United States Court of Appeals 

For the First Circuit 

No. 16-2391 

UNITED STATES OF AMERICA, 

Appellee, 

v. 

LEDA GIGGEY, 

Defendant, Appellant. 

APPEAL FROM THE UNITED STATES DISTRICT COURT 

FOR THE DISTRICT OF MAINE 

[Hon. John A. Woodcock, Jr., U.S. District Judge] 

Before 

Kayatta, Selya and Barron, 

Circuit Judges. 

 Matthew S. Erickson on brief for appellant. 

 Richard W. Murphy, Acting United States Attorney, Renée M. 

Bunker, Assistant United States Attorney, Appellate Chief, and 

Benjamin M. Block, Assistant United States Attorney, on brief for 

appellee. 

August 14, 2017 
- 2 - 

SELYA, Circuit Judge. Controlled substances continue to 

cast a dark shadow over a large segment of American society. That 

situation is made even worse by the proliferation of new 

permutations of such substances. Synthetic cathinones, 

colloquially known as bath salts, represent one of these 

permutations, and we recently had occasion to warn that their 

illegal use was becoming a mounting problem in the District of 

Maine. See United States v. Coombs, 857 F.3d 439, 443 & n.1 (1st 

Cir. 2017). 

When drug offenses involve drugs not listed in the 

relevant tables incorporated in the sentencing guidelines, those 

drugs are converted into their marijuana equivalent for sentencing 

purposes. See USSG §2D1.1, cmt. nn.6 & 8. This appeal requires 

us, for the first time, to pass upon the method and manner in which 

that conversion is effected with respect to synthetic cathinones. 

The court below used a conversion metric grounded in its finding 

that methcathinone is the drug referenced in the sentencing 

guidelines that is most closely related to the synthetic cathinone 

alpha-pyrrolidinopentiophenone (alpha-PVP). Using this metric, 

the court sentenced defendant-appellant Leda Giggey to a 72-month 

term of immurement. Discerning no clear error, we affirm. 

I. BACKGROUND

We briefly rehearse the facts and travel of the case, 

drawing upon the plea agreement, the uncontested portions of the 
- 3 - 

presentence investigation report, and the transcript of the 

disposition hearing. See United States v. Del Valle-Rodríguez, 

761 F.3d 171, 173 (1st Cir. 2014); United States v. Dietz, 950 

F.2d 50, 51 (1st Cir. 1991). Between 2012 and 2015, the defendant 

procured 2,120.75 grams — more than 21,000 individual doses — of 

synthetic cathinones, some from local suppliers and some from 

China. During this period, she became one of the foremost dealers 

of bath salts in Aroostock County, Maine. After some time had 

gone by, law enforcement officers threw a monkey wrench into her 

drug-distribution business: they executed a search warrant at her 

residence and found 1.07 grams of alpha-PVP, a drug ledger, two 

digital scales, and a cellular telephone replete with 

incriminating text messages. The defendant's arrest followed 

apace. 

In due course, the defendant pleaded guilty to 

conspiracy to distribute and possession with intent to distribute 

controlled and analogue substances. See 21 U.S.C. §§ 813, 

841(a)(1), 846. Federal drug laws classify proscribed drugs in 

five separate schedules, which are updated on an annual basis. 

See id. § 812(a). Because alpha-PVP was not listed on any of these 

schedules until March of 2014, see Schedules of Controlled 

Substances: Temporary Placement of 10 Synthetic Cathinones into 

Schedule I, 79 Fed. Reg. 12,938, 12,941 (Mar. 7, 2014) (codified 

at 21 C.F.R. § 1308.11), the government prosecuted the defendant 
- 4 - 

under the Controlled Substance Analogue Enforcement Act of 1986 

(Analogue Act), Pub. L. No. 99-570, §§ 1201-1204, 100 Stat. 3207-

13, 3207-13 to -14 (codified at 21 U.S.C. §§ 802(32), 813). The 

Analogue Act facilitates the regulation of new drugs which, though 

not currently outlawed, exhibit substantial similarities to a 

controlled substance found in either Schedule I or II.1 See 21 

U.S.C. § 802(32)(A). The Analogue Act defines a "controlled 

substance analogue" as: 

[A] substance (i) the chemical structure of 

which is substantially similar to the chemical 

structure of a controlled substance in 

schedule I or II; (ii) which has a stimulant, 

depressant, or hallucinogenic effect on the 

central nervous system that is substantially 

similar to or greater than the stimulant, 

depressant, or hallucinogenic effect on the 

central nervous system of a controlled 

substance in schedule I or II; or (iii) with 

respect to a particular person, which such 

person represents or intends to have a 

stimulant, depressant, or hallucinogenic 

effect on the central nervous system that is 

substantially similar to or greater than the 

stimulant, depressant, or hallucinogenic 

effect on the central nervous system of a 

controlled substance in schedule I or II. 

