Cactus Chemistry By Species 2014 Light

174 Pages·2014·3.03 MB·English

by  Keeper Trout

Cactus Chemistry: By Species
rT uo ts’ toN es
no
Cactus Chemistry
By Species
4102
iL hg t
sA semelb d yb
eK eper rT uo t
& rf iesdn
1
PDF generated 9 January 2014 (adapted from the illustrated PDF) Minor typo corrections 1apr14
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Cactus Chemistry
By Species
oC pyrightyM 3102 ,4102© driaticrP oduction s (where applicable).
Copyrighted 2007 by Mydriatic Productions; 1997-1999 by Trout’s Notes & Better Days Publishing
Previously published entitled
Distribution of the Alkaloids & Triterpenoids Reported in CaCtaCeae; By Species (1997) and as
Trout’s Notes #C-10 Cactus Chemistry Summary: By Species (1999 and later).
This version merges, updates, corrects and replaces all previous versions.
tI i n s owes ctiono 2 fS acred Cacti t4 he ditionaP rt C Cactus Chemistry
Produced by yM driaticrP oduction;s a division of eB tteraD yuP s lb ihs ing
©eR 4102 productionw ithoutw rittena uthoriaz tioni p s rohiib ted. lA lr ightr s ees rev d.
Acquiring & processing the references needed for a comprehensive treatment has postponed the planned
release date so dramatically that I have decided to make this version available while the fnal book
takes shape. Due to the ongoing nature of research and this subject that book could be a never ending
project to complete so the fnal book will be a compromise formed by time, life & literature access.
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2
Cactus Chemistry: By Species
“ It is pertinent to mention that all of the Trichocereus species, which have been reported to contain alkaloids, grow
in a rather limited geographical area confned to Argentina.”
Djerassi et al. 1956 JACS 78: 2312-2315.
Table of Contents
iD striub ti no fo aklA iol sd , rT iterpeion sd & to her Cmo puo sdn i n the CaCtaCeae 4
Cactus tamonox y a dn an mes i n this row k 5
hT e Cactus Species 7
Leguminosae 67
cA tiiv ty &( yM thygolo ) toN es 87
rT aid tiano l tE has-lon uo rces 89
eR ef recn es 9
ednI x 421
Cactus hP een thyal mien s: AaT ub al r eK y t o their Structura l roF mual s 651
Cactus sI uqo iilon en s: AaT ub al r eK y t o their Structura l roF mual s 061
Structura l taelb sI uqo iilon en s i n apl haeb tica l ro ed r 461
Smo e Cactus rT iterpeion sd , Sterslo & Simial r eloM cuel s 61
AaT ub al r eK y t o their Structura l roF mual s 61
Smo e to her anon akl iol ad l melo cuel s 071
hW at is Cactus Sil me ? 271
Betaal isn 371
Bimo ien rasl 371
Spien s 371
3
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Distribution of Alkaloids, Triterpenoids &
other Compounds Reported in the CaCtaCeae
esA mlb ede & ditedyb eK eperrT out hydrolyez o ro therwies a lteros mec omponent.s
tI i i s mportantt ou nderts andt hata lla lak loidc oncentration s hT e concentration sgiev n are a s they were reported in the
caneb h ighlyav rialb e.hT ic s aneb t her eus lto fm anyf actor.s literature. Many were calculated as the fnal yield of highly
eG netice ,s niv ronmenta , gep , artas mpledw , eatherh , ealth , purifed and repeatedly recrystallized alkaloids and will there-
timeo fy earo rt imeo fd aya , ndw hethert hep lantw s ere foreeb l owav lue.s
wildo rc ultiav tedh , aev a lleb enn oteda f s actorp s otentially Identifcation criteria can be found in the occurrence lists
capable of infuencing the alkaloid content and/or composi- under indiiv dual alak loid entrie.s rP( eiv ouls y releaes d in an
tioni np lant.s arb idgedf orma 9-C s Appendix A)
uS tsb antialav riationc s aneb e ncounteredab es do nt heav ri- hT ius s pplementall its ingi p s rimarilyo ft hea lak loidt & s riter -
etyl , ocalf orma , geg , rowthts agea ndo therf actor.s penoidr s eportedf romc actia lthoughw eh aev t aek nt hel ieb rty
nA o ivb ouub s tf reuq entlyo ev rlooek df acti t s hata nalyis o s f ofi ncludingos mea dditionalc ompounda s ndr eporti s ndicating
ac actuc s anr eallyo nlyt ellu a s ob utt hea ctualm ateriali nh and either that alkaloids were present but not identifed or else that
undergoinga nalyis a s ndc anes rev a n s om oret hana p roab lb e alkaloids seemed to be absent. Many fruit or fower pigments,
guidelinef orw hateb THGIM t hec aes w itha notherps ecimen carob hydratem , ucilagep & olyphenolicts udiew s ereo mitted.
