/ ;11/1/"T1I A7"1 fe..;'rNR' / R L /J()/Jd"'~ e / /1'8) CACTUS . 50. A COMPREHENSIVE TABULAR SUMMARY·

Rachel Mala and Jerry L. McLaughlin

Department of Medicinal Chemistry and Pharmacognosy School of Pharmacy and Pharmacal Science Purdue University. West Lafayette, Indiana 47907 U.S.A.

ABSTRACT. The puhlished lilin be ohtained by consuhinF the referrnces cited. The survey i.< belined to be complete Ihrou,h 1980. and the authors requtSt' notifIcation of omilled references. Botanical synonymsmay.be misleadinj!.and readers are referred to the included taxonomic rdere"""s (7 . 9.10. 12.1.3. 28. 30. 46.95. 151) .

• ucturr presented at the VIII Simposio Internacional de Quimica de ProduclOs Naturales. Institulo Tecnol6,ico y de Estudios Superiores de Monte""}". ~8/4/198J. Much ()f this research has bttn sup­ ported by l!rants from Ihe Cactus and Succulent Society of America.

Iable 1. Occurrence of Alkaloids in the Caetaceae as Reported in the Literature

Criteria of Botanical Name Common Name Habitat Content Identif iea­ Re1erences . tion Ariocarpus agavOides Magueyitos lula and lama­ ,Hordeuine tlc.Sc.Bc...... 19 (Caslaiieda)E.F. Anderson (little ulipas (Mexico) ag~ves) ! - Methyl-3,4-dime thoxy­ phenet hylamine - tlc.gc.gc-ms ~.~-Dimethyl-4-hydroxy- - 3-methoxyphenelhylamine ~lc,gc,gc .... s

Ariocarpu8 fissuratuB Peyote Zacatec.as and tlc,mp,mmp, 102 var. lloydl1 (Rose) Chaute Coahuila iT Mars~ (Mexico) ~-Methyltyramlne tlc

Ariocarpus f1 SOuTatuB living rock. Zacatecas and Hordenine mp 47,102,112 var .. fissuratu6 (Engel.) chautle, Coahuila Schum. peyote, BU­ (Mexico); ~Methyltyramin~ tlc nami or dry le.x.as . whiske)" ~-Methyl-3.4-dimethoxy- pezufia de phenet hylamine tlc ,mp.mmp venado, peyote cimar ron, star cactus, star rock

Arioc.arpus kotsLnou­ Pe..zuna de Northern and !lordenine ~lc,mp._p 109.127 ~(Lem.) Schum. venac!o, pata Central Mexico iT .de veRBdo. chaute.peyott ~-Methy1tyramine tlc,mp,anp, ir

Ariocllrpus ~ Chaute, San Luis POLosi Hordenine tlc.mp,mmp, 11.47,107, Scheid. Anha1on iUIII choulle, (Mexico) ir, 130,131. PI' lsmat ic"," Lem. pe yote !!-~I..chyl tIc Imp,ramp 155 ir ~-Methyl-3. 4-dimethoxy­ tlc,mp,mmp, phenet hylamin~ ir

~-Methyl-4-methoxyphene- tlc,mp,lamp, r.hylamine ir - 96

Table 1. (cont inued)

Criteria of , Botanical Name Common 'Name Habitat Alkaloid Cont ent Ident 1f1ca­ References tion

Ar10carEus "cha~harD6tru6 Chaute Nuevo Leon Hordenine tlc,gc,8C-mS 22 Boed. (Mexico) ~-Methyltyramine tlc,gc~gc-m5

~,~-Dimethyl-3,4-di- tlc,gc,gc--ms methoxyphenethylamine

~-Methyl-3,4-dimetboxy- tlc.gc,gC-tDS I phenet hvlamine

Ar10carpus trigonus Chaut e Mex1cD ~-Methyl-3,4-dimethoxy- Llc.,mp,mmp, 145 (Web. ) Schum. p hen ethy lam ine uv,1r ,nmr

Hordenine tlc,mp,mmp, ir ~-Methyltyramine tIc

Azureocereus a~acuchens1s Peru Tyramine tlc,mp,mmp 81 Johns ir

Backebergia militaris Guerrero, 3,4-Dimethoxyphenethyla­ tIc ,mp. iT ,ms 97,121,149 (Andot) Bravo ex Sanchez Michoacan mine Mejorada (Mexico) Hel1amine tlc,mp, ir. DiS ,m1k.es 3-Hethoxytyramine tlc,mp,mmp, ir,as \ Lemaireocereioe tlc,mp,mmp, , 1r ,ms ,mikes

Carnegiea gigantea Saguaro, Arizona, Cal1­ Carnegine gC,mp 14,16-18,26 (Engel. ) Br. and R. sajuaro, forn1a (USA); 58,59,138, pitahaya SODora (Mexico) gC,mp - 140,149 Salsol1dine mp,mmp,ir, nmr ,gc-ms 3-Methoxytyramine gc-ms gc__ 3,4-Dimethoxyphenethyl­

Arizonine tlc,mp,mmp, iT ,nmr ,m5 gc-ms tIc

Cereus aethiops Argent ina, Hordenine t le ,mp ,mmp, ir 13b Hs1ol. Brazil Tyramine tlc,mp,mmp,1r

Cand1cine t.lc,mp,mmp

Cereus alacriEortanus Braz 11 and Hordenine iT 2 Pfeilf. Paraguay

---Cereus forbe611 O. Cordoba, Cata­ Tyramine ir.nmr,ms 2 marcs, 1\JcuUlan (Argent ina) -

I Cereus !!laucus SD. Tyramine gc 2 I I '''"o~ Hordenine gc Table 1. (continued)

Criteria of Botanical Name Common Name Hallitat Alkaloid Content Ident1f ica- Ref ere.nces tion

~ Jamacaru DC. Brazil Caffeine (unconfinned) No ~eported 25,45

Tyramine tlc,mp,ir,ms

Cereus Eeruv ianul; (L.) Southeastern Tyramine gc 2 , 32,131 Mill. South America Hordenine gc