Id. 

 1 Schedule I is reserved for drugs with "no currently accepted 

medical use." 21 U.S.C. § 812(b)(1). Schedule II covers drugs 

which, although they may have an accepted medical use, are such 

that "[a]buse of the drug . . . may lead to severe psychological 

or physical dependence." Id. § 812(b)(2). Schedules III, IV, and 

V cover drugs of decreasing levels of potential abuse and 

dependence. See id. § 812(b)(3)-(5). 
- 5 - 

Drug quantity is an important integer in the sentencing 

calculus for most controlled substance offenses. See United States 

v. Dunston, 851 F.3d 91, 94 (1st Cir. 2017). The sentencing 

guidelines implement this concept through, inter alia, the use of 

a Drug Quantity Table, see USSG §2D1.1(c), and Drug Equivalency 

Tables, see id. §2D1.1, cmt. n.8(D). 

As a practical matter, less commonly used drugs and new 

drugs are frequently not referenced in these tables. In such 

cases, the drug must be converted into the marijuana equivalent 

quantity of the most closely related controlled substance listed 

in the guidelines. Here, the government argued that methcathinone 

(a Schedule I controlled substance) was the appropriate comparator 

for alpha-PVP. The defendant countered that pyrovalerone (a 

Schedule V controlled substance) was more closely related to alphaPVP than methcathinone and, therefore, was the appropriate 

comparator. The defendant's sentence turned, to a large extent, 

on the outcome of this dispute: if methcathinone was deemed to be 

the proper comparator, the defendant's guideline sentencing range 

(GSR) promised to be appreciably higher. 

The district court convened the disposition hearing on 

November 8, 2016. Drug quantity was hotly contested in motion 

papers filed prior to the hearing. As matters turned out, the 

district court had confronted this same quandary in an earlier 

case. See United States v. Brewer, No. 1:15-cr-00003, 2016 WL 
- 6 - 

3580614 (D. Me. June 28, 2016). Rather than reinventing the wheel, 

the court opted to incorporate by reference its previous analysis, 

which found methcathinone to be the most closely related controlled 

substance to alpha-PVP for sentencing purposes.2 On that basis, 

the court found the defendant responsible for the equivalent of 

805.89 kilograms of marijuana.3

With this finding as the linchpin, the court made certain 

offense-level adjustments (not relevant here), calculated the 

defendant's total offense level (30), and placed her in criminal 

history category I. These subsidiary findings yielded a GSR of 

97-121 months. After considering the factors limned in 18 U.S.C. 

§ 3553(a), the court imposed a downwardly variant sentence of 72 

months' imprisonment. This timely appeal ensued.4

 2 Neither party has objected to the district court's reliance 

upon Brewer, and the defendant has raised no arguments other than 

those raised in Brewer. Because the district court relied on 

Brewer without making any new findings or adding any new analysis, 

our references to the district court's decision in this case 

necessarily refer to its findings and analysis in Brewer. 

3 The court also found the defendant responsible for an 

additional drug quantity after converting certain opioids into 

their marijuana equivalent. This incremental increase in overall 

drug quantity has no bearing on the issues before us. 

4 The plea agreement contains a waiver of the defendant's 

right to appeal from any sentence of 57 months or less. Given the 

length of the sentence imposed, this waiver has no effect on the 

defendant's appeal. 
- 7 - 

II. ANALYSIS

At the outset, we pause to review the methodology used 

to determine drug quantity for crimes involving prohibited drugs 

not specifically referenced in the sentencing guidelines. To 

begin, the guidelines provide a series of base offense levels for 

controlled substance offenses. See USSG §2D1.1. The most common 

controlled substances (for example, heroin, cocaine, marijuana, 

and the like) appear in the Drug Quantity Table, which specifies 

particular base offense levels depending upon the drug type and 

quantity involved in a given offense. See id. §2D1.1(c). Many 

less common drugs are assigned ratios in the Drug Equivalency 

Tables, which permit conversion of a given quantity of any of these 

controlled substances into its "equivalent quantity of 

mari[j]uana." Id. §2D1.1, cmt. n.8(A)(i); see United States v. 

