Amended Opinion
Dеfendant-Appellant Abdirashid Mohamed Hassan appeals from the November 28, 2005 judgment of the United States District Court for the Eastern District of New York (Garaufis, J.), convicting him, following a jury trial, of one count of conspiracy to import cathinone, in violation of 21 U.S.C. §§ 952(a), 963, one count of conspiracy to distribute and to possess with intent to distribute cathinone in violation of 21 U.S.C. §§ 841(a), 846, one count of conspiracy to launder money in violation of 18 U.S.C. § 1956(a)(1), (h), and forty-one substantive counts of money laundering, in violation of 18 U.S.C. § 1956(a)(1). On *113 appeal, Hassan argues that: (1) the district court erred in its instructions to the jury; (2) the statute and regulations governing cathinone do not provide fair warning as to what conduct is unlawful; (3) the evidence was insufficient to support his convictions; (4) the government’s failure to correct false and misleading testimony denied him a fair trial; (5) trial counsel provided ineffective assistance; (6) the district court erred in admitting a chemist’s testimony and exhibits regarding the testing of three samples of khat; and (7) the district court’s sentencing determination was erroneous and unreasonable. Because we conclude that the evidence was insufficient to convict Hassan of the forty-one substantive counts of money laundering, in violation of 18 U.S.C. § 1956(a)(1), we REVERSE the judgment on these counts, and direct the district court to enter an order of acquittal. Because we conclude that the district court made a fundamental error in its jury instructions, we now VACATE the judgment as to the remaining counts. 1
I. BACKGROUND
A. Khat
Hassan was convicted of controlled substance and money laundering offenses involving cathinone, a stimulant that is sometimes present in “khat.” Khat is the leaf of the plant
catha edulis,
a shrub that grows in parts of East Africa and the Arabian Peninsula.
See
United States Food and Drug Administration, Basis for the Recommendation for Control of Cathinone into Schedule I of the Controlled Substance Act 9 (Nov. 5,1992) [hereinafter “FDA Report”];
United States v. Hassan,
03-cr-567, slip op. at 1,
While “khat is ... ingested as regularly in East African countries (such as Somalia,
*114
where the defendant is from) as coffee is ingested in the United States,”
id.
at 8,
Khat itself is not a controlled substance under United States law. However, khat is subject to an unusual and, indeed, unique dual regulatory scheme that employs a distinction based upon the chemical composition of khat. “When khat contains cathinone, khat is a Schedule I substance,” and “[w]hen khat does not contain cathinone, but does contain cathine, khat is a Schedule IV substance.” Schedules of Controlled Substances: Placement of Cathinone and 2, 5-Dimethoxy-4-ethylampheta-mine Into Schedule I, 58 Fed.Reg. 4316, 4317 (Jan. 14, 1993);
see also United States v. Caseer,
B. Hassan’s Trial
1. The Evidence
The evidence at trial demonstrated that Hassan had been importing khat into the *115 United States for several years with the assistance of a United States Customs broker named Patrick Fuller. Fuller provided Hassan with counterfeit customs stamps, which helped release goods from United States Customs quickly and without inspection. Hassan’s khat shipments were falsely labeled as printed matter, or similar material, and used fake return addresses. Hassan, who was first introduced to Fuller in 1997 or 1998, was one of Fuller’s principal clients. Fuller estimated that he helped Hassan import two to three shipments of khat per week, and Hassan paid Fuller $1,500 for each successful shipment. Hassan also took Fuller to London and introduced him to a man named Omar Hashi who told Fuller that he was Hassan’s khat supplier.
Fuller worked with several other khat importers, including a man named Mohamed Hassan — -no relation to defendant — who cooperated with the government [hereinafter “the cooperator”]. The cooperator testified that, like a number of other khat importers, he regularly took waybills to Fuller to be stamped with the counterfeit customs stamps. In 2002, another khat importer, Ahmed Mussa, introduced the cooperator to a man named Le-ban. The cooperator met with Leban several times, but, ultimately, the two did not successfully negotiate a deal. The cooperator later identified defendant Hassan as Leban in a photo array; however, when asked to idеntify Leban in the courtroom during trial, the cooperator failed to identify defendant Hassan as Le-ban.
Prior to his arrest in 2003, Hassan had two khat-related encounters with law enforcement authorities. On April 4, 2001, Hassan was briefly detained at John F. Kennedy Airport (“JFK”) when he and another individual tried to pick up two shipments of khat from a cargo facility. At the time, Hassan told United States Customs Special Agent Paul Kastava that he thought that khat was legal in the United States, because it was legal in Great Britain. In response, Special Agent Kastava informed Hassan that khat is illegal in the United States. 3 However, Kastava did not inform Hassan that khat is illegal because it is, or can be, a controlled substance. Rather, he simply told Hassan that khat is illegal.
Although the shipment of khat was seized, Hassan was not arrested. The government argues, and the district court found, that testimony about this encounter supports the argument that Hassan knew “that khat contains a controlled substance.”
Hassan,
03-cr-567, slip. op. at 12,
Hassan’s second encounter with law еnforcement regarding khat was on May 9, 2002, at a bond hearing for fellow khat importer Ahmed Mussa. Having been caught importing khat into the United States, Mussa was not charged with violating United States drug laws, but rather was charged with importing merchandise *116 into the United States, by means of a false statement to Customs, in violation of 18 U.S.C. § 542. Hassan, who described himself as a friend of Mussa’s family who did not know Mussa himself, testified briefly at the hearing and co-signed a bond on Mussa’s behalf. The bond did not identify the charges against Mussa. During the hearing, the prosecutor and Mussa’s attorney both made reference to the fact that “the underlying conduct here was importation of drugs” and “the underlying offense involves drugs.”