~ validus Haw. I:. Bolivia ·to 3-Nitrotyramine mp, tic ,uv,1r. 111 Argent ina nmr,lIls

Cereus pe ruv ianu5 ~- Southeastern Tyramine tr,ms 2. truosus DC . South America

Coryphantha bumamma Morelos. Hordenine tlc,gc-ms 20,23 (Ehren. ) Br . and R. Guerrero (Mexico) ~-M e thyl-3,4-d1methox y- tlc,gc-ms

~-Meth y l-4-methoxyphen- ethylamine t.lc..gc-ms

Coryphantha calipensis Calipan ~-Methyl-3,4-dimethoxy- 21,23,156 H. Bravo (Mexico) phenethyla..ine tlc,gc-ms,mp, ir , mmp .. . I Normacromerineo tlc,gc:-ms,lnp, ""p, ir

6-D-Methylnormacro- mp,t.lc,ms,gc, merlne (calipamine) nmr .

6-0-Methylmacromerine mp, t1c. gc. IDS, nmr

~,~-Dimethyl - 3,4,-d1me- thoxyphenethylamine tlc',gc-ms . ~ Hordenine tlc,gc..",s

~-Methyltyram1ne tlc,gc-IIlS

Cornhantha corn!!era Central Mexico 4-Methoxyphenethylamine tIe,lIe . .- . -' 60 (DC.) Lem. ~Methyl - 3,4-dimethox ~- . ­ phenethylam1ne tIc,gc

4-Methoxy-B-hydroxy­ phenethylamine tlc, gc

I Hordenine tIc I I tIc

tIc B-D-MethyIsynephriRe 1 Table 1. (continued)

CriteriB of Botanical Name Common Name . Habitat Alkaloid Content Ident1fica- References tioD

Coryphantha eornifers North Mexico; ~-Methyl-4-~ethoxy- 60 (DC . ) ·Br. snd R. var. W. Texas (USA) phenethy18mine tlc,mp ..mnp, eehinus (Engel. ) L- ir Ben50n ~-MethyI-3.4-di~ethoxy- phenethylamine tlc,mp,mmp. ir

Mac romer ille gC,ms I 4-Methoxy-B-hydroX)­ phenethy1amine nmr,ms

Hordenine tlc.mp,tmnp, ir

~-Methyltyran1ne tlc,1bp,tnmP, ir P-Q-Methylsynephrine tlc,nmr,ms

-. Synephrine tlc . I Cor:il~hantha Northern l1exico ~-Methyl-3.4-dimethoxy- duranguensis phenethylamine tlc,ge 60 (Rtinl\e) BT. and R. Hordenine tle,ge

~l1ethyltyramine tlc,~e . Synephrine tlc,ge

Corvphantha e1ephana- I l-1ichoacan ~-Methyl-3,4-dimethoxy- I tidens Lem. I (Mexico) phenethylamine tle,!!e 60 I tic ­ .I I 4-MethoxY-6-hydroxyphen I ethylamine tlc,se I i Hordenine tlc,ge I ~-l1ethy1tyramine , tIc Synephrine tIc

~-Methyl-4-Methoxy- . I I I phenethylamine tic Coryphantha Vera Cruz N.N-Dimethvl-3.4-dime- 23,125 ETeen...,oodi1 H. Bravo (Mexico) th;xy?henethylamine tle,ge-ms I Hordenine tlc,ge-tns

l\ormac romer ioe tlc.gc-ms

~-Meth)'I-3 ,4-dimethoxy- mp,mmp,ir phenethy1amine t.lc.gc-ms

B-Q-Methylsynephrine tIc ,gc-...

Synephrine tIc

o-2-l1et hy Ino",.• e ro- tlc,1r,ms. merine runr Table 1. (continued)

Criteria of I Identi fica­ . Botanical N~me Common Name I. Habi~at Al kaloid Content References J I tion Coryphantha macroroeris Dona Ana Southern N. Macro~er1ne ir,nmr.ms,uv 15.~9,77 (Engel.) Lem. Mexico, \Je6tern Texas (USA); Chihuahua (Mexico)

Coryphantha macromeris Dona Ana; Northern Mexico; Nonnacromerine tlc,mp,mmp 2,5,8,77-79 var .. rur-vonii l. Benson dumpling S. Texas (USA) cactus N-Me~hyl-3,4-dimethoxy- ir,nmr,tlc, phenet hylamine' mp,l1J'np,it', nmr,tI'Is

~-Me~hylme~Bnephrine dc

~-Methyl-4-methoxy- tlc,m.p,mmp, phenethylamine ir,nmr, l:e-9

Hordenine ~lc ,mp,mcp, ir ,nmr ,ms

Macromerine tlc,mp,mmp, ir,nmr

~-MethyltyrBmine t.lc,mp,mmp, ir ,nmr

Metanephrine tlc,mp,mmp, ir,nmr

N-Formylnormacromerine tlc,mp,mmp, , ir,nmr

Tyramine tle,lIlp,mmp, ir,se Synephrine tlc -

Corvphantha missour1­ M1ssouri pin­\Jest ern USA Hordenine tlc,!Dp,mmp, 122 ensis (Sloleet) Br. and R. cusion ir,ms

~-Methyltyram1ne tIc ,mp,mmp, 1r,1I15

Tyramine tIc ,ms

N-Methyl-3,4-dimethoxy­ tlc,1D5 phenethylam1ne

Co'ryphantha oHonis Central Mexico 4-MethoxyphenethylBmine tlc,se 60 (PfeH.) Lem. Hordenine tlc,se

~-Me~hyltyramine tle,se

Synephrine tlc,se

CoryphanthB pectinata Southern Texas N-Methyl-3,4-dimethoxy­ tle,se 41,60 (Engel.) Br. and R. (USA) ethylamine

