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Amphetamine
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!D
"D"A
"ethamphetamine
!al#ia di#inorum
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%olatile substances
&lossary
Amphetamine
Chemistry
Physical form
Pharmacology
!ynthesis and precursors
"ode of use
'ther names
Analysis
(ypical purities
Control status
Pre#alence
!treet price
"edical use
Bibliography
Further reading
!)*(+!, 'FD(
A synthetic substance- *ormally seen as a .hite po.der, it acts as a stimulant of the
central ner#ous system /C*!0- )t is belie#ed that amphetamine .as first manufactured in
the 1223s by the &erman chemist euckart, although e#idence for this is lacking- )t
appears that, as in the case of methamphetamine, systematic studies of its chemistry did
not come about until the early t.entieth century- Amphetamine has some limited
therapeutic use, but most is manufactured in clandestine laboratories in +urope- )t is
under international control and closely related to methamphetamine-
Chemistry
Amphetamine /CA!4533467480 is a member of the phenethylamine family, .hich
includes a range of substances that may be stimulants, entactogens or hallucinogens-
(hus, amphetamine is *,94methylphenethylamine-
According to ):PAC, the fully systematic name is *,94methylbenzeneethanamine- (he
asymmetric 94carbon atom gi#es rise to t.o enantiomers- (hese t.o forms .ere
pre#iously called the ;<=4 or l4stereoisomer and the ;>=4 or d4stereoisomer, but in modern
usage are defined as the ?4 and !4stereoisomers-
"olecular structure
"olecular formula@ C8H15*
"olecular .eight@ 15A-7
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Physical form
Amphetamine base is a colourless #olatile oil insoluble in .ater- (he most common salt
is the sulfate /CA!463415480@ a .hite or off4.hite po.der soluble in .ater- )llicit products
mostly consist of po.ders- (ablets containing amphetamine may carry logos similar to
those seen on "D"A and other ecstasy tablets-
Amphetamine!)*(+!, 'FD(
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Pharmacology
Amphetamine is a C*! stimulant that causes hypertension and tachycardia .ith feelings
of increased confidence, sociability and energy- )t suppresses appetite and fatigue and
leads to insomnia- Follo.ing oral use, the effects usually start .ithin 53 minutes and last
for many hours- ater, users may feel irritable, restless, anBious, depressed and
lethargic- )t increases the acti#ity of the noradrenaline and dopamine neurotransmitter
systems- Amphetamine is less potent than methamphetamine, but in uncontrolled
situations the effects are almost indistinguishable- (he !4isomer has greater acti#ity than
the ?4isomer- )t is rapidly absorbed after oral administration- After a single oral dose of
13 mg, maBimum plasma le#els are around 3-37 mgC- (he plasma half4life #aries from D
to 17 hours and is dependent on the urinary pH@ alkaline urine decreases the rate of
elimination- A maEor metabolite is 14phenyl474propanone, .ith smaller amounts of D4
hydroByamphetamine- Analysis of amphetamine in urine is confounded because it is a
metabolite of methamphetamine and certain medicinal products- Acute intoBication
causes serious cardio#ascular disturbances as .ell as beha#ioural problems that include
agitation, confusion, paranoia, impulsi#ity and #iolence- Chronic use of amphetamine
causes neurochemical and neuroanatomical changes- Dependence F as sho.n by
increased tolerance F results in deficits in memory and in decision4making and #erbal
reasoning- !ome of the symptoms resemble those of paranoid schizophrenia- (hese
effects may outlast drug use, although often they resol#e e#entually- )nEection of
amphetamine carries the same #iral infection hazards /e-g- H)% and hepatitis0 as are
found .ith other inEectable drugs such as heroin- Fatalities directly attributed to
