Ensing, Jacob Geert

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   University of GroningenComposition and characterization of illicit cocaine seized at The Netherlands AntillesEnsing, Jacob GeertIMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite fromit. Please check the document version below.Document VersionPublisher's PDF, also known as Version of recordPublication date:1990Link to publication in University of Groningen/UMCG research databaseCitation for published version (APA):Ensing, J. G. (1990). Composition and characterization of illicit cocaine seized at The Netherlands Antilles.s.n.CopyrightOther than for strictly personal use, it is not permitted to download or to forward/distribute the text or part of it without the consent of theauthor(s) and/or copyright holder(s), unless the work is under an open content license (like Creative Commons).The publication may also be distributed here under the terms of Article 25fa of the Dutch Copyright Act, indicated by the “Taverne” license.More information can be found on the University of Groningen website: https://www.rug.nl/library/open-access/self-archiving-pure/taverne-amendment.Take-down policyIf you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediatelyand investigate your claim.Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons thenumber of authors shown on this cover page is limited to 10 maximum.Download date: 08-06-2022SI]I{HARYThe coca shrub,  Erythroxylum coca,  is  growing mainly in the rsarmand  rno i s t  va l l eys  o f  t he  Andes  moun ta i ns .  F rom anc ien t  t imes ,  t hel eaves  o f  t he  coca  sh rub  have  been  used  f o r  med i c i ne  as  we l l  asfo r  p l easu re .  I n  t he  m id  1800 ' s  t he  ma in  ac t iwe  subs tance  wasisolated f rom the coca leaves and th is substance was ca11ed"coca ine "  .  Because  o f  i t s  anes the t i c  p rope r t i es ,  coca ine  wassuccess fu l l y  app l i ed  du r i ng  su rge ry ,  bu t  i t s  use  was  l a t e rove r t aken  by  syn the t i c  anes the t i c s .  Th rough  t he  yea rs ,  howeve r ,c o c a i n e  d e v e l o p e d  a n  e n o r m o u s  p o p u l a r i t y  a s  a n  i l l i c i t  d r u g .Du r i ng  t he  c l andes t i ne  coca ine  p rocess ing ,  mo re  o r  l ess  c rudec o c a i n e  b a s e  i s  f i r s t  o b L a í n e d ,  w h i  I e  a  c o c a i n e  s a l t  ( m o s t l ycoca ine .HC l )  can  be  f o rmed  i n  a  subsequen t  r e f i ne r y  s t ep .  "C rack "re fe r s  t o  a  mo re  re f i ned  f o rm  o f  coca ine -base  (mo re  t han  90 *c o c a i n e ) ,  w h i c h  i s  u s u a l l y  p r e p a r e d  f r o m  c o c a i n e . H C l .  C o c a i n e -base is  norrnal ly  smoked and i ts  ef fects appear to be much hígherand  more  add i c t i ve  t han  t hose  ob ta i ned  a f t e r  t he  sno r t i ne  o fcoca ine  .  HC1  .I n  t he  1980 ' s  bo th  t he  i l l ega l  t r ade  and  t he  use  o f  coca ine  basei n c r e a s e d  d r a s t i c a l l y  i n  T h e  N e t h e r l a n d s  A n t i 1 1 e s .  A s  a  r e s u l L ,mo re  c rude  coca ine  samp les  we re  subm i t t ed  t o  ou r  l abo ra to r y .  Th i sa1  I  owed  us  t o  t ake  a  c l ose r  I  ook  a t  t he  accompany ing  m ino ralkalo ids in the samples,  some of  which having an unknowní d e n L i L y  a L  c h a c  t i m e .  B e c a u s e  o f  c h e i r  p e r s i s c i n g  p r e s e n c e  Í nthe  i l l i c i t  coca ine ,  t he  i den [ i f i ca t i on  o f  t he  na tu ra l  congene rsí s  o f  g rea t  impo r tance  i n  o rde r  t o  ge t  mo re  i ns i gh t  abou t  t heo r i g i n  o f  L h e  i l l i c i t  c o c a i n e .  