~-Methyl-3,4-d1methoxy- tle,ge phenethylam1ne . Mac r o :nf" T ine ~lc,ge

4-Methoxy-e~hydroxy- tIc .ge phenethylamine

Hordenine tIc

~-Me:h ~ lt~Tacine tlc Criteria of Botanical Name Common Name Habitat Alkaloid Content Identifica- IReference. tion

Synephrine tIc , S-Q-MethylsynephriDe tIc

Cor:n~ha n t ha Eose lseriana Nuevo Leon, 4-Methoxyphenethylamine tlc,gc 60 (Dietr.) Br. and R. 2.acatec8S, Coahuila Horden:lne tle,ge (Mexico) I ~-Heth y ltyramine tle,ge

Synephrine tle,ge

CorYEhantha ~ Central Mexico N-Hethyltyramine tlc,ge-ms 23 (DC.) Br. and R. Hordenine tlc ,gC-1D6

CorYEhantha ramillosa Southern i exas ~-Methyl-4-methoxy- tlc,mp,mmp, 137 Cutal<.. (USA); and phenethylamine ir northcentral Hexico ~-Methyltyramine tlc,mp,mmp ir Synephr:lne tlc,mp,mmp ir S-Q-Hethylsynephrine tlc,mp,mmp, ir Hordenine t.lc,mp.,tDmp, ir

CoryEhantha viviEara Manitoba to Hordenine tle,ge-1IlS 14,23 (Nutt. ) Eng. Alberta (Cana­, da); Kansas, Texa.s, Colorado (USA) l.riteria 01 Botanical Name Common Name -Habitat Alkaloid Content Ident1fiea- References tion -

CoryEhantha vivipara Arizona (USA) Hordenine tlc.,lDp,mmp, 62 (Nutt. ) Br- and R. var .. ir ari%onitl (Engelm.) W.T. Marahall

Doliehothele baum1i iamaulipas Doliehotheline tIc 34 (&oed.) Werd. and F. (Hexieo) Boyb.

Dol1ehothele Iongimamma Peyot1l10, Cent.ral Hex_ieo Dolichothel in" tIc 34,80,124,127 (DC.) Br. and R. peyote - --"­ Longima=ine nmr,ms,ir,uv. - mp,mmp

Longimammosine nmr,ms,ir,uv, mp,l!lID.p

Longimammid ine nmr ,ms., 1r tU~. mp, mmp

Longimammat ine nmr,m5,ir,uv, mp,mmp

LongimallllJlamine nmr.m5,1r,uy. mp,m:np

Nonnacrocerine tlc,mp,mmp,1r

Synephrine tlc,mp,1IDp,1r Table 1. (continued)

Criteria of Botanical liame Common Name Ilabitat Alkaloid Content Ident1fica- Reference. , tion

Dol1chothele melaleLca Oaxaca (Mexico) Dolichotheline tIc: 34 (I~ar. ) Craig

Dolichothele sphaerica peyote Southern Te.xa& Dolichotheline tlc,il',DmI', 33,134,135 (Dietr.) Br. "and R. (USA) ; liorthern lOS Mexico 8-Q-Methylsynephrine tIc,ir, omr, ms ,mp,mmp

~-Methyltyramine tlc,11',nmr, mS,t!lp,mmp

Synephrine tlc, 11' ,nmr. ms Imp ,Dlnp

B-Q-Ethylsynephrine tlc,ir,nmr, (artifact) ms,mp,mmp

~-Methylphenethylamine tlc,ir,nmr, ms,mp,'CIllp

Dolichothele surculos& Tamaulip"s dol1chotheline tIc: 34 \ {Boed.) F. BUJ

Hordenine ir,mp,tlc.

~p,nmr,1D8

. ~-Methyltyramine 1r,mp,tlc, mmp,nmr,tnS

Synephrine ir,mp,tlc, mmp ,nmr,1D.S

Dolic:otheline tIc -

Dolichothele uberiformis peyote Central Mexico Dol1chotheline tIc: 2,80,126,127, (Zucc. ) Br. and R. 130,131,155 Ub1ne ms,nmr,1r, mp,mmp

Hordenine tIc

~-Methyltyramine tIc

Longimammatine tIc

Synephrine ir,mp,tlc

Uber1ne ms,nmr,uv

Long imammamine tIc

. ~-Methyl-3,4-dimethoxy- tlc:,mp,mmp phenethylaroine

N-Methyl-4-methoxy- tlc,mp,mmp phenethylamine

Normae rome r1ne 11' ,mY,mmp. tIc: .

Echinocereus cineTBscens Central Mexico !-Hethyl-J.4-dimethoxy- tlc,gc,ir, 27 (DC.) Riimpler phenethylamine ..5

~-~-Dimethyl-3,4-dimeth- tlc,gc,1r, oxyphenethylamine ms Table 1. (continued) ICriteria of Botanical J(ame Common Name Habitat Alkaloid Content IldentHica­ References tion ,

E.chinocereus lIlerkerl1 Durango, ~.~- Dimethyl-3.4-dimeth- mp,mmp,Sc-ms, Hlldm. Coahuila, San oxyphenet hylamine ir Luis Potosi (Mexico) ~-Methyl-3.4-dimethoxy- mp.m:np,gc-ms. phenethy la'mine ir

3,4-Dimethoxyphenethyl­ gc-ms amine

3-Hethoxyt.yramine gC"'1l15

Hordenine gc-ms

/' ­ Salsoline gc-ms ,/ r

ft Q Echinocereus tr1g1o­ claret cup S. Texas K ,N -DimethylhistB­ tlc,uv. ir. 43 chidatus Engelm var. (USA) mine ncr,ms,mp,mmp paucispinus Engelm. ex W.T. Harshall

Ech1nops1s evriesii Southern Brazil; Hordenine ir 2,55,131 (Turpin) Zucco Uruguay; Entre Rios (Argen­ tina)

Echinops1s rhodotricha Paraguay and Hordenine tlc,gc-1IlS 6 K. Schum. Northern Argen­ t ina Tyramine tlc,gc-ms