amphetamine are rare- (he estimated minimum lethal dose in non4addicted adults is 733
mg-
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!ynthesis and precursors
(he most common route of synthesis is by the euckart method-(his uses /P7P, B"K,
phenylacetone0 and reagents such as formic acid, ammonium formate or formamide to
yield a racemic miBture of the ?4 and !4enantiomers- A much less common, but
stereoselecti#e, method is by reduction of the appropriate diastereoisomers of
norephedrine or norpseudoephedrine- (hese precursors /14phenyl474propanone,
norephedrine and norpseudoephedrine0 are listed in (able ) of the :nited *ations 1822
Con#ention Against )llicit (raffic in *arcotic Drugs and Psychotropic !ubstances- (he
corresponding +: legislation is set out in Council ?egulation /++C0 *o 56GGC83 /as later
amended0, .hich go#erns trade bet.een the +: and third countries-
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"ode of use
Amphetamine may be ingested, snorted and, less commonly, inEected- :nlike the
hydrochloride salt of methamphetamine, amphetamine sulfate is insufficiently #olatile to
be smoked- Hhen ingested, a dose may #ary from se#eral tens to se#eral hundreds of
milligrams depending on the purity-
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'ther names
(he term amfetamine /the )nternational *on4Proprietary *ame@ )**0 refers to a racemic
miBture of the t.o enantiomers- Amfetamine is also the name reIuired by Directi#es
6AC6AC++C and 87C7GC++C for the labelling of medicinal products .ithin the +:-
DeBamfetamine is the )** for the /!04*,94methyl4benzeneethanamine enantiomer also
kno.n as />04*,94methylphenethylamine- e#amfetamine is the /?04*,494
methylbenzeneethanamine enantiomer also kno.n as /<04*,94methylphenethylamine-
'ther commonly used chemical names include 14phenyl474aminopropane and
phenyliospropylamine- Amphetamine is sometimes included .ith methamphetamine and
other less common substances /e-g- benzphetamine0 under the generic heading of
JamphetaminesK- Hundreds of other synonyms and proprietary names eBist /see, for
eBample, http@CC...-chemindustry-comCchemicalsC13A577-html0- J!treetK terms include
speed, base and .hizz-
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Analysis
(he "arIuis field test produces an orangeCbro.n coloration- (he !imon test produces a
red coloration that .ill distinguish amphetamine /a primary amine0 from secondary
amines such as methamphetamine /blue coloration0- (he mass spectrum sho.s little
structure .ith a maEor ion at mCz L DD- )dentification by gas chromatography<mass
spectrometry can be impro#ed by *4deri#atisation, e-g- using carbon disulfide to form the
isothiocyanate- :sing gas chromatography, the limit of detection in urine is M13 NgC-
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(ypical purities
(he purity of po.ders #aries considerably across +urope- (he mean retail purity of
amphetamine in 7311 ranged from A O /!lo#enia0 to 72 O /the *etherlands0 /(able
PPP42, part /i00- (ablets may contain up to D3 mg of the acti#e drug- '#er the period
7336<11 the purity of amphetamine has fallen in 1G countries and increased in D /)taly,
Portugal, !lo#akia and Hungary0 amongst those pro#iding sufficient information for trend
analysis- )n +urope, the most common cutting agents are caffeine, glucose and other
sugars, less commonly ephedrine or ketamine-
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Control status
(he ?4 and !4enantiomers /le#amfetamine and deBamfetamine respecti#ely0 as .ell as
the racemate /a A3@A3 miBture of the ?4 and !4stereoisomers0 are listed in !chedule )) of
the :nited *ations 18G1 Con#ention on Psychotropic !ubstances-
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Pre#alence
Among young adults /1A4 to 5D4year4olds0, lifetime pre#alence of amphetamines use
#aries considerably bet.een countries, from 3-1 O to 17-D O, .ith a .eighted +uropean
