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Aphetonin, efedrina, ephedrin, ephedrine,
ephedrinum, ephetonin, erythro-2-methylaminoI-
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
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"
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
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 yetbeen 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.
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.
Hikino, Hiroshi, Kuniaki Ogata, Yoshimasa
Kasahara, and Chohachi Konno. 1984.
Pharmacology of ephedroxanes. Journal of
Hofmann, H., K. Opitz, and H. J. Schnelle. 1955. Die
Wirkung des nor-c-Ephedrins. ArzneimittelForshung
Kalix, P. 1991. The pharmacology of psychoactive
alkaloids from Ephedra and Catha. Journal of
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
Wolfes, 0.1930. Uber das Vorkommen von dNorisoephedrin
in Catha edulis. Archiv derPharmazie 268:81-83.