### F I LE D U. S . COURT OF AP PE ALS E LEVE NTH CI RCUI T Jul y 08, 2005 T HOM AS K. KAHN C L E RK [ P UB L I S H] I N THE UN I TE D STATE S C OU RT OF APPE ALS F O R T H E E L E V E N T H C IR C U IT

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________________________ D . C . D oc ke tN o. 02- 00185- C R - 1- C B - 002 U N I T E D S T A T E S O F A M E R I C A , P la in tif f - A p p e lle e , v ersu s R ON AL D K E I T H B R OWN, D efen d an t s-A p p el l an t s.

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________________________ D . C . D oc ke tN o. 02- 00185- C R - 1- C B - 001 U N I T E D S T A T E S O F A M E R I C A , P la in tif f - A p p e lle e , v ersu s KE VI N L AY NE B R OWN, D e f e n d a n ts - A p p e lla n ts .2 ________________________ A pp ea l s f

rom the U ni t ed S t at es D i stri ctC ou rt f o rth e So u th e rn D i s tr i c to f A l ab a ma

_________________________ ( Ju l y 8, 2005) B e f o r e A N D E R S O N , C A RN E S a n d R O N E Y , C ir c u it J u d g e s . C A RN E S , C i rc ui tJudg e: T w o b r o th e r s , R o n a ld a n d K e v in B r o w n , w e r e c o n v ic te d o f c o n s p ir a c y to di s tr i but e 1, 4- but a ne di ol , a n a l l e ge d c ontr ol l e d s ubs t a nc e a na l ogue , i n vi ol a t i on of 2 1 U .S .C . § 8 4 6 . W h e th e rth e c h e m ic a l s tru c tu r e o f th a t s u b s ta n c e is “s u b s ta n tia lly s i mi l a r ” t o th e c h e mi c a l s tru c tu r e o f th e s c h e d u l e I c o n tr o l l e d s u b s t a n c e g a mma hydrox ybutyr i c a ci d (G H B ), such thati ti s a“ control l ed subst ance anal og ue” a s defi ned b y 21 U . S . C . § 8 02 (32)(A ), w as the key quest i on attri al and i ti s the key q u e s tio n in th is ap p e a l. T he B r ow ns ha ve br oughtus a num be rof c ont e nt i ons a r i s i ng f

r om the di s put e ove rw he the r1, 4- but a ne di ol i s s ubs t a nt i a l l y s i m i l a rt o G H B . S om e of th e m i n v o l v e D a u b e r tv . M e rr e l l D o w Ph a r ma c e u t i c a l s , I n c . , 5 0 9 U . S. 5 7 9 , 1 1 3 S. C t . 27 86 (199 3), and q uest i on the di stri ctcourt ’ s rul i ng s on the adm i ss i on of expert t e s t i m ony . T he othe r s i nvol ve w he the rthe e vi de nc e w a s s uf f i c i e ntt o c onvi c tthe B r o wn s a n d wh e th e rth e a n a l o g u e th e o ry e m b o d i e d i n 2 1 U. S . C . § § 8 0 2 ( 3 2 ) ( A)3

a n d 8 1 3 is u n c o n s titu tio n a l. I. A. R on al d and K evi n B row n o w ned and op er at ed tw o Int ernetw ebsi t es that a d v e r tis e d a n d s o ld p r o d u c ts f o rh u m a n c o n s u m p tio n c o n ta in in g v a ry in g a m o u n ts of 1, 4-bu t anedi ol , an i nd ustri al sol ventthati n rec entye ar s has been foun d t o b e a d e p r e s s a n ta n d c a n b e u s e d a s a “ d a t e r ap e ” d ru g . O v e ra tw o - y e a rp e r i o d , FBI a ge nt s us e d a n unde r c ove re - m a i l a c c ountt o pur c ha s e f r om the B r ow ns ap p r o x im a te ly 2 3 .5 g a llo n s o f p r o d u c ts c o n ta in in g 1 ,4 - b u ta n e d io l. T h e n , in conj un ct i on w i th a nat i on w i de op er at i on coordi nat ed by the D epartm entof Just i ce , l a w e nf or c e m e ntof

f i c e r s e xe c ut e d s e a r c h w a rr a nt s f orthe B r ow ns ’ r e s i de nc e s a nd a nothe rhous e w he r e the drugs w e r e thoughtt o be ke pt . T he y f ound 200 ga l l ons of 1, 4- but a ne di ol , s om e pur e a nd s om e di l ut e d, a s w e l l a s ha ndw r i tt e n not e s a nd r e c ip e s f o rp r e p a r in g 1 ,4 - b u ta n e d io l p r o d u c ts . A n i nd i ctm entw as re turned chargi ng the B row ns w i th o ne coun tof c ons pi r a c y t o di s tr i but e a nd pos s e s s w i th i nt e ntt o di s tr i but e 1, 4- but a ne di ol , a nd w i th e i ghtc ount s of

di s tr i but i on a nd pos s e s s i on w i th i nt e ntt o di s tr i but e 1, 4- b u ta n e d io l, in v io la tio n o f 2 1 U .S .C . § § 8 4 1 ( a ) ( 1 ) , 8 1 3 , a n d 8 4 6 . T he pa r t i e s e nt e r e d i nt o a j oi ntbe nc h tr i a l a gr e e m e ntunde rw hi c h the4

gove rnm e ntdr oppe d the e i ghtpos s e s s i on c ount s a ga i ns tthe B r ow ns . I n pl a c e of the i ndi c tm e nt , the gove rnm e ntf i l e d a s upe r s e di ng i nf

or m a t i on c ha r gi ng the B r ow ns w i th c ons pi r a c y t o di s tr i but e a nd pos s e s s w i th i nt e ntt o di s tr i but e 1, 4- b u t an ed i o l . T h e g o v ern m en tal so so u g h tcri m i n al fo rfei tu re o f th e B ro w n s’ pr ope r ty . T he B r ow ns a gr e e d t o s t i pul a t e t o a l l the f a c t s e xc e ptthe c e ntr a l one of w he the rthe c he m i c a l s truc tur e of 1, 4- but a ne di ol i s “ s ubs t a nt i a l l y s i m i l a r ” t o the c he m i c a l s truc tur e of

G H B s o a s t o br i ng the c he m i c a l c om pound w i thi n the defi ni t i on of “ control l ed subst ance anal og ue” und er21 U . S . C . § 8 02 (32)(A ). T hat o n e f a c tu a l is s u e w a s le f

t f o rtr ia l. I n a s u b s e q u e n t jo in t a m e n d m e n t to th e a g r e e m e n t, th e B r o w n s w a iv e d th e ir ri gh tt o app ea l any r es ul t i ng conv i ct i on and sent ence , exce ptas t o cert ai n speci fi ed i s s ue s . T he r e l e va nte xc e pt e d i s s ue s f orpr e s e ntpurpos e s a r e w he the r1, 4- b u t an ed i o l i s su b st an t i al l y si m i l ar t o G H B as d efi n ed b y § 8 0 2 (3 2 )(A )(i ), an d th o se addi t i on al i ss ues a ri si ng fr om “ any rul i ng s by the di stri ctcourtaddres si ng that i ss ue. ” B. T h e g o v e rn m e n t’s p o s itio n th r o u g h o u t th is p r o s e c u tio n h a s b e e n th a t, pu rs uantt o 2 1 U . S . C . § 8 02 (32)(A ), 1, 4-bu t anedi ol i s a“ control l ed subst ance anal og ue” of G H B , w hi ch C on gres s a dd ed t o the st atut ory l i stof sc hedu l e I5

c ontr ol l e d s ubs t a nc e s i n 2000. S e e H i l l ory J . F a r i a s a nd S a m a ntha R e i d D a t e - R ape D rug P r ohi bi t i on A c tof 2000, P ub. L . N o. 106- 172, § 3( a ) , 114 S t a t . 7. U nde rthe C on trol l ed S ub st ance A nal og ue E nforcement A ctof 19 86 (“ the A nal og ue A ct ”) , 21 U . S . C . §§ 80 2 and 81 3, som e c hem i ca l com po un ds thatar e notthem se l ves l i st ed as sc hedu l e I control l ed subst ance s a re t erm ed “ control l ed subst ance an alo g u e[ s]” a n d trea ted as th o u g h th ey w er e s ch ed u le I s u b stan ce s. Id . § 8 1 3 (“A c ontr ol l e d s ubs t a nc e a na l ogue s ha l l , t o the e xt e nti nt e nde d f orhum a n c ons um pt i on, b e tr e a te d , f

o rth e p u rp o s e s o f

a n y F e d e r a l la w a s a c o n tr o lle d s u b s ta n c e in sch ed u l e I. ”). T h e A n al o g u e A ctd efi n es a “ co n tro l l ed su b st an ce an al o g u e” as a subst ance : ( i ) the c he m i c a l s truc tur e of w hi c h i s s ubs t a nt i a l l y s i m i l a rt o the chem i ca l structure of acontrol l ed subst ance i n schedul e I or II ; ( i i ) w hi c h ha s a s t i m ul a nt , de pr e s s a nt , orha l l uc i noge ni c e f f e c ton the c e ntr a l ne r vous s y s t e m tha ti s s ubs t a nt i a l l y s i m i l a rt o orgr e a t e rtha n the st i m ul ant , depres sa nt , or hal l uci no geni c e ff ec ton the ce ntra l nervou s s ys t em of a c on trol l ed subst ance i n schedul e I or II ; or ( iii) w ith r e s p e c t to a p a r tic u la rp e r s o n , w h ic h s u c h p e r s o n r e p r e s e n ts ori nt e nds t o ha ve a s t i m ul a nt , de pr e s s a nt , orha l l uc i noge ni c e f f e c ton the c e ntr a l ne r vous s y s t e m tha ti s s ubs t a nt i a l l y s i m i l a rt o orgr e a t e rtha n the st i m ul ant , depres sa nt , or hal l uci no geni c e ff ec ton the ce ntra l nervou s s ys t em of a c on trol l ed subst ance i n schedul e I or II . I d . § 8 0 2 ( 3 2 ) ( A ) . W e h a v e n e v e rd e c id e d w h e th e r§ 8 0 2 ( 3 2 ) ( A ) s h o u ld b e r e a d d is ju n c tiv e ly6

orc onj unc t i ve l y . T he di s tr i c tc our tc onc l ude d tha tm os tc our t s “ ha ve r e a d the s t a tut e i n the c onj unc t i ve w hi c h r e qui r e s the gove rnm e ntt o pr ove c l a us e ( i ) a nd e i the rc l a us e ( i i ) or( i i i ) . ” U ni t e d S t a t e s v. B r ow n, 279 F . S upp. 2d 1238, 1240 ( S . D . A l a . 2003) ( c i t a t i on om i tt e d) ; a c c or d U ni t e d S t a t e s v. T ur c ott e , 405 F . 3d 515, 5 2 2

