine unchanged (Roth et

al. 1994, 812*). The effective oral dosage is 5 to

10 mg.

The closely related ephedra alkaloids have

similar effects but vary in their potency (Reti 1953). Pseudoephedrine is significantly weaker,

while the related ephedroxanes tend to have

depressant effects (Hikino et al. 1985). Pseudoephedrine

can be used to produce methcathinone,

which in the United States is smoked as "speed" or

snuffed like cocaine (it is also used as a substitute

for cocaine) (Glennon et al. 1987).

Although Catha edulis does contain d- norisoephedrine,

it is not the plant's primary active constituent,

as was previously assumed (Wolfes 1930).

However, cathinoneCathinone, or Benzoylethanamine is a monoamine alkaloid found in the shrub Catha edulis (khat) and is chemically similar to ephedrine, cathine and other amphetamines. Cathinone differs from amphetamine by possessing a ketone oxygen atom on the β position of the side chain., the psychoactive constituent

in khat leaves, is metabolized into ephedrinene

(Brenneisen et al. 1986; Kalix 1991). Norephedrine,

the nor-form (a threo-isomerEach of two or more compounds with the same formula but a different arrangement of atoms in the molecule and different properties.) of ephedrine, lacks

a methyl group on the side chain. Up to 90% of

norephedrine is excreted unchanged (Cho and

Segal 1994, 58).

Removing the hydroxyl group from the

ephedrine molecule by either reduction or ~hydroxylation

yields amphetamine (Cho and Segal

1994,57). Amphetamine is one of the most highly

effective stimulants known. Numerous derivatives

have been developed from amphetamine (e.g.,

Ritalin, methamphetamine, MDMA; cf. herbal

ecstasy). In addition to their stimulating effects,

several of these substances also induce

empathogenic and even hallucinogenic effects

(Cho and Segal 1994). Amphetamine has not yet

been found to occur in nature.
Commercial Forms and Regulations

Ephedrine is available as anhydrous ephedrine

(ephedrinum anhydricum), ephedrine hemihydrate,

or (most often) ephedrine hydrochloride

([ +] -ephedrine-HCL). Ephedrine and ephedrine

preparations (medicinal drugs) require a prescription.

Because ephedrine is now regarded as a

precursor substance for the illegal synthesis of

MDMA, it is only rarely prescribed and is strictly

controlled. In Germany, only combination preparations

(cough medicines) in which a single

dosage may not exceed 10 mg of ephedrine can be

purchased in a pharmacy without prescription

(Roth et al. 1994, 812*). A number of high-profile

cases, including one in which a young professional

athlete died after ingesting ephedrine before training,

resulted in the banning of most ephedrine

preparations in the United States in 2004.

Literature

See also the entries for Catha edulis, Ephedra

gerardiana, Ephedra sinica, and Ephedra spp.

Brenneisen, R., S. Geisshusler, and X. Schorno. 1986.

Metabolism of cathinoneCathinone, or Benzoylethanamine is a monoamine alkaloid found in the shrub Catha edulis (khat) and is chemically similar to ephedrine, cathine and other amphetamines. Cathinone differs from amphetamine by possessing a ketone oxygen atom on the β position of the side chain. to (-)-norephedrine

and (-)-norpseudoephedrine. Journal of

Pharmacy and Pharmacology 38:298-300.

Cho, Arthur K., and David S. Segal, eds. 1994.

Amphetamine and its analogs:

Psychopharmacology, toxicology and abuse. San

Diego: Academic Press.

Costa, E., and S. Garattini, eds. 1970. Amphetamine

and related compounds. New York: Raven Press.

Glennon, R., M. Yousif, N. Naiman, and P. Kalix.

1987. Methcathinone, a new and potent

amphetamine-like agent. Pharmacol. Biochem.

Behav.26:547-51.

Hikino, Hiroshi, Kuniaki Ogata, Yoshimasa

Kasahara, and Chohachi Konno. 1984.

Pharmacology of ephedroxanes. Journal of

Ethnopharmacology 13:175-9l.

Hofmann, H., K. Opitz, and H. J. Schnelle. 1955. Die

Wirkung des nor-c-Ephedrins. ArzneimittelForshung

5:367-70.

Kalix, P. 1991. The pharmacology of psychoactive

alkaloids from Ephedra and Catha. Journal of

Ethnopharmacology 32:201-8.

Panse, E, and W. Klages. 1964. Klinischpathologische

Beobachtungen bei chronischem

MiBbrauch von Ephedrin. Archiv fur Psychiatrie

und Neurologie 206:69 ff.

Prokop, H. 1968. Halluzinose bei Ephedrinsucht. Der

Nervenarzt 1968:71 ff.

Reti, L. 1953. Ephedra bases. In The alkaloids:

Chemistry and physiology, ed. R. H. E Manske

and H. L. Holmes, 339-62. New York: Academic

Press.

Wolfes, 0.1930. Uber das Vorkommen von dNorisoephedrin

in Catha edulis. Archiv der

Pharmazie 268:81-83.

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