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Ask Dr. Shulgin Online September 26, 2001

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ARCHIVE:September26,2001 AcaciasandNatural Amphetamine

DearDr.Shulgin:
AreyoufamiliarwithAcaciaberlandieriandA. rigidulawhichwerenotedtocontainvariousa methylbphenethylamines?Doyouhaveany ideasastowhatthebotanicaloriginsofthese structuralcarbonskeletonsmightbe?The literaturecitationsarePHYTOCHEM.(1998), 49(5),1377andPHYTOCHEM.(1997),46(2), 249. Auto

Dr.AlexanderShulgin
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ASKAQUESTION BROWSEARCHIVE RETURNTO CURRENTQ/A

BuyBooksby Alexander&Ann Shulgin!

DearAuto:
IamfamiliarwiththeliteratureconcerningthesetwoWest TexasAcaciaspecies,butnotwiththeplantsthemselves.Ihad boththesePHYTOCHEMISTRYpapersinmyAcaciafilebutI mustadmitthatIhavesomeverymixedfeelingsaboutthem. Whatcaughtmycuriosityimmediatelywasthecasual indifferenceshowntowhatiscertainlyanextraordinary discovery.Here,amongstsome40orsoalkaloidsfoundineach ofthesetwospecies,therewerefiveamphetaminesthathad heretoforebeenthoughttobeinventionsofman.Twoofthese areScheduleIIdrugs,AmphetamineandMethamphetamine. TwoareScheduleIdrugs,N,NDimethylamphetamineand4 Methoxyamphetamine.Andthefifthoneisamajorhuman metaboliteofAmphetamine,4Hydroxyamphetamine.Tomy knowledge,noneofthesehadeverbeforebeenreportedas beingnaturalplantalkaloids.Thisunprecedenteddiscovery elicitedonlyapassinglineofcommentintheearlierofthetwo papers. Myfirstthoughtsastooriginweredirectedtowardsthewell knownnaturalhydroxylatedamphetaminessuchas norephedrine,ephedrineandNmethylephedrine.Iknowthat ephedrineandpseudoephedrine,frequentprecursorsinthe illegalsynthesisofmethamphetamine,canbereducedto methamphetamineasanartifactofanalysis.Thesample insertionconditionsofthegaschromatographcaneffectthis conversion.Butthen,therewasnomentionofanyofthese hydroxylatedalkaloidsasbeingpresentineitherAcacia. Mightacontaminatedroundbottomedflaskhavebeen purchasedatagaragesaleoutsideanabandonedmethlaband servedasthesourceofthese"manmade"compounds? Unlikely,eveninTexas. Evenmoredramatic,oneoftheseamphetamines,the4 Methoxyamphetamine,istheincreasinglynotoriousPMAthatis appearingasoneofthelethal"Ecstasy"offeringsintherave scene. SeveralmonthsagoItriedtocontact,individually,thetwo principalauthors,bybothemailandpersonalsnailmail,andI havereceivednoresponseasyet. Thereiscertainlyprecedentforadrugwhichwasoriginally manmade,tobediscoveredinaplant.N,N Dimethyltryptamine(DMT)wasfirstsynthesizedbyManske,in Canada,inthe1930s.Itwasovertwentyyearslaterthatit wasdiscoveredinaplantfromSouthAmerica.Butsuchan eventusuallyevokesconsiderablecommentary.Hereitseems thatanexcitingstoryisbeingignored.AmImissing something? Dr.Shulgin TermsofUse

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Ask Dr. Shulgin Online September 26, 2001

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