– 2 3 (7 th C ir. 2 0 0 5 ). B ec au se b o th p ar ti es ac ce p t th e d istrict co u rt’s c o n ju n c tiv e r e a d in g o f

th e s ta tu te , w e w ill a s s u m e f o rp u rp o s e s o f

th is ap p e a l th a t it is th e c o rr e c t o n e . T he B row ns have conceded al l al on g that1, 4-bu t anedi ol has the sa m e e ff ec t on a pe r s on’ s c e ntr a l ne r vous s y s t e m a s G H B a nd the r e by m e e t s c l a us e ( i i ) of § 802( 32) ( A ) . I n f

a c t , the y s t i pul a t e d i n the di s tr i c tc our ttha tw he n i nge s t e d 1, 4- b u ta n e d io l is a c tu a lly tr a n s f o r m e d in to G H B b y tw o n a tu r a lly o c c u rr in g e n z y m e s . T ha tl e a ve s onl y the que s t i on of w he the r1, 4- but a ne di ol m e e t s c l a us e ( i ) . T he g o v e rn m e n t s a y s it d o e s ; th e B r o w n s s a y it d o e s n o t. C. D ur i ng the thr e e - da y be nc h tr i a l the gove rnm e ntputon tw o w i tne s s e s a nd th e d e f e n s e p u t o n o n e . A ll th r e e o f th e w itn e s s e s te s tif

ie d o n th e § 8 0 2 ( 3 2 ) ( A ) ( i) is s u e : w h e th e rth e c h e m ic a l s tru c tu r e o f 1 ,4 - b u ta n e d io l is “s u b s ta n tia lly s im ila r ” to th a to f G H B. T h e g o v e rn m e n t c a lle d D r . J a m e s D e F r a n c e s c o , a f o r e n s ic d ru g c h e m is t w ith7

th e D ru g E n f

o r c e m e n t A g e n c y . D e F r a n c e s c o h o ld s a P h .D . in p h y s ic a l- o r g a n ic c he m i s try a nd ha s c onduc t e d s e ve r a l s tudi e s of 1, 4- but a ne di ol a nd G H B . T he g o v e rn m e n t a ls o c a lle d D r . R ic h a r d I rw in , a b io c h e m is t w ith th e N a tio n a l I n s titu te o f E n v ir o n m e n ta l H e a lth S c ie n c e s , a b r a n c h o f th e N a tio n a l I n s titu te s o f H e a lth . I rw i n hol ds a P h. D . i n bi oc he m i s try a nd i s the a uthorof a pe e r - r e vi e w e d pape ron 1, 4-bu t anedi ol . T ho se tw o w i tness es w er e qual i fi ed as expert s i n chem i stry w ith o u t o b

je c tio n f r o m th e d e f

e n s e . D eF ra nces co expl ai ned thatthe si m i l ar i t i es and d i ff er ence s i n the chem i ca l s truc tur e s of

1, 4- but a ne di ol a nd G H B c oul d be de t e r m i ne d by vi s ua l l y c om pa r i ng tw o - d im e n s io n a l r e p r e s e n ta tio n s o f th e a to m ic s tru c tu r e s o f th e tw o c h e m ic a ls . B a s e d on tha tvi s ua l c om pa r i s on, both D e F r a nc e s c o a nd I rw i n c onc l ude d tha t1, 4- but a ne di ol a nd G H B a r e s ubs t a nt i a l l y s i m i l a rbe c a us e the y di f f e ronl y i n the

“ fu n ct i o n al g ro u p s” fo u n d o n th e ri g h tsi d e o f th e m o l ecu l es. D eF ra nces co and Irw i n exp l ai ned thatbo th 1 , 4-bu t anedi ol and G H B ar e c om pos e d of

c a rbon, oxy ge n, a nd hy dr oge n a t om s , a nd e a c h one ha s a n a l c ohol f unc t i ona l gr oup on i t s l e f te nd. T he m ol e c ul e s di f f e r , how e ve r , on the r i ghts i de be c a us e a 1, 4- but a ne di ol m ol e c ul e ha s a s e c ond a l c ohol f unc t i ona l gr oup, m a ki ng it a d ia lc o h o l, w h ile a G H B m o le c u le h a s a c a rb o x y lic - a c id f u n c tio n a l g r o u p . D e s pi t e thos e di f

f e r e ntf unc t i ona l gr oups , D e F r a nc e s c o a nd I rw i n w e r e of the8

op i ni on thatthe chem i ca l structures of the tw o sub st ance s a re subst ant i al l y s i m i l ar a n d th a t1 , 4 - b u t a n e d i o l i s , th e r e f o r e , a c h e mi c a l a n a l o g u e o f G H B. D e F r a n c e s c o a n d I rw in a ls o e x p la in e d h o w 1 ,4 - b u ta n e d io l is c o n v e r te d in to G H B i n the hu m an bo dy by tw o n atural l y occ urri ng enzy m es . Irw i n t es t i fi ed that th i s m e t ab o l i c c o n v e r s i o n i s a c ru c i a l f a c ti n c o m p a r i n g th e two s u b s t a n c e s . He al so t ol d the courtthatthe ef fe ctof G H B on the bo dy i s t o d epre ss the ce ntra l ne r vous s y s t e m , w hi l e 1, 4- but a ne di ol i t s e l f ha s no e f

f e c ton the c e ntr a l ne r vous sy st em . O nce i ng es t ed, ho w ever , 1, 4-bu t anedi ol i s r api dl y c on vert ed t o G H B . In f a c t , G H B c a n be de t e c t e d i n the bl oods tr e a m w i thi n tw o m i nut e s a f t e r1, 4- bu t anedi ol i s i ng es t ed. A pers on ca n sl ow do w n, bu tca nn otprevent , the i nt ernal c o n v e r s io n o f

1 ,4 - b u ta n e d io l to G H B . B e c a u s e 1 ,4 - b u ta n e d io l is c o n v e r te d in to G H B soon af

t eri ng es t i on , consum i ng i thas the sa m e e ff ec ton the bo dy as c ons um i ng G H B . I nde e d, the r e a s on pe opl e t a ke ( ora dm i ni s t e rt o othe r s ) 1, 4- b u t an ed i o l i s th ati ti s co n v ert ed i n t o , an d p ro d u ces th e sam e d ep ressan teffects as, G H B . I rw in a c k n o w le d g e d th a t th e f a c t o n e c o m p o u n d m e tab o liz e s in to a n o th e ris no tenou gh by i t se l f t o est abl i sh subst ant i al si m i l ar i ty betw ee n thei r c hem i ca l s truc tur e s . N one the l e s s , he t e s t i f i e d tha tthe m e t abol i c c onve r s i on of 1, 4- b u ta n e d io l in to G H B is im p o r ta n t w h e n c o n s id e r in g th e d e g r e e o f s im ila r ity9

be tw e e n the m . T ha ti s be c a us e the c he m i c a l s truc tur e of 1, 4- but a ne di ol m us tbe “b as ically id en ti ca l” to th at o f G H B in o rd erfo r it t o “fitin to th e G H B re ce p to r[ s]” a n d p r o d u c e th e s a m e e f f e c t. D e F r a nc e s c o a nd I rw i n pr ovi de d no a ddi t i ona l m e thodol ogy orba s i s f or th ei r o p i n i o n s, an d th ey ci t ed n o stu d i es o r o th er o b j ect i v e d at a. D u ri n g cro ssexam i nat i on Irw i n st at ed thathi s det erm i nat i on s abo utw hether c hem i ca l c o m p o u n d s a r e s u b s ta n tia lly s im ila ris a “g u t le v e l th in g ” o rb a s e d o n “in tu itio n ,” buthe l a t e re xpl a i ne d tha tw ha the m e a ntw a s tha ti tw a s a j udgm e ntba s e d on th ir ty y e a r s o f

le a rn in g a n d e x p e r ie n c e a s a c h e m is t. A tthe c onc l us i on of

the gove rnm e nt ’ s c a s e , the B r ow ns m ove d t o ha ve the t es t i m on y of the go vernm ent ’ s tw o exp ert s e xcl ud ed un der D aubertand F eder al R ul e of E vi dence 702 . T hey a rgued the t es t i m on y di d n otm ee tthe D aubert st andards because i tw as un sc i ent i fi c a nd coul d n otbe t es t ed. T he di stri ctcourt d e n ie d th e irm o tio n . F o rits c a s e in c h ie f