withint heas meps ecie.s In every case posible, the original research reports were
iD fferencem s ightis mplyeb uq antitatiev ub ta ref reuq ently ues d for the entrie s eb low ub t in a few ints ance s we relied
found to eb uq alitatiev a swell hs ould enough as mpling seb on es condh- and lits ing swhen the primary os urce paper wa s
performed. unaav ilalb e.nI( ts ancea s rei ndicatedi nt het etx . )
hT e trend in the literature i sa loo kat one as mpling ,os me- )?%( indicate sob th that the entry wa sfrom a es condh- and
time suis ng ab tched material ,sand then moev on to the netx lits inga ndd idn oti ncludea p ercentage.
ps ecie.s hT oes which haev had ind- epth woruk p sperformed
ford ifferentc ollectiona s nda td ifferentt imeo s fy earus s ggets lA os i ncludeda ren oteo s fos mee rrora s ppearingi nt hel iter -
thi shs ould eb undertaek n for any ps ecie s that ha sonly one aturea( ni ncompletel its .) hT ees a rei ncludedis mplyt oh elpt he
pulb ihs eda nalyis .s reader evaluate and resolve the conficts they may fnd between
What should always be kept in mind when encountering thil s its a ndo ther.s hW ilem aik ngn on otea t s ot heos urcef or
any ps ecie s where a is ngle giev n alak loid compois tion and any of these erroneous entries, they (and the reference that
concentrationi ts s atedt hii s ndicatet s hatas idps ecieh s ao s nly wa scited )were included in hope sof reducing the numeb r of
eb ena nalyez dt hato neis nglet ime. erroreb s ingp erpetuatedi nt hef uture.eW d on otus ggets p eople
nA alyis s inov liv ng different tius e swithin a is ngle plant is mply taek u sat our word oev r highly reps ected authoritie s
haev conis ts ently produced diev rgent reus lt sus ggets ing that and offcial databases; we do suggest that in these instances
dits riub tiona NIHTIW g iev nps ecimeni a s los a na ev nuew or - they loo kat the primary reference sgiev n and determine the
thy of greater ind- epth epx loration. eM cs aline ues r salready truthf ort hemes lev .s
utiliez t hiu s neuq ald its riub tionyb r emoiv nga ndi ngets ingo nly nO e point we would liek to maek concerning os me of the
theo uterp ortiono s fg reent ius ef romt hec actuT s richocereus disparities between various researchers is that Agurell &
pachanoia w ,s hilew ats efulo fm ucho fi tc s ontaineda lak loid , coworkers specifcally did not look for any quaternary amines
it generates material that contains a greater percentage of and therefore would not haev detected any eev n if prees nt in
mecs aline yb weight than would the intact plant. aS dly much theirm aterial.
of thi swor ki snot pulb ihs ed and due to the current illegality tI i a s los i mportantt on otet hatos mew orek ru s es dy oungc ul-
of us ch practice sw( hether as cramental or recreational )will tivated material grown from seed while others used adult feld
proab lb yn eev reb p ulb ihs edi nd etail. collected ps ecimen.s hT e claim ha s eb en prees nted ,without
nI m anyc aes n s ote noughav rialb ea s ren otedt ou nderts and any indication of it sab is ,sthat analytical reus lt sare identical
the reported differences. eW would suggest that detailed eb tweent hees es to s fas mpleub s tt hea av ilalb ew ora k w s illeb
information about the actual source, the specifc part or parts detailedw ithind oen s otus pportt hata es rtioneb yonda r ough
inev ts igatedy( oungo ro ldt ius ec s anp roduceuq ited ifferent uq alitatiev generaliaz tion. oB th haev av lue for underts anding
reus lt sa scan different internal ts ructure ,)sthe date and time thec hemits ryo ft hep lantub s ti nn oc aes c ant hea nalyis o s fa
of day they were collected and detail saob ut how they were giev nps ecieo s rps ecimeneb r elialb ye tx rapolatedt oi ndicate
procees dt ROI R P oi nev ts igationeb comer egardeda iv s tali n- what will eb found in anything other than what wa sanalyez d
formationt oi ncludea longw itht hen ormalp roceduralw oruk p. ont hed ayt hati tw aa s nalyez d.