Hassan was arrested on April 16, 2003. Investigating agents from the Bureau of Immigration and Customs Enforcement traced a United Parcel Service (“UPS”) delivery of khat to an office building at 19 West 22nd Street in New York City (the “office building”). Immediately after the package was delivered by the UPS driver, and signed for by co-defendant Mahamed Mahamed (the “co-defendant”), Special Agent Stephen Lee went to the office building and asked the co-defendant to take him to the UPS package. The co-defendant showed Special Agent Lee the package, which had been placed on the floor of a closet adjacent to the office building’s lobby. In response to questioning, the co-defendant told the investigating agents that Hassan was responsible for arranging shipments of khat to the office building, that the codefendant would sign fоr the packages, and that the two men would split the contents. Hassan arrived shortly thereafter and was arrested. Hassan initially told the agents that he was at the office building to pick up a key to the co-defendant’s residence, where a sick relative was staying. After further questioning, Hassan acknowledged that he had previously run into trouble with U.S. Customs when he tried to pick up khat at Newark Airport. 4
After he was arrested, Hassan allowed agents to search his backpack and apartment. Among other things, the backpack contained $12,642 in cash, a UPS airway bill addressed to the office building, and receipts for postal money orders. The backpack also contained notebooks and date books which appeared to be records of khat transactions, listing names of couriers and known co-conspirators, city names, and calculations. In Hassan’s apartment, investigating agents found more money order receipts and UPS air waybills addressed to the office building, as well as a luggage tag bearing the name and address of an individual who had been arrested three months earlier at JFK for smuggling khat in his luggage. After Hassan’s arrest, investigating agents obtained additional records of money orders purchased by Hassan between December 21, 1998, and May 15, 2000, payable to his khat supplier in London, Omar Hashi.
At trial, the government offered evidence attempting to connect Hassan to other importations of khat. A customs officer testified that on June 3, 2000 he had sеized khat from the bags of Robert Lightbody, a citizen of the United Kingdom, who was attempting to enter the United States at JFK. Customs records showed that an individual of the same name also arrived in the United States on November 8, 1999; Lightbody’s name appeared in one of Hassan’s calendars for that date, along with the notation “Light-body, 400 plus 120.”
The government also presented the testimony of a Drug Enforcement Administration (“DEA”) chemist, Brian Hall. Hall *117 testified about analyses he performed on three packages of khat to determine the chemical composition of the khat, i.e., whether the khat contained either cathinone or cathine. Hall did not analyze the package of khat that was seized the day that Hassan was arrested, and thus provided no testimony as to the chemical composition of that khat shipment. Instead, Hall testified about three packages of khat that the DEA had seized after Hassan was arrested. None of the packages were addressed to Hassan. However, the first package was apparently seized at the office building. The other two packages were seized at a UPS facility. Hall testified that each of the samples that he tested from these three packages contained both cathinone and cathine. He also testified that cathinone, which cannot be detected without chemical testing, begins to lose its potency within 48 to 72 hours, when it starts to break down into cathine.
2. Procedural History
The case was tried before a jury from July 11, 2005, to July 14, 2005. On the first day of trial, Hassan filed a motion in limine seeking to prevent the prosecution or its witnesses from stating, inter alia, that khat is a controlled substance. The government conceded that “khat in and of itself, without any cathinone[,] is not necessarily a controlled substance,” but pointed out that khat “may contain” cathinone. The district court ruled that the government “would not be permitted to introduce evidence that khat per se is a controlled substance.”
Hassan,
03-cr-567, slip. op. at 15,
In addition to the testimony of several law enforcement officers to the effect that khat itself is illegal because it is a controlled substance, the customs broker Patrick Fuller also testified to the effect that khat itself is illegal in the United States because it is a controlled substance. He testified that he pleaded guilty to “[cjonspiracy to import khat,” that khat is “a controlled substance, so that falls under drugs,” and that “my charges is [sic] conspiracy to import khat.” Additionally, the cooperator indicated that he pleaded guilty to “importing forbidden stuff to the United States.” When asked to clarify what he meant by “forbidden stuff,” the cooperator responded, “[t]he khat.”
While Hassan’s trial counsel did not explicitly object to this testimony, he did try to highlight the inaccurate nature of this testimony through his cross-examination. After hearing Special Agent Lee inaccurately testify that khat is illegal in the United States because it is on the controlled substance list, Hassan’s attorney sought to contradict Special Agent Lee’s testimony to this effect by presenting the actual wording of the Controlled Substances Act to the witness. However, after the prosecutor objected to this line of *118 questioning, stating that it “is beyond the scope of my direct,” the district court sustained the government’s objection. In response to the district court’s decision to sustain the objection, Hassan’s counsel asked to “respond for the record.” However, the district court denied this request, stating, “[wje’ll put it on the record later. Let’s keep going.” Later in the trial, after Fuller also testified that khat is a controlled substance, Hassan’s counsel again tried to undermine these statements by questioning Fuller about the chemical composition of khat. Again, the government objected to this questioning, and the district court sustained the government’s objection.
