Opinion ID: 3009491
Heading Depth: 3
Heading Rank: 2

Heading: Organic Composition

Text: On the second aspect of methamphetamine sentencing, both Bogusz and O'Rourke challenge the district court's tacit assumption that the methamphetamine was D-methamphetamine as opposed to L-methamphetamine. The two are grossly different in physiological effect and, as we shall see, this difference is reflected in the Guidelines drug equivalency tables by a factor of 250 to 1. An initial failure of the parties to appreciate the chemistry involved and thus to inform the district court of the scientific basis for this contention requires us to consider whether Bogusz and O'Rourke have waived any issue regarding the distinction between D-and L-methamphetamine. Discussion of the principles of organic chemistry that underlie this issue is necessary before the problem created by the distinction between D- and L-methamphetamine can be understood. See United States v. Ammar, 714 F.2d 238, 261-64 (3d Cir.) (pre-Guidelines case discussing chemical difference between D- and L-heroin), cert. denied sub nom. Stillman v. United States, 464 U.S. 936 (1983). The methamphetamine molecule, like most organic molecules, exists in different isomeric forms. Isomers are compounds that have the same molecular formula but different structural formulas. Harold Hart, Organic Chemistry: A Short Course 15 (6th ed. 1983) (Organic Chemistry Text). Just as people are either right- or left-hand dominant, a molecule can sometimes exist in right- and left-handed forms. See Organic Chemistry Text at 125-26; Roger A. Hegstrom & Dilip K. Kondepudi, The Handedness of the Universe, Scientific American, Jan. 1990, at 108 (Hegstrom & Kondepudi Article); United States v. Patrick, 983 F.2d 206, 209 (11th Cir. 1993). A molecule that exhibits the property of handedness is called a chiral molecule.7 The two forms of the chiral molecules are called enantiomers.8 Each enantiomer is labelled either Dextro or Levo, or D or L. Hegstrom & Kondepudi Article at 109. The difference is determined by the optical rotation of light. D is right-handed and L is left-handed. One is the mirror image of the other; that is, they are mirror symmetrical. Id. Although enantiomers only differ with respect to chirality, the human body is highly sensitive to enantiomeric differences. Id. For example, the thalidomide birth defects of the 1960's resulted because one enantiomer of thalidomide stopped morning sickness while the other caused birth defects. Id. at 109-10.9 7 . Chirality was discovered in 1847 by Louis Pasteur. See Hegstrom & Kondepudi Article at 108; Organic Chemistry Text at 127. 8 . Thus, enantiomers are isomers that are not identical with their mirror image; that is, the enantiomers are nonsuperimposable. Organic Chemistry Text at 121-25. For example, the mirror image of a right hand is not another right hand but a left hand. Id. 9 . Not all enantiomers have such disparate effects on the human body. See, e.g., New Jersey v. Cathcart, 589 A.2d 193, 198 (N.J. App. Div. 1991) (discussing the similar effects of D- and L- cocaine); United States v. Puglisi, 790 F.2d 240, 242 (2d Cir.) (same), cert. denied, 479 U.S. 827 (1986); United States v. Bockius, 564 F.2d 1193, 1195 (5th Cir. 1977) (same); United States v. Orzechowski, 547 F.2d. 978, 985 (7th Cir. 1976) (same), cert. denied, 431 U.S. 906 (1977). Methamphetamine exists in these two isomeric forms.10 L-methamphetamine is a compound that produces little or no physiological effect when ingested. Carroll, 6 F.3d at 743. D-methamphetamine, on the other hand, produces the physiological effect desired by its users. Id. The text of U.S.S.G. § 2D1.1 differentiates only between methamphetamine and methamphetamine (actual). We have previously discussed that distinction as it involves drug purity, not organic structure. The question now posed is whether the isometric structure of methamphetamine, as well as the net quantity of methamphetamine hydrochloride, is relevant to Guidelines sentencing. The Guidelines do not differentiate between the D- and L- isomers of methamphetamine in the text of section 2D1.1, but only in the commentary to it. There, in the Drug Equivalency Tables, L-methamphetamine is treated far less severely than either methamphetamine or methamphetamine (actual): methamphetamine (actual) by a factor of 250, methamphetamine by a factor of 25. See U.S.S.G. § 2D1.1 comment.(n.10) (Drug Equivalency Table) (one gram of L-methamphetamine is equivalent to 40 grams of marijuana, one gram of methamphetamine is equivalent to one kilogram of marijuana, and one kilogram of 10 . The Eleventh Circuit, in United States v. Carroll, 6 F.3d 735, 743 (11th Cir. 1993), described a third form of methamphetamine: DL-methamphetamine. Standard texts, however, seem to recognize only two chemical forms of methamphetamine with DL-methamphetamine merely being a combination of the two forms. See Organic Chemistry Text at 127 (defining a racemic mixture as a 50:50 mixture of enantiomers). Our analysis would be unaffected if a third form does exist. methamphetamine (actual) is equivalent to 10 kilograms of marijuana).11 With this chemical background in mind, we consider first whether the issue raised by this distinction in their physiological effect was fairly raised before the district court. Bogusz and O'Rourke never used precise chemical terms in arguing this question. They lumped this issue together with their arguments on purity when they objected to sentencing based upon an unanalyzed substance. Nevertheless, we