Espostoa huanucensis Peru , Tyramine tlc,mp,mmp, 96 R1tt. ir

~-Methyltyramine tlc,mp,mmp, 1r

Hordenine tlc,mp,mmp, .­ il'

GymnOC8CtuS aquirreanus S. Coahuila Hordenine tlc,lIlp,mmp. 153 Glas8 and FOBter (Mexico) ir

~-Methylphenethyl- t1c amine - ~-Methy1tyramine t1c

Gvmnocactus beguinii Coahuila, Zaca Hordenine tlc 153 (Web. ) »ackbg. Texas (Mexico) ~-Methylphenethyl- tlc amine

~-Methyltyramine tIc

Gvmnocactus horripilus Hida1go(Hexico) ~-Methylphenethy1- tlc,mp,~Pt (Lem. ) Backbg. amine ir

Hordenine t1c

Gymnocactus knuth1anu8 San Luis Potos 1 ~-Hethy1phenethy1- t1c 41,153 (Boea'. ) &ckbg. (Mexico) amine

Gvmnocactus mandr8~ora Hexico ~-~ethy1phenethyl- t1c 153 (Fric) »ckbg. amine

~-~ethyltyramine t1c Table 1. (continued) --- Criteria of Botanical Name Common Name Habitat Al k.aloid Content 1dent if1ca­ Ref erenc.es tion , Cvmnocactus roseanu& Mexico Hordenine tlc,mp,1III1p 153 val'. From el Chif1on, ir Mexico ~-Methy1phenethy1- t1c amine

~-Methyltyramine tIc

Gvmnocactus viereckii 'Iamaulipas ~-Methylphenethyl- t lc 153 (IJerd . ) Backbg. (Mexico) amine

G~nocalvcium ~1bbosum Argent ina Hescaline Chemical 54,130 (Haworth) Pfeiffer testa

Lophophorine

Gvmnocal~c1um lee.anum Argentina and Tyramine gc 32,54 (Hook. ) Br. and R. Uruguay ~-Methyltyramine gc

Hordenine ms ,gc

Mescaline chemical tests (uncon­ firmed)

Anhalonine chem1cal testa

, Lophophorine chemical ...... ----­ te5ts

Gymnocalvc1U1D sch1c1

Han isia adscendes Cacto Bahia (Brazil ) Caffeine (uncon! irn>ed) None re- 45 (Gurke) Bt. and R. ported

Hel ianthocereus huascM Catamarca (Ar- Hordenine lr,mp 2 (IJeb. ) Backbg. gent 1na)

HelianthocereuEi EBsacans ATgent1n8; Hordenine ms 2 (IJeb.) Backbg. Southern Boliv­ ia

~minoT Backbg. S. Peru 3,4-D1.met hox)"phenethyl- t1c,BC 35 amine

Mescaline tlc,gc

~-PhenethyIa~ine tlc

Corypalline t 1c

Horden 1ne t1c

)-Methoxytyramine tIc

-~-Hethyltyra~1ne t1c lyrat:1ine tlc

Pellot ine tIc Criteria BOlanical Name Common Name Habitat Alkal01d Content Ident if1ca­ References tion

Lobiv1a alegriana S.E: Peru Hordenine tIc Backbg. ~-Methyltyramine tIc

Tyramine tIc

Lobivia surea (Br. Cordoba (Ar­ Hordenine tIc 44 and R.) Backbg. gent ins) ~-Methyltyramine tIc

Tyramine tIc

Lobivia .backeberg11 La Paz Hordenine mp,mmp,ir, 44 (Werd.) Baekbg. (Bolivia) tIc

~-Methyltyramine mp,mmp,ir" tIc

Tyramine tIc

LobiviB binghamiana s. E. Peru Hordenine mp,mmp, 1r" 44 tIc Backbg.

~-Methyl tyramine "'P,mmp,ir, tIc

Tyramine tIc

Lobivia huashua (Weber) Argentina Hordenine tIc 44 W. T. Marshall ~-Methyityramine tIc

Tyramine tIc

Lobivla pentlandU s. Peru; N. Hordenine mp,mmp,ir 44 (Hook.) Br. and R. Bolivia tIc

~-Methyltyramine tIc

Tyramine tIc

Leocereus bahiensis Cacto" rabo Bahia (BrazU) Caffeine (uneon­ none 45 Br. and R. de raposa f1l111ed) reported

Lophocereus schottii Senita, Southern Ari­ Lophocerine mp,ir,etc. 36,39,40,41, (Engel.) Br. and R. Totem pole zona (USA); 57,114,115,120 cactus, can.. Sonora, Baj a PUocereine mp,x-ray,ir, 130.149 cancerina Califomis, etc. (Mexico) PUoceredine mp,ir,etc.

Lophocereus schottii Mexico P 1locereine mp,mmp,ir 37 (Eng.) Br. and R. var. australis (K. Brand) Borg.

Lophocereus gatesii Baja CalHor­ P ilocereine llc,mp,mmp, 37 M.E. Jones nia (Mexico) ir

Lophocereu8 schott i (Enp.) Totem pole Baja Califor­ Pilocereine tIc ,mp,tIlIIlp t 154 Dr. and R. forma mon­ cactus nia (Mexico) ir strosus Gates ~nd--- mierkl eyanus C. Lindsey Table 1. (continued)

I Cr1t er 1a of i, Iiotanleal Name COlDlDOn Name Habitat A1 kalold Content Ildent1fICa­ References tion

Lophophora dlffusa Peyote Mexico Pellotlne tIc 2~.1~7 (Crolzat) H. Bravo Lophophorine tIc i ,I > Anhalamlne tIc

Anhalonldlne tIc \

Mescaline tIc Q-Methylpellotine tIe ,gc-ms I

Lophophora ulillamsii Biznaga, North central Tyramine tIc 1.2.12,2~,~7- (L."..) Coult. challote. Mexico; south 53,63-71.73­ peyote,mes­ Texas (USA) ~-Methyltyramine tlc,mp.m:mp, 76,60,62-66. cal.dry lr 68.69.91-9~. whi.key.tuna 100,101,103. de tierra. Hordenine tlc,mp,mmp, 118,130.131, sen1, ho, lr 139-1~ .l~ 7 k.amab•• devll'a; Cand Ic ine tIc root,

Chaute Iiesealine mp.-P

Anhalamine 1II)l.-P

Lophophorine lIIp.mmp . mp .lDIDP ~liethylpellotlne ge.8 8 - ....