T h e  b o t a n i c a l  b a c k g r o u n d ,  t h eg row ing  a rea ,  t he  na tu re  o f  t he  i l l i c i t  p roduc t i on  p rocess  e t c .nay  be  re f l ec ted  t o  some  ex ten t  i n  t he  cha rac te r i s t i c s  o f  i l l i c i tc o c a i n e .  T h i s  p r o m p t e d  u s  t o  e s t a b l i s h  t h e  i d e n t i t y  o f  L h e s em ino r  a l ka l o i ds  encoun te red .In Chapter 2 the unknown minor a lkalo ids,  v is ib le dur ing TLCana l ys i s ,  a re  desc r i bed  and  í nves t i ga ted .  The  subs tances  gavei somer i za t i on  du r i ng  l r o r k -up ,  p roduc ing  con fus i ng  ana l y t i ca lr esu l t s ,  wh i ch  pa r t l y  appea red  t o  be  due  t o  deco rnpos i c i on .  A f t e ri nves t i ga t i ng  ex i s t i ng  s i n i l a r i t i e s  w i t h  known  coca ine  congene rs ,t he  subs tances  we re  i den t i f i ed  as  t r ux i l l i nes :  Fo r  t he  f i r s t  t ime104farmthe, I e di lerTET ,rudeack"90rine -ghert o fbaseThisrinorinouTle i n,nêÍsthei c i tthey were observed,  isolated and ident i f ied usíng TLC. The spotwith the highest abundance showed the same retention behaviour asa very recent ly  obtained reference sample of  o- t ruxi l l ine.Truxi l l ines are bui l t  up f rom two 1-nethylecgonine moiet ies,which are connected through an acid.  This acid may be ei thert ruxi l l ic  or  t ruxin ic acid.  The t ruxi l l ines can also beconsidered as the dinerÍzat ion producc of  two molecules ofc innamoylcocaine,  in whÍch the 2X2 carbon atoms at  the doublebonds in the c innamic acid moiety form a 4-membered r ing.Al though the possib le existence of  the t ruxi l l ines was postulatedmore than 100 years ago,  these substances had not  yeÈ beeniden t i f i ed  un t i l  ve r y  r ecen t l y .  I t  has  been  sugges ted  t ha tt ruxin ic acid may exist  in 6 and t ruxi l l ic  acid in 5 isomericforms. However,  we bel ieve that  s ince there are 4 addi t ionalenant iomeric st ructures for  t ruxin ic acid,  the tota l  nurnber ofposs ib l e  t r ux i l l i nes  i s  15 .  Because  t he  t r ux i l l i nes  a re  f o rmed  i nthe coca 1eaf ,  their  presence as wel l  as their  quant i tat iveprof i le in the i l l ic i t ly  produced cocaine may furnish importantinformat ion about i ts  background.Chapter 3 descr ibes the detect ion and isolat ion of  3 unknowncongeners,  observed dur ing gas chromatographic analysis ofi l l i c i t  coca ine .  Once  i so l a ted .  t he i r  i den t iÈ i es  we re  es tab l i shedÈo be norcocaine,  N-formylnorcocaine and N-benzoylnorecgonineme thy l  es te r ,  r espec t i ve l y .The f i rs t  two substances menËioned can be considered as oxidat ionproducts of  cocaine,  whereas the laËter rnay be a t ransformat ionproduct  of  norcocaine.  The re lat ive amount of  N-benzoylnorecgonine nethyl  ester  Ís  dependent on the pH dur ing theproduct ion.  We qrere the f i rs t  to detect  these N-subst i tutedsubscances  i n  i l l i c i t  coca ine ,  wh i l e  no t i c i ng  t ha t  N - f o rmy l -norcocaine even never has been descr ibed.  Because oxidat ion(bleaching) Ís  one of  the rout inely performed steps dur ing theprocessing of  i l l ic i t  cocaine,  i t  is  very conceivable that  th isstep is  responsible for  the presence of  the 3 congeners.  We couldprove that  they can be formed by oxidat ion of  pure cocaine underl abo ra to r y  cond iÈ ions .  The i r  p resence  i n  i l l i c i t  coca ine  i svar iable and so these substances are verv valuable for  thecha rac te r i za t i on  o f  coca ine  samp les .TLCr,ave.ca1r t e rÍ S 'ineIn the fourth ChaPter an approach is  being presented for  thef i nge rp r i n t i ng  o f  coca ine  samp les ,  i ' e '  che  cha rac te r i zaË ion  bymeans of  the minor const i tuents.  