DOCSLIB.ORG

Impurity Analysis of MDA Synthesized from Unrestricted Compounds

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Impurity Analysis of MDA Synthesized from Unrestricted Compounds Impurity Analysis of MDA Synthesized from Unrestricted Compounds Katherine Cooper Master of Science (Research) School of Mathematical and Physical Sciences University of Technology Sydney 2019 CERTIFICATE OF AUTHORSHIP/ORIGINALITY I, Katherine Cooper declare that this thesis, is submitted in fulfilment of the requirements for the award of Master of Science (Research), in the School of Mathematical and Physical Sciences at the University of Technology Sydney. This thesis is wholly my own work unless otherwise reference or acknowledged. In addition, I certify that all information sources and literature used are indicated in the thesis. This document has not been submitted for qualifications at any other academic institution. This research is supported by the Australian Government Research Training Program. Production Note: Signature removed prior to publication. Katherine Cooper 16 July 2019 __________________________________ This is a conventional thesis format. pg. ii Acknowledgements I’d like to thank my primary supervisor Scott Chadwick for your no-nonsense, practical, and helpful advice throughout my degree. Thank you for always being available and willing to help someone who started a chemistry degree with very limited organic chemistry knowledge. Your patience and guidance are very much appreciated, and I would not have finished without you. I’d like to thank my secondary supervisor Andrew McDonagh for sharing your knowledge and apparent love for your job. Thank you for your encouragement and reassurance. Your contribution especially regarding NMR interpretation is much appreciated. I’d like to thank Erin Heather for your help with mass spectral interpretation and expertise regarding things you’d only just overcome yourself, as well as your friendly and approachable demeanour. I’d like to thank the laboratory technical staff. Thank you for answering my silly questions while I learn my way around the labs. Thank you for helping me and teaching me with the procedures and interpretation of the various analytical instruments I needed. pg. iii Table of Contents ACKNOWLEDGEMENTS ...................................................................................................................... III TABLE OF CONTENTS .......................................................................................................................... IV LIST OF FIGURES AND TABLES ............................................................................................................ VI LIST OF ABBREVIATIONS ..................................................................................................................... X ABSTRACT ......................................................................................................................................... XI 1. INTRODUCTION .............................................................................................................................. 1 1.1 ILLICIT DRUGS IN SOCIETY ......................................................................................................................... 1 1.2 ILLICIT DRUGS IN AUSTRALIA ..................................................................................................................... 2 1.3 AMPHETAMINE-TYPE STIMULANTS (ATS) .................................................................................................... 7 1.3.1 Effects of ATS Use ....................................................................................................................... 8 1.4 PROFILING ............................................................................................................................................. 9 1.5 ANALYTICAL TECHNIQUES ........................................................................................................................ 10 1.5.1 Fourier Transform Infra-Red Spectroscopy ............................................................................... 10 1.5.2 Gas Chromatography – Mass Spectrometry (GCMS) ................................................................ 11 1.5.3 Nuclear Magnetic Resonance ................................................................................................... 13 1.6 ADDITIONAL TECHNIQUES ....................................................................................................................... 14 1.6.1 Raman Spectroscopy ................................................................................................................ 14 1.6.2 2D- Gas Chromatography ......................................................................................................... 15 1.6.3 Isotope Ratio Mass Spectrometry ............................................................................................. 16 1.7 IMPURITIES .......................................................................................................................................... 16 1.8 PROFILING OF OTHER ILLICIT SUBSTANCES .................................................................................................. 18 1.9 MDA ................................................................................................................................................. 26 1.9.1 Synthesis Routes ....................................................................................................................... 26 1.9.2 Profiling of MDA ....................................................................................................................... 27 1.10 AIMS AND OBJECTIVES ......................................................................................................................... 