hT ew ordd“ rieda ,” a s ne ax mplec , anm eana n umeb ro ft hing.s
oF ri nts ancef , reeez d- riedm ateriala ppeart s og iev l owery ields aC ctic anos metimeeb s h ighlyav rialb ei na ppearance.s hT i s
thand oec s arefuld ryinga ndts andarde tx ractionub s tw hether wor kattempt sto prees nt multiple image sof is ngle ps ecie sin
thii s t s her MRON emaint s oeb e av luated. haib tata ndg rownu nderd ifferentis tuationo s ri nm ultipleh ands
E xtraction approach can also generate differing results. wheneev r pois lb e. nO e clear adav ntage to thi seb ing a FDP
eL ngthyh eatingd uringoS hx lete tx ractionc anc aues c hange s i sthe elimination of concern saob ut minimiiz ng cots through
compared to a room temperature os a keb ing ues d. iS milarly limitingt hen umeb ro fc olorp hotot s hata rei ncluded.
theu es o fa cidd s uringe tx ractionw , hileav lualb ec , anr eadily
4
Cactus Chemistry: By Species
Aviso concerning the results of Djerassi
Cactus taxonomy and names in this work
aM yn species haev eb e n rean me d mutl ipel times ; a partia l tI shuo dl emphasiez d that mso t , i f ton a ,l fo the triterpeion sd
il st fo syynon ms ro pio tn s fo pto etn ia l cufno si no is icn ul ed .d ievn stiag te d yb djerAssi a( dn to her row ek rs ) ew re primarily
elP ase see BAckeBerg , BrAvo , Britton & rose, Anderson, artiaf cts fo their isalo ti no a dn aan yl tica l prco eud re . iW th ylno
Hunt or the specifc botanical authority listed for more nomen- ev ry ef w ecx eptisno , it is ton maed cel ar i f ayn fo them actuayl
cal tura l ro tamonox ic ed taisl . eix st i n the pal tn s a ,dn i f s ,o h wo much is there . nI thso e ef w
Some names have been changed so many times over the cases hw ere it eod s appear that they actuayl may eix st i n the
course of their analytical history that it can be diffcult to locate pal tn , it is as ylno a ev ry sma l pro ti no fo the tto a l triterpeion sd
cmo prehesn iev irofn mati no auob t hw at has eb e n puilb she .d recevo re d hT( e usua l suo rce rof these triterpeion sd & sterslo
hT e sbo curi gn fo aan yl tica l accuo tn s yb the prilo ef rati no fo aw s iv a aci d hyrd ylo sis fo the cro respidno gn ylg cso ates).
syynon ms precul id gn eef f ctiev iedn ix gn is a n uedn r appreciate d While it might therefore be debated as to whether these
prelbo m . hT is is ton il mite d t o pal tn s . yM rf ie dn noJ aH an aylg ceno s are reayl prpo eryl il ste d as cactus cmo peno tn s , sicn e
pio tn e d uo t a particual ryl amusi gn series fo an mes chaegn s . they are products arising from the hydrolysis of the mixe d
In a sweeping revision of Amphibia Bufo alvarius had its sapino n rf acti ,no it aw s ed eme d impro tatn t o icn ul ed them as
an me chaegn d t o Cranopsis alvaria i n .602 aL ter i n 602 the they appear to have valuable chemotaxonomic signifcance.
an me aw s chaegn d aag i ,n yb impil cati ,no t o Ollotis alvaria .
nI 802 it eb came Incilius alvarius . cnI reid ylb the ylno eno tonA her pio tn ccno ersn djerAssis’ aakl iol d ievn stiag tisno .
fo its histro ica l syynon ms ton resurrecte d i n that prco ess aw s aM yn species they repro te d as eb i gn ed iov d fo aakl iol sd ew re
Phrynoidis alvarius . eF w iedn ix gn seriv ces fo puilb catisno ca n later shown to contain alkaloids (sometimes in appreciable
successuf yl maan eg t o icn ul ed a l nwonk syynon ms fo either amuo tn s .) hW iel ton id smissi gn the pso siib il ty fo iidn iv ud a l
pal tn s ro ain masl causi gn a rf amg etn e d access t o the ctno etn s variati o n bet ween samples, we suspect their al ka l oi d
of scientifc papers. screening technique played a signifcant role in at least some
In many cases chemical work does not refect the current fo the id sparate resutl s .
