Structural determination of the principal byproduct of the lithium-ammonia reduction method of methamphetamine manufacture

Journal of Forensic Sciences

Volumn 50, Issue 1, 2005, Pages 87-95

  Person, Eric C ^a   Meyer, Jennifer A ^b   Vyvyan, James R ^b  

^a Washington State Patrol   (United States)

^b WESTERN WASHINGTON UNIVERSITY   (United States)

Author keywords

Byproduct; Forensic chemistry; Forensic science; Manufacture; Methamphetamine; Nuclear magnetic resonance; Reduction

Indexed keywords

1 (1',4' CYCLOHEXADIENYL) 2 METHYLAMINOPROPANE; ALKALI METAL; AMMONIA; EPHEDRINE; LITHIUM; METHAMPHETAMINE; PROPYLAMINE; PSEUDOEPHEDRINE; UNCLASSIFIED DRUG;

ARTICLE; BIRCH REDUCTION; CHEMICAL STRUCTURE; DRUG MANUFACTURE; GAS CHROMATOGRAPHY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REDUCTION; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 11844304192     PISSN: 00221198     EISSN: None     Source Type: Journal    
DOI: 10.1520/jfs2004204     Document Type: Article

References (23)

1. Methamphetamine byproduct from birch reduction tentatively identified. J Clandestine Lab Invest Chem Assoc 1997;7(2):7-10.
2. Dawson N. The sodium-ammonia "Nazi" method of methamphetamine synthesis: an historical overview, methodology and case reviews. J Clandestine Lab Invest Chem Assoc 1995;5(3):12-4.
3. Ely RA. Lithium-ammonia reduction of ephedrine to methamphetamine: an unusual clandestine synthesis. J Forensic Sci 1990;35(3):720-3.
4. Hall SS, Lipsky SD, Small GH. Selective lithium-ammonia reduction of aromatic ketones and benzyl alcohols: mechanistic implications. Tetrahedron Lett 1975;21:1853-4.
5. Small GH, Minnella AE, Hall SS. Lithium-ammonia reduction of benzyl alcohols to aromatic hydrocarbons: an improved procedure. J Org Chem 1975;40(21):3151-2.
6. Birch AJ, Smith H. Reduction by metal-amine solutions: applications in synthesis and determination of structure. Q Rev Chem Soc 1958;XII:17-33.
7. Dal Cason TA. A review of the birch reduction method. Clandestine Laboratory Investigating Chemists Association Monograph 1998:1-3.
8. Smith M. Dissolving metal reductions. In: Augustine RL, editor. Reduction. New York: Marel Dekker, 1968:95-108.
9. March J. Advanced organic chemistry: reactions, mechanisms, and structure. New York: John Wiley & Sons, 1992.
10. Birch AJ. Reduction by dissolving metals. Part I. J Chem Soc 1944:430-6.
11. Birch AJ. Reduction by dissolving metals. Part II. J Chem Soc 1945:809-13.
12. Birch AJ. The reduction of organic compounds by metal-ammonia solutions. Q Rev Chem Soc 1950;IV:69-93.
13. Watt GW. Reactions of organic and organometallic compounds with solutions of metals in liquid ammonia. Chem Rev 1950;46:317-79.
14. Marshal WP, Logan BK. The presence of N-methyl-1-(1-(1′,4′- cyclohexadienyl))-2-propanamine, a birch reduction product, in methamphetamine positive toxicology samples. Abstracts of the Society of Forensic Toxicologists Annual Meeting; 2003 Oct. 20-24; Portland, OR. Portland, OR: Society of Forensic Toxicologists, 2003.
15. Bremer N, Woolery R. The yield of methamphetamine, unreacted precursor and birch by-product with the lithium-ammonia reduction method as employed in clandestine laboratories. Midwest Association of Forensic Scientists Newsletter 1999;Fall 1999:8-16.
16. Person EC, Knops LA. Clandestine ammonia generation. J Clandestine Lab Invest Chem Assoc 2004;14(1):20-7.
17. Moffat AC, Osselton MD, Widdop B, editors. Clarke's analysis of drugs and poisons. 3rd ed. Grayslake, IL: Pharmaceutical Press, 2004.
18. Shaferstein R, editor. Forensic science handbook. Upper Saddle River, NJ: Prentice Hall, 1988.
19. ASTM Designation E1969-01: Standard guide for microcrystal testing in the forensic analysis of methamphetamine and amphetamine. West Conshahocken, PA: American Society for Testing and Materials (ASTM), International, 2001.
20. Silverstein RM, Bassler GC, Morrill TC. Spectrometric identification of organic compounds. 5th ed. New York: John Wiley & Sons, Inc., 1991.
21. Pretsch E, Bühlmann P, Affolter C. Structure determination of organic compounds. 3rd ed. Heidelberg: Springer, 2000.
22. Pavia DL, Lampman GM, Kriz GS. Introduction to spectroscopy. 3rd ed. Orlando, FL: Harcourt College Publishers, 2001.
23. Zvilichovsky G, Gbara-Haj-Yahia I. Birch reduction of (-)-ephedrine. Formation of a new, versatile intermediate for organic synthesis. J Org Chem 2004;69(16):5490-3.