29 2. MATERIALS AND METHODS ........................................................................................................... 31 2.1 INSTRUMENTATION ............................................................................................................................... 31 2.2 CHEMICALS .......................................................................................................................................... 31 2.3 SYNTHESIS ........................................................................................................................................... 31 2.3.1 Synthesis of MDA HCl from Helional ......................................................................................... 32 2.3.2 Synthesis of MDA HCl from Piperonal ....................................................................................... 33 3. RESULTS ........................................................................................................................................ 35 3.1 SYNTHETIC ROUTES CONSIDERED ............................................................................................................. 35 3.2 CHARACTERISATION PROCEDURE .............................................................................................................. 35 3.3 SYNTHESIS OF MDA FROM HELIONAL ....................................................................................................... 36 3.3.1 Synthesis of 3-Benzo[1,3]dioxol-5-yl-2-methyl-propionaldehyde oxime from helional ............ 36 3.3.2 Synthesis of 3-Benzo[1,3]dioxol-5-yl-2-methyl-propionamide (MMDPPA) from 3- Benzo[1,3]dioxol-5-yl-2-methyl-propionaldehyde oxime .................................................................. 40 3.3.3 Synthesis of MDA free base from MMDPPA ............................................................................. 44 3.4 SYNTHESIS OF MDA FROM PIPERONAL ...................................................................................................... 49 3.4.1 Synthesis of 5-(2-Nitro-propenyl)-benzo[1,3]dioxole from piperonal ....................................... 50 3.4.2 Synthesis of 1-Benzo[1,3]dioxol-5-yl-pronan-2-one (MDP2P) from 5-(2-Nitro-propenyl)- benzo[1,3]dioxole .............................................................................................................................. 51 3.4.3 Synthesis of MDA from 1-Benzo[1,3]dioxol-5-yl-pronan-2-one ................................................ 54 pg. iv 4. DISCUSSION 4.1 EXPERIEMENTAL CONSIDERATIONS ..................................................................... 60 4.2 SYNTHESIS COMPARISON ........................................................................................................................ 62 4.2 IMPURITY ANALYSIS ............................................................................................................................... 63 5. CONCLUSION ................................................................................................................................ 66 5.1 Future Work ................................................................................................................................. 67 APPENDIX A- GAS CHROMATOGRAPHS ............................................................................................. 69 APPENDIX B- NMR SPECTRA .............................................................................................................. 73 APPENDIX C- MASS SPECTRUMS OF THE IMPURITIES FOUND IN 3-BENZO[1,3]DIOXOL-5-YL-2-METHYL- PROPIONALDEHYDE OXIME .............................................................................................................. 76 APPENDIX D- MASS SPECTRUMS OF THE IMPURITIES FOUND IN 3-BENZO[1,3]DIOXOL-5-YL-2-METHYL- PROPIONAMIDE ..............................................................................................................................
Load more

Recommended publications
  • Comparison of the Use of Aqueous and Nonaqueous Buffers in Association with Cyclodextrin for the Chiral Separation of 3,4-Methyl
    3904 Electrophoresis 2005, 26, 3904–3909 Yu-San Huang1 Comparison of the use of aqueous and nonaqueous Chung-Chen Tsai1 Ju-Tsung Liu2 buffers in association with cyclodextrin for the Cheng-Huang Lin1 chiral separation of 3,4-methylenedioxymeth- 1Department of Chemistry, amphetamine and related compounds National Taiwan Normal University, A comparison of the use of aqueous and nonaqueous buffers in association with b-CD Taipei, Taiwan for the chiral separation of (R)- and (S)-3,4-methylenedioxymethamphetamine and 2Forensic Science Center, related compounds is described. The (R)- and (S)-isomers of 3,4-methylenedioxy- Military Police Command, Ministry of National Defense, methamphetamine (MDMA) and its major metabolite 3,4-methylenedioxy- Taipei, Taiwan amphetamine (MDA) were prepared. Under aqueous and nonaqueous buffer condi- tions and based on the CZE and MEKC modes, the order of migration of (R)-MDA, (S)-MDA, (R)-MDMA, and the (S)-MDMA enantioisomers were determined. Several electrophoretic parameters, including the concentration of b-CD (aqueous, 25–60 mM; nonaqueous, 20–150 mM) used in the electrophoretic separation and the amount of organic solvents required for the separation, were optimized. Keywords: Aqueous and nonaqueous buffers; Capillary electrophoresis; Enantioseparation; 3,4- Methylenedioxymethamphetamine DOI 10.1002/elps.200410374 1 Introduction (2)-methamphetamine can also be extracted from a Vicks Inhaler [4] and that (2)-methamphetamine is used 3,4-Methylenedioxymethamphetamine (MDMA) was first in certain prescription drugs [5]. To avoid errors in judg- synthesized (1912) and patented (1914) by Merck Phar- ment, an enantiomeric analysis would be highly desir- maceuticals. The toxicity of MDMA was examined in able.