At the close of the government’s case, Hassan moved for a judgment of acquittal under Federal Rule of Criminal Procedure 29(a). The district court denied the motion, but deferred consideration of Hassan’s constitutional challenge to the regulatory scheme for post-trial briefing. Hassan rested without presenting a defense case.
At the charging conference, defense counsel objected to the following language in the proposed jury charge for Count One:
While you must find that the defendant knew it was drugs he was conspiring to bring into the United States, you need not find that the defendant knew or believed that it was cathinone, as long as the government proves that he knew and intended that some controlled substance would be imported into the United States.
Defense counsel argued that this charge was far too broad, because the government’s burden was to prove that Hassan intended to import or distribute cathinone, and not merely khat. The court overruled these objections, but agreed “in the interest of fairness” to change the instruction slightly to indicate that the jury need not find that the defendant believed he was importing “a drug called” cathinone. 'The charge as delivered also contained the following language, which the government characterizes as a “reminder that cathinone was the controlled substance at issue in the case”:
While you must find that the defendant knew it was a controlled substance he was conspiring to bring into the United States, you need not find that the defendant knew or believed that it was a drug called cathinone, as long as the government proves that he knew and intended that some controlled substance would be imported into the United States. As I told you earlier, cathinone is a controlled substance.
Similar language in the charge for Count Two was not modified after trial counsel’s initial objection. After brief deliberations, the jury found Hassan guilty on all counts.
Following his conviction, Hassan moved again for a judgment of acquittal under Rule 29 and also for a new trial under Rule 33. Fed.R.Crim.P. 29, 33. On October 12, 2005, the district court denied these motions in a written opinion.
Hassan,
03-er-567, slip. op. at 1-18,
In his Rule 33 motion, Hassan argued that he should be granted a new trial because the government had repeatedly violated the court’s pre-trial ruling by referring to khat as a controlled substance and discussing cathine. The district court rejected this argument on several grounds. First, the district court found that the examples cited by Hassan were “not direct violations of the in limine order.” Second, the district court concluded that, even if the order were deemed violated, Hassan had not carried his burden, because it would not be a manifest injustice to let the verdict stand in light of the substantial evidence of his guilt. Third, the district court found that Hassan had “effectively waived” any objection pursuant to Rule 33, by failing to object at trial to the relevant testimony and by failing to request a limiting instruction on this issue.
The district court sentenced Hassan to eighty-seven months’ imprisonment and three years of supervised release on each count, to run concurrently, and imposed a special assessment of $4,400. The court also ordered a $21,100 forfeiture.
This appeal followed. We agreed to consider the case on аn expedited basis, and, in an order filed on May 9, 2007, after oral argument, we granted Hassan’s motion for bail pending appeal. See 18 U.S.C. § 3143(b). We now reverse the judgment of the district court as to the forty-one substantive counts of money laundering in violation of 18 U.S.C. § 1956(a)(1) because we find that the evidence was insufficient to sustain those convictions, and vacate the judgment of the district court on the remaining counts, because we find that the district court made a fundamental and prejudicial error in its jury instructions.
II. DISCUSSION
Almost all of the issues raised by Hassan in this appeal are intertwined in that they all implicate scienter. Thus, while sufficiency of the evidence is a threshold issue that may obviate other challenges,
see United States v. Allen,
A. Due Process Challenge
1. Standard of Review
We review
de novo
challenges to the constitutionality of a statute.
United States v. Giordano,
2. The Controlled Substance Act is Not Unconstitutionally Vague as Applied to Hassan
Hassan contends that the Controlled Substance Act (“CSA”) is unconstitutional as it applies to khat, 21 U.S.C. § 841, because it violates the Due Process Clause of the Fifth Amendment by failing to provide the defendant with fair warning that *120 his conduct is unlawful. Specifically, Hassan argues that a person of ordinary intelligence would not be able to determine— even upon close inspection of the relevant statute and regulations — that the importation or distribution of khat is , unlawful, that khat may contain a controlled substance, the nature of that controlled substance, or the sеriousness of a khat-related offense. Hassan roots his argument in the fact that the CSA does not explicitly mention the word “khat” while other botanical sources are listed in the CSA; that the chemicals that are mentioned in the CSA relating to khat — cathinone and cathine— are obscure and unknown to the average person; and that because cathinone rapidly deteriorates into cathine, it is impossible to know without chemical testing whether these chemicals are present in any particular supply of khat. Furthermore, Hassan notes that the obscurity of the CSA as it relates to khat is especially troublesome given that khat is legal and socially accepted in a large portion of the world, including Hassan’s native Somalia, and that its effects are that of a relatively mild stimulant similar to caffeine.
Hassan’s argument is an issue of first impression in our Circuit. The First, Sixth, and Eighth Circuits, however, have all rejected due process challenges to the khat-related regulatory scheme in the CSA.
See Caseer,
The vagueness doctrine requires that, in order to be constitutional, a statute must “give the person of ordinary intelligence a reasonable opportunity to know what is prohibited” and “provide explicit standards for those who apply [it].”
Grayned v. City of Rockford,
We believe, as the district court found, that what saves the statute at issue here — the CSA as it relates to khat — from constitutional trouble is the fact that scienter is required for a conviction.
