/ ;11/1/"T1I A7"1 fe..;'rNR' / R L /J()/Jd"'~ e / /1'8) CACTUS ALKALOIDS. 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 lil
• 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 Alkaloid 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 Hordenine 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 tyramine 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) Gigantine gC,mp - 140,149 Salsol1dine mp,mmp,ir, nmr ,gc-ms 3-Methoxytyramine gc-ms gc__ 3,4-Dimethoxyphenethyl amine
Arizonine tlc,mp,mmp, iT ,nmr ,m5 gc-ms Dopamine 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 phenethylamine
~-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 Synephrine 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 Macromerine 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-
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 Anhalamine 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 . Pellotine 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 Anhalonidine (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 I. A,urrlJ. S. and J. lundmom. 1968. Appartnt intrrmrdiatrs in the loids. VII. Alkaloids ofCrhinoct"rruJ mrrlrri. J. Phorm Sci. 58: 1413. bio~yntksi, of me,catinr and rrlaud trtrahydroi.oquinolinrs. ChnrL ~ . Al'urdl. S. 1969. Cact.cra. alkaloids. VIII . N·Nrthyl-4-mrthoxv Commlln. 1968: 1638 . phen<1hylaminr from L,pidoro'yphDnlho ",,,ronii 181. and R.l 2. Arun:lJ. S. 1969. Cact.accar alkaloids. I. Lloydio. 32. 206. Backbg: CxprrirTllio. 25: 1132. 3. 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