Lead Opinion
OPINION OF THE COURT
Appellants, Donald Bogusz (“Bogusz”) and John O’Rourke (“O’Rourke”), appeal criminal sentences imposed on them by the United States District Court for the District of New Jersey.
I. Background
Because this appeal focuses on sentencing, only a summary of the facts material to the sentencing issues is needed. On August 29, 1991, a federal grand jury returned an indictment against twelve individuals, including Bogusz and O’Rourke, charging them with participation in a scheme to manufacture and distribute methamphetamine. Bogusz located and obtained glassware and phenylacetic acid, a methamphetamine precursor, for the methamphetamine production process. O’Rourke served as a “plumber.” In that capacity, he unclogged drains that became blocked during the methamphetamine manufacturing process.
Bogusz and O’Rourke received methamphetamine as part of the consideration for their services. O’Rourke received four of the eight pounds of methamphetamine produced while he worked on the pipes and Bogusz got one pound. The methamphetamine produced was described as “sticky” and “like caramel” indicating its poor quality. In fact, Bogusz gave half of his methamphetamine to a co-conspirator and returned the other half because of its poor quality.
On' March 17, 1992, Bogusz pled guilty under a plea agreement to a conspiracy to distribute more than two pounds of phenyla-cetic acid, a listed chemical, knowing that it would be used to manufacture methamphetamine, a controlled substance, in violation of 21 U.S.C.A. § 841(d)(2) (West Supp.1994). On May 14, 1992, after a jury trial, O’Rourke was convicted of a conspiracy to manufacture methamphetamine with intent to distribute in violation of 21 U.S.C.A. § 846 (West Supp. 1994) and possession with intent to distribute in excess of one kilogram of methamphetamine in violation of 21 U.S.C.A. § 841(a)(1) (West Supp.1994).
At Bogusz’s sentencing, the district court adopted a recommendation in the probation office’s Presentence Report (the “PSR”) to apply a higher base offense level than the one stipulated in Bogusz’s plea agreement. Bogusz and the government had stipulated to a base offense level of 24, applying U.S.S.G. § 2Dl.ll(d)(3); but the PSR recommended applying U.S.S.G. § 2D1.1 with a base offense level of 34. Using a cross-reference from section 2Dl.ll(e)(l) to section 2D1.1, the district court decided the base offense level was 34. Because phenylacetic acid is not included in section 2Dl.l’s Sentencing Table, use of section 2D1.1 required conversion of the phenylacetic acid quantities to those of a substance on the table. The probation officer preparing the PSR converted the eight pounds of phenylacetic acid to two pounds of methamphetamine, the amount of methamphetamine produced from the pheny-lacetic acid.
The PSR also recommended that sentencing be based upon “methamphetamine (actu
At O’Rourke’s sentencing, the district court again adopted the PSR’s recommendation to apply U.S.S.G. § 2D1.1 and again decided that the methamphetamine was methamphetamine (actual). Based on the eight pounds of methamphetamine produced when he worked on the pipes, O’Rourke received a base offense level of 38, see U.S.S.G. § 2Dl.l(c)(3), but the district court granted O’Rourke a four point offense level reduction for his mitigating role. See U.S.S.G. § 3B1.2(a). Using a criminal history category of II and an offense level of 34, the Guidelines put O’Rourke in a sentencing range of 168 to 210 months imprisonment. See U.S.S.G. Ch. 5, Pt. A (Sentencing Table). O’Rourke was sentenced to concurrent sentences of 168 months imprisonment on each count. Both Bogusz and O’Rourke filed timely notices of appeal.
II. Jurisdiction and Standard of Review
The district court had subject matter jurisdiction over these criminal eases pursuant to 18 U.S.C.A. § 3231 (West 1985). We have appellate jurisdiction over this consolidated appeal under 28 U.S.C.A. § 1291 (West 1993) (review of final decisions) and 18 U.S.C.A. § 3742 (West 1985) (review of sentences).
Under the Guidelines, we review a district court’s findings of fact for the limited purpose of determining whether they are clearly erroneous. United States v. Miele,
III. Discussion
Bogusz raises four challenges to the district court’s sentences. O’Rourke joins with
A. Guidelines’ Treatment of Methamphetamine
To apply U.S.S.G. § 2D1.1, a sentencing court must first determine whether the substance in question is methamphetamine or methamphetamine (actual). This determination involves two related issues. We must first consider whether the methamphetamine that Bogusz and O’Rourke helped produce was “pure” methamphetamine, a necessary condition for its classification as methamphetamine (actual), and then the more complex question of whether the government must also prove that the substance is D- or L-methamphetamine.