an me en vogue . eW haev tfo e n el tf an mes as ecn uo tn ere d iw th It was specifcally fawed with regards to detecting mescaline,
erof f ts maed ylno t o reud ce cufno si .no nI this prco ess ew haev susb tacn es iw th simial r sulo ib il ties ro ayn en utra l aakl iol sd .
empyol e d hw at mayn may ejbo ct t o as uo tad te d an mes. djerAssis’ primary criteria rof ed tecti gn aakl iol sd :
hT is row k is a cmo peidn um fo puilb she d aan yl tica l accuo tn s 1) The residue remaining from an initial ethanolic extract
invol ving cacti rather than being a taxonomic treatment o f uow dl rof m a n aakl il en sulo ti no hw e n etx racte d iw th ether .
cacti . tI s uj st as il ek yl that the iwolof gn are presetn e d h-wo :.dE[ toN a l aakl iol sd are sulo elb i n ether & ton a l aakl iol sd rof m
eev r they ew re aan yl ez d tha n iw th hw at is won their presetn aakl il en sulo tisno ].
accepte d an me . 2) Al kaloids could be isolated and obtained as crystaline
Please be aware therefore that our use of one specifc name materia.l
evo r aton her eod s ton en cessariyl iidn cate ayn arg eemetn iw th )3 soP itiev aM yer test . pA( paretn yl ton use d i n mayn cases)
ro acovd acy fo that pal cemetn .
nI a un meb r fo to her cases edlo r s“ pil tter ” syynon ms ew re djerAssi sometimes noted the presence of unidentifed mate-
ed il eb rateyl preserev d t o preev tn ul mpi gn rf mo sbo curi gn smo e riasl ub t i n mayn cases there aw s ivbo uo syl materia l presetn
itn eresti gn aan yl tica l resutl s . they id d ton eal rob ate no ro ievn stiag te uf rther.
A il sti gn fo syynon ms is asl o icn ro pro ate d s o this shuo dl ton djerAssi repeated ly made the claim that al kal oi ds an d
cause ayn prelbo ms . eF eabd c k is ew cl mo e.d triterpeion d ylg cso ied s are ton uof dn i n the same pal tn . hW iel
this is ivbo uo syl icn ro rect i f maed as a alb ekn t statemetn
Some useful trivia when considering trace or lo w amounts, it might prove
0.0X % indicates X miligrams per 10 grams. (i.e. 0.1 % true that the presecn e fo susb tatn ia l amuo tn s fo either may
iidn cates 01 miil rg ams per 01 rg ams). precul ed al reg amuo tn s fo the to her simutl aen uo syl eb i gn
%10.0 yb rd y tw . is 5.4~ rg ams fo aakl iol d per 01 puo sdn present. A systematic overview and evaluation is neede d
rd y tw . i[ e. . 01 m g per 01 mg ] before drawing any frm conclusions.
” 5 to 25+ mg. per 100 grams of fresh ” iidn cates apprixo mateyl
rf mo %10.0~ t o evo r %30.0 yb ew t tw .
eR pro te d aw ter ctno etn i n smo e cacti has raegn d rf mo 26 t o
.%59 rA uo dn %09 aw ter yb ew ihg t is cmo m.no
aM yn etn ries ab se d no ib ao ssays fo av rieties fo nwonk actiev
species ew re mo ittte d rf mo this row .k
roM e ed taisl no thso e a dn mayn fo the to her species that are
icn ul ed d i n this row k ca n eb uof dn i n the paeg s fo Sacred
Cacti Part A and/or Part B
5
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Trout’s Notes
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Some Other Succulents
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Cactus Chemistry By Species
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6
Cactus Chemistry: By Species
The Cactus Species Ariocarpus fssuratus (engeLmann) k.sChumann
“chaute”, “chautle”, “peyote cimarrón”, “peyote” (said to
be erroneous) stAndley 1924: 933
sA semelb d yb eK eper rT uo t & rf iesdn
Hordenine (200 mg of sulfate from 1 kg dry) HeFFter
1894b
cA atn hco ereus petn aunog s (L.) Britton & rose N-Methyltyramine (%?) diAz et al. 1977
(Now Acanthocereus tetragonus (l.) Hummelinck) See comments in the Activity Notes.