!I..1!-Dimethyl-3­ ge.8c-,.. methoxytyramine Dopamine 8c.8c..... ­ Epinine gC,gc-ms

3-liethoxytyramlne gc.8c -ma

3.~-Dimethoxyphen- 8c .8c-­ ethyl..amine

3.~-Dlhydroxy-5- 8e.ge-a methoxyphenethylamlne

3-Demethylmescallne ge,ge-Jall

!I.-liethyl~3-hydroxy-~. ge.8e-_ 5-dimethoxyphenethyl­ amine

!I..~-Dimethyl-3-hydroxy- ge,Be-as ~.5-dimethoxyphenethyl- amine

~-Formyl-3-hydroxy-~.5- gc-1nS dlmethoxyphenethylamine

!I.-Acetyl-3-hydroxy-4.5­ gc-ma dimethoxyphenethylamlne . ~-P.et hy lrnescaline mp,mmp

gc-_ -N-Formylmescallne, ~-Acetylme5callne. mp,mmp ~-Formylanhalamlne gc-"", Cr1~er1a of Botanical Name Common Name I Habitat Alkaloid Content Ident1fica- Reference5 I II tion ~-Acetylahalam~ne gc-IIIS , Iooanhalamine Be .8c-ms

Anhallnine "'P,-p

~-Formylanhalinine gc-IIIS

Anhal1c!ine "'P,-p

Anhalotin.. 1r.tlJIlr. uv

Isoanhalid1ne gc:.gc-ms

Anhalonidine "'P,1IIIIIP

~-Formylanhalon1dine gc-ms

lsoanhalon1dln.. gc,gc-IDS

£-Methylanhalon1d1ne mp,mmp

~-Formyl-~Methylan- ge-ms halonldlne

Isopellot lne Ic,le-DIS

Anhalonine "'P,1IIIIIP

~-Formylanhalonine ge-IIIS

~-Acetylanhalonine gc-ms - . Lophotine 1r.n.mr ,UY Peyophorine tlc,Be,1r.1IA

tHescaline 6uec in:lJllld .. gC-1IIII !Mescaline mal:lJlllde gc-. ­ !Mescaline c1tr1mide ge-IIUI

Mescaline male:lJlllde ge-as

iMescaline isocitr1m1de gc-ms lactone

Peyoglutam ge.....

Hesealo~ .... ge-all

Hescaloll)'llc acid ge

Hescaloruvlc acid ge

Peyoxyl1e acid ge

Pryoruvle acid ge

Peyon1ne ge

PeyoglWIJIl ge

Choline tle,le.ir Tablr 1. (continued)

Criteria of Botanical Name Common NaUle· Habttat Alkaloid Content Identifica- References tion

Kammillaria elonsata goldrn atar Hlldago (He.x- Hordenine tlc ...p ....p 152 DC. ico) tIc Synephrinr tIc ,mp ,mmp" tIc

S-Q-Methylsynephrine tIc

Tyramine tIc

~-Methyltyramine tIc

Mamm1llar ia he ~ der1i Buna ge, New Mexico, E-Hethyl-3.4-dimethoxy­ tlc,gc-ms 19 Muehl. b izn.ga d .. Texas (USA) phenethylamine chlli1106, chil1to.nip­ pIe cactus

Kammillarh 1I1icrocarE8 Ar izona (USA) ~-Hethyltyramine tlC,lIIp.mmp, 61 Eng. 1r

Hordenine tlc,mp ,temp. 1r

Me.locactua delessert!­ Jalapa (Mexico) Tyramine tlc 35 auUB LeDI..

Melocactu8 msxon11 El RAncho. Tyramine tlc 35 (Rose) GUrlt-e--­ Sal...... , (Cuatema~a)

Notocactua otton1. BrazU. Argen- Hordenine ac-ms 32 (Lem. ) Berg. ex Ilcltbg. t ina, Uruguay ADd Knuth.

Cbrellonia denesr1i Peyote Ta:maul1pas, San Tyramine tlc.mp,1EmIP, 19.41,108 J'ric, Vicente. C1udad ir Victoria (Me.x­ 11,,0)

~-Hethylt y ramine tlc,mp,m:mp, ir

Hordenine tlC,IIIP,_p 1r

Opunt 1a 8urant iBca Argentina and Hordenine gC-lll$ 32 • Lindlry Uruguay

Opuntia ~ Eng. Club cholla Northwestern ~-Methylt y ramine 1r.tlc,~. 150 Dagger cholla and Central IIIIIlp Mexico; N_ Hu:ico (USA) Hordenine tIc

Tyramine tlc

Opunt1a imbricate S.W. USA to Tyramine tlc.mB 104 &"• Cent ral Hexico 3-Hethoxytyramine t.lc,Q . Hesc.- e tIc ,IU 3.4-D1Joethoxy-S­ tIc,.. phenethylamine

Opuntia invlcte Lower Califor- Tyramine tIc 104 Ilrandrqee oia (t'.exlco) Table 1. (continued)

Criteria of Botanical Name Common Name Habitat Alkaloid Content Ident1fica­ References , tion

~-Methyltyramine tIc

Hordenine tIc

Opuntia kleiniae DC. TexaB ( USA) Tyramine tIc 104 to Central Mexico ~-Methyltyramine tIc -

Opuntia maldonesis Punta Ballena Hordenine ge,ID5 32 Are ch. (Uruguay)