    [Show full text]
  • Application of High Resolution Mass Spectrometry for the Screening and Confirmation of Novel Psychoactive Substances Joshua Zolton Seither [email protected]
    Florida International University FIU Digital Commons FIU Electronic Theses and Dissertations University Graduate School 4-25-2018 Application of High Resolution Mass Spectrometry for the Screening and Confirmation of Novel Psychoactive Substances Joshua Zolton Seither [email protected] DOI: 10.25148/etd.FIDC006565 Follow this and additional works at: https://digitalcommons.fiu.edu/etd Part of the Chemistry Commons Recommended Citation Seither, Joshua Zolton, "Application of High Resolution Mass Spectrometry for the Screening and Confirmation of Novel Psychoactive Substances" (2018). FIU Electronic Theses and Dissertations. 3823. https://digitalcommons.fiu.edu/etd/3823 This work is brought to you for free and open access by the University Graduate School at FIU Digital Commons. It has been accepted for inclusion in FIU Electronic Theses and Dissertations by an authorized administrator of FIU Digital Commons. For more information, please contact [email protected]. FLORIDA INTERNATIONAL UNIVERSITY Miami, Florida APPLICATION OF HIGH RESOLUTION MASS SPECTROMETRY FOR THE SCREENING AND CONFIRMATION OF NOVEL PSYCHOACTIVE SUBSTANCES A dissertation submitted in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY in CHEMISTRY by Joshua Zolton Seither 2018 To: Dean Michael R. Heithaus College of Arts, Sciences and Education This dissertation, written by Joshua Zolton Seither, and entitled Application of High- Resolution Mass Spectrometry for the Screening and Confirmation of Novel Psychoactive Substances, having been approved in respect to style and intellectual content, is referred to you for judgment. We have read this dissertation and recommend that it be approved. _______________________________________ Piero Gardinali _______________________________________ Bruce McCord _______________________________________ DeEtta Mills _______________________________________ Stanislaw Wnuk _______________________________________ Anthony DeCaprio, Major Professor Date of Defense: April 25, 2018 The dissertation of Joshua Zolton Seither is approved.
    [Show full text]
  • Pharmacology Notebook 1 PDF (Searchable)
    The Shulgin Lab Books December 2012 May 2018 Pharmacology Lab Notes #1 (1960 - 1976) A Bit About This Document: While undertaking the work of investigating the chemistry and pharmacology of many varied psychoactive substances, Alexander “Sasha” Shulgin kept detailed notebooks. His documentation covered not only on his own personal research, but the research of friends and acquaintances. This book, the first of the “Pharmacology” series, represents mostly sub-acute work-ups of various substances and subjective responses by Shulgin and his research group. It covers the time frame of 1960 to 1976. The Creation of This Document: The project to undertake the transcribing of Shulgin’s Lab Books was started in 2008 by a team of volunteers and staff at Erowid, along with members of Team Shulgin. Various books were transcribed without a clear idea of how to present the information as a final product; eventually this format was chosen and a volunteer began work assembling the document. Each page was painstakingly transcribed from scanned images. All the hand-drawn “dirty pictures” (molecule drawings) and graphs were edited from the original scans and combined with drawn-in marks, outlines, and arrows to form this searchable PDF. Most of the names in this document have been redacted and pseudonyms put in their place. Names are presented as much as possible as they were in the original book, for example “Robert Thompson” is also “Robert”, “R.Thompson”, and “RT”. Initials are frequently used, and no two people share names or initials so the reader can keep track of who’s who. Words highlighted in yellow are words that the transcription team could not decipher.