“ o rg a n o ” , “ p i t a h a y a ” , “ p i t a h a y a m o r a d a ” ,
“pitahaya naranjadas”, “night-blooming cereus”,
Ari ocarpus fissuratus var. fissuratus (rose)
“barb-wire cactus ” Powell & weedin 2004 & stAndley
marshaLL
1924
3,4-Dimethoxy-N-methylphenethylamine (Major alka-
See comments in Activity Notes
loid. 0.004% dry wt.) norquist & mclAugHlin 1970
Hordenine (0.006% by dry weight) mclAugHlin 1969
Anhalonium elongata See as rA ico arpus triunog s
N-Methyltyramine (visual estimate of 10 mg from 1.92
hnA ainol um uoj rad in aun m lewin was determined to contain an kg dry) mclAugHlin 1969
unidentifed but pharmacologically active alkaloid; lewin 1894b. It
cannot be demonstrably linked to Lophophora jourdaniana Ariocarpus fssuratus var. hintonii see as rA ico arpus rb aaov un s
HABermAnn. [See comment under] Anderson 1980 ssp . hitn ino i
Anhalonium lewinii Hennings See as poL hpo hro a iw il amsii
Ariocarpus fssuratus var. yol id i (engeLmann)
Anhalonium prismaticum lemAire See as rA ico arpus retusus
Anhalonium williamsii rümPler See as poL hpo hro a id uf sa sChumann
Anhalonium williamsii (lemAire) lemAire See as poL hpo hro a Hordenine (no quantifcation) mclAugHlin 1969
id uf sa [See BruHn & Holmstedt 1974 for details] N-Methyltyramine (no quantifcation) mclAugHlin 1969
Anisocereus foetidus (mAcdougAll & mirAndA) mArsHAll Ariocarpus furfuraceous see rA ico arpus retusus (most regard as
See as tP erco ereus eof tiud s retusus var. furfuraceous; lacks published analysis)
Anisocereus gaumeri (Britton & rose) BAckeBerg
See as tP erco ereus (?) ag umeri Ariocarpus hintonii see as rA ico arpus rb aaov un s ssp . hitn ino i
Aporocactus fagelliformis (L.) Lemaire rA ico arpus tok schuo eb yaun s (Lemaire) sChumann
“for del cuerno”, “foricuerno”, “for del látigo”, “hierba “pezuña de venado” (Nuevo León) stAndley 1924: 933
de la alferecía”, “junco”, “junquillo”, “cuerno”, “rat-tail 78% water by weight
cactus” Standley 1924: 917 Hordenine (0.059% dry wt.) neAl et al. 1971b
Flowers contained Betanin (35.4% of total), Phyllocactin N-Methyltyramine (0.015% dry wt.) neAl et al. 1971b
(59.8% of total) & an unidentified Betacyanin. Reported to contain Betalains as pigments.
PiAttelli & imPerAto 1969 woHlPArt & mABry 1968 cited dreiding 1961
See comments in Activity Notes See Activity Notes for additional comments.
rA ico arpus aag iov ed s (CastañeDa) e.F.anDerson rA ico arpus retusus sCheiDweiLLer
3,4-Dimethoxy-N-methylphenethylamine (trace) “chaute”, “chautle”, “peyote” (said to be an erroneous name)
N,N-Dimethyl-3-methoxytyramine (trace) stAndley 1924: 933
Hordenine (Over 50% of 1-10 mg of total alkaloids/ 100 86% water by weight . BrAgA & mclAugHlin 1969
gm. fresh.) BruHn & BruHn 1973 3,4-Dimethoxy-N-methylphenethylamine (0.00047% dry
wt.) neAl & mclAugHlin 1970
rA ico arpus rb aaov un s hernanDez & anDerson Hordenine (0.02% dry wt.: 214 mg from 1.19 kg dry) BrAgA
Lacks published analysis. & mclAugHlin 1969
See comments in Activity Notes. N-Methyl-4-methoxyphenethylamine (0.00045% by dry
weight) neAl & mclAugHlin 1970
rA ico arpus rb aaov un s ssp . hitn ino i (stuppy & tayLor)
N-Methyltyramine (0.0016% by dry weight, i.e. 18.5 mg
anDerson & Fitz mauriCe
from 1.19 kg.) BrAgA & mclAugHlin 1969
Lacks published analysis. [neAl & mclAugHlin 1970, did not report the latter compound.]