, th e d e f e n s e c a lle d D r . J o h n S te e le , w h o h o ld s a P h .D . in p la n t p a th o lo g y a n d w o r k s a s a f r e e la n c e c o n s u lta n t in th e f ie ld o f c h e m is try . W he n the B r ow ns s oughtt o ha ve S t e e l e qua l i f i e d a s a n e xpe r ti n c he m i s try , the gove rnm e ntobj e c t e d, c ont e ndi ng tha the w a s notqua l i f i e d be c a us e he ha d no chem i stry degree. T he di stri ctcourtpo stpo ned i t s rul i ng on thati ss ue. T he court10

d eci d ed th atb ecau se i tw as a b en ch tri al th e co u rtw o u l d h ear al l th e t est i m o n y, i ncl ud i ng S t ee l e’ s, and d et erm i ne l at erw hether i tshou l d b e tre at ed as expert te s tim o n y . S t e e l e t e s t i f

i e d t o hi s opi ni on tha t1, 4- but a ne di ol a nd G H B a r e not s u b s ta n tia lly s im ila r . H is o p in io n w a s b a s e d o n h is a n a ly s e s o f th e tw o c h e m ic a ls us i ng a “ T a ni m ot o c oe f f i c i e nt ” m e thod. T hi s m e thod i nvol ve s i s ol a t i ng the s ubs truc tur e s i n e a c h of the c he m i c a l m ol e c ul e s t o be c om pa r e d, the n di vi di ng the nu m ber of c om m on substructures betw ee n the tw o com po un ds by the t ot al nu m ber of substructures , w hi ch prod uces a num er i ca l re sul tbetw ee n zer o and on e hun dred pe r c e nt . S t e e l e c l a i m e d tha tthe r e s ul t i ng f i gur e w a s a qua nt i t a t i ve m e a s ur e of the p e r c e n ta g e o f

s tru c tu r a l s im ila r ity b e tw e e n th e tw o c h e m ic a ls . C a l c u l a t i n g th e T a n i m o t o c o e f f i c i e n tb o th m a n u a l l y a n d th r o u g h two c o m p u te rp r o g r a m s th a t ap p ly it ( C h e m F in d e r4 a n d C h e m I D P lu s ) , S te e le c onc l ude d tha tthe s i m i l a r i ty be tw e e n the c he m i c a l s truc tur e s of 1, 4- but a ne di ol a nd G H B i s l e s s tha n f

i f ty pe r c e nt . M or e s pe c i f i c a l l y , S t e e l e opi ne d tha t1, 4- but a ne di ol a nd G H B s ha r e s e ve n outof f i f t e e n t ot a l s ubs truc tur e s . T he qua nt i t a t i ve m e a s ur e of the i rs truc tur a l s i m i l a r i ty , i n hi s vi e w , i s s e ve n di vi de d by f if te e n , o r4 6 .7 % . B e c a u s e S te e le d e f in e d “s u b s ta n tia l” to m e a n ab o v e f if ty p e r c e n t, in h is o p in io n 1 ,4 - b u ta n e d io l is n o t s u b s ta n tia lly s im ila rto , a n d th u s n o t a11

c o n tr o lle d s u b s ta n c e a n a lo g u e o f , G H B . B oth of the gove rnm e nt ’ s e xpe r t s t e s t i f i e d tha tthe T a ni m ot o c oe f f i c i e nt coul d n otbe used t o q uant i fy ac cura t el y the degree of s tructural si m i l ar i ty betw ee n tw o si m pl e s ub st ance s l i ke 1, 4-bu t anedi ol and G H B . D eF ra nces co ac kn ow l edged th a t h e h a d tr ie d tw o o f

th e c o m p u te rp r o g r a m s th a t u tiliz e d th e T a n im o to coef fi ci entand they produ ce d res ul t s i ncon si st entw i th h i s opi ni on thatthere w as s ubs t a nt i a l s i m i l a r i ty . H e s ugge s t e d tha tthe s of tw a r e pr ogr a m s m i ghti nc l ude othe rc he m i c a l pr ope r t i e s apa r tf r om m ol e c ul a rs truc tur e , w hi c h w oul d e xpl a i n the in c o n s is te n c y . I rw i n a l s o r e

j e c t e d the us e of

the T a ni m ot o c oe f

f i c i e nt s t o c om pa r e the chem i ca l structures of m ol ec ul es . H e t es t i fi ed thati n h i s thi rty- ye arca re erhe had ne ve rhe a r d of

a ny c he m i s tus i ng the T a ni m ot o c oe f f i c i e ntthe ory t o c om pa r e the d eg ree o f si m i l ari ty b etw een tw o k n o w n , si m p l e co m p o u n d s. S i m i l arl y, D eF ra nces co t es t i fi ed thathe w as un aw ar e of other c hem i st s or s ci ent i st s w ho used th e T a n i m o t o c o e f

f i c i e n tm e th o d t o a s s e s s th e s tru c tu r a l s i m i l a r i ty b e twe e n two si m pl e c om po un ds l i ke the tw o i nv ol ved i n thi s c as e. Iti s notan ac ce pt ed m eth o d o l o g y fo r su ch co m p ari so n s. A tthe c onc l us i on of

the e vi de nc e , the B r ow ns a ga i n m ove d t o ha ve D e F r a nc e s c o’ s a nd I rw i n’ s t e s t i m ony e xc l ude d unde rD a ube r ta nd R ul e 702. T he12

d is tr ic t c o u r t d e n ie d th e m o tio n a n d to o k th e c a s e u n d e rc o n s id e r a tio n . D. O n J u n e 1 7 , 2 0 0 3 , th e d is tr ic t c o u r t is s u e d a m e m o r a n d u m o p in io n w ith f in d in g s o f

f a c t. U n ite d S ta te s v . B r o w n , 2 7 9 F . S u p p . 2 d 1 2 3 8 ( S .D . A la . 2 0 0 3 ) . T he di s tr i c tc our tf

ound tha tthe opi ni ons of the gove rnm e nt ’ s e xpe r tw i tne s s e s on th e q u e s tio n o f

s u b s ta n tia l s im ila r ity w e r e r e le v a n t a n d r e liab le . I d . a t 1 2 4 4 . T h e c o u r t d e c lin e d to r e c o g n iz e th e d e f e n s e w itn e s s , S te e le , a s a n e x p e r t in the ar eaof control l ed subst ance s bec ause of hi s “ l ac k o f e xp ert i se . ” I d. at12 45 . It a ls o f o u n d th a t h is m e th o d o lo g y ( th e T a n im o to c o e f f ic ie n t) w a s b o th u n r e liab le and u nrel i abl y app l i ed t o the fa ct s of thi s c as e. Id. at12 48 , 12 50 . T he court de s c r i be d how S t e e l e ha d c r i t i c i z e d the gove rnm e nt ’ s e xpe r t s f orus i ng nonqua nt i t a t i ve m e thods , w hi l e a tthe s a m e t i m e c onc e di ng tha the w a s “ nota w a r e of th e m e th o d s o f

o th e rc h e m is ts ” o rw h e th e ro th e rc h e m is ts u s e d th e T a n im o to coef fi ci ent . Id. at12 48 , 12 50 . T he di stri ctcourtal so foun d thatS t ee l e had

“ m a ni pul a t [ e d] ” hi s us e of the T a ni m ot o c oe f

f i c i e nt , “ i m pe r m i s s i bl y e m pha s i z [ i ng] th e d if f e r e n c e s b e tw e e n ” th e tw o s u b s ta n c e s b y c o u n tin g a “c o m p o u n d f o u n d in G H B , bu tno t[1, 4-bu t anedi ol ] , se vera l t i m es . ” I d. at12 48 . F urther, the court f o u n d th a t S te e le ’s te s tim o n y b a s e d o n th e c o m p u te rp r o g r a m s w a s u n r e liab le b e c a u s e h e d id n o t e v e n k n o w h o w th e p r o g r a m s d e f in e d “s im ila r ity .” I d . a t 1 2 5 0 .13

F o ra ll o f th e s e r e a s o n s , th e c o u r t r e f u s e d to c o n s id e rS te e le ’s te s tim o n y a s r e liab le e x p e r t o p in io n , th o u g h it d id c o n s id e rth e te s tim o n y a s e v id e n c e . I d . a t 1 2 4 5 . In i t s r ol e a s f

ac t fi nd er , the di stri ctcourtconcl ud ed thatthe go vernm enthad p r o v e n b e y o n d a r e a s o n ab le d o u b t th a t th e c h e m ic a l s tru c tu r e o f 1 ,4 - b u ta n e d io l is su b st an t i al l y si m i l ar t o th ato f G H B an d , acco rd i n g l y, 1 , 4 -b u t an ed i o l i s a c o n tr o lle d s u b s ta n c e a n a lo g u e o f G H B . I d . a t 1 2 4 5

– 5 0 . O n th a t b a s is , th e c o u r t foun d the B row ns gu i l ty of c on spi ra cy t o d i stri bu t e acontrol l ed subst ance a n a lo g u e f

o rh u m a n c o n s u m p tio n . I d . a t 1 2 5 0 . A tthe s e nt e nc i ng he a r i ng, the di s tr i c tc our ts e nt e nc e d R ona l d B r ow n t o 87 m o n th s i m p ri so n m en tan d K ev i n B ro w n t o 1 3 5 m o n th s i m p ri so n m en t . Ital so e nt e r e d a j udgm e ntof

f or f e i tur e a ga i ns tthe B r ow ns ’ pr ope r ty . T he B r ow ns sep arat el y ap p eal ed th ei r co n v i ct i o n s, b u tw e co n so l i d at ed th e ap p eal s. II. T h e B r o w n s r a is e s e v e r a l is s u e s . T h e y a r g u e th a t u n d e rD a u b e r t v . M e rr e ll D ow P harm ac eut i ca l s, Inc. , 50 9 U . S . 57 9, 11 3 S . C t . 27 86 (199 3), and F eder al R ul e of E vi de nc e 702, the di s tr i c tc our ts houl d notha ve a dm i tt e d the opi ni on te s tim o n y o f