See Caseer,
Nonetheless, while we believe the statute is constitutional, we are sympathetic to Hassan’s argument because the statutory scheme, as it relates to khat, is troubling. Here, rather than including the words “khat” or
“catha edulis
” in the applicable regulations, the regulatory scheme references only khat’s key chemical ingredients, cathine and cathinone. In contrast to the regulatory treatment of khat, Congress did list four botanical sources — сannabis, coca, peyote, and poppy — in the CSA in addition to their chemical ingredients.
5
We agree ■with Hassan, and the district court, that it would be helpful to people, who actually resort to statutes and regulations to determine whether their conduct is lawful, for Congress, through the statutory or regulatory scheme, to include the word “khat” in the CSA. However, we do not believe that Congress was required to do so.
See Hussein,
As the Sixth Circuit emphasized in
Caseer,
while the due process challenges raised in khat cases are unique, they nonetheless implicate serious constitutional concerns because “[w]hen a statute is precise on its face yet latently vague, the danger of persons being caught unaware of the criminality of their conduct is high.”
*122
B. Sufficiency of the Evidence
Because sufficiency of the evidence is a threshold issue that may obviate other challenges,
see Allen,
1. Standard of Review
We review
de novo
challenges to the sufficiency of the evidence.
United States v. Rangolan,
Nevertheless, Hassan’s burden, while heavy, is “not an impossible one.”
United States v. Jones,
2. The Evidence was Sufficient to Convict Hassan of the Khat Conspiracy Charge
“To sustain a conspiracy conviction, the government must present some evidence from which it can reasonably be inferred that the person charged with conspiracy knew of the existence of the scheme alleged in the indictment and knowingly joined and participated in it.”
Rodriguez,
As we noted earlier, khat may sometimes, but does not always, contain one or two stimulants that are controlled substances under U.S. law: cathinone and cathine.
See
21 C.F.R. §§■ 1308.11(f), 1308.14(e);
see also
21 U.S.C. § 812. In this case, Hassan was convicted on two khat related conspiracy charges: conspiracy to import
cathinone,
in violation of 21 U.S.C. §§ 952(a), 963, and conspiracy to distribute and to possess with intent to distribute
cathinone,
in violation of 21 U.S.C. §§ 841(a), 846. The government’s evidence at trial clearly established, and Hassan does not dispute, that Hassan knowingly conspired to import and distribute
khat.
Therefore, Hassan knew of and knowingly joined and participated in the scheme alleged. The only matter in dispute is whether the government presented evidence sufficient to demonstrate that Hassan “knowingly engaged in the conspiracy with the
specific intent
to commit the offenses that were the objects of the conspiracy.”
United States v. Samaria,
That is, because “[conspiracy is a specific intent crime ... [p]roof that the defendant knew that
some
crime would be committed is not enough.”
United States v. Morgan,
As we previously explained, khat itself is not a controlled substance.
See
*124
Argaw,
What differentiates this case from the khat cases that other circuits have confronted is that there was
no direct evidence
that any of the khat Hassan imported
actually contained a controlled substance
— cathinone, in this case.
Cf. Caseer,
Because of the lack of direct evidence, the government sought to prove the requisite intent in several ways. First, the government presented testimony about Hassan’s encounter with Agent Paul Kastava at JFK in 2001; second, it presented evidence about Hassan’s presence at a bond hearing for Ahmed Mussa; and third, it presented evidence that Hassan
*125
tried to bring the khat into the country expeditiously. While all of this evidence indicates that Hassan believed it was illegal to import khat into the United States, none of it, alone, supports what is required by law, i.e., “that the defendant knew- he possessed [the]
controlled substance
[charged, cathinone], (even [if] he was either mistaken about or did not know its exact identity).”
Hussein,
Although neither the government nor the district court lingered on this point, we begin by noting that Hassan’s potential awareness, from his time living in Somalia, of the stimulant effect of khat was not enough to put him on notice that khat contained cathinone, or indeed some other controlled substance.
Contra United States v. Sheikh,
We now turn to the evidence that the government argues supports the jury’s finding that Hassan was guilty of conspiring to import and distribute cathinone. First, Hassan was present at a bond hearing for a fellow khat importer, Ahmed Mussa. At that hearing, importation of khat was referred to at least twice as importation of a “drug” and it was compared to marijuana for the purposes of sentencing. Hassan participated in part of the hearing, being asked to come to the front of the room to testify. A jury could reasonably conclude that he was present in the room when khat, drugs, and marijuana were referenced. This is close to sufficient circumstantial evidence from which a jury could rationally conclude that Hassan knew that khat contained a controlled substance.
Second, the government argues that the speed with which Hassan attempted to bring the khat into the United States and the fact that he hired people to help him get khat out of Customs quickly — using Fuller’s fraudulent stamps to secure quick release of the packages and employing overnight delivery services — indicate that he knew he was importing the controlled substance cathinone. This evidence could have been construed in light of testimony that, over time, cathinone degrades into weaker chemicals. Transport speed is therefore directly related to cathinone’s pоtency, and the faster khat is shipped, the greater the probability that it will contain cathinone when it arrives at its intended destination. Combined with proof that Hassan spent between $3,000 and $4,500 a week to ensure that the khat was imported with sufficient speed, the jury was free to infer that Hassan intended to deal not merely in khat, but khat with cathinone, specifically. The impact of this cumulative evidence is weakened, however, because there is nothing in the record with respect to how much time it actually took to ship the khat to the United States, i.e., how *126 much time had elapsed between the moment the khat was picked in Northeast Africa and the time it arrived in the United States. Nevertheless, it does aid the government’s case. Further, because Hassan’s importation methods included efforts to conceal the nature of his packages, the shipping evidence adds to Hassan’s presence at the bond hearing to help show that Hassan knew cathinone to be a regulated substance.