1. Methamphetamine (Actual)
The difference between methamphetamine and methamphetamine (actual) is highly significant for sentencing purposes: methamphetamine (actual) is subject to an offense level ten times greater than methamphetamine. See U.S.S.G. § 2D1.1, comment, (n. 10) (Drug Equivalency Table) (one gram of methamphetamine (actual) is treated as the equivalent of ten grams of marijuana while one gram of methamphetamine is equivalent to one gram of marijuana); see also United States v. Lande,
The district court defined methamphetamine (actual) as “pure methamphetamine.”
Well, pure is how you define “pure.” I’m defining it, “pure,” as uncut product, not whether the product was good product or bad product. Now that may be erroneous, in which case I’ll be reversed on appeal. But the fact of the matter is that a caramel-like mess to me is not the critical point; the point is, that’s what came out of the manufacturing process, and it had not yet been cut.
Bogusz Appendix at 85. Bogusz and O’Rourke argue that methamphetamine (actual) refers to the percentage purity of the end product. That is, they argue that methamphetamine (actual) refers to the net amount of methamphetamine hydrochloride present in the substance upon which sentencing is based.
The Guidelines’ commentary defines methamphetamine (actual) as “the weight of the controlled substance, itself, contained in the mixture or substance.” U.S.S.G. § 2Dl.l(c), comment.(n.*).
Unfortunately, the commentary to the Guidelines is susceptible to either interpretation of “pure,” and each has case law support. Compare United States v. Macklin,
At oral argument, the government argued that adoption of the appellants’ interpretation would reward them for being “poor cooks.” Transcript of Oral Arguments at 46. This contention reflects a fundamental misunderstanding of methamphetamine production and the Guidelines’ treatment of it. Sentencing for methamphetamine drug offenses is intended to punish all cooks equally. Sentencing under methamphetamine (actual) punishes particularly good cooks and then-employers more severely. Methamphetamine, as produced through normal chemical processes, contains a number of impurities. See Spencer,
The government’s reliance on Chapman v. United States,
After consideration of the text and commentary of the Guidelines, existing case law and the peculiar sentencing scheme for methamphetamine, we hold that methamphetamine (actual) refers to the net amount of methamphetamine hydrochloride produced and not the gross amount of uncut methamphetamine. Thus, methamphetamine (actual) refers to the net amount of methamphetamine hydrochloride after all impurities, waste, byproducts, or cutting agents are removed.
The government argues that Bogusz and O’Rourke did not show that the methamphetamine “contained a cutting agent, waste product, or any substance other than the controlled substance itself.” Brief of Appellee at 46. In essence, the government is arguing that defendants bear the burden of showing the portion of the substance that is not methamphetamine (actual). This argument fails. Although the purity of a methamphetamine product does not bear on a defendant’s guilt or innocence and, thus, does not invoke the “beyond a reasonable doubt” standard of In re Winship,
In some situations, a chemical analysis of the substance that indicates its purity may be required for the government to meet this
In this ease, some of the evidence produced at trial supports the district court’s tacit finding of 100% purity. Trial testimony showed that the defendants were in possession of a functional recipe, proper equipment, and requisite chemicals. There was, however, other evidence on the color and consistency of the product which indicated poor quality and could have supported a finding of impurity. Manufactured methamphetamine is not 100% pure regardless of the sophistication of the equipment. Therefore, the government cannot rely solely on the nature of the production process and assume that the total product is pure methamphetamine which calls for sentencing under methamphetamine (actual). Instead, we think there should be a finding, based on evidence, on how much methamphetamine hydrochloride is included in the mixture that constitutes the end product. Because the district court failed to make such a finding, we will remand for further fact finding on the purity of the product.
2. Organic Composition
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-meth.amphetamine. 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,
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. Heg-strom & Dilip K. Kondepudi, The Handedness of the Universe, Scientific American, Jan. 1990, at 108 (“Hegstrom & Kondepudi Article”); United States v. Patrick,
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-
Methamphetamine exists in these two isomeric forms.
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 isomeric 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 gram of methamphetamine (actual) is equivalent to 10 kilograms of marijuana).
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. Deninno,
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,
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.
In United States v. Carroll,
An isolated literal reading of U.S.S.G. § 2Dl.l(e) does offer some support to the Carroll majority’s separation of the 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.
Accordingly, we hold that the references to methamphetamine and methamphetamine (actual) in the Drug Quantity Tables of U.S.S.G. § 2Dl.l(c) refer solely to quantities of D-methamphetamine. In order to calculate a base offense level under section 2Dl.l(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.