conclude that Bogusz's and O'Rourke's objections to sentencing based on the unanalyzed substance produced at the methamphetamine laboratory fairly raised and preserved the issue for appeal. Even if Bogusz and O'Rourke were raising the issue for the first time on appeal, we could nevertheless review the trial court's findings for plain error. See Fed. R. Crim. P. 52(b) (Plain errors or defects affecting substantial rights may be noticed although they were not brought to the attention of the court.). We believe that under these circumstances the district court's interpretation of the Guidelines would be plain error. Because of the objections at sentencing, this case differs factually from United States v. Peninno, 29 F.3d 572, 580 (11th Cir. 1994), in which the United States Court of Appeals for the Eleventh Circuit refused to consider a similar claim because of 11 . The Drug Equivalency Tables are generally used only when a controlled substance is not listed in the Drug Quantity Table, U.S.S.G. § 2D1.1(c), or when it is necessary to combine different controlled substances. See U.S.S.G. § 2D1.1, comment.(n.10); cf. Ammar, 714 F.2d at 263 (upholding heroin conspiracy conviction without distinguishing between D- and L- isomers because statute did not distinguish them). the appellant's complete failure to object at sentencing. Moreover, considering the gross disparity in sentencing, we disagree with the Peninno court's holding that the determination of methamphetamine type is entirely a factual question that cannot rise to the level of plain error. Id. The Fifth Circuit recently defined a plain error as one so obvious that [a] failure to notice it would seriously affect the fairness, integrity, or public reputation of the judicial proceeding and result in a miscarriage of justice. United States v. Hoster, 988 F.2d 1374, 1380 (5th Cir. 1993) (quoting United States v. Surasky, 974 F.2d 19, 21 (5th Cir. 1992), cert. denied, 113 S. Ct 1948 (1993)); see also United States v. Olano, 113 S. Ct. 1770, 1776 (1993). We recognize that the term plain error normally implies an error that is apparent as well as unjust. See United States v. Atkinson, 297 U.S. 157, 160 (1936).12 Here, however, we think that the egregiousness of the 12 . Rule 56 is sometimes said to require a plain error to be an obvious error. See United States v. Blythe, 944 F.2d 356, 359 (7th Cir. 1991) (relying exclusively on Justice Scalia's dissenting opinion in Pretez v. United States, 111 S. Ct. 2661, 2678 (1991)). The Supreme Court, however, has defined plain errors as errors that are obvious, or [that] otherwise seriously affect the fairness, integrity or public reputation of the judicial proceedings. Atkinson, 297 U.S. at 160. In United States v. Olano, 113 S. Ct. 1770 (1993), the Supreme Court, discussing Rule 52(b), stated that appellate review is available only when: (1) there is an error; (2) the error is plain; and (3) the error affects substantial rights. Id. at 1776-77. Plain is synonymous with clear or, equivalently, obvious. . . . At a minimum, the Court of Appeals cannot correct an error pursuant to Rule 52(b) unless the error is clear under current law. Id. at 1777 (internal citations and quotations omitted). Though the present error was not obvious, we think it was clear; thus, even if Bogusz's and O'Rourke's failure to appreciate the technical chemical basis for their objection was a waiver, we injustice that would result if the distinction between the two isomers is not recognized outweighs the failure of Bogusz and O'Rourke to articulate clearly the principles of organic chemistry that underlie their objections to the district court's application of the Guidelines.13 Thus, considering the magnitude of the difference in sentencing that could result from the application of the wrong organic isomer, we think the sentencing court's failure to make this determination would result in a grave miscarriage of justice.14 We will thus consider whether the distinction between (..continued) think the requirements of Rule 52(b) would be met because of the great difference in the effect of the two substances that the commentary to U.S.S.G. § 2D1.1(c) recognizes when it distinguishes them by a conversion factor of 250 to 1. 13 . Moreover, a sentencing scheme that imposes the same penalty on a person who produces a compound with little or no effect as a person who produces a potent mind-altering drug would seem irrational. When interpreting the Guidelines, we apply traditional canons of statutory construction. Thus, we will not interpret the Guidelines in a manner that leads to irrational results when alternative interpretations consistent with the objectives of the Sentencing Reform Act are available. See, e.g., Griffin v. Oceanic Contractors Inc., 458 U.S. 564, 575 (1982). The Sentencing Reform Act intended to create an effective, fair sentencing system. U.S.S.G. Ch. 1, Pt. A intro. comment. To achieve this end, . . . Congress sought proportionality in sentencing through a system that imposes appropriately different sentences for criminal conduct of differing severity. Id. 14 . Because the Guidelines' confusing textual use of the term actual and its unexplained distinction between the two isomers in the commentary's reference to the equivalency table, we cannot criticize the district court for failing to appreciate this problem. Some commentators suggest that lawyers generally possess an appalling degree of scientific illiteracy, which ill equips them to educate and guide the bench. Andre