Finally, the government introduced evidence that Hassan knew khat could be seized at Customs. Of course, “[n]ot all items that may be seized by the U.S. Customs Services, however, are classified as controlled substances .... ”
Caseer,
All this should make clear that we have deeply serious concerns regarding the sufficiency of the evidence in this case. We nevertheless find that the evidence — when viewed collectively — permits a finding of guilt.
See Autuori,
3. The Evidence was not, However, Sufficient to Convict Hassan of the Substantive Money Laundering Charges
Hassan was also charged with forty-one substantive counts of money laun
*127
dering, in violation of 18 U.S.C. § 1956(a)(1), based on money orders he purchased between December 21, 1998, and May 15, 2000. To sustain the substantive money laundering charges, the government must establish that Hassan (1) knowing that the property involved in а financial transaction represented the proceeds of some form of unlawful activity, (2) conducted or attempted to conduct a financial transaction, (3) which in fact involved the proceeds of specified unlawful activity, (4) either with (a) the intent to promote the carrying on of specified unlawful activity or (b) the knowledge that the transaction was designed at least in part to conceal or disguise the nature, location, source, ownership, or control of the proceeds of specified unlawful activity.
See
18 U.S.C. § 1956(a);
United States v. Gotti
The third requirement is dis-positive in this case. To sustain the substantive money laundering charges, in stark contrast to the conspiracy charges, the government must show not simply that Hassan laundered money that he believed to be the proceeds of cathinone sales, but that the funds he laundered were in fact the proceeds of cathinone sales. As the government conceded at oral argument, “[w]e don’t have any seizures from that time period, so there’s no direct evidence” to show that the underlying transactions actually involved the proceeds of cathinone trafficking. Moreover, there is no circumstantial evidence to show that Hassan actually trafficked in cathinone during this period. Instead, the government relies on the abundant evidence of Hassan’s khatrelated activities. For instance, the government argues that the money laundering charges are supported by the notebooks and date books Hassan kept detailing his khat transactions. In, addition, the government contends that the fact that Hassan’s declared income was an amount far less than the value of the money orders he purchased supports an inference that he used the proceeds of unreported khat sales to purchase the money orders. However, none of this evidence speaks to whether Hassan actually imported cathinone during this time period. Because cathinone can disappear from khat in a matter of days, and must be imported from the Horn of Africa or the Arabian Peninsula, the mere presence of khat in the United States certainly does not support an inference that cathinone is present.
See United States v. Muse,
No. 06-cr-600,
4. The Evidence was Sufficient to Convict Hassan of Conspiring to Launder Money.
Hassan was also charged with one count of conspiracy to launder money, in violation of 18 U.S.C. § 1956(h). “In order to establish that a defendant conspired to launder monetary instruments in violation of 18 U.S.C. § 1956(h), the government must show that the defendant agreed to: 1) conduct a financial transaction; 2) in
*128
volving the proceeds of specified unlawful activity; 3) knowing that the property involved in the transaction represented the proceeds of some form of unlawful activity; and 4) knowing that the financial transaction was designed in whole or in part to conceal or disguise the nature, source, location, ownership, or control of those proceeds.”
United States v. Henry,
The evidence presented at trial was sufficient to sustain a conviction on this count, which charged Hassan with conspiring to launder money “between December 1998 and April 2003.” The money orders, unreported income, date books, and notebooks allowed the jury to infer that Hassan agreed to conduct various financial transactions, knowing that the transactions were structured to disguise the nature and source of the funds involved. Having found the evidence sufficient to convict Hassan of the cathinone conspiracy charges, the jury could have easily inferred that Hassan believed that the funds related to cathinone trafficking. Because the government presented money orders purchased by Hassan in November 2002, after his participation in the bond hеaring and following his encounter with Agent Kastava, the jury was able to also conclude that Hassan knew cathinone was a regulated substance during the period charged in the indictment. However, as we explain below, we believe there was a fundamental and prejudicial error in the district court’s instructions to the jury on scienter. Because we fear that this error may have affected the jury’s determination on this issue, we vacate the judgment of the district court, and remand for a retrial on the one count of conspiracy to launder money, in violation of 18 U.S.C. § 1956(h). For the same reasons, discussed in further detail below, we also vacate the judgments on the one count of conspiracy to import cathinone, in violation of 21 U.S.C. §§ 952(a), 963, and the one count of conspiracy to distribute and to possess with intent to distribute cathinone, in violation of 21 U.S.C. §§ 841(a), 846.
C. Erroneous Jury Instructions
1. Standard of Review
We review
de novo
a claim of error in jury instructions, “reversing only where, viewing the charge as a whole, there was a prejudicial error.”
United States v. Aina-Marshall,
The government’s claim sweeps too broadly. At the charging conference, defense counsel clearly raised an objection to the jury instructions that dealt with precisely the issues now before us. With respect to Count One, importation, defense counsel stated:
The only controlled substance involved in this case is cathinone. If it’s not cathinone, we’ve stipulated cathine could not be regarded, khat is not a controlled substance. I don’t know — -they can’t argue heroin or cocaine. There is no evidence of anything other than cathinone. This ... broadens it so wide .... I just think the sentence should be deleted.