D e F r a n c e s c o a n d I rw in . T h e y a r g u e th a t th e d is tr ic t c o u r t s h o u ld h a v e r e c o g n iz e d S te e le a s a n e x p e r t a n d c o n s id e r e d h is te s tim o n y a c c o r d in g ly . T hey a rgue thatthei r c on vi ct i on s c anno tbe sust ai ned b ec ause there w as14

i ns uf f i c i e nte vi de nc e t o f

i nd be y ond a r e a s onabl e doubttha t1, 4- but a ne di ol a nd G H B a r e s ubs t a nt i a l l y s i m i l a r . F i na l l y , K e vi n B r ow n a l s o a r gue s tha tthe A na l ogue A c ti s unc ons t i tut i ona l be c a us e i tvi ol a t e s the non- de l e ga t i on doc tr i ne of A rt i cl e I . III. A. B ef ore w e t ake up the B row ns’ fi rs tcont ent i on , w hi ch i s thatthe di stri ct courtcom m i tt ed D auberterror, w e nee d t o exp l ai n w hy i ti s di ff i cul tt o p er suade a c our tof appe a l s t o r e ve r s e a di s tr i c tc our t ’ s j udgm e nton D a ube r tgr ounds . T he th e m e th a t s h ap e s ap p e lla te r e v ie w in th is a r e a is th e lim ite d n a tu r e o f it. “A ll e vi de nt i a ry de c i s i ons a r e r e vi e w e d unde ra n abus e - of - di s c r e t i on s t a nda r d. ” G e n. E l ec . C o. v. Joi ner, 52 2 U . S . 13 6, 14 1, 11 8 S . C t . 51 2, 51 7 (19 97 ). A s aprac t i ca l m a tt e r , the abus e of

di s c r e t i on s t a nda r d m e a ns tha ta di s tr i c tc our tha s a r a nge of c h o ic e . R a s b u ry v . I n te rn a l R e v e n u e S e r v . ( I n r e R a s b u ry ) , 2 4 F .3 d 1 5 9 , 1 6 8 ( 1 1 th C i r . 1994) ( “ [ U ] nde rthe abus e of di s c r e t i on s t a nda r d of

r e vi e w the r e w i l l be oc c a s i ons i n w hi c h w e a f f i r m the di s tr i c tc our te ve n though w e w oul d ha ve gone the othe rw a y ha d i tbe e n ourc a l l . ” ) ; U ni t e d S t a t e s v. K e l l y , 888 F . 2d 732, 745 ( 11th C i r . 1989) ( “ T he abus e of di s c r e t i on s t a nda r d ha s be e n de s c r i be d a s a l l ow i ng a r ange of choi ce for the di stri ctcourt , so l on g as thatchoi ce do es no tconst i tut e a15

c l e a re rr orof

j udgm e nt . ” ) . T he s i z e of tha tr a nge — the a m ountof di s c r e t i on ac corded— depend s on the i ss ue bei ng deci ded b y the court . W e r ec og ni ze a s ig n if ic a n t r a n g e o f

c h o ic e f o rth e d is tr ic t c o u r t o n e v id e n tia ry is s u e s , w h ic h is to sa y w e def

ert o i t s dec i si on s t o a consi derabl e e xt ent . S ee M cC orvey v. B axt er H e a l thc a r e G r oup, 298 F . 3d 1253, 1257 ( 11th C i r . 2002) ( “ [ O ] urr e vi e w of e v id e n tia ry ru lin g s b y tr ia l c o u r ts . . . is v e ry lim ite d .” ( q u o ta tio n o m itte d ) ) . W e de f e rt o di s tr i c tc our t s on the i re vi de nt i a ry rul i ngs f ora tl e a s ta c oupl e of r e a s ons . O ne i s tha tthe di s tr i c tc our t ’ s r ol e i n pr e s i di ng ove rtr i a l pr oc e e di ngs m e a ns the di s tr i c tc our ti s i n the be s tpos i t i on t o de c i de the m a tt e r . P i e r c e v. U n d e rw o o d , 4 8 7 U .S . 5 5 2 , 5 6 0 , 1 0 8 S . C t. 2 5 4 1 , 2 5 4 7 ( 1 9 8 8 ) . “I n h e r e n t in th is [ ab u s e o f d is c r e tio n ] s ta n d a r d is th e f ir m r e c o g n itio n th a t th e r e a r e d if f ic u lt evi dent i ary rul i ng s thatturn o n m att er s uni qu el y w i thi n the pu rvi ew of the di stri ct c o u r t, w h ic h h a s f

ir s t- h a n d a c c e s s to d o c u m e n ta ry e v id e n c e a n d is p h y s ic a lly pr oxi m a t e t o t e s t i f

y i ng w i tne s s e s a nd the j ury . ” U ni t e d S t a t e s v. J e rni ga n, 341 F . 3d 1273, 1285 ( 11th C i r . 2003) . B e i ng a tthe tr i a l a s the pr oc e e di ngs oc c ura nd the e vi de nc e unf

ol ds , a tr i a l j udge ha s a n a dva nt a ge ous f a m i l i a r i ty w i th the pr oc e e di ngs a nd “ m a y ha ve i ns i ght s notc onve y e d by the r e c or d” aboutthe e v id e n c e a n d th e is s u e s r e la tin g to it. P ie r c e , 4 8 7 U .S . a t 5 6 0 , 1 0 8 S . C t. a t 2 5 4 7 . D up l i ca t i ng thatfa m i l i ar i ty a nd tho se i nsi gh t s a tthe appel l at e l evel i s i m prac t i ca l16

a nd of t e n i m pos s i bl e . I d. ; s e e ge ne r a l l y W i l t on v. S e ve n F a l l s C o. , 515 U . S . 277, 289, 115 S . C t . 2137, 2144 ( 1995) ( “ [ T ] he r e vi e w i ng a tt i tude tha ta c our tof appe a l s t a ke s t ow a r d a di s tr i c tc our tde c i s i on s houl d de pe nd upon the r e s pe c t i ve i ns t i tut i ona l a dva nt a ge s of tr i a l a nd appe l l a t e c our t s . ” ( c i t a t i on a nd quot a t i on o m itte d ) ) . A s e c ond r e a s on w e gi ve c ons i de r abl e de f e r e nc e t o the tr i a l c our ton e vi de nt i a ry i s s ue s i s tha ti ti s of t e n notpos s i bl e t o pr e c i s e l y c a l i br a t e rul e s f orthe m a n y d if f e r e n t c ir c u m s ta n c e s th a t c a n a r is e . H o w to ap p ly e v id e n tia ry ru le s in a ll pos s i bl e s c e na r i os i s nota m a tt e ra m e nabl e t o c l os e r e gul a t i on, be c a us e the c i r c um s t a nc e s tha ta r i s e dur i ng tr i a l “ i nvol ve m ul t i f a r i ous , f l e e t i ng, s pe c i a l , na rr ow fa ct s thatut t er l y r es i stgeneral i za t i on . ” P i er ce , 48 7 U . S . at56 1– 62 , 10 8 S . C tat 2 5 4 8 ( q u o ta tio n o m itte d ) . E v id e n tia ry is s u e s o f te n d o n o t in v o lv e a “g e n e r a lly r e c u rr in g , p u r e ly le g a l m a tte r ” o ra “q u e s tio n r e a d ily r e s o lv e d b y r e f e r e n c e to g e n e r a l l e g a l p r i n c i p l e s a n d s t a n d a r d s a l o n e . ” Bu f o r d v . U n i t e d St a t e s , 5 3 2 U . S. 59 , 65 , 12 1 S . C t . 12 76 , 12 80 (200 1) (j ust i fy i ng defe re nt i al re vi ew of a part i cul ar se nt enci ng gu i del i nes i ss ue). Inst ea d, they a l m ostal w ay s pre se nta quest i on that “g r o w s o u t o f

, a n d is b o u n d e d b y , c a s e - s p e c if ic d e ta ile d f

a c tu a l c ir c u m s ta n c e s . A nd the fa ct -bou nd nature of the deci si on l i m i t s the val ue of appel l at e c ou rt p r e c e d e n t . . . .” I d . a t 6 5 , 1 2 1 S . C t. a t 1 2 8 0

– 8 1 .17

W h a t is tru e ab o u t th e r e v ie w o f e v id e n tia ry is s u e s in g e n e r a l ap p lie s w ith eq u al o r ev en g reat er fo rce t o D au b erti ssu es i n p art i cu l ar, an area w h ere th e ab u se of di s c r e t i on s t a nda r d thr i ve s . S e e K um ho T i r e C o. v. C a r m i c ha e l , 526 U . S . 137, 152–53, 119 S . C t . 1167, 1176 ( 1999) ; U ni t e d S t a t e s v. A br e u, 406 F . 3d 1304, 1305–07 ( 11th C i r . 2005) ( pe rc ur i a m ) ; M c C l a i n v. M e t abol i f e I nt ’ l I nc . , 401 F . 3d 1233, 1238 ( 11th C i r . 2005) ; U ni t e d S t a t e s v. F r a z i e r , 387 F . 3d 1244, 1258–59 ( 1 1 th C ir . 2 0 0 4 ) ( e n b a n c ) . I m m e r s e d in th e c a s e a s it u n f o ld s , a d is tr ic t c o u r t is m o r e f a m ilia rw ith th e p r o c e d u r a l a n d f a c tu a l d e ta ils a n d is in a b e tte rp o s itio n to d e c id e D a u b e r t is s u e s . T h e ru le s r e la tin g to D a u b e r t is s u e s a r e n o t p r e c is e ly ca l i brat ed and m ustbe appl i ed i n cas e- spec i fi c e vi dent i ary c i rc um st ance s thatoft en defy general i za t i on . A nd w e don ’ tw antt o d eni grat e the i m po rt ance of the tri al a n d e n c o u r a g e ap p e a ls o f ru lin g s r e la tin g to th e te s tim o n y o f e x p e r t w itn e s s e s . A ll o f th is e x p la in s w h y “th e ta s k o f e v a lu a tin g th e r e liab ility o f e x p e r t te s tim o n y is uni que l y e ntrus t e d t o the di s tr i c tc our tunde rD a ube r t , ” a nd w hy “ w e gi ve the di s tr i c tc our t‘ c ons i de r abl e l e e w a y ’ i n the e xe c ut i on of i t s duty . ” R i nk v. C hem i no va, Inc. , 40 0 F . 3d 12 86 , 12 91 (11th C i r. 20 05 ) ( ci t at i on s om i tt ed); ac cord F ra zi er , 38 7 F . 3d at12 59 . T hati s true w hether the di stri ctcourtadm i t s or e xcl ud es e x p e r tt e s t i mo n y . J o i n e r , 5 2 2 U . S. a t1 4 1

– 4 2 , 1 1 8 S. Ct . a t5 1 7 ; i d . a t1 4 2 , 1 1 8 S. C t. a t 5 1 4 ( “A c o u r t o f

ap p e a ls ap p ly in g ‘ab u s e - o f - d is c r e tio n ’ r e v ie w to [ D a u b e r t]18

rul i ng s m ay no tca t egori ca l l y di st i ng ui sh betw ee n rul i ng s a l l ow i ng expert te s tim o n y a n d ru lin g s d is a llo w in g it.” ) . A n d it is tru e w h e r e th e D a u b e r t is s u e is o u tc o m e d e te r m in a tiv e . I d . a t 1 4 1