B. Section 2Dl.ll’s Cross Reference to 2D1.1
Bogusz alone raises the next Guidelines issue. He argues that the district court erred in applying U.S.S.G. § 2D11 under section 2Dl.ll’s cross-reference to it. He contends that section 2D1.1 does not apply to violations of 21 U.S.C.A. § 841(d). Bogusz pled guilty to distribution of a precursor chemical knowing that it would be used to manufacture a controlled substance but was sentenced for conspiracy to unlawfully manufacture the quantity of the controlled substance that was produced from the precursor chemicals he delivered.
Bogusz relies primarily on United States v. Voss,
Since Voss, the Guidelines have been amended and section 2D1.11 now clearly applies to violations of section 21 U.S.C.A. § 841(d). See U.S.S.G. § 2D1.11 (Unlawfully Distributing, Importing, Exporting or Possessing a Listed Chemical; Attempt or Conspiracy). We sympathize with the concern the Voss majority expressed,
Unless there is a showing of contrary intent, we must “follow the clear unambiguous language of the Guidelines.” United States v. Wong,
However, the use of section 2D1.11 requires us to consider a constitutional issue. If the Voss majority’s interpretation of the pre-1991 Guidelines was correct, Bogusz’s sentence would conflict with the Ex Post Facto Clause. U.S. Const, art. I, § 9, cl. 3. The prohibition against the passage of ex post facto laws includes, inter alia, “[ejvery law that changes the punishment and inflicts a greater punishment than it was when committed.” Calder v. Bull,
Bogusz was sentenced under the 1991 Guidelines for conduct that occurred from early April to early May 1990. The 1991 Guidelines became, effective November 1, 1991. Therefore, if the 1990 Guidelines would have resulted in a lower sentence, the Ex Post Facto Clause would require its application. See United States v. Spiropoulos,
The Ex Post Facto Clause requires us to interpret the pre-1991 Guidelines and meet the question posed by Foss, one this Court has not previously decided under the pre-1991 Guidelines. After thorough consideration, we find ourselves in agreement with those courts that have rejected the view of the Foss majority.
C. Bogusz’s Plea Bargain
Finally, Bogusz argues that the government violated the terms of his plea bargain by arguing for affirmance of the district court’s sentence in this appeal.
In Santobello v. New York,
The stipulations attached to the plea bargain between Bogusz and the government state that “the applicable federal sentencing guideline is section 2D1.11(3) carrying a base offense level of 24.” The government argues that the district court was correct in sentencing Bogusz based on methamphetamine (actual) as opposed to methamphetamine. Brief of Appellee at 41-49. Bogusz claims that the government’s presentation of this argument violates the plea agreement.
Bogusz’s plea agreement did not explicitly address the post-conviction conduct of either party. See, e.g., United States v. Gonzalez,
A reasonable person in Bogusz’s position may have understood the stipulation to include an agreement not to argue against the stipulation on appeal. Cf. Moore v. Foti,
Moreover, the government does not directly argue against the stipulation; instead, it contends only that the district court’s definition of methamphetamine (actual) is correct. This issue is separate and distinct from the stipulation. Similarly, Bogusz has not breached his plea agreement by arguing directly for his own interpretation of methamphetamine after he had stipulated to an unrelated Guidelines’ provision. Our adversarial system of justice relies heavily on the presentation of opposing views by both parties, on appeal as well as at trial. Thus, we are reluctant to deny any party the right to advance its interpretation of law. Under the circumstances before us, we hold that the government did not violate the letter or the
IV. Conclusion
For the reasons discussed above, the sentences imposed on Bogusz and O’Rourke will be vacated and their cases remanded for resentencing in a manner consistent with this opinion. In all other respects, the orders of the district court are affirmed.
Notes
. O’Rourke also appeals his conviction. In that respect, he argues: (1) that the district court erred in refusing to sever his trial from his co-defendants and (2) that the variance between the proof at trial and the indictment unduly burdened him. Upon review, we hold that these issues lack merit.
. Unless otherwise stated, all references to the Guidelines are to the 1991 version, the Guidelines in effect at the time of the appellants’ sentencing. See 18 U.S.C.A. § 3553(a)(4) (West 1985).
. Section 2D1.1 subjects methamphetamine (actual) to a more severe base offense level. What the phrase methamphetamine (actual) means is an issue in these appeals which we discuss infra in Part III-A.
. Prior to the 1991 amendments, the Guidelines also used the term pure instead of actual. See U.S.S.G. App. C., amend. 395.
. In this respect, the Guidelines’ treatment of methamphetamine and PCP is contrary to the gross weight method of calculating the quantity of all other controlled substances. See Chapman v. United States,
.It has sometimes been suggested that giving the government a second chance to make the requisite showing that it was unable to achieve originally is inconsistent with the Double Jeopardy Clause of the Fifth Amendment. This Court, however, has held that “sentencing proceedings are not ... so trial-like as to implicate the Double Jeopardy Clause.” Wilmer v. Johnson,
. Chirality was discovered in 1847 by Louis Pasteur. See Hegstrom & Kondepudi Article at 108; Organic Chemistry Text at 127.