    [Show full text]
  • INTERNATIONAL COLLABORATIVE EXERCISES (ICE) Summary Report
    INTERNATIONAL QUALITY ASSURANCE PROGRAMME (IQAP) INTERNATIONAL COLLABORATIVE EXERCISES (ICE) Summary Report SEIZED MATERIALS 2017/1 INTERNATIONAL QUALITY ASSURANCE PROGRAMME (IQAP) INTERNATIONAL COLLABORATIVE EXERCISES (ICE) Table of contents Introduction Page 2 Comments from the International Panel of Forensic Experts Page 2 NPS reported by ICE participants Page 4 Codes and Abbreviations Page 6 Sample 1 Analysis Page 7 Identified substances Page 7 Statement of findings Page 12 Identification methods Page 23 Summary Page 29 Z- Scores Page 30 Sample 2 Analysis Page 33 Identified substances Page 33 Statement of findings Page 38 Identification methods Page 49 Summary Page 55 Z- Scores Page 56 Sample 3 Analysis Page 60 Identified substances Page 60 Statement of findings Page 66 Identification methods Page 77 Summary Page 83 Z- Scores Page 84 Sample 4 Analysis Page 88 Identified substances Page 88 Statement of findings Page 90 Identification methods Page 96 Summary Page 102 Test Samples Information Samples Comments on samples Sample 1 SM-1 was prepared from a seizure containing 43.1 % (w/w) 3,4-methylenedioxypyrovalerone base. The test sample also contained lactose. Sample 2 SM-2 was prepared from a seizure containing 23.7 % (w/w) Cocaine base. The test sample also contained lactose with methylecgonine, benzoylecgonine and cinnamoyl cocaine as minor components. Sample 3 SM-3 was prepared from a seizure containing 55.7 % (w/w) MDMA. The test sample also contained lactose. Sample 4 SM-4 was a blank test sample prepared from plant material and contained no substances from the ICE menu. Samples Substances Concentrations Comments on substances Sample 1 3,4-Methylenedioxypyrovalerone 43.1 % Lactose 0 % Sample 2 Cocaine 23.7 % Lactose 0 % Sample 3 3,4-Methylenedioxymetamfetamine (MDMA) 55.7 % Lactose 0 % Sample 4 [blank sample] This report contains the data received from laboratories participating in the current exercise.
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 9,034.442 B2 Chang Et Al
    USOO9034442B2 (12) United States Patent (10) Patent No.: US 9,034.442 B2 Chang et al. (45) Date of Patent: *May 19, 2015 (54) STRENGTHENED BOROSILICATE GLASS CO3C 21/002: CO3C 17/30; CO3C 17/32: CONTAINERS WITH IMPROVED DAMAGE CO3C 2217/78; CO3C 2218/111; CO3C 3/04; TOLERANCE C09D 179/08: C09D 161/00; C09D 177/00 USPC ............. 501/53, 55, 68; 428/34.1, 34.4, 34.6, (71) Applicant: Corning Incorporated, Corning, NY 428/410; 215/12.1 (US) See application file for complete search history. (72) Inventors: Theresa Chang, Painted Post, NY (US); Steven Edward DeMartino, Painted (56) References Cited Post, NY (US); Andrei Gennadyevich U.S. PATENT DOCUMENTS Fadeev, Elmira, NY (US); John Stephen Peanasky, Big Flats, NY (US); 2,106,744 A 2f1938 Hood et al. Robert Anthony Schaut, Painted Post, 2.691,548 A 10, 1954 Feucht et al. NY (US); Christopher Lee Timmons, (Continued) Big Flats, NY (US) (73) Assignee: Corning Incorporated, Corning, NY FOREIGN PATENT DOCUMENTS (US) CN 24.83332 Y 3, 2002 (*) Notice: Subject to any disclaimer, the term of this CN 1963650 A 5/2007 patent is extended or adjusted under 35 (Continued) U.S.C. 154(b) by 0 days. OTHER PUBLICATIONS This patent is Subject to a terminal dis claimer. ASTM, "Standard Specification for Glasses in Laboratory Appara tus.” Designation E438-92 (Reapproved 2006). http://enterprise2. (21) Appl. No.: 14/052,048 astm.org/DOWNLOAD/E438-92R06. 1656713-1.pdf.* (22) Filed: Oct. 11, 2013 (Continued) (65) Prior Publication Data US 2014/OO34544A1 Feb. 6, 2014 Primary Examiner — Ellen S Wood (74) Attorney, Agent, or Firm — Dinsmore & Shohl LLP Related U.S.