– 4 3 , 1 1 8 S . C t. a t 5 1 7 . T o b e s u r e , r e v i e w u n d e ra n ab u s e o f d i s c r e t i o n s t a n d a r d d o e s e n t a i l r e v i e w, a n d g r a n tin g c o n s id e r ab le le e w a y is n o t th e s a m e th in g a s ab d ic a tin g ap p e lla te re spon si bi l i ty. W e w i l l re vers e w hen the di stri ctcourt ’ s D aubertrul i ng do es a mo u n tt o a n ab u s e o f

d i s c r e t i o n th a ta f

f e c t e d th e o u t c o me o f

a tr i a l . Se e Fe d . R. E v i d . 1 0 3 (a); A b reu , 4 0 6 F . 3 d at1 3 0 6 ; F razi er, 3 8 7 F . 3 d at1 2 6 6 n . 2 0 . A n ab u se of di s c r e t i on c a n oc c urw he r e the di s tr i c tc our tappl i e s the w r ong l a w , f ol l ow s the w rong procedure, base s i t s dec i si on on cl ea rl y e rr on eous fa ct s, or com m i t s acl ea r error i n j ud gm ent . S ee M cC l ai n, 40 1 F . 3d at12 38 ; F ra zi er , 38 7 F . 3d at12 59 ; se e a ls o M o o r e rv . D e m o p o lis W a te rw o r k s & S e w e rB d ., 3 7 4 F .3 d 9 9 4 , 9 9 6

– 9 7 ( 1 1 th C i r. 20 04 ) ( per c uri am ); U ni t ed S t at es v. B row n, 33 2 F . 3d 13 41 , 13 43 (11th C i r. 20 03 ); Jones v. Int ’ l R i di ng H el m et s, L t d. , 49 F . 3d 69 2, 69 4 (11 th C i r. 19 95 ). In the D a ube r tc ont e xt , i f

one of thos e ty pe s of

s e r i ous e rr oroc c ur , w e m a y c onc l ude th atth e d i stri ctco u rth as n o tp ro p erl y fu l fi l l ed i t s ro l e as g at ek eep er. W e h av e al so foun d thata di stri ctcourtabuses i t s di sc re t i on w here i tfa i l s t o actas a gat ekee per b y e s s e n tia lly ab d ic a tin g its g a te k e e p in g r o le . M c C la in , 4 0 1 F .3 d a t 1 2 3 8 & n .3 ( r e v e r s in g w h e r e th e d is tr ic t c o u r t s ta te d it d id n o t h a v e s u f f ic ie n t s c ie n tif

ic19

k n o w le d g e to e x c lu d e th e e v id e n c e ) . B. In D au b ertth e S u p rem e C o u rtex p o u n d ed o n th e d i stri ctco u rt ’ s ro l e as a g a te k e e p e rin d e te r m in in g w h e th e re x p e r t te s tim o n y o n s c ie n tif ic m a tte r s is a d m is s ib le u n d e rR u le 7 0 2 . 5 0 9 U .S . a t 5 8 9 , 1 1 3 S . C t. a t 2 7 9 4

– 9 5 . I t s a id th a t a di stri ctcourt“ m ustensure thatany a nd al l sc i ent i fi c t es t i m on y or e vi dence a dm i tt e d i s notonl y r e l e va nt , butr e l i abl e , ” a nd tha tthe c ourtm us ts c r e e n out

“ expert ” t es t i m on y thati s notsuff i ci ent l y r el i abl e or trustw orthy for the fa ct fi nd er t o con si der. S ee i d. at58 9, 11 3 S . C t . at27 95 . T he B row ns sa y the di stri ctcourt m a de a c l e a re rr orof

j udgm e nti n nots c r e e ni ng outa s unr e l i abl e the opi ni ons of th e g o v e rn m e n t’s tw o w itn e s s e s , o p in io n s th e c o u r t a d m itte d a s e x p e r t te s tim o n y . T he opi ni on t e s t i m ony of thos e tw o e xpe r t s , the B r ow ns a r gue , f a i l e d t o m e e tthe r e l i abi l i ty s t a nda r ds of

D a ube r ta nd R ul e 702. R u l e 7 0 2 st at es: I f s c i e nt i f i c , t e c hni c a l , orothe rs pe c i a l i z e d know l e dge w i l l a s s i s tthe tr ie ro f f a c t to u n d e r s ta n d th e e v id e n c e o rto d e te r m in e a f a c t in is s u e , a w i tne s s qua l i f

i e d a s a n e xpe r tby know l e dge , s ki l l , e xpe r i e nc e , tr a i ni ng, or e duc a t i on, m a y t e s t i f

y the r e t o i n the f

or m of a n opi ni on orothe rw i s e , i f ( 1) the t e s t i m ony i s ba s e d upon s uf f i c i e ntf a c t s orda t a , ( 2) the t e s t i m ony i s the prod uctof re l i abl e pri nci pl es and m etho ds, and (3) the w i tness has app l i ed the pri nci pl es and m etho ds re l i abl y t o the fa ct s of the ca se . F e d. R . E vi d. 702.20

T he S upr e m e C our ti n D a ube r ts e touta l i s tof “ ge ne r a l obs e r va t i ons ” f or det erm i ni ng w hether e xp ertt es t i m on y i s s uffi ci ent l y r el i abl e t o b e a dm i tt ed un der R ul e 702. 509 U . S . a t593, 113 S . C t . a t2796. T hos e ge ne r a l obs e r va t i ons f oc us on four pri m ary i nq ui ri es abou tthe expert ’ s theory or t ec hn i qu e: (1) w hether i tca n be ( a nd ha s be e n) t e s t e d; ( 2) w he the ri tha s be e n s ubj e c t e d t o pe e rr e vi e w a nd publ i c a t i on; ( 3) w ha ti t s know n orpot e nt i a l r a t e of e rr ori s , a nd w he the rs t a nda r ds c o n tr o llin g its o p e r a tio n e x is t; a n d ( 4 ) w h e th e rit is g e n e r a lly a c c e p te d in th e f ie ld . I d. a t593–94, 113 S . C t . a t2796. T he vi sual as se ss m entm etho d u se d b y the go vernm ent ’ s w i tness es on l y m et o n e o f th e f o u rD a u b e r t f

a c to r s . D e F r a n c e s c o a n d I rw in c o n c e d e d th a t th e ir m e th o d a n d c o n c lu s io n s w e r e n o t q u a n tita tiv e o rte s tab le b y th e s c ie n tif ic m e th o d . Inst ea d, they w er e bas ed on vi sual com pari sons of the m ol ec ul arm od el s c om bi ned w ith e x p e r t k n o w le d g e o f c h e m is try . D u r in g c r o s s - e x a m in a tio n , I rw in c ha r a c t e r i z e d hi s opi ni on a s be i ng a “ gutl e ve l thi ng” a nd ba s e d on i ntui t i on, buthe l at erexpl ai ned thathe used tho se t erm s t o ref ert o the kn ow l edge and exp er i ence he had g ai ned from thi rty y ea rs as a c hem i st . T he go vernm entprod uced no papers or stud i es i n w hi ch the m etho do l og y or opi ni on s of D eF ra nces co and Irw i n w er e subj ec t ed t o p ee r r evi ew . T hei r m etho d d i d, ho w ever , m ee tthe general ac ce pt ance f a c t or . D e F r a nc e s c o a nd I rw i n t e s t i f i e d tha tthe i rm e thod i s ge ne r a l l y a c c e pt e d,21

and the di stri ctcourtcr edi t ed thei r t es t i m on y thati ti s. “ T he cr edi bi l i ty of a w i tne s s i s i n the pr ovi nc e of the f a c t f i nde r , ” a nd w e “ w i l l notor di na r i l y r e vi e w the f a c t f i nde r ’ s de t e r m i na t i on of c r e di bi l i ty . ” U ni t e d S t a t e s v. C ope l a nd, 20 F . 3d 412, 4 1 3 ( 1 1 th C ir . 1 9 9 4 ) ( p e rc u r ia m ) . T h e B r o w n s h a v e n o t c h a lle n g e d th e c r e d ib ility of the s e tw o e xpe r t s , a nd w e s e e nothi ng i n the r e c or d t o c onvi nc e us tha tthe d is tr ic t c o u r t c le a r ly e rr e d in f in d in g th a t th e y w e r e c r e d ib le . T he qu es t i on , then, i s w hether e xp ertop i ni on evi dence thatdo es no tm ee t thr e e of the f ourD a ube r tf

a c t or s ne ve r the l e s s c a n be a dm i tt e d. I n the r i ght c i r c um s t a nc e s , the a ns w e rt o tha tque s t i on i s “ y e s . ” T he S upr e m e C our tm a de c le a rin its D a u b e r t o p in io n th a t th e f a c to r s it s e t o u t th e r e w e r e n o t to b e r ig id ly appl i e d, butw e r e i ns t e a d t o s e r ve a s gui de l i ne s f orf e de r a l di s tr i c tc our t s appl y i ng R u l e 7 0 2 . T h e C o u r ts a i d , “ [ t ] h e i n q u i ry e n v i s i o n e d b y R u l e 7 0 2 i s , we e m pha s i z e , a f

l e xi bl e one , ” D a ube r t , 509 U . S . a t594, 113 S . C t . a t2797; “ [ m ] a ny f a c t or s w i l l be a ron the i nqui ry , a nd w e do notpr e s um e t o s e touta de f i ni t i ve c h e c k lis t o rte s t,” id . a t 5 9 3 , 1 1 3 S . C t. a t 2 7 9 6 . T h e d e c is io n in K u m h o T ir e e lab o r a te d o n th e f le x ib le n a tu r e o f

th e in q u iry . T here the C ou rtpo i nt ed ou tthat“ D aubert ’ s l i stof spec i fi c f ac t ors nei ther ne c e s s a r i l y nore xc l us i ve l y appl i e s t o a l l e xpe r t s ori n e ve ryc a s e . ” I d. a t141, 119 S . C t . a t1171. W he the rthe D a ube r topi ni on f a c t or s a r e e ve n pe r t i ne ntt o a s s e s s i ng22

re li ab il ity in a g iv en ca se w il l “ d ep en d [] o n th e n atu re o f th e iss u e, th e e x p er t’ s part i cul arexpert i se , and the subj ec tof hi s t es t i m on y. ” I d. at15 0, 11 9 S . C t . at 11 75 (i nt ernal m arks om i tt ed). B ec ause the appl i cabi l i ty of the D aubertfa ct ors d e p e n d s o n th e in d iv id u a l f a c ts in a p a r tic u la rc a s e , th e C o u r t s a id th a t it c o u ld : ne i the rrul e out , norrul e i n, f ora l l c a s e s a nd f