. 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.
. Not all enantiomers have such disparate effects on the human body. See, e.g., New Jersey v. Cathcart,
. 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.
.The Drug Equivalency Tables are generally used only when a controlled substance is not listed in the Drug Quantity Table, U.S.S.G. § 2D 1.1(c), or when it is necessary to combine different controlled substances. See U.S.S.G. § 2D1.1, comment, (n.10); cf. Ammar,
. Rule 52 is sometimes said to require a plain error to be an obvious error. See United States v. Blythe,
. 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.,
.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) (discussing the difficulties experienced by judges in determining the admissibility of expert evidence).
. Judge Bright lamented the complexity and confusion apparent in the Guidelines' treatment of methamphetamine. Carroll,
. 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.
. See United States v. Lande,
. The Voss majority also expressed concern over treating section 841(d) violators the same as actual drug manufacturers. The Guidelines, as amended since Voss, cross reference to section 2D 1.1 only when the "offense involved unlawfully manufacturing or attempting to manufacture a controlled substance....” U.S.S.G. § 2D1.11(c)(1). Section 841(d) can be violated by conduct not meeting this requirement. Therefore, we do not believe that the Sentencing Commission acted irrationally by equating the penalties for these offenses. In fact, the theory behind all inchoate penalties is based on some belief in equivalent culpability.
. See United States v. Leed,
. The government argues that Bogusz raised this issue for the first time in his reply brief. In response, the government filed a motion to strike this argument or, in the alternative, for leave to file a surreply brief. We denied these motions. We do not usually consider questions first raised in this manner. Here, however, the issue Bogusz raises became apparent only after the government filed its brief. Accordingly, Bogusz had no
Concurrence Opinion
concurring and dissenting.
I join in all parts of the majority’s opinion except for part 111(A)(1). Because I believe the majority has adopted the wrong test for determining the purity of methamphetamine, I respectfully dissent from that portion of its opinion.
As the majority recognizes, the Sentencing Guidelines provide two ways for sentencing a defendant convicted of unlawfully manufacturing methamphetamine. Under U.S.S.G. § 2Dl.l(c) cmt. * (1991), the court first looks to “the entire weight of any mixture or substance containing a detectable amount of the controlled substance.” Next, the court is instructed to determine the weight of the pure form of the controlled substance contained within the mixture, otherwise known as “methamphetamine (actual).” These weights are then translated into offense levels by use of the Drug Quantity Table, and the higher of the two offense levels is used in determining the appropriate sentence.
The issue here is how much methamphetamine (actual) was contained in the substance manufactured by the defendants. Appellants contend that methamphetamine (actual) means only the amount of pure methamphetamine, free of all impurities, while the government argues that any uncut substance containing methamphetamine is methamphetamine (actual), regardless of its purity. The majority, while acknowledging that both views are supported in the caselaw, concludes that “methamphetamine (actual) refers to the net amount of methamphetamine hydrochloride produced and not the gross amount of uncut methamphetamine.” Majority at 87.
I disagree with this conclusion. Precursor chemicals used in the manufacture of methamphetamine cost money and may be difficult to obtain. Consequently, it is counterin-tuitive to conclude that every rational “cook” would not seek the highest possible yield of methamphetamine hydrochloride from those chemicals. The mere fact that the cook bungles the recipe and produces a sticky, caramel-like substance of low purity, which no user wishes to purchase, should not diminish punishment vis-a-vis the “good” cook whose product is more pure and highly salable.
Moreover, the majority’s holding also places an unwarranted burden upon the government to obtain an enhanced sentence based on the amount of methamphetamine (actual). Under the majority’s rule, the government must now have every sample of methamphetamine analyzed and its purity determined; the mere fact that the drug is uncut is no longer sufficient. First, we must recognize that criminal defendants who operate “meth cooks” in garages, barns and, as here, basements, are not scientists who sit around discussing the molecular structure of their creations. Bogusz was a mechanic who got the phenylacetie acid for the “cook” and O’Rourke was a truck driver who cleaned out the drains at the “cook.” Second, “meth” is not produced under laboratory conditions and is almost never pure. Third, in cases like this one, where the specific batch of drugs at issue is never recovered and tested, the defendant will avoid an enhanced sentence altogether, even when it is undisputed that the drugs were uncut.
I would simply avoid these problems altogether and hold that methamphetamine (actual) refers to the uncut output of the manufacturing process, regardless of its purity. See United States v. Macklin,