    [Show full text]
  • Tryptamine Derivatives by Liquid Chromatography–UV Absorption and –Electrospray Ionization Mass Spectrometry
    ANALYTICAL SCIENCES JUNE 2009, VOL. 25 759 2009 © The Japan Society for Analytical Chemistry Simultaneous Separation and Detection of 18 Phenethylamine/ Tryptamine Derivatives by Liquid Chromatography–UV Absorption and –Electrospray Ionization Mass Spectrometry Yao HSIAO,* Ju-Tsung LIU,** and Cheng-Huang LIN*† *Department of Chemistry, National Taiwan Normal University, 88 Sec. 4, Tingchow Road, Taipei, Taiwan **Forensic Science Center, Military Police Command, Department of Defense, Taipei, Taiwan The optimal conditions for the separation and detection of a mixture of 18 phenethylamine/tryptamine derivatives were determined, using liquid chromatography/UV-absorption (LC/UV) and liquid chromatography/electrospray ionization mass spectrometry (LC/ESI MS) methods, respectively. Complete separation could be achieved within ~25 min using gradient elution (A, 0.1% formic acid aqueous solution/pH 2.5; B, acetonitrile). The limit of detection (LOD at S/N = 3) obtained by LC/UV-absorption (absorption wavelength, 280 nm) was in the range from 0.3 to 3 mg/mL. In contrast, when the LC/ESI MS method was used, the LODs for primary, secondary and tertiary amines were in the ranges 0.1 – 3.0, 0.1 – 0.2, and 0.05 – 1.8 mg/mL, respectively. The lower LOD obtained for a tertiary amine can be attributed to the fact that its ionization efficiency (during the ESI process) is better than the others. In order to improve the LOD of a primary/secondary amine, a derivatization procedure was used in which the chemical structure was altered to a secondary/tertiary amine, via a reaction with acetic anhydride. As a result, the LODs for primary/secondary amines could be significantly improved.
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 9,347,961 B2 Karlsen Et Al
    US009347961 B2 (12) United States Patent (10) Patent No.: US 9,347,961 B2 Karlsen et al. (45) Date of Patent: May 24, 2016 (54) TEST KIT FOR THE QUANTITATIVE 2008/0058351 A1* 3/2008 Tung ..................... CO7B 59,002 514,259.3 DETERMINATION OF NARCOTC DRUGS 2008/0287.495 A1 * 1 1/2008 Tung .................... CO7D 317.64 514,321 (71) Applicant: CHIRONAS. Trondheim (NO) 2009.006870.6 A1 3/2009 Freudenschluss ......... C12P1/02 435,713 (72) Inventors: Morten Salihi Karlsen, Trondheim 2009/0093.422 A1* 4/2009 Tung .................... CO7D :S. (NO), Huiling Liu, Trondheim (NO); 2009/0208413 A1* 8, 2009 Reis ..................... CO7D 243/24 Jon Eigill Johansen, Tiller (NO) 424f1.81 2009/0291 152 A1* 1 1/2009 Tung .................... CO7D 417/12 (73) Assignee: CHIRONAS. Trondheim (NO) 424,722 2010/0130723 A1* 5, 2010 Latham .................... CO7K 1/10 c - r - 530/342 ( ) Notice: Subject tO any disclaimer, the term of this 2012. O156139 A1 ck 6, 2012 Katz-Birull . A61 K 31 136 patent is extended or adjusted under 35 4249.3 U.S.C. 154(b) by 0 days. 2014/0227792 A1* 8, 2014 Johansen ............. A61K 31,137 436.8 (21) Appl. No.: 14/414,146 FOREIGN PATENT DOCUMENTS (22) PCT Filed: Jul.19, 2013 EP 2551675 A1 1, 2013 JP 2008266.149 A * 11 2008 (86). PCT No.: PCT/EP2013/065.323 WO 2004.056398 A1 T 2004 WO 2006091885 A2 8, 2006 S371 (c)(1), WO 201102415.6 A1 3, 2011 (2) Date: Jan. 12, 2015 OTHER PUBLICATIONS (87) PCT Pub. No.: WO2014/013063 Thomas Berget al: “C labelled internal standards.A solution to mini PCT Pub.