ora l l t i m e the appl i c abi l i ty of the f a c t or s m e nt i one d i n D a ube r t , nor[ c oul d i t ] now do s o f ors ubs e t s of ca se s c at egori ze d b y c at egory of e xp ertor by ki nd of evi dence. T oo m uch depend s upo n the part i cul arci rc um st ance s of the part i cul arca se ati ss ue. Id. at15 0, 11 9 S . C t . at11 75 . T hi s m ea ns thatexpertt es t i m on y thatdo es no tm ee t al l or m ostof the D aubertfa ct ors m ay som et i m es be adm i ss i bl e. T he S up re m e C ou rtsa i d i n K um ho T i re thatthe qu es t i on of “ w hether D a ube r t ’ s s pe c i f

i c f a c t or s a r e , ora r e not , r e a s onabl e m e a s ur e s of r e l i abi l i ty i n a p a r tic u la rc a s e is a m a tte rth a t th e la w g r a n ts th e tr ia l ju d g e b r o a d la titu d e to d eter m in e.” I d . at 1 5 3 , 1 1 9 S . C t. at 1 1 7 6 . W e a re to re v iew th e d istrict co u rt’s deci si on on ho w t o d et erm i ne re l i abi l i ty w i th the sa m e abu se of di sc re t i on st andard tha tw e us e t o r e vi e w i t s ul t i m a t e c onc l us i on. I d. a t152, 119 S . C t . a t1176 (“ [T ] h e tri al j u d g e m u sth av e co n si d erab l e l eew ay i n d eci d i n g i n a p art i cu l ar case ho w t o g o abo utdet erm i ni ng w hether part i cul arexpertt es t i m on y i s r el i abl e. ”) ; se e a l s o A br e u, 406 F . 3d a t1307 ( “ T he di s tr i c tc our tha s w i de l a t i tude i n de c i di ng how t o d et erm i ne re l i abi l i ty. ”) ; U ni t ed S t at es v. M aj ors, 19 6 F . 3d 12 06 , 12 15 (11th C i r. 19 99 ).23

I n thi s c a s e , the i s s ue w a s w he the rthe c he m i c a l s truc tur e s of 1, 4- but a ne di ol a nd G H B a r e “ s ubs t a nt i a l l y s i m i l a r . ” A f t e rhe a r i ng the t e s t i m ony of the gove rnm e nt ’ s tw o e xpe r tw i tne s s e s , the c our tf ound tha tD e F r a nc e s c o’ s a nd I rw i n’ s opi ni ons w e r e “ ba s e d on the i rknow l e dge , s ki l l , a nd e xpe r i e nc e ” a nd on “s u f f ic ie n t f a c ts a n d d a ta .” B r o w n , 2 7 9 F . S u p p . 2 d a t 1 2 4 4 . I n lig h t o f its de t e r m i na t i on tha tthe i rt e s t i m ony aboutthe ge ne r a l a c c e pt a nc e of the i rm e thod w as cr edi bl e, the courtconcl ud ed that“ bo th [expert s] em pl oyed an acc ept ed m e thod. ” I d. M or e ove r , i tf ound tha tthe e xpe r t s ha d appl i e d tha tm e thodol ogy r e l i abl y . I d. W e c a nnots a y tha tthe c our tabus e d i t s di s c r e t i on i n a l s o c onc l udi ng tha tthe s pe c i f

i c D a ube r tf

a c t or s ( s uc h a s t e s t abi l i ty a nd pe e rr e vi e w ) w e r e not r e q u ir e d in th is p a r tic u la rs itu a tio n . N o rc a n w e s a y th a t its k e y c r e d ib ility de t e r m i na t i on w a s c l e a r l y e rr one ous . G i ve n the c i r c um s t a nc e s of thi s c a s e , a nd gi ve n the he a vy thum b— r e a l l y a thum b a nd a f i nge rortw o— tha ti s puton the di s tr i c tc our t ’ s s i de of

the s c a l e , w e c onc l ude tha ti tw a s nota n abus e of di s c r e t i on t o adm i tthe expertop i ni on s of the tw o g ov ernm entw i tness es i n thi s c as e. O urc onc l us i on i s c ons i s t e ntw i th the “ l i be r a l thrus tof the F e de r a l R ul e s a nd thei r genera l approach of rel axi ng the tra di t i on al barr i er s t o o pi ni on t es t i m on y. ” D aubert , 50 9 U . S . at58 8, 11 3 S . C t . at27 94 (i nt ernal m arks and ci t at i on om i tt ed); s e e a l s o J oi ne r , 522 U . S . a t142, 118 S . C t . a t517 ( “ [ T ] he F e de r a l R ul e s of24

E v id e n c e a llo w d is tr ic t c o u r ts to a d m it a s o m e w h a t b r o a d e rr a n g e o f s c ie n tif ic t es t i m on y than w ou l d h ave been adm i ss i bl e und erF ry e . . . . ”) . T ho se barr i er s a re even m ore r el axed i n a bench tri al si tuat i on , w here the j ud ge i s s ervi ng as f a c tf in d e ra n d w e a r e n o t c o n c e rn e d ab o u t “d u m p in g a b a rr a g e o f q u e s tio n ab le s c i e nt i f i c e vi de nc e on a j ury . ” A l l i s on v. M c G ha n M e d. C orp. , 184 F . 3d 1300, 13 10 (11th C i r. 19 99 ); se e a l so i d. (r ec og ni zi ng thatthe j ury “ w ou l d l i kel y be e ven l e s s e qui ppe d tha n the j udge t o m a ke r e l i abi l i ty a nd r e l e va nc e de t e r m i na t i ons a nd m o r e lik e ly th a n th e ju d g e to b e a w e s tru c k b yth e e x p e r t’s m y s tiq u e ” ) . T h e r e is l e s s ne e d f

orthe ga t e ke e pe rt o ke e p the ga t e w he n the ga t e ke e pe ri s ke e pi ng the g a te o n ly f

o rh im s e lf

. C. W e turn oura tt e nt i on now t o the B r ow ns ’ w i tne s s , D r . S t e e l e . R ul e 702 r e qui r e s , a m ong othe rthi ngs , tha t : ( 1) a w i tne s s be “ qua l i f i e d a s a n e xpe r tby know l e dge , s ki l l , e xpe r i e nc e , tr a i ni ng, ore duc a t i on” a nd ( 2) hi s t e s t i m ony be “ the prod uctof re l i abl e pri nci pl es and m etho ds” thatw er e r el i abl y app l i ed t o the fa ct s a t ha nd. F e d. R . E vi d. 702. T he di s tr i c tc our tde t e r m i ne d tha tS t e e l e w a s not qu al i fi ed as an experti n con trol l ed subst ance s a nd thatthe m etho d h e use d t o rea ch hi s opi ni on w a s both unr e l i abl e a nd unr e l i abl y appl i e d. T he B r ow ns c ha l l e nge thos e c onc l us i ons . P utt i ng the i ra r gum e nt s i n the be s tl i ght , the B r ow ns c ont e nd25

tha tthe di s tr i c tc our tabus e d i t s di s c r e t i on, by r e l y i ng on c l e a r l y e rr one ous f a c t s or m a ki ng a c l e a re rr orof

j udgm e nt , w he n i tr e f

us e d t o qua l i f

y S t e e l e a s a n e xpe r ta nd w he n i tc onc l ude d tha tS t e e l e ’ s T a ni m ot o c oe f f i c i e ntm e thod w a s unr e l i abl e a nd u n r e liab ly ap p lie d . T he di stri ctcourtdi d n otabuse i t s di sc re t i on i n d ec l i ni ng t o q ual i fy S t ee l e a s an expert . A s the di stri ctcourtexpl ai ned, S t ee l e’ s a ca dem i c w ork and profes si on al experi ence re l at ed m ore t o p l antpatho l og y a nd bo t any than t o chem i stry . S ee B r ow n, 279 F . S upp. 2d a t1244–45. T hough w e r e c ogni z e tha tS t e e l e doe s ha ve experi ence i n chem i stry , w e c an fi nd no abuse of di sc re t i on i n l i gh tof the fa ctthat S t e e l e ha s onl y w or ke d w i th 1, 4- but a ne di ol a nd G H B “ on i s ol a t e d pr oj e c t s ” a nd that“ he do es no tpo ss es s al i ce nse t o w ork w i th con trol l ed subst ance s. ” I d. at 1245. M or e ove r , e ve n i f w e w e r e t o a gr e e w i th the B r ow ns tha tS t e e l e s houl d ha ve been qu al i fi ed as an expert , w e w ou l d st i l l re j ec tthei r a rgum entthatthe di stri ct courterre d i n fi nd i ng hi s m etho d u nrel i abl e a nd un re l i abl y app l i ed. T he di stri ct courtfoun d thatS t ee l e’ s m etho do l og y w as un re l i abl e bec ause i tprod uces

“ skew ed” a nd “ bi za rr e a nd curi ou s” re sul t s w hen rel at i vel y s i m pl e m ol ec ul es ar e a t is s u e , a s in th is c a s e . I d . a t 1 2 4 8

– 4 9 ; s e e id . a t 1 2 4 8 ( “T h e s k e w e d r e s u lts c onvi nc e d the c our ttha tthe T a ni m ot o c oe f f i c i e nti s nota r e l i abl e i ndi c a t orof26

s truc tur a l s i m i l a r i ty w he n a s s e s s i ng tw o s i m pl e l i ne a rm ol e c ul e s w i th onl y one di f f e r i ng f unc t i ona l gr oup . . . . ” ) ; i d. a t1249 ( di s c us s i ng thr e e e xa m pl e s of “b iz a rr e a n d c u r io u s ” r e s u lts ) . F or a num ber of r ea sons, the di stri ctcourtal so foun d thatS t ee l e had appl i ed hi s m etho do l og y i n an u nrel i abl e w ay . T he courtexpl ai ned thatS t ee l e had o v e r e m p h a s iz e d th e d if

f e r e n c e s b e tw e e n th e tw o c h e m ic a ls b y u n n e c e s s a r ily do ub l e- coun t i ng a s ub structure pres enti n G H B bu tno ti n 1 , 4-bu t anedi ol . Id. at 1 2 4 8 . I t f

o u n d th a t S te e le ’s s o le r e lia n c e o n th e T a n im o to c o e f f ic ie n t a n d h is