Demers, 842 F.3d 8, 12 (1st Cir. 2016). In such instances, 

sentencing courts "[u]se the offense level that corresponds to the 

equivalent quantity of mari[j]uana [in the Drug Quantity Table] as 

the base offense level for the [actual drug] involved in the 

offense." USSG §2D1.1, cmt. n.8(A)(iii); see United States v. 

Hurley, 842 F.3d 170, 171-72 (1st Cir. 2016). 

Although the Drug Quantity Table and the Drug 

Equivalency Tables together cover a broad array of controlled 

substances, these tables do not exhaust the universe of prohibited 

drugs. When either a controlled substance or a controlled 
- 8 - 

substance analogue does not appear in either of the tables, the 

sentencing court must calculate the offender's base offense level 

using the marijuana equivalent of "the most closely related 

controlled substance" that is referenced in the tables. USSG 

§2D1.1, cmt. n.6; see Hurley, 842 F.3d at 171-72. To determine 

which drug is most closely related, three factors must be 

considered. They include 

(1) whether the unreferenced controlled 

substance has a chemical structure that is 

substantially similar to a controlled 

substance referenced in the guidelines; 

(2) whether the unreferenced controlled 

substance has a stimulant, depressant, or 

hallucinogenic effect on the central nervous 

system that is substantially similar to the 

stimulant, depressant, or hallucinogenic 

effect of a controlled substance referenced in 

the guidelines; 

(3) whether a lesser or greater quantity of 

the unreferenced controlled substance is 

needed to produce a substantially similar 

effect on the central nervous system as a 

controlled substance referenced in the 

guidelines. 

See USSG §2D1.1, cmt. n.6. 

Once the proper comparator has been identified, the 

court calculates the unreferenced drug's marijuana equivalent 

using the marijuana equivalent value assigned to the comparator in 

the Drug Equivalency Tables. See id. §2D1.1, cmt. nn.6 & 8. The 

offender's base offense level is then established by comparing 
- 9 - 

this deduced marijuana equivalent quantity to the appropriate tier 

in the Drug Quantity Table. See id. §2D1.1(c) & cmt. nn.6 & 8. 

In the case at hand, the defendant challenges the 

district court's selection of methcathinone as the appropriate 

comparator for alpha-PVP on two distinct grounds. First, she 

asserts that the district court erred by restricting its search 

for a comparator drug to Schedule I and II controlled substances. 

Second, she asserts that the court erred in finding that 

methcathinone was more closely related to alpha-PVP than 

pyrovalerone. We evaluate these claims of error separately. 

A.

The defendant's first claim of error posits that the 

sentencing court impermissibly limited its search for an alphaPVP comparator to the universe of Schedule I and II controlled 

substances. As a result, the defendant says, the court excluded 

her preferred comparator, pyrovalerone, which is a Schedule V 

controlled substance. This amounts to a challenge to the district 

court's application of the sentencing guidelines, and we review 

the sentencing "court's interpretation and application of the 

sentencing guidelines de novo." United States v. Walker, 665 F.3d 

212, 232 (1st Cir. 2011). 

In this case, the district court, adopting its findings 

in Brewer, 2016 WL 3580614, at *11, concluded that, as a matter of 

law, only a Schedule I or Schedule II controlled substance can be 
- 10 - 

considered the most closely related drug to a controlled substance 

analogue not referenced in the sentencing guidelines. The plain 

language of the sentencing guidelines supports the conclusion that 

an analogue comparator must be a controlled substance selected 

from either Schedule I or II. The commentary to the relevant 

sentencing guideline states, in an application note, that "[f]or 

purposes of this guideline 'analogue' has the meaning given the 

term 'controlled substance analogue' in 21 U.S.C. § 802(32)." USSG 

§2D1.1, cmt. n.6. The statute, in turn, defines a controlled 

substance analogue as a substance that is "substantially similar" 

in chemical structure, pharmacological effect, and intended effect 

to "a controlled substance in schedule I or II." 21 U.S.C. 

§ 802(32)(A) (emphasis added); see McFadden v. United States, 135 

S. Ct. 2298, 2303-05 (2015). 

It is a familiar tenet that the text of a statute 

"furnishes the most reliable guide to its interpretation." United 

States v. Suárez-Gonzáles, 760 F.3d 96, 99 (1st Cir. 2014). The 

same respect is accorded to the text of the sentencing guidelines. 