    [Show full text]
  • Armenia Criminal Code As of 23 May 2018
    Strasbourg, 12 March 2021 CDL-REF(2021)022 Opinion No. 1026 / 2021 Engl. only EUROPEAN COMMISSION FOR DEMOCRACY THROUGH LAW (VENICE COMMISSION) ARMENIA CRIMINAL CODE AS OF 23 MAY 2018 (*) (*) Translation provided by the Armenian authorities This document will not be distributed at the meeting. Please bring this copy. www.venice.coe.int CDL-REF(2021)022 - 2 - CRIMINAL CODE OF THE REPUBLIC OF ARMENIA (Adopted on 18 April 2003) GENERAL PART SECTION 1 CRIMINAL STATUTE CHAPTER 1 TASKS AND PRINCIPLES OF CRIMINAL LEGISLATION Article 1. Criminal legislation of the Republic of Armenia 1. The criminal legislation of the Republic of Armenia consists of this Code. New laws that envisage criminal liability shall be included in the Criminal Code of the Republic of Armenia. 2. The Criminal Code of the Republic of Armenia is based on the Constitution of the Republic of Armenia and on principles and norms of international law. Article 2. Tasks of the Criminal Code of the Republic of Armenia 1. Tasks of the Criminal Code of the Republic of Armenia shall be as follows: to protect human and citizens’ rights and freedoms from criminal encroachments, rights of legal entities, property, environment, public order and security, constitutional order, peace and safety of humanity, as well as to prevent crimes. 2. For the purpose of implementing these tasks, the Criminal Code of the Republic of Armenia stipulates the ground for criminal liability and the principles of criminal legislation, determines what acts dangerous to the public are deemed to be crimes and defines the types of punishment and other criminal-law enforcement measures for commission thereof.
    [Show full text]
  • Synthetic Cathinones Are B-Keto (‘Bk’) Analogs of Amphetamine
    Why am I here today? The Drugs Named In These Books PIHKAL TIHKAL The Essential Amphetamines • PMA (para-methoxy-amphetamine) • 55 Chemicals, all variations • 2,4-DMA (2,4-dimethoxy-amphetamine) • 3,4-DMA (3,4-dimethoxy-amphetamine) of Tryptamines, Among • MDA (3,4-methylenedioxy-amphetamine) • MMDA (3-methoxy-4,5-methylendioxy-amphetamine) them, • MMDA-3a (2-methoxy-3,4-methylendioxyamphetamine) • MMDA-2 (2-methoxy-4,5-methylendioxyamphetamine) • TMA (3,4,5-trimethoxyamphetamine) – DMT • TMA-2 (2,4,5-trimethoxyamphetamine) • DMMDA (2,5-dimethoxy-3,4-methylenedioxyamphetamine) – LSD • DMMDA-2 (2,3-dimethoxy-4,5-methylenedioxyamphetamine) • TeMA (2,3,4,5-tetramethoxyamphetamine) The Magical “Half Dozen” • Mescaline (3,4,5-trimethoxyphenethylamine) • DOM (2,5-dimethoxy-4-methylamphetamine, DOM being short for desoxy methyl, referring to the removal of the Oxygen atom from the Methoxy group on the "4" carbon. • 