a#erage of A-A O /(able &P!41, part /iii00- ast year use of amphetamines in this age
group ranges from 3 O to 5-8 O, .ith most countries reporting pre#alence le#els of 3-A<
7-3 O- )t is estimated that about 1-G million /1-5 O0 young +uropeans ha#e used
amphetamines during the last year- /(able &P!47, part /ii00-
Among 1A4 to 164year4old school students, lifetime pre#alence of amphetamines use
ranged from 1 O to G O in the 7D +: "ember !tates and *or.ay .ith +!PAD sur#eys
in 7311- 'nly Belgium, Bulgaria and Hungary reported pre#alence le#els of more than D
O /(able +P+473 part /i00-
?outine monitoring of amphetamine use among the general population in +urope does
not distinguish amphetamine from methamphetamine, use of .hich has historically been
restricted to the Czech ?epublic and, more recently, !lo#akia-
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!treet price
)n 7311, mean price of amphetamine at consumer le#el ranged bet.een +:? 2
/Belgium0 to 71 /!.eden0 per gram in +"CDDA reporting countries reporting information
/(able PPP4D, part /i00- "ean retail prices of amphetamines fell /1A O0 o#er the period
7336<11 in +: countries reporting sufficient data for trend analysis /Figure PPP410-
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"edical use
Amphetamine has occasional therapeutic use in the treatment of narcolepsy and
attention deficit hyperacti#ity disorder /ADHD0-
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Bibliography
)#ersen, - /73360, !peed, +cstasy, ?italin@ the !cience of Amphetamines, 'Bford
:ni#ersity Press, 'Bford-
King, - A- and "cDermott, !- /733D0, JDrugs of abuseK, in@ "offat, A- C-, 'sselton, "- D-
and Hiddop, B- /eds-0 Clarke$s Analysis of Drugs and Poisons, 5rd edn, %ol- 1, pp- 5G<
A7, Pharmaceutical Press, ondon-
"offat, A- C-, 'sselton, "- D- and Hiddop, B, /eds-0 /733D0, Clarke$s Analysis of Drugs
and Poisons, 5rd edn, %ol- 7, Pharmaceutical Press, ondon-
:nited *ations /73360, "ultilingual Dictionary of *arcotic Drugs and Psychotropic
!ubstances under )nternational Control, :nited *ations, *e. Pork-
:nited *ations /73360, ?ecommended "ethods for the )dentification and Analysis of
Amphetamine, "ethamphetamine and their ?ing4!ubstituted Analogues in !eized
"aterials /re#ised and updated0, "anual for :se by *ational Drug (esting aboratories,
:nited *ations, *e. Pork-
:nited *ations 'ffice on Drugs and Crime /73350, +cstasy and Amphetamines &lobal
!ur#ey 7335, :nited *ations 'ffice on Drugs and Crime, %ienna
/http@CC...-unodc-orgCpdfCpublicationsCreportQatsQ7335438475Q1-pdf0-
:nited *ations 'ffice on Drugs and Crime /733D0, Horld Drug ?eport 733D, %ol- 1@
Analysis, :nited *ations 'ffice on Drugs and Crime, %ienna
/http@CC...-unodc-orgCpdfCHD?Q733DC#olumeQ1-pdf0-
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Further reading
(he follo.ing publications ha#e been proposed for further reading by ?eitoB national
focal points- (hey represent a shortlist of key publications on the drug in each "ember
!tateR-
!hulgin, A- (- and !hulgin, A- /188G0, (ihkal@ the continuation, (ransform Press,
Berkeley-
!hulgin, A- (- and !hulgin, A- /188A0, Pihkal@ a chemical lo#e story, (ransform Press,
Berkeley-
R Please note that not all national focal points ha#e pro#ided references so the list abo#e
cannot be considered eBhausti#e- "oreo#er, inclusion in this list does not imply that the
+"CDDA endorses these publications- (he #ie.s eBpressed in these publications are
those of the authors and do not necessarily reflect those of the +"CDDA-
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About the +"CDDA
(he +uropean "onitoring Centre for Drugs and Drug Addiction /+"CDDA0 is the
reference point on drugs and drug addiction information in +urope- )naugurated in
isbon in 188A, it is one of the +:Ks decentralised agencies- ?ead more SS
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