... The officer sat on the stand, testified that khat was a controlled substance. ... The chemist witness went further, he even said cathine, I found cathine, and it’s on schedule four .... What if the jury heard that and they say *129 oh that cathine business, it might have been cathine.
Hassan’s trial counsel thus made clear that he believed that portions of the jury charge should be stricken so as to assure that the jury did not convict Hassan, improperly, on the basis of his conspiring to import “some controlled substance” other than cathinone. Although Hassan did not explicitly reiterate his objection to the jury instruction relating to Count II, the same charging language was at issue in both drug counts. There was no reason for Hassan to limit his challenge to Count I, nor for the court to believe he was doing so. It is true that, as' the government argues, if Hassan had specifically objected to the charge for Count II, the court may have made the same modifications to the scienter instruction as it did for Count I. However, that is immaterial on this appeal, because Hassan is arguing that — even as modified — the charge for Count I was erroneous:
The government also claims that the arguments being raised on appeal are not preserved because trial counsel, after objecting to the jury instructions, failed to propose alternative language. This argument also fails. Rule 30(d) requires only that a party “inform the court of the specific objection,” Fed.R.Crim.P. 30(d), and does not require that a party propose alternate language in order to preserve a challenge for appeal. As the cited portion of counsel’s statements indicates, the substance of the claim now being raised on appeal was squarely raised below: counsel made it clear to the trial court that he objected to the charge because he believed it permitted the jury to convict Hassan based on a finding that Hassan intended to import and distribute khat or khat containing cathine.
Cf. United States v. Masotto,
2. The District Court Made a Fundamental Errоr in its Jury Instructions
“A jury instruction is erroneous if it misleads the jury as to the correct legal standard or does not adequately inform the jury on the law.”
Anderson v. Branen,
We begin by noting that, in this case, the instruction to the jury on the requirement of intent is critical for two reasons. First, as noted above, scienter is what preserves the relevant statutory and regulatory scheme from a successful due process challenge. Second, Hassan has been charged only with conspiracy, and thus the government does not need to prove that Hassan ever actually imported or pos
*130
sessed cathinone with intent to distribute, but only that he
intended
to do so.
See United States v. Morgan,
Count One charged Hassan with conspiring to import cathinone, a Schedule I controlled substance, in violation of 21 U.S.C. §§ 952(a), 963. As to Count One, the district court instructed the jury that in order to convict Hassan, the jury “must find that the defendant knew it was a controlled substance he was conspiring to bring into the United States,” and explained that the jury “need not find that the defendant knew or believed that it was a drug called cathinone, as long as the government proves that he knew and intended that some controlled substance would be imported into the United States.” Count Two charged Hassan with conspiring to possess with intent to distribute cathinone in violation of 21 U.S.C. §§ 841(a)(1), 846. As to Count Two, the district court instructed the jury that, in order to convict Hassan, the jury had to find that Hassan “acted with the specific intent of possessing the controlled substance,” and explained that “[t]he government need not, however, prove that the defendant knew the exact nature of the controlled substance in his possession. It is enough that the government proves that the defendant knew that he possessed some kind of a controlled substance.”
Hassan argues that the charges to the jury on the conspiracies to import and distribute cathinone were erroneous and not accurate explanations of the law, because they left open the possibility that the jury could convict Hassan on an improper basis — either on the basis that he intended to import and distribute khat (which is not a controlled substance) or on the basis that he imported or distributed cathine (which, as the government has acknowledged, was not the controlled substance which Hassan was charged with possessing in the indictment). Hassan points out that the district court did not explain to the jury that khat itself is not a controlled substance, or that defendant’s intent to import or possess khat could not be the basis for his conviction without proof that he intended to import or possess khat with cathinone. Furthermore, the district court did not explain to the jury that cathine is a different, and less serious controlled substance, and could not be the basis for Hassan’s conviction of the crimes charged in the indictment.
Hassan contends that the problems with the jury instructions are of particular import, because at trial, government witnesses repeatedly suggested — incorrectly, and without correction by the court — that khat itself is a controlled substance. Because khat is not, per se, a controlled substance, the district court ruled before trial that the “[gjovernment would not be permitted to introduce evidence that khat is per se a controlled substance.” Nonetheless, at trial numerous government witnesses suggested that khat was in fact a controlled substance. For example, Special Agent Kastava testified that khat is “an illegal substance in the United States,” Special Agent Lee testified that khat is a “narcotic” and “is on the controlled substance list,” Special Agent Villanucci testified that he arrested Hassan for “[ijmportation of khat” and arrested an *131 other individual earlier for “attempting to import khat,” Fuller testified that he pled guilty to “[cjonspiracy to import khat,” and that khat is “a controlled substance,” and Mohamed Hassan testified that he pled guilty to importing “forbidden stuff ... [t]he khat.” 9 Furthermore, a government witness also discussed the illegality of khat with cathine. Specifically, the DEA chеmist testified that khat may contain cathine, that cathine is a Schedule IV controlled substance, and that the khat tested in connection with this case in fact contained both cathine and cathinone. Despite this repeated testimony, the district court did not clarify to the jury that Hassan was charged with importing or possessing khat with, cathinone, not khat, nor khat with cathine. Thus, Hassan argues that these statements by witnesses, combined with the jury instructions, allowed the jury to believe that it could convict Hassan because he intended to import and possess khat, or intended to import and possess khat with cathine.