“ s tubborn r e f

us a l . . . t o s uppl e m e nthi s opi ni on by vi s ua l l y a s s e s s i ng” the c h e m ic a ls “r e e k e d o f

b ia s .” I d . a t 1 2 5 0 . T h e c o u r t f u r th e rf o u n d th a t S te e le d id no tkn ow , and cou l d n otexpl ai n, ho w the com pu t erprog ra m s he use d d ef i ned

“ si m i l ar i ty. ” I d. B ec ause S t ee l e di d n otkn ow ho w the com pu t erprog ra m s def i ned “s im ila r ity ,” th e r e s u lts w e r e o f q u e s tio n ab le v a lu e . I d . T h e c o u r t e x p r e s s e d its “a m a z [ e m e n t] th a t D r . S te e le w o u ld s ta k e h is p r o f e s s io n a l r e p u ta tio n o n th e r e s u lts o f a p r o g r a m w ith o u t k n o w in g h o w it w o r k s .” I d . I t s a id th a t S te e le ’s “[ c ]o m p le te ac ce p tan ce o f [ th e c o m p u ter p ro g ra m m er ’s] su b jectiv e d ef

in it io n o f ‘sim il ar ity’” a m o u n te d to “b lin d r e lia n c e d e v o id o f m e r it.” I d . E v e n if a ll o f th a t w e r e n o t e n o u g h b y its e lf , th e B r o w n s ’ a r g u m e n ts w o u ld st i l l fa i l gi ven the un i qu e c i rc um st ance s of thi s c as e. B ec ause thi s w as a bench27

tr i a l , the di s tr i c tc our tw a s notonl y the ga t e ke e pe rbuta l s o the f a c t f i nde r . T he d is tr ic t c o u r t a s g a te k e e p e rd id n o t e x c lu d e a n y o f S te e le ’s te s tim o n y . I n s te a d , it al l ow ed S t ee l e t o t es t i fy , expl i ci t l y r es ervi ng for l at erthe det erm i nat i on of w hether hi s t es t i m on y c om pl i ed w i th D aubertand R ul e 702 . T he courtl at erdet erm i ned thati tw as “ un w i l l i ng t o q ual i fy D r. S t ee l e a s a n exp ertw i th k no w l edge i n the ar ea of c ontr ol l e d s ubs t a nc e s , e s pe c i a l l y [ 1, 4- but a ne di ol ] a nd G H B . ” N e ve r the l e s s , the court“ st i l l consi der[ ed] D r. S t ee l e’ s t es t i m on y, bu thi s l ac k o f e xp ert i se i n the ar ea s u b s ta n tia lly a f

f e c t[ e d ] th e w e ig h t” th e c o u r t g a v e it. I d . a t 1 2 4 5 . I n o th e rw o r d s , the c our t - a s - ga t e ke e pe rl e tthe c our t - a s - f a c t f i nde rc ons i de rS t e e l e ’ s t e s t i m ony , but the c our t - a s - f

a c t f i nde rde c i de d nott o gi ve i tm uc h w e i ght . T ha tm e a ns the f a c tf in d e rh e a r d th e te s tim o n y th e B r o w n s s o u g h t to h a v e a d m itte d , a n d th e ir c o m p la in t r e a lly is ab o u t th e w e ig h t g iv e n to th a t te s tim o n y . Q ue s t i ons aboutthe w e i ghtgi ve n t o t e s t i m ony , a s di s t i ngui s he d f r om the i ss ue of i t s a dm i ss i bi l i ty, ar e f or the fa ct fi nd er . S ee U ni t ed S t at es v. H ernand ez , 141 F . 3d 1042, 1052 ( 11th C i r . 1998) . “ I f the di s tr i c tc our t ’ s a c c ountof the e vi de nc e i s pl a us i bl e i n l i ghtof the r e c or d vi e w e d i n i t s e nt i r e ty , the c our tof appe a l s m a y notr e ve r s e i te ve n though c onvi nc e d tha tha d i tbe e n s i tt i ng a s the tr i e ro f f a c t , i tw o u l d h a v e w e i g h e d th e e v i d e n c e d i f f e r e n t l y . ” A n d e r s o n , 4 7 0 U . S. at57 3– 74 , 10 5 S . C t . at15 11 . W e c ert ai nl y c anno tsa y thatthe di stri ctcourtTh eB ro wn s alsoarguethat th ee vide nc eis ins uf fi c ient b e c a

us etheg ov e rnment’ s o nly 1 e vide nc e—th ee xpe rt

te stimony

—s ho uld havebe e n e xclude d unde r D a ub e rt . Thisargument, however, mere ly

rec asts their Da

ubert a rgument, which wehave already dealt with. See Par

t III .B, supra. 28 c le a r ly e rr e d w ith r e g a r d to th e w e ig h t it g a v e S te e le ’s te s tim o n y . I V. T he B r ow ns a l s o a r gue tha tthe i rc onvi c t i on m us tbe r e ve r s e d be c a us e the evi dence w as i nsuffi ci entt o con vi ctthem . T hey c on t end thatthe di stri ctcourt c o u ld n o t r e a s o n ab ly c o n c lu d e th a t th e g o v e rn m e n t p r o v e d b e y o n d a r e a s o n ab le doubtthe onl y c ont e s t e d e l e m e ntof the of f e ns e : w he the rthe c he m i c a l s truc tur e of 1 ,4 - b u ta n e d io l is s u b s ta n tia lly s im ila rto th a t o f G H B . T h e y m a k e tw o a r g u m e n ts abou tthi s. F i rs t , K evi n B row n argues thatthe di stri ctcourti m prop er l y c on si dere d the m et abol i c c on vers i on of 1, 4-bu t anedi ol i nt o G H B on the qu es t i on of subst ant i al s i m i l a r i ty . S e c ond, the B r ow ns a r gue tha te ve n i f i tw a s pr ope rt o c ons i de r1, 4- but a ne di ol ’ s c onve r s i on i nt o G H B , the gove rnm e nts t i l l f a i l e d t o pr ove be y ond a re as on abl e dou btthatthe chem i ca l structures of 1, 4-bu t anedi ol and G H B ar e subst ant i al l y s i m i l ar . 1 W e r e vi e w de novo w he the rs uf f i c i e nte vi de nc e s uppor t s a c onvi c t i on, but w e r es ol ve al l re as on abl e i nfer ence s i n favor of the verdi ct . U ni t ed S t at es v. O rt i z, 31 8 F . 3d 10 30 , 10 36 (11th C i r. 20 03 ) ( per c uri am ). “ In re vi ew i ng the suff i ci ency of the evi dence i n sup po rtof a c on vi ct i on i n a cr i m i nal ca se fol l ow i ng a non -j ury29

tri al , w e m u std et erm i n e w h eth er th e ev i d en ce, co n stru ed i n th e l i g h tm o st f a vor abl e t o the gove rnm e nt , w oul d pe r m i tthe tr i e rof f a c tt o f i nd the de f

e nda nt gui l ty be y ond a r e a s onabl e doubt . ” U ni t e d S t a t e s v. B ur s ty n, 878 F . 2d 1322, 1324 ( 11th C i r . 1989) ( pe rc ur i a m ) . “ I ti s notourf unc t i on t o m a ke c r e di bi l i ty c hoi c e s or t o pa s s upon the w e i ghtof the e vi de nc e . ” U ni t e d S t a t e s v. T urne r , 812 F . 2d 1552, 1 5 6 3 (1 1 th C i r. 1 9 8 7 ). In st ead , w e m u stsu st ai n th e v erd i ct“ w h ere th ere i s a r e a s onabl e ba s i s i n the r e c or d f or ” i t . P a rke rv. S c r ap M e t a l P r oc e s s or s , I nc . , 386 F . 3d 99 3, 10 10 (11th C i r. 20 04 ) ( qu ot at i on om i tt ed). W e a re no tpers uaded b y K evi n B row n’ s a rgum entthat , i n d ec i di ng w hether the tw o s ubs t a nc e s w e r e s ubs t a nt i a l l y s i m i l a r , the di s tr i c tc our ts houl d notha ve c ons i de r e d the m e t abol i c c onve r s i on of 1, 4- but a ne di ol i nt o G H B . A s the go vernm ent ’ s tw o exp ert s t es t i fi ed, the re ady m et abol i c c on vers i on do es evi dence s u b s ta n tia l s im ila r ity . I rw in e x p la in e d w h y : “T h is s tru c tu r e h a s to b e b a s ic a lly i d e n t i c a l t o th i s s tru c tu r e i n o r d e rf o rth e [ 1 , 4 - b u t a n e d i o l ] t o b e c o n v e r t e d t o GH B and for i tt o fi ti nt o the G H B re ce pt or. A nd so i n thatcont extthati nfl uences — that basi ca l l y r equi re s thatthe structures be very si m i l ar . ” H i s t es t i m on y i s i n acc ord w i th, and B row n’ s c on tra ry ar gu m entconfl i ct s w i th, w hatw e s ai d i n U ni t ed S t at es v . F is h e r , 2 8 9 F .3 d 1 3 2 9 ( 1 1 th C ir . 2 0 0 2 ) , c e r t. d e n ie d , 5 3 7 U .S . 1 1 1 2 , 1 2 3 S . C t. 903 ( 2003) . T he r e , i n r e j e c t i ng a voi d f

orva gue ne s s c ha l l e nge t o the A na l ogue30

A c t , w e s t a t e d tha tthe f a c tthe c om pound G B L c onve r t s i nt o G H B upon i nge s t i on m e a n s th a t th e c h e m ic a l s tru c tu r e s o f th e tw o c o m p o u n d s a r e s u b s ta n tia lly s im ila r . I d. a t1339; s e e a l s o U ni t e d S t a t e s v. W a s ha m , 312 F . 3d 926, 931 ( 8th C i r . 2002) ( hol di ng, i n the c our s e of r e j e c t i ng a voi d f

orva gue ne s s c ha l l e nge t o the A na l ogue A ct , thati ti s proper t o con si der m et abol i c c on vers i on i n d et erm i ni ng the structural s i m i l a r i ty of