See id. Here, the plain language of both the statute and the 

application note indicate that the proper comparator for an 

unreferenced controlled substance analogue must be drawn from 

Schedule I or II. See 21 U.S.C. § 802(32)(A); USSG §2D1.1, cmt. 

n.6; see also United States v. Emerson, No. 2:15-cr-17, 2016 WL 
- 11 - 

1047006, at *5 (D. Vt. Mar. 10, 2016) (terming any other result 

"absurd"). 

But there is more to the story. Here, the district court 

— after stating that the controlled substance analogue must be 

chosen from the ranks of Schedules I and II — prudently assumed, 

favorably to the defendant, that pyrovalerone (the Schedule V 

controlled substance identified by the defendant) was eligible for 

consideration in the search for a suitable comparator to 

alpha-PVP. The court then proceeded to examine both methcathinone 

(the Schedule I controlled substance identified by the government) 

and pyrovalerone in order to determine which drug was most closely 

related to alpha-PVP. It was only after this detailed examination 

of the competing candidates proposed by the parties that the court 

concluded that methcathinone was the proper comparator. 

That ends this aspect of the matter. As we recently 

explained, "courts should not rush to decide unsettled issues when 

the exigencies of a particular case do not require such definitive 

measures." Privitera v. Curran (In re Curran), 855 F.3d 19, 22 

(1st Cir. 2017). So it is here: the sentencing court's 

prophylactic approach obviates the need for us to make a definitive 

holding as to whether the proper comparator for a controlled 

substance analogue can be chosen only from the possibilities 

presented by Schedules I and II. Because the sentencing court 

went the extra mile and thoroughly considered the Schedule V drug 
- 12 - 

proposed by the defendant in its search for the proper comparator, 

it would be gratuitous to decide whether the court's search should 

have been limited to Schedules I and II. Given the breadth of the 

inquiry actually undertaken by the court, any error in stating 

that the search should be restricted to Schedules I and II was 

manifestly harmless. See, e.g., United States v. Alphas, 785 F.3d 

775, 780 (1st Cir. 2015) (explaining that "an appellate court may 

deem such an [alleged] error harmless if, after reviewing the 

entire record, it is sure that the error did not affect the 

sentence imposed"). 

B.

This brings us to the defendant's plaint that the 

sentencing court erred in determining that methcathinone was the 

controlled substance referenced in the sentencing guidelines that 

corresponds most closely to alpha-PVP. Typically, findings of 

fact at sentencing are reviewed for clear error. See, e.g., 

Walker, 665 F.3d at 232. It is an open question in this circuit, 

though, whether a district court's selection of the most closely 

related controlled substance is a factual or a legal determination. 

Withal, we do not write on a pristine page. Several of 

our sister circuits have held that such a determination is a 

factual matter and, thus, engenders review only for clear error. 

See, e.g., United States v. Novak, 841 F.3d 721, 730 (7th Cir. 

2016); United States v. Malone, 828 F.3d 331, 337 (5th Cir. 2016); 
- 13 - 

United States v. Ramos, 814 F.3d 910, 918 (8th Cir. 2016); United 

States v. Chowdhury, 639 F.3d 583, 585-86 (2d Cir. 2011) (per 

curiam). We share this view, and we proceed to assay the district 

court's "comparator" finding for clear error.5 That standard of 

review is deferential: it requires that we accept findings of fact 

and inferences drawn therefrom unless, "on the whole of the record, 

we form a strong, unyielding belief that a mistake has been made." 

Demers, 842 F.3d at 12 (quoting Cumpiano v. Banco Santander P.R., 

902 F.2d 148, 152 (1st Cir. 1990)). 

Here, the district court did not clearly err. The court 

methodically subjected the two proposed comparators 

— methcathinone and pyrovalerone — to the prescribed tripartite 

test: it inspected and contrasted the chemical structure, 

pharmacological effect, and potency of each drug. What is more, 

the court painstakingly conducted this inquiry through the prism 

of competing expert testimony and evidentiary proffers purporting 

to show which drug should be deemed more closely related to 

alpha-PVP. 

 5 While we review the district court's factfinding on the 

designated factors only for clear error, we reserve the right, in 

an appropriate case, to review the net result of that combined 

factfinding on a less deferential standard. Cf. Ornelas v. United 

States, 517 U.S. 690, 691, 699 (1996) (explaining that factual 

findings underlying probable cause determinations are reviewed for 

clear error but determination of "ultimate question[]" as to 

whether probable cause exists is reviewed de novo). 
- 14 - 

In its analysis, the court determined that both 

methcathinone and pyrovalerone were substantially similar in 

chemical structure to alpha-PVP (even though pyrovalerone was 

somewhat "more similar . . . in its chemical structure"). The 

court next determined, based principally on the proffered expert 

testimony, that both drugs were substantially similar in 

pharmacological effect to alpha-PVP. Last — but far from least — 

the court determined that methcathinone more closely resembled 

alpha-PVP in potency. In this regard, the court stated that 

"[a]lpha-PVP is more potent than methamphetamine, and thus is at 

least as potent as methcathinone."6 The court found that the 

defendant had not proven pyrovalerone to be as potent. 