Opuntia schottl1 Dog cholla Texlls (USA) Tyramine tlc,ms 104 Engelm. to Northern Mexico ~-Methyltyramine tlc,ms,ir,mp

Hordenine tlc,ma,1r,mp

Opuntia spinosior Cane chella Aruona. Ii"", Meseafine tlc.mikes,mp. 80.116 (Engelm. ) Toumay Mexico (USA) ; "t:::o::::::::::= ir..... Northern Mexico Tyramine tlc,mp,1r,ms

3-Methoxytyramine t1c.mp.ir,_

3.1, -DiJDe t hoxyphenethyl­ tlc,ea amine

Opunt ia Iltanlyi Enge lm . Aruona; Ii.... Tyramine tIc, 104 var·. kunzei (Rose) L. Mexico (US.}); Benso-n--- Northern Mexico ~-Methyltyram1ne tlc,ms,1r,mp. mmp

Opunt1a stanlyi var. Arizona, New Tyramine tIc 104 Btanlyi Engelm. Mexico (USA); - Northern Hexico ~-Methyltyramine tIc

Opunt1a subulata Valparaiso 3-Methoxytyramine tIc 101, (MUhlenpfordt) (Chile) Enge1m.

Opunt1a ver1sicolor Arizona, lie" Tyramine tIc 104 Engelm. Mexico (USA) ~-Hethyltyramine tIc

Hordenine tIc

Opunt1a vulgaris Hiller Coast and i8­ Hordenine ge,IDs 32.42 lands of Brazil; Uruguay; Argen­ tina; interior of Paraguay; Cuba, India. South Africa; Australia (natur aUled)

Opuntia whipplei Arizona, Hew 3.I,-Dimethox yphenethyl­ tIc 104 Engelm. 4 Bigelow Mexico (USA) amine . Pachvcereus ~rsinatu& Organo HUdalgo. PUocereine mp,mrtlp,ir.uv 37,H,130 DC.) Br. and R. Queretaro, Guanajuato

( (Mexico) T.ble 1. (continued)

Crit ..ria cf 1I0tanlcal NBJlle COllmlOn Name liabitat A1kBlold content ldent if1ea­ References: tion

PaehycereuB p ..eten-.bo- Cardon, h ..eho, c;hlhuahua , 50no­ Ca",egine (pee tenine) lIIp 25.127,138, riginum (Engel.) Br. and carve. orlano, ra, Cal1ma, and 146,149 i.. pitahayo Baja Cal1fornia 3-Bydroxy-'-methoxy- ge-_ (Hexleo) phenet11ylamine

5alsol1dine tlc,lILa,i.r, I-P J 3,4-Dimethoxyphen- ge-... ethy lamine

Hel ialIIine ~.ttlc,BC, hplc, ir,nmr. ms

3-lIethot<~ tyram1ne tlc,ge,hplc,

~e_a

Arizonine tlc,gc,hplc, gc-lllS \

5alsoline tlc,hplc,BC, ge-1lls

Isosalsoline tle,gc,bplc:, ge_o; \

Paehyeereu8 pringleii Cardon Sonora, Tehuanine tIe,_pt_·,ir, 98,149 \ (5. Wate.) Br. and i.. Nayarit, lIaja ..1u. I California (Mexico) , Bel ialIIine tlc,1IlP,••,1r. ..lu.

Lemaireoeereine tle,mlke. Weberine tlc,..lu. - 1 Pachycereu8 veb..rl CardOD, Puebla, Oaxaca PeUctine tlc,WIJ>,1r 37,99,1109 (Coult.) Br. and i.. eandebobe, (Hexico) "andelabro Weberldine tlc,lIIp,uv.1r. ., , nmr,1Ds,a1k.e:.

Anhalonldine "'I'.-p,1r

jehuanine tlc,-.p,uv .. lr• ...... 1u.

- BelialIIine tlc,.."uv,lr. IDIlr."•a1k.d . .-.-. _ .- - .

~-Heth y 1he11amine tlc,.p,uv,lr, (oxymethy leorypalline) nmr ,,'lDs,mikes \ Non ehuanine tlc,mp,uv,lr, nmr,ms,mlkes I

Len.alreocereine tlc,mp,uv,lr, nmr,ms,mlkes

lIeberine tlc,mp,uv,1r, nmr ,tr:s,mi ke5 I

~ r o ..us teh.e'!ntepe- Mex ico lepenine not reported 72 cannus Mac Iiou£. and II. .~ Bravo l.,haunine not reporte~ Table 1. (continued)

Criteria of Botanical Name Common Name Habitat Alkaloid Content Ident1fica­ Reference. t ion

PelecYEhon aselliformis Peyot illo. San Luis Hordenine tlc.gc..... 6.110 Ehren. peyote. hat­ Potosi (Hexico) I­ .... ; chet cactus, Anhalidine tlc,gc-ms peot illo. p 1ote, peyote Pell

~-Hethylmescaline tlc.ms,gc

3,~-DimethoXyphen- tIc, IllS, gc ethylamine

~-~lethyl-3, ~-dilJlethoxy- tIc, ms, gc phenethylamine

3-Pemethyltrlchocereine mp, -p, ir DIU

PeleeH>hora EseudoEeeti­ Palmillas Hordenine gc-ms 19 nata Bckbg. (Mexico)

Pereskia aculeata tropical Tyramine tIc 35 Miller America (Venezuela)

Peresk1a autumnalis Guatemala B-Phenethylamine tIc 35 (Eichlam) Rose Tyramine tIc

Pereskia corrugate Unkno"" 3,4-Dimethoxy­ tIc, ge 35 Cutak , phenethylamine Mescaline tIc, ge 3-Methoxytyramine tIc Tyramine tlc

Pereskia eubensis Cuba Tyramine tIc 35 Br. and Ii.