2C-B (2,5-dimethoxy-4-bromophenethylamine) • 2C-E (2,5-dimethoxy-4-ethylphenethylamine) • 2C-T-2 (2,5-dimethoxy-4-ethylthiophenethylamine) • 2C-T-7 (2,5-dimethoxy-4-(N)-propylthiophenethylamine) 2-CB • Rusko • Venus • Bees • Nexus • Spectrum 2-cb Trip Report 2-CE- “EUROPA” 2C-E Dosages 2C-B Dosages Oral Threshold 2 - 5 mg Oral Light 5 - 10 mg Threshold 2 - 5 mg Common 10 - 15 mg Strong 15 - 30 mg Light 5 - 15 mg Heavy 25 - 40 mg Onset : 20 - 90 minutes Common 15 - 30 mg Duration : 6 - 10 hours Strong 25 - 50 mg Normal After Effects : 2 - 6 hours 2C-E Dosages Insufflated (tentative) Oral 2C-I Dosages Threshold 1 mg Light 1 - 3 mg Threshold
    [Show full text]
  • Chiral Separation of 3,4-Methylenedioxymeth- Amphetamine and Related Compounds in Clandestine Tablets and Urine Samples by Capil
    Electrophoresis 2003, 24, 1097–1104 1097 Yu-San Huang1 Chiral separation of 3,4-methylenedioxymeth- Ju-Tsung Liu2 Li-Chang Lin1 amphetamine and related compounds in Cheng-Huang Lin1 clandestine tablets and urine samples by capillary 1Department of Chemistry, electrophoresis/fluorescence spectroscopy National Taiwan Normal University, The R-(2)- and S-(1)-isomers of 3,4-methylenedioxymethamphetamine (MDMA) and Taipei, Taiwan 2Military Police School, its metabolite 3,4-methylenedioxyamphetamine (MDA) were prepared, identified by Command of the Army Force gas chromatography/mass spectrometry (GC/MS) and then used as standards in of Military Police, a series of capillary electrophoresis (CE) experiments. Using these R-(2)- and S-(1)- Department of Defense, isomers, the distribution of (RS)-MDA and (RS)-MDMA stereoisomers in clandestine Wuku, Taipei, Taiwan tablets and suspect urine samples were identified. Several electrophoretic parameters, such as the concentration of b-cyclodextrin used in the electrophoretic separation and the amount of organic solvents required for the separation, were optimized. Keywords: Capillary electrophoresis / Chiral separation / Clandestine tablet / Designer drug / Gas chromatography-mass spectrometry / Urine EL 5350 1 Introduction and identification of enantiomers would be helpful in clinical and forensic analysis because different enantio- The increasing distribution of 3,4-methylenedioxymeth- mers have different pharmacological activities. Hence, it amphetamine (MDMA) derivatives in the illicit market has would be desirable to develop an assay that is capable became a serious social problem. 3,4-Methylenedioxy- of rapidly separating and identifying these enantiomers amphetamine (MDA), which is the major metabolite of in clandestine tablets and in biological fluids such as urine CE and CEC MDMA, along with N,N-dimethyl-3,4-methylenedioxy- or blood more accurately.