After a thorough review of the record, we conclude that 

the district court did not clearly err in finding that 

methcathinone is the drug referenced in the sentencing guidelines 

that is most closely related to alpha-PVP. The district court 

found the government's expert evidence more persuasive, and we 

have said that "[w]hen dueling experts have each rendered a 

coherent and facially plausible opinion, the trial court's 

decision to adopt one and reject the other cannot be clearly 

 6 This finding is of a piece with the defendant's admission 

at sentencing that alpha-PVP "is a powerful, highly addictive 

poisonous chemical that left me with a mind riddled with poor 

judgment." 
- 15 - 

erroneous." United States v. Jordan, 813 F.3d 442, 447 (1st Cir. 

2016). That is precisely the situation here. 

In an effort to undermine the district court's 

factfinding, the defendant emphasizes that pyrovalerone was found 

to be closer in chemical structure. This emphasis, however, 

ignores the district court's supportable findings regarding the 

two remaining guideline factors. When all is said and done, a 

sentencing court is not obliged "to match substances under each of 

the factors." Chowdhury, 639 F.3d at 586. So, for example, a 

substance that is not the best fit in terms of chemical structure 

may still be the most appropriate comparator because of 

substantially similar pharmacological effect and potency. See 

Novak, 841 F.3d at 730. 

In this instance, the district court, after taking each 

of the three prongs of the test into consideration, found that, on 

the whole, methcathinone was the most closely related controlled 

substance to alpha-PVP. Pertinently, the district court gave 

significant weight to potency, finding that alpha-PVP packed a 

punch comparable to methcathinone, and that there was no proof 

that pyrovalerone was as powerful. Put simply, the court's 

rationale rests heavily (and logically) on the similarity in 

potency between methcathinone and alpha-PVP. The plausibility of 

this rationale is not weakened simply because the court "did not 

weigh the factors as the [defendant] would have liked." Coombs, 
- 16 - 

857 F.3d at 452. The short of it is that the court's careful 

calibration of the decisional scales gives us confidence that its 

analysis was not clearly erroneous. See United States v. Platte, 

577 F.3d 387, 394 (1st Cir. 2009) (finding no clear error when 

drug quantity determination was "supported by a sensible (though 

not inevitable) view of the record"). 

In all events, the defendant's argument fails on its own 

terms. Her factual challenge hinges on the notion that 

pyrovalerone would be a better choice as a comparator than 

methcathinone, not that methcathinone is an implausible choice (a 

point the defendant freely concedes when she states, in her 

appellate brief, that "there is ample evidence on the record to 

support the sentencing [c]ourt's finding"). This approach runs 

headlong into the settled rule that "where there is more than one 

plausible view of the circumstances, the sentencing court's choice 

among supportable alternatives cannot be clearly erroneous." 

United States v. Ruiz, 905 F.2d 499, 508 (1st Cir. 1990). 

In a last-ditch effort to turn the tables, the defendant 

invokes the rule of lenity. She argues that because both 

methcathinone and pyrovalerone could be recognized as comparators, 

we should mandate the use of the latter because doing so will 

result in a markedly diminished sentence. This argument is 

hopeless. 
- 17 - 

"The rule of lenity generally applies to criminal 

statutes that are subject to more than one plausible interpretation 

and demands that the interpretation more favorable to the defendant 

prevail." Suárez-Gonzáles, 760 F.3d at 101. When statutory 

ambiguity is wholly absent, any "concerns that may be redressed 

through an application of the rule of lenity" are also absent. 

United States v. Aponte-Guzmán, 696 F.3d 157, 160 (1st Cir. 2012); 

see Suárez-González, 760 F.3d at 101. Here, the defendant advances 

no claim of statutory ambiguity but, rather, merely reprises her 

factbound claim that pyrovalerone is a better comparator to alphaPVP than methcathinone. Seen in this light, the defendant's 

attempt to embrace the rule of lenity necessarily fails. 

III. CONCLUSION

We need go no further. For the reasons elucidated above, 

the sentence is 

Affirmed.