The government makes a number of arguments concerning the evidence in this case. First, the government argues that Hassan misreads the jury instructions, taking one sentence out of context, and that a review of the entire charge shows that Hassan’s argument has no merit. While the government concedes that witnesses testified that khat is an unlawful controlled substance, it nonetheless dismisses this testimony as “not literally false” given the fact that khat is a controlled substance when it contains either cathinone or cathine, like the khat at issue.
But cf. Argaw,
But the question before us is not, as the government suggests, whether this trial testimony was literally false, but rather whether, in light of the testimony, the judge’s instructions failed to present the jury with a correct explanation of the law. The government argues that Hassan takes a single sentence in the jury instructions out of context and that the charge as a whole properly instructed the jury that an element of each charged crime was the intent to import or possess the controlled substance cathinone, regardless of whether Hassan knew the substance by name. The government is correct that references to *132 cathinone appear frequently in the jury instructions:
[Reading from the indictment:] “Count One: Conspiracy to Import Cathinone .... [defendant] did knowingly and intentionally conspire to import into the United States ... a substance containing cathinone.”
“I instruct you that cathinоne is a controlled substance under the law and for the purposes of these statutes.”
“Before you may convict the defendant of conspiracy to import cathinone as charged in the indictment, the government must establish each of the following elements beyond a reasonable doubt.”
“[Y]ou need not find that the defendant knew or believed that it was a drug called cathinone, as long as the government proves that he knew and intended that some controlled substance would be imported into the United States. As I told you earlier, cathinone is a controlled substance.”
[From the indictment:] “Count Two: Conspiracy to Possess with Intent to Distribute Cathinone .... [defendant] did knowingly and intentionally conspire to distribute and possess with intent to distribute a controlled substance, which offense involved a substance containing cathinone .... ”
“I have already instructed you that cathinone is a controlled substance under the law.”
“[Y]our decision as to whether the defendant conspired to commit a particular unlawful act, either distribution of cathinone or possession with intent to distribute cathinone, must be unanimous.”
“The elements of possession with intent to distribute are: First, that the defendant possessed cathinone; Second, that the defendant knew that he possessed a controlled substance; and Third, that the defendant possessed cathinone with intent to distribute it.”
“The elements of the crime of distribution of cathinone are: First, that the defendant distributed cathinone; Second, that the defendant distributed the cathinone knowingly.”
Moreover, cathinone is the only controlled substance identified in the jury instructions.
The government therefore argues that the purpose and the effect of the jury instruction was to inform the jury that Hassan need not know that the controlled substance at issue was named cathinone, so long as Hassan realized it was a controlled substance. While we agree that this was likely the district court’s purpose in stating the jury instructions as it did, we disagree with the government as to the effect that the instructions may have had. We emphasize, again, that in this case the scienter requirement is what prevents the entire regulatory scheme, as it relates to khat, from being unconstitutional. Therefore, we must scrutinize the instructions regarding scienter, and the context in which they were given, very closely. Here, we believe that the jury instructions failed to correctly inform the jury that a bare intent to import or possess khat, or khat with cathine, would not be sufficient to sustain Hassan’s conviction. Instead, in light of the evidence presented to the jury throughout the trial, the jury may have very well convicted Hassan on the erroneous belief that khat is a controlled substance, or on the basis of a belief that Hassan must have known, at a minimum, that he was importing with intent to distribute cathine. We therefore find that there was a fundamental error in the jury instructions. Furthermore, given how close we believe the sufficiency of the evidence was in this case, and the essential role that the scienter requirement played *133 in our due process analysis, this error was not harmless.
We аre also unpersuaded by the government’s remaining arguments. First, the government argues that the charge as a whole was adequate because cathinone was the only substance identified as a controlled substance in the jury charge. While this is so, as we explained above in detail, the jury also heard inaccurate testimony to the effect that khat 'is- illegal, along with accurate testimony that cathine is also illegal. The district court’s jury instruction thus left open the possibility that the jury would convict on one of these alternative bases. Second, the government argues that it is inconceivable that Hassan intended to import anything other than cathinone in light of his overnight delivery methods. This is obviously not true. Hassan’s customers may have preferred fresh khat containing cathine, or simply fresh khat containing no controlled substances. Despite the expedited means of delivery, there was absolutely no evidence in the record of when the khat arrived, much less that it arrived in the United States within 48-72 hours of it being cut. See U.S. Drug Enforcement Administration, Fact Sheet, Khat, AKA: Catha Edulis, http://www.dea.gov/pubs/ pressrel/pr072606a.html (last visited Aug. 10, 2008)(stating that “[cjathinone ... dissipates within 48 hours of harvest”); FDA Report 11-12 (stating that khat leaves have been reported to lose their effect within three days of harvesting).
Finally, and perhaps most troubling, the government cites our decision in
United States v. Morales, 577
F.2d 769, 776 (2d Cir.1978), to argue that Hassan could have been lawfully convicted by the jury even if the jury found that he intended to import an illegal substance with
cathine,
and not an illegal substance with
cathinone.