A. Moenssens et al., Scientific Evidence in Criminal Cases 7 (3d ed. 1986) the left- and right-handed isomers of methamphetamine is material to the Guidelines sentences that can be legally imposed on Bogusz and O'Rourke. In United States v. Carroll, 6 F.3d 735 (11th Cir. 1993), the Court of Appeals for the Eleventh Circuit sought to separate methamphetamine's purity from the effect of its isomers. In that case, the defendant's sentence was based on methamphetamine that contained 50% D- and 50% L-methamphetamine. Id. at 743. The Court of Appeals held, the distinction between methamphetamine and [methamphetamine (actual)] refers to the relative purity of any methamphetamine compound; it does not refer to a particular form of methamphetamine. Id. at 744. Thus, the 50% D- and 50% L-methamphetamine compound could be 100% pure for purposes of calculating methamphetamine (actual). Judge Bright dissented from the majority's drug quality issue. Id. at 747. Because the Guidelines caused great confusion due to the convoluted chemical rhetoric required by their application in this area, Judge Bright would have affirmed the lower court's conclusion that purity should be based on the quantity of D-methamphetamine. Id. at 749.15 An isolated literal reading of U.S.S.G. § 2D1.1(c) does offer some support to the Carroll majority's separation of the (..continued) (discussing the difficulties experienced by judges in determining the admissibility of expert evidence). 15 . Judge Bright lamented the complexity and confusion apparent in the Guidelines' treatment of methamphetamine. Carroll, 6 F.3d at 749 (Bright, J., dissenting). We add our voice to his lament. purity problem from the difference in the effect of the two isomers. We think, however, that such a separation for purposes of Guidelines' sentences would obliterate the distinction between the effect of the two isomers that the Guidelines' commentary recognizes in any case in which the Drug Equivalency Tables are not used. Considering the difference between the physiological effect of the two isomers, along with the Sentencing Commission's recognition of that difference in its use of conversion factors with a 1 to 250 ratio, the disparity in sentencing that would result seems to us contrary to one of Congress's primary goals in passing the Sentencing Reform Act--the substitution of uniformity for disparity in sentencing.16 We think the Guidelines should not be construed in a way that results in so greatly irrational a disparity. To illustrate, under Carroll, a defendant convicted of one gram of pure L-methamphetamine would have a base offense level of 16 with a Guidelines range of 21 to 27 months imprisonment. See U.S.S.G. Ch. 5, Pt. A (Sentencing Table) (assuming a criminal history category of I). Another defendant sentenced for one gram of pure L-methamphetamine and an additional 200 grams of marijuana (thus, requiring conversion under the Drug Equivalency Table) would have a base offense level of 6 and a sentencing range of zero to six months. See U.S.S.G. 16 . The Sentencing Reform Act of 1984 sought to achieve reasonable uniformity in sentencing by narrowing the wide disparity in sentences imposed for similar criminal offenses committed by similar offenders. U.S.S.G. Ch. 1, Pt. A, intro. comment. Ch. 5, Pt. A (Sentencing Table) (again, assuming a criminal history category of I). Accordingly, we hold that the references to methamphetamine and methamphetamine (actual) in the Drug Quantity Tables of U.S.S.G. § 2D1.1(c) refer solely to quantities of D-methamphetamine. In order to calculate a base offense level under section 2D1.1(c) for L-methamphetamine, the substance in question must first be converted into marijuana equivalents. See U.S.S.G. § 2D1.1, comment.(n.10) (noting that the Drug Quantity Tables do not include all substances and that the Drug Equivalency Tables should be used for those that are not included). Because no determination of the isomeric composition of methamphetamine was made at sentencing, this issue must also be considered on remand. We again remind the government that it has the burden of production and persuasion on this issue and that the proper standard for the burden of persuasion is a preponderance of the evidence. The type of proof required to satisfy this standard will also vary from case to case.17 In 17 . See United States v. Lande, No. 94-8038, 1994 WL 627425, at -2 (10th Cir. Nov. 9, 1994) (affirming a district court's finding of D-methamphetamine based upon circumstantial evidence); United States v. Wessels, 12 F.3d 746, 754 (8th Cir. 1993) (reversing a district court for taking judicial notice that methamphetamine was D-methamphetamine), cert. denied, 115 S. Ct. 105 (1994); Patrick, 983 F.2d at 210 (requiring the government to prove that conviction was based upon D-methamphetamine). We do not think that this standard will create either an insurmountable burden or a meaningless hurdle for the government but, rather, merely recognizes the distinctions between the organic compositions and purity levels of methamphetamine the Guidelines require. We think some evidence of the quantity of each isomer some cases, the evidence will include a chemical analysis or expert testimony. In others, circumstantial evidence of which isomer is present may be sufficient to meet the preponderance of the evidence standard. See United States v. Koonce, 884 F.2d 349, 352-53 (8th Cir. 1989) (affirming D-methamphetamine determination based on circumstantial evidence of defendant's prior methamphetamine shipment).