Peresk1a godseff1ana tropical 4-Hethoxy-B-hydroxy­ tIc 35 (Sand.) Knuth America phenethylamine

Pereskia grandifol1a BrazIl 3-Methoxytyramine tlc 35 Haw. Tyramine tIc

Pereskia grandiflora Unknown e-Hydroxymescaline, tle 35 Hort. i Tyramine tIc

Pereskia Eititache Mexico; -. B-Phenethylamine tIc 3.5 (Karvinsky) Br. and R. Guatamala? Tyramine tlc

Pereskia tamEicana Tampico 3;4-Dimethoxy­ tlc,gc 35 Web. (Mexico) phenethylami ne Hescaline tlc.gc 4-Methoxy-f-hydroxy­ tIc phenethvlamine B-Phenethylamine tIe Tyramine tIc

PereskioEsis chaEi.tle Oaxaca 4-Methoxy-B-hydroxy­ tIc 35 (Web.) Br. and R. phenethylamine Abbey B-Phenethylamine tIc 3-Me thoxyt~' ramine tIc l:vramine tIc

Peresk10Esis scandens Yucatan 3.4-Dimethoxy-f­ tlc.gc 35 Br. and R. (Mexico) phenethylamine Mescaline tle,ge lyramine tIc Table 1. (continued) Criteria of Botanical Name Common Name Habitat Alkaloid Content ldentifica- References tion

Pilocereu. goun~llei Chique-chique Pernambuco Caffeine (unconfirmed) None 45 (Web . ) Byl. and Rowl. Bahia reported "(Brazil)

P110cereus chrvsacanthus Tehuacan, ~-Methyl-3,4-dimethoxy- tlc,ge,iT, 27 (\Jeb. ) Byl. and Rowl. Puebla, phenethylamine mp, IDS Oaxac.a (Mexico)

Pilosocereus guerreronis Guerrero N-Methyl-3,4-dimethoxy- tlc,gc,gc-ms 87 (Bckbg. ) Byl. and ROI.·l. (Me xico) - phenethYlamine

~,~-Dimethyl-3,4-dimeth- tlc,gc.,gc-ms oxyphenethylamine

Q-Methylcorypalline tlc,ms,gc

PilosocereuB maxonii [I Rancho, ~-Metbyl-3,4-dimethoxy- tlc,mp,mmp, 123 (Rose) Byles I> Rowley Salama phenethylamine ir,ms (Guatemala) ~- :le thyl-3-methoxy- tlc,Ul:p,uv,ms, tyramine IIIIIlp,ir ~,~-Dimethyl - 3-methoxy- tlc,mp,tmnp, tyramine iT ,ms 3,4-Dimethoxy- tIc IDS phenethylamine Tyramine tIc N-~ethyltyrBmine tIc

Pseudolobivia 'kermesina 3,4-Dimethoxy-S- tIc ,ms 44 Kainz phenethylamine Tyramine tlc,ms,mp,1r , Pterocereus gaumert Yucatan Pterocereine tlc ,ms,nmr, 106 (Br. and R.) HacDoug. (Mexico) uv,mp,ir and Hir. Deglucopterocereine tlc,ms.nmT, uv,mp,ir

Selenicereus grandiflo- Night bloom- Jamaica, Cuba, Cactine (uncharacterized) gc 14,130,140 .!.!!! (L. ) Br. and R. ing cereus, Haiti, Mexico reina de 18 noche

Solisi.. pectinate Cochinito, Tehuacan. Hordenine gC-m£ 19,127 (B. Stein) Br. and R. peyotillo, Puebla, ~-Methylryramine gC-m£ peyote OaxaCA, (Mexico) -.- Stet sonia ~ (S.D. ) Northwestern Mescaline tIc ,gc''"1IlS -"!',1l3,130 IIr . aDd R. Argentina Tyramine tIc , gc ...... Coryneine -tIc .IC-IDS (tr.) tlc,gc-ms Anhalidine (tr. ) tlc,gc-ms Oxycandicine tlc.gc-ms ~-Methyltyramine tIc , gc-ms \ 3-Methoxytyramine tlc,EC-ms 3,4-Dimethoxy- tlc.gc-ms phenethylamine

Trichocereus bridgesii La Paz Mescaline tlc ,mp, iT ,1115 2 (S.D. ) Br. and R. (Bolivia) 3,4-Dimethoxy- tIc ,'IDS phenethylamine 3-Methoxytyramine tlc,ir,ms Tyramine tlc,IDS

Tr1chorereus'camar8uen- Bolivia Tyra llO ine tlc,ms 2 ~ Card. 3,4-Dimethoxyphene- t.lc ,1:1.5 thylamitle 3-Methoxytyramine tIc .m& ~-Meth y ltyramine tlc,gc 'Iable 1. (continued)

Criteria of lIotanlc.1 Name Co...on Name Habltat, Alka101d Content Ident1flce­ RefereDcee tiOD

Trlchocereu8 candieans Northwestern Candleine lIIP,lIIIIIJ' 2,53,96, (C1ll. ) Br. and It. Argentina Hordenine t1e,lIIP.1r 128,130 !-Methyltyrallline tIc ,lIIP. lr Tyramine tle

Trlehocereus ehllensi& Atacama, Candldne tIc, lIIP,lIIIIIJ', 29 (Colla.) Br. and R. Curleo (Chile) ir

'Irlchocereus eourantll Bahia 1I1anee, !-Methyltyramine tIc, ge-1llS 6 (I<.. Sch.) Bckbg. Rl0 Negro. Rio gC-1lls Colorado !-Methyl-3-methoxytyre- tIc, mine (Argentina) 3,4-Dlmethoxyphenethyl­ t1e, gC-1II6 amine Tyramine tIc. ge-ms 2-!1ethoxytyramine tIc, ge""'"

Triehoeereua cU%coensis Cu%eo (Peru) )-Hethoxytyramine "1:1e, gC-1ll8 6 IIr. and It. Tyramine t1e. gC-1ll8 He8ea11ne tIc, ge-1d 3-Hydroxy-4.5-d1methoxy­ tIc, gc-ms phenethylamine

TrlehoeereuB fu1vlanus Chile . Tyramine tIc, ge-ma 6 Ititt. !-l1ethy1tyramlne tIc, ge ...... He8ealine tIc, ge-1d .-. TrlehocereuB 1amprochlo­ Northern Hordenine tIc.1r -2,130. .!..!!.! (!.em.) Argentlna, 133.160 BekbS· Candiclne unreported Bolivla

Trlehoeereua lcnuthlanus feru Tyramine t1c.se..... 6 Bekbg. 3-Methoxytyramlne tIe,ge......