First, as stated previоusly, we believe the jury instructions, in light of testimony at trial, created a real possibility that the jury may have convicted Hassan on the erroneous belief that khat, itself, was a controlled substance, and therefore this argument is unpersuasive. Second, the government conceded .at trial that it was not trying an “any” controlled substance charge, but rather, was limiting itself to trying a cathinone-related charge, as listed in the indictment. Moreover, the government’s attempt to use
Morales
to argue that any error in. the jury instructions was harmless runs squarely into Hassan’s constructive amendment claim. A conviction based on cathine, rather than cathinone, would have been an impermissible constructive amendment of the indictment.
See United States v. Wozniak,
By making this charging decision, Hassan’s alleged intent to import and possess this Schedule I substance was critical to a conviction.
See Wozniak,
We understand that the khat-related regulatory scheme poses unique and complicated issues for the government, defendants, and district courts. We are not unsympathetic to those problems. In this case, however, given the terms of the indictment, the misleading evidence allowed at trial concerning the illegality of khat, and the potentially confusing evidence concerning cathine, the jury instructions were clearly erroneous. Furthermore, the jury instructions were not harmless. Under the circumstances of this case, to be valid, the jury charge needed to explain explicitly to the jury that (1) khat itself is not a controlled substance and Hassan cannot be convicted simply for intending to import or possess with intent to distribute khat; (2) if the jury found that Hassan had the intent to import and possess khat with cathine, that too would not be sufficient to convict Hassan; and (3) that the government is bound by the scienter burden it assumes in the crimes it charges — the government was required to prove here that Hassan had the intent to import and possess khat with cathinone.
D. Remaining Claims
We are reversing and ordering an entry of acquittal on forty-one of Hassan’s substantive money laundering charges, and vacating and remanding to the district court for retrial on all remaining charges. Therefore, we need not consider Hassan’s remaining arguments that he was denied a fair trial because the government failed to correct false and misleading testimony, his trial counsel was ineffective, the district court erred in admitting the DEA chemist’s testimony and the exhibits regarding the testing of three samples of khat, and that his sentence was erroneous and unreasonable.
III. CONCLUSION
Because we conclude that the evidence was insufficient to convict Hassan of the forty-one substantive counts of money laundering, in violation of 18 U.S.C. § 1956(a)(1), we REVERSE the judgment on these counts, and direct the district court to enter an order of acquittal. Because we believe there was a fundamental error in the jury instructions that was not harmless, we VACATE Hassan’s conviction on the remaining counts and remand to the district court for retrial, if the government should wish to pursue the matter.
Notes
. As noted, this amended opinion replaces in its entirety our earlier decision in
United States
v.
Hassan,
. Hassan argues that cathine's listing as a controlled substance is no longer valid because a temporary listing cannot substitute indefinitely for the required rulemaking process. Because Hassan was not charged with a cathine offense, we do not reach this issue.
. Kastava thus misstated the law regarding khat to Hassan. Khat itself is not illegal, rather, only khat containing cathinone or cathine is illegal. See supra Part 1(A).
. As stated previously, it was actually at JFK, not Newark, that Hassan had run into previous trouble with U.S. Customs.
. We are aware that, similar to khat, "magic mushrooms” are not listed in the CSA while their psychedelic ingredients, psilocybin and psilocyn, are. Thus, we agree with the First Circuit that there is no reliable pattern here.
Hussein,
. Testimony that occurred at trial supports this position: The cooperator (Mohamed Hassan), a witness who had made his career in the khat trade, testified that he had never heard of "cathinone;” and the government’s DEA chemist testified that he had never heard the term cathinone until trained by the DEA.
. “This is not to suggest that in all Controlled Substances Act prosecutions the government must prove beyond a reasonable doubt that the defendant had actual knowledge that the substance at issue is controlled. For substances such as cocaine that are controlled per se under the controlled substances schedules and for which there are no due process fair-warning concerns, constructive knowledge inferred from the listing of the substance in the controlled substances schedules may suffice. However, when a targeted item, such as khat, is not itself listed in the controlled substances schedules, due process requires that the government prove beyond a reasonable doubt that the defendant had
actual knowledge
that the targeted item contained a controlled substance regulated under federal drug abuse laws.”
Caseer,
. The government also proffered "evidence” that we do not believe supports its case that Hassan was guilty of conspiring to import and distribute a Schedule I drug. The government presented evidence that it tested several packages of khat that were obtained after Hassan’s arrest, and the DEA chemist testified that these packages contained both cathinone and cathine. Assuming arguendo both that the chemist’s testimony was admissible as relevant, and that DEA forms recording the three additional seized packages were admissible hearsay — two assumptions about which we have grave doubts — this additional evidence does not help show even that Hassan intended to import khat, nor does it support an inference that the seized packages were connected to the charged conspiracy. The government provided no evidence, for instance, about how these packages were addressed and labeled, from where they were mailed, how long they were in transit, or any other information that would have provided stronger circumstantial proof that these packages were connected to Hassan
And while Agent Kastava testified that he told Hassan that khat was illegal in the United States — a statement which is in fact inaccurate, as khat is only illegal when it contains a controlled substance — he did not testify that he told Hassan it was illegal because it could contain controlled substances, or more importantly, for the purposes of this case, cathinone. As such, this evidence has little use.
. Defense counsel actually highlighted some of this testimony when objecting to the jury instructions, but the judge indicated that a law enforcement officer’s testimony that khat was a controlled substance was a matter "for the jury.” We are troubled by this comment; regardless of how the legal status of khat is characterized, it is a legal issue for the judge to decide, and clarify for the jury, not a question of fact reserved for the jury.