1, 4- but a ne di ol a nd G H B ) ; U ni t e d S t a t e s v. R obe r t s , 363 F . 3d 118, 124–26 ( 2d C i r . 2004) ( s a m e ) ; i d. a t126 n. 4 ( “ W e e m pha s i z e tha tthe f a c ttha t1, 4- but a ne di ol m e t abol i z e s i nt o G H B i s s i gni f i c a ntnotbe c a us e i tm e a ns tha tthe chem i ca l s a re i dent i ca l , bu tbecause i ti nd i ca t es thatthe re adi l y a sc ert ai nabl e pre i nge s t i on s i m i l a r i ty be tw e e n 1, 4- but a ne di ol a nd G H B

— the m e r e tw o- a t om d if f e r e n c e b e tw e e n th e m o le c u le s — is a s im ila r ity o f a m a te r ia l a n d r e le v a n t s o r t, g iv e n th e p u rp o s e o f

th e A c t.” ) . A s t o th e B ro w n s’ o th er arg u m en t , v i ew i n g th e ev i d en ce i n th e l i g h tm o st f a v o r ab le to th e g o v e rn m e n t, a s w e m u s t, w e c o n c lu d e th a t th e r e w a s a r e a s o n ab le basi s i n the re cord for the di stri ctcourt ’ s dec i si on . F i rs t , i tw as un di sput ed that 1, 4- but a ne di ol r api dl y m e t abol i z e s i nt o G H B w he n i ti s i nge s t e d a nd, a s w e ha ve e x p la in e d , th a t is a v a lid p ie c e o f e v id e n c e o n th e q u e s tio n o f s u b s ta n tia l s im ila r ity . S e c ond, the gove rnm e ntpr e s e nt e d the e vi de nc e of tw o w e l l - qua l i f

i e d e xpe r t s , w ho bo th u nequ i vo ca l l y s t at ed thei r opi ni on s that1, 4-bu t anedi ol i s acontrol l edIn Bonner v. Prichard, 661 F.2d 1206, 1207 ( 11th Cir. 1981) (en ba nc), w e adopte d as 2 binding prece dent all Fif

th Circuit decisions handed down prior to October 1, 1981. 31 subst ance anal og ue of G H B because i thas asubst ant i al l y s i m i l archem i ca l structure. T hese expert s t es t i fi ed thatw hi l e the subst ance s a re no ti dent i ca l , they ar e s ub st ant i al l y s i m i l arbecause they a re “ i dent i ca l exce ptfor the t erm i nal c a rb o n s ” ; th a t is , in th e te r m in a l f u n c tio n a l g r o u p o n th e irr ig h t s id e . T h is t e s t i m ony i s s uf

f i c i e ntt o s uppor tthe f

a c t f i nde r ’ s de t e r m i na t i on tha t1, 4- but a ne di ol and G H B ar e s ub st ant i al l y s i m i l arand the re sul t i ng concl usi on thatthe B row ns ar e g u ilty o f v io la tin g 2 1 U .S .C . § 8 4 6 . T he f a c ttha tthe B r ow ns pr ovi de d s om e e vi de nc e t o the c ontr a ry thr ough the t es t i m on y of S t ee l e does notun derm i ne ou r c on cl usi on . T hata def endanthas pr ovi de d s om e t e s t i m ony t o s uppor thi s the ory of the c a s e i s note nough t o s how i nsuffi ci entevi dence, because the fa ct fi nd eri s f re e t o rej ec tthatt es t i m on y. C f. U ni t e d S t a t e s v. K e l l e y , __ F . 3d __, 2005 W L 1403400, a t*6 ( 11th C i r . 2005) ( i n a s u f f ic ie n c y o f

th e e v id e n c e c h a lle n g e , r e je c tin g th e d e f

e n d a n t’s a r g u m e n t th a t a gove rnm e ntw i tne s s ’ t e s t i m ony w a s unbe l i e vabl e be c a us e i tc ontr a di c t e d the de f e nda nt ’ s w i tne s s ’ t e s t i m ony ) ; L i be r ty M ut . I ns . C o. v. F a l gous t , 386 F . 2d 248, 2 5 3 ( 5 th C ir . 1 9 6 7 ) ( “J u ry f in d in g s o n c o n f

lic tin g e v id e n c e a r e b in d in g o n th is C our t , w hi c h a c c e pt s a s true tha tve r s i on of the t e s t i m ony the j ury m i ght re as on abl y have a do pt ed i n rea chi ng i t s ver di ct. . . . ”) . 232

F i n al l y, th e B ro w n s’ arg u m en tth ata reaso n ab l e d o u b tm u stex i stb ecau se sc i ent i st s c ou l d l egi t i m at el y di sa gree abou tw hether 1, 4-bu t anedi ol and G H B ar e subst ant i al l y s i m i l ari s w i tho utm er i t . W hen w e r evi ew w hether there w as s uf f i c i e nte vi de nc e t o uphol d a c r i m i na l c onvi c t i on, i ti s notne c e s s a ry tha tone h u n d r e d p e r c e n t o f

th e e v id e n c e p o in t to g u ilt. N o rd o w e a s k w h e th e rth e o n ly po ss i bl e ver di ctthe fa ct fi nd ercoul d h ave r ea ched i s gui l ty. O ur re vi ew i s notthat se ar chi ng . W e m ustho l d thatthe evi dence und er l yi ng the conv i ct i on w as s u f f ic ie n t “s o lo n g a s a r e a s o n ab le tr ie ro f f a c t, c h o o s in g a m o n g r e a s o n ab le i nt erpret at i on s of the evi dence, coul d fi nd gu i l tbeyond a r ea sonabl e dou bt . ” U ni t ed S t at es v. P i nei ro, 38 9 F . 3d 13 59 , 13 67 (11th C i r. 20 04 ) ( ci t i ng U ni t ed S t a t e s v. L l ue s m a , 45 F . 3d 408, 409–10 ( 11th C i r . 1995) ) . I ns t e a d of r e - w e i ghi ng th e e v id e n c e a n d m a k in g c r e d ib ility d e te r m in a tio n s o u r s e lv e s , w e d e c id e o n ly w he the rthe r e i s a r e a s onabl e ba s i s i n the r e c or d t o s uppor tthe ve r di c t . H e r e , the d is tr ic t c o u r t r e a s o n ab ly c o u ld , a n d d id , f in d th e g o v e rn m e n t’s e x p e r ts b e lie v ab le . T h e irte s tim o n y p r o v id e d a r e a s o n ab le b a s is f o rc o n c lu d in g b e y o n d a r e a s o n ab le d o u b t th a t th e c h e m ic a l s tru c tu r e s o f 1 ,4 - b u ta n e d io l a n d G H B a r e s u b s ta n tia lly si m i l arfor purpo se s of 21 U . S . C . § 8 02 (32)(A )( i ). V. L a s t l y , K e vi n B r ow n a r gue s tha tthe s t a tut e unde rw hi c h he w a s c onvi c t e d,33

21 U . S . C . § 813, vi ol a t e s the non- de l e ga t i on doc tr i ne of A rt i c l e I of

the C ons t i tut i on, a nd tha tthe di s tr i c tc our te rr e d i n de ny i ng hi s m ot i on t o di s m i s s on tha tba s i s . B e c a us e B r ow n ha s w a i ve d hi s r i ghtt o appe a l thi s i s s ue , w e w i l l not c o n s id e rit. A s pa r tof

the j oi ntbe nc h tr i a l a gr e e m e ntB r ow n e nt e r e d i nt o w i th the g o v e rn m e n t, h e a g r e e d to w a iv e h is r ig h t to ap p e a l is s u e s a r is in g f r o m h is conv i ct i on and sent enci ng , w i th l i m i t ed except i on s. T he on l y e xcept i on that B r o w n c o u ld c o n c e iv ab ly a r g u e e n c o m p a s s e s h is n o n - d e le g a tio n a r g u m e n t is e xc e pt i on ( d) : “ T he s ol e l e ga l a nd f a c tua l i s s ue of

w he the r , pur s ua ntt o T i t l e 21, U ni t e d S t a t e s C ode , S e c t i on 802( 32) ( A ) ( i ) , the c he m i c a l s truc tur e of 1, 4- B ut anedi ol i s s ub st ant i al l y s i m i l art o the chem i ca l structure of the S chedul e I c ontr ol l e d s ubs t a nc e G H B , i nc l udi ng a ny rul i ngs by the di s tr i c tc our ta ddr e s s i ng th a t is s u e .” B r ow n’ s a r gum e ntaboutthe c ons t i tut i ona l i ty of the A na l ogue A c tdoe s not go t o the “ s ol e l e ga l a nd f a c tua l i s s ue of

w he the r. . . the c he m i c a l s truc tur e of 1, 4- B ut anedi ol i s s ub st ant i al l y s i m i l art o the chem i ca l structure of the S chedul e I control l ed subst ance G H B . ” B row n d oes notcont end thathi s w ai ver w as un kn ow i ng or i nv ol un t ary. S ee U n ite d S ta te s v . B u s h e r t, 9 9 7 F .2 d 1 3 4 3 , 1 3 5 0 ( 1 1 th C ir . 1 9 9 3 ) ( s ta tin g th a t a34

k n o w i n g an d v o l u n t ary w ai v er o f th e ri g h tt o ap p eal w i l l b e en fo rced ). B ecau se B row n’ s non -del egat i on ar gu m enti s c l earl y out si de the except i on s t o the appeal w a i ve r , he ha s w a i ve d hi s r i ghtt o r a i s e i t . S e e , e . g. , U ni t e d S t a t e s v. W e a ve r , 275 F .3 d 1 3 2 0 , 1 3 3 3 ( 1 1 th C ir . 2 0 0 1 ) . V I. F o r th e fo reg o i n g reaso n s, w e co n cl u d e th atth e d i stri ctco u rtd i d n o tab u se its d is c r e tio n in its e v id e n tia ry d e c is io n s a n d th a t th e r e w a s s u f f ic ie n t e v id e n c e to s u p p o r t th e B r o w n s ’ c o n v ic tio n s . K e v in B r o w n ’s n o n - d e le g a tio n a r g u m e n t is fore cl osed by hi s app ea l w ai ver. AF F I R ME D.