Trlchocereus macrogonu9 South Amerlea Hescallne t1c,1IlS.1r 2,130 (S.D.) Rice. . - 3,4-Dlmethoxyphen­ ethylamine t1c._ ' ­.

)-lIethoxytyramlne tIc .lIIS Tyramlne tlc ,ms

'Irlehocereus manguln1i Paraguay Tyramlne tle.gc-1IlB 6 Bckbg. !-Hethyltyramlne tlc,gc-ms Hordenlne tle,Be-1DS 3-Melhoxytyramine tIe ,Be-IDS Table 1. (continued)

Criteria of Botanical NalD

Trichoe"r"us E8ehanoi Ciganton Peru and tit!sea1ine t1e,mp,II:II1p,ir 2,),31,90 Br. and R. Equador .... 119,148 3,4-D1methoxyphenethyl­ t1e,....,ir amine

Hordenine tIe ,111& TYramine t1c,ms.8e 3-Methoxytyramine tle,mBt'ir,gc. mp,mm.p 3,5-Dimethoxy-4­ hydroxyphen­ tIc ,IllS ethy1amine 3,4-Dimethoxy-5­ tIc ..... hydroxyphen­ ethylamine

Triehocereu8 E8sBeana Bolivia; Candie1ne tlc,mp,mmp,lr 105 (Web.) Hr. and R. Argentina TYramine tle

~-Methyltyramine tIc Bordenine tIc

TriehocereuB p:eruv1anu8 Peru Tyramine tlc,ms,mp,lIIDp. 2,117 Br. and R. ir 3-Methoxytyram1ne tlc.,'IIlS,lDp.1IDIP. ir . tit!sca1ine ....tIc ,1Dp,'DDp, lr. 3, 4-Dimethoxyphen­ tIc.... ethy1amine 3, s-Dimethoxy-4-hydroxy­ tlc,"'P,mmp.ir. phenethylamine ... 2-Ch1oromesca1ine tlc,1Dp,mmp,1D.8 ~ (artifact) uv,nmr.m.1kea

TrichocereuB ~ur2ure.o- Sierra C.ordoba , Tyramine tlC;gc-ms 6 pHOBUB Wgt. (Argentina) ~-Hethy1tyram1ne t1c.ge....,.

Trlehoeereu8 santiaguen- Santiago del Tyramine t1c.8c...... 6 _1& (Speg.) Bckbg. Estero Hordenin" tle,Bc...... (Argentina)

Triehocereu8 eehicken- Northwestern Hordenine tle,.. 2 dant~i1 (Web.) Br. and R. Argentina !-Methy1tyramine tIc. Be

TriehoeereuB altort_bergii Coquimbo Hordenine t1c.8e...... 6 Bckbg. (Chile) !-tit!thy1tyramine tIe ,Be.....

Triehocereu. IIEaebianu8 'Western Candieine ir 2.96.130 (t-.) iUcc. Argentina Bordenine mp,....P.i.r !-Meth!ltyramine tlc Tyra.m1ne tic

tlc.le__ Trichoeereua _triogoaue Merdo~ •• San Bordenine I 6 (SIl.) Br. and I.. Juan (Argentina) Table 1. ("ontinued) Criteria of &Otani"al llame Common Name Habitat Alkaloid Content Identif1ca- Referen"e. tion

TTi"ho"ereutl taguimba- &olivia Iie."a1ine t1".I.,.... 6 1£%1 a18 Card. Hordenine t1".I"_

3.~-D1metboxyphenethy1- t1".I"__ amine 3-Methoxytyramine t1<:.I"_

TTi"bo"ereua tere"h..- c..rdon llorthveatern Tr1"hoc:ereine ~ 2.S6.: dd1 (Pa",.) Br. and )t. grande ArgentinA 12,..132 He.."aline t1"...,lr Anha.lonine -

Tr1c:ho"ereue tbe1esonua Catamar"a. Hordenine tl".I"'" 6 (Web.) Br. and K. Tu"umatl (Argentina) !-Methy1tyrain1.ne tl".I"'"

Tri"ho"ereu8 the1egonoi- llorth Hordenine tl".I".... 6 dee (Speg.) Br. and K. ArgentinA

Tri"hoc:ereua tunarienei8 &olivia Tyramine tl".I"-" 6 Card. Hordenine t1",I"_

Trlc:ho"ereua v81idua Bolivia Me."aline tl".I"'" 6 (Houv.) B"kbg-.-­ . Tr1"ho"ereutl verdermann- Tuph:a. Mes"aline t1".ir... 3 ~B"kbl. Char"oma 3.~-D1methoxypheD- tl",ir,_ (Bolivi.a~ ethylamine Tyramine tl"... .3-Methoxytyramine tle,ir... 3.5-D1methoxy-4-bydroxy- t1c.... phenethylsmine

T\1rbin1car~. p.eudo- San Lute Hordenine tle.le 19 ...eroc:bele (kkbl') F. Poto.i Jltnb and JI"kbl' (Mexi"o)

W1Ssine1.a er1na"u Uruguay HordeDiDe Ie." 32 (B4w.) D.Ii. Porter ­ .. ­. . - ._.._-_.---- Wigg1De1a aa"TO"antha Uruguay Hordenine - --­ - Ie.," ·"32 (Arec:b.) D.H. Porter

Wiggins is tephra"aotha Uruguay Hordenine I"." 32 (L. and 0.) D.H. Porter

REFERENCES

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