    [Show full text]
  • Us 2019 / 0142851 A1
    US 20190142851A1 ( 19) United States (12 ) Patent Application Publication ( 10) Pub . No. : US 2019 /0142851 A1 CHADEAYNE (43 ) Pub. Date : May 16 , 2019 ( 54 ) COMPOSITIONS COMPRISING A 2017 , provisional application No. 62/ 587, 410 , filed PSILOCYBIN DERIVATIVE AND A on Nov. 16 , 2017 , provisional application No . 62 /587 , CANNABINOID 395 , filed on Nov . 16 , 2017 . (71 ) Applicant: CaaMTech , LLC , Issaquah , WA (US ) Publication Classification (51 ) Int . Ci. ( 72 ) Inventor: Andrew R . CHADEAYNE , Issaquah , A61K 31/ 675 ( 2006 .01 ) WA (US ) A61K 31 / 4045 (2006 . 01 ) A61K 31/ 4406 ( 2006 .01 ) (21 ) Appl. No. : 16 / 192, 736 A61K 31/ 05 (2006 . 01) A61K 31 / 192 (2006 .01 ) ( 22 ) Filed : Nov . 15 , 2018 A61K 31 /353 ( 2006 . 01) (52 ) U . S . CI. Related U . S . Application Data CPC .. A61K 31/ 675 ( 2013 .01 ) ; A61K 31/ 4045 (60 ) Provisional application No . 62/ 613 , 360 , filed on Jan . (2013 . 01 ) ; A61K 31/ 353 (2013 .01 ) ; ACIK 3 , 2018 , provisional application No. 62 /609 , 115 , filed 31/ 05 (2013 . 01 ) ; A61K 31/ 192 (2013 . 01 ) ; on Dec . 21 , 2017 , provisional application No . 62/ 598 , A61K 31 /4406 ( 2013 . 01 ) 767, filed on Dec . 14 , 2017 , provisional application No . 62 /595 ,336 , filed on Dec . 6 , 2017 , provisional ( 57 ) ABSTRACT application No . 62 / 595 , 321 , filed on Dec . 6 , 2017 , This disclosure pertains to new compositions and methods provisional application No . 62 /593 ,021 , filed on Nov . comprising a psilocybin derivative . In one embodiment, the 30 , 2017 , provisional application No . 62 / 592, 320 , compositions disclosed herein are used for a method of filed on Nov . 29 , 2017 , provisional application No .
    [Show full text]
  • 3,4-Methylenedioxyamphetamine (MDA) Analogues Exhibit Differential Effects on Synaptosomal Release of 3H-Dopamine and 3H-5-Hydroxytryptamine
    PharmacologyB/ochem/,nry& Behav/m-,VoL 38, pp. 505-512. o Pergamon Pressplc, 1991. Printed in the U.S]_. 3,4-Methylenedioxyamphetamine (MDA) Analogues Exhibit Differential Effects on Synaptosomal Release of 3H-Dopamine and 3H-5-Hydroxytryptamine DENNIS J. McKENNA, *l X.-M. GUAN* AND A. T. SHULGINt *Department of Neurology & Neurological Sciences, Stanford University Medical Center, Stanford, CA 94305 \ p1483 Shulgin Road, Lafayette, CA 94549 x Received 16 August 1990 McKENNA, D. J., X.-M. GUAN AND A. T. SHULGIN. 3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptasomal release of ZH-dopamine and SH-$-hydroxytryptamine. PHARMACOL BIOCHEM BEHAV 38(3) 505-512, 1991.--The effect of various analogues of the neurotoxic amphetamine derivative, MDA (3,4-methylenedioxyamphetamine) on car- rier-mediated, calcium-independent release of ZH-5-HT and 3H-DA from rat brain synaptosomes was investigated. Both enantiomers of the neurotoxic analogues MDA and MDMA (3,4-methylenedioxymethamphetamine) induce synaptosomal release of 3H-5-HT and 3H-DA in vitro. The relea._ of 3H-5-HT induced by MDMA is partially blocked by 10 -6 M fluoxetine. The (+) enantiomers of both MDA and MDMA are mote potent than the ( - ) enantiomers as releasers of both _H-5-HT and 3H-DA. Eleven analogues, dif- feting from MDA with respect to the nature and number of ring and/or side chain substituents, also show some activity in the re- lease exper/rnents, and are more potent as releasers of 3H-5-HT than of 3H-DA. The amphetamine derivatives ( n-)fenfluram/ne, (-+)norfcnfluramine, (±)bIDE, (-*)PCA, and d-methamphetamine are all potent releasers of 3H-5-HT and show varying degrees of activity as 3H-DA releasers.
    [Show full text]