Fi rst ,  the var ious cocainecongeners are evaluated for  their  use as parameEer for  cocainecharacter izat ior i .  Subsequent ly,  a GC analysis is  developed'  whichenab led  us  t o  de tec t ,  bes ides  coca ine ,  6  congene rs  i n  aquant i tat ive manner,  and their  abundance l tas exPressed relat iveto the most prominent congener present in the sample underinvescigat ion.  Ïhe resui t ing Parametsers could then be expressedg raph i ca l l y  i n  so - ca l l ed  p i c t og rams '  o r  numer i ca l l y '  I n  t o t a l '  71saurples were examined by th is f ingerpr int ing approach'  Thesesamples were col lecEed over a few years and assurned to beunrelated.  The resul ts of  the GC analysis was surpr is ing:  A fewsamp les  showed  s im i l a r i t i e s  i n  t he i r  f i nge rp r i n t s '  whe reas  t hela rge  ma jo r i t y  showed  no  s im i l a r i t y  a t  a l l '  Th i s  i s  exemp l i f i edby  a  subd i v i s i on  o f  t he  ana l yzed  samp les  i n  d i f f e ren t  ca tègo r i es 'based on the number and types of  congeners found'  According tothese observat ions i t  is  c lear that  the method wi l l  be veryuse fu l  f o r  t he  cha rac te r i za t i on  o f  i 1 l - i c i t  coca ine 'Addi t ional ly  i l lustrat ive is  the example of  2 cocaine samplespossessing Ëhe same f ingerpr int  and also hawing the same cocaÍnebase content .  One sample or ig inated f rom a cocaine dealer  and theother one f rorn a user.  The thus deternined s imi lar i ty  gavevaluable support  to the forensic invest igat ion 'The f i f th chapter  star ts wi th a d iscussion on the format ion oft he  na tu ra l  congene rs  i n  t he  coca - l ea f :  T ropacoca ine '  c Í s -  andtrans'  c innamoylcocaine,  and the t ruxi l l ines '  Especia l ly  theformat ion of  the t ruxi l - l ines is  not  fu11y understood at  themoment.  However,  the presence of  the natural  congeners can serveto prove the natural  or ig in of  the cocaine 'Cocaine may also be prepared synthet ical ly  but  such products maydist inguish i tsel f  f rom natural  cocaine by the Presence of  thed i a s t e r e o i s o m e r s  p s e u d o - ,  a l l o - ,  a n d  a l l o p s e u d o c o c a i n e ,respec t i ve lY .Based on the techniques which are descr ibed in the foregoingChap te r s ,  a  p rocedu re  f o r  che  cha rac te r i za t i on  o f  i l l i c i t  coca ineis suggested.  This procedure is  based on the or ig in and contentof  the cocaine,  the presence of  natural  congeners ( t ruxi l l inesand GC parameters) ,  the presence of  synthet ic  lsomers '  as wel l  as106rr thelon byocaÍnercalnewhichÍ n aLativeunder:essed1 1 ,  7 1ïhese:o beA fews theif iedr l e s ,1g toverynples:aÍneI thegaven o frdthetheervenaytheine,ringrÍne:entLnes. a sthe presence of adulterat ion.since every batch of cocaine possesses i ts own unique character,the characterizatron of ' l ' ic i t  cocaine may provide importantinformatlon concerning its background, and may offer valuablecrues regarding the i l 'egal production method and transportat ionrou tes .Ïhe value of the proposed nethodology for the latter tvo areasshould be further establÍshed, although i t  is crear that wÍth theidentl f icat ion of the cocaine congeners, together r.7ith the GCflngerprint ing approach, a nerÍ research area is created for thecharac ter iza t ion  o f  i l l i c i t  coca ine .IO7

Composition and characterization of illicit cocaine seized at The Netherlands Antilles

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Composition and characterization of illicit cocaine seized at The Netherlands Antilles

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