See comments in Activity Notes. Reported with no detectable alkaloids in smolenski et al.
1973.
Ariocarpus denegrii (Fric) mArsHAll
Retusin (a favonoid) & β-Sitosterol were recovered by
See as rbO einog a ed en rg ii
dominguez et al. 1968. This was the frst isolation of
Ariocarpus disciformis (decAndolle) mArsHAll
retusin (tetramethylated quercetrine); formerly known
See as Strmo cob actus id scirof mis
as a synthetic compound (gomm & nierenstein 1931).
See Activity Notes for additional comments.
7
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rA iocarpucs s aphirots ris BoeDeCker More recently Opuntia cylindrica reverted to an older
(Originally misspelled Ariocarpus scapharostrus) synonym Australocylindropuntia cylindrica.
Hordenine (Major alkaloid of 4 in 0.012% total alkaloids) Authenticated Opuntia cylindrica was determined to contain
N-Methyltyramine (no quantifcation) no measurable alkaloid in Agurell 1969b [Obtained via
3,4-Dimethoxy-N,N-dimethylphenethylamine (no quant.) European commercial sources].
3,4-Dimethoxy-N-methylphenethylamine (no quant.)
BruHn 1975b (Cultivated: California) uA ts rocylindropuntiae ax ltata Berger
[Considered varietal to Opuntia subulata in Hunt 2006]
rA iocarput s rigonus (weBer) sChumann 3,4-Dimethoxyphenethylamine (less than 0.01% dry wt.)
3,4-Dimethoxy-N-methylphenethylamine (0.007% dry) 4-Hydroxy-3,5-dimethoxyphenethylamine (Less than
Hordenine (Major alkaloid. 0.013% dry weight) 0.01% dry wt.) mA et al. 1986 (ostoLaza #84284)
N-Methyltyramine (trace)
sPeir et al. 1970 uA ts rocylindropuntiap achypu s K. sChumann
[Tyramine has been listed in error; the reference cited, sPeir et [sic as Opuntia pachiypus]
al. 1970, did not report it from this species.] The claim for the presence of Mescaline was made by
cAycHo jimenez 1977 (page 91) but no reference was cited
Ariocarpus williamsii (lemAire) voss
and nothing was included to support his assertion.
See as oL phophoraw illiamis i
uA ts rocylindropuntiaus ub lata (mühLenpForDt)
Armatocereus humilis (Britton & rose) BAckeBerg
See as eL maireocereuh s umilis engeLmann
Armatocereus laetus (HBk.) BAckeBerg 3-Methoxytyramine (no quantifcation)
See as eL maireocereul s aetus An unidentifed alkaloid was also present.
meyer et al. 1980
Oddly the entire genus Astrophytum lacks published analysis
88% of the daily CO2 uptake occurred through the leaves
during the daytime but some occurred at night (under well
tsA rophytuma ts eria s ( zuccArini) lemAire
watered conditions)
“star cactus”, “peyote” (stAndley 1924: 955)
Nobel & Hartsock 1986
Unpublished analysis failed to show the presence of alkaloids
(Martin Terry 2005; personal communication) Aylostera pseudodeminuta (BAckeBerg) BAckeBerg
See as eR ub tiap es udodeminuta
tsA rophytumm yriots igma Lemaire
“mitra” (San Luís Potosí), “birreta de obispo” (Coahuila) tzA eik umr itteri (BöDeker) BöDeker
“bonete”, “peyote cimarrón” (Durango) stAndley 1924: (Plants greenhouse grown in Czechoslovakia)
955 N-Methyltyramine (0.0031%)
Appears listed as containing unidentifed alkaloid(s) but 3-Methoxytyramine (Less than 0.0001%)
either the entry included no reference (ex. soulAire Hordenine (Less than 0.0001%)
1947) or else the reference that was cited (Brown et al. N,N-Dimethyl-3,4-dimethoxyphenethylamine (0.0036%)
1968) did not mention the species. Mescaline (0.0009%)
Anhalidine (0.0008%)
See comments on the Astrophytum species in Activity Notes. Pellotine (0.0026%)
ŠtArHA 1994 (All % above are by fresh wt.)
uA ts rocylindropuntiac ylindrica LamarCk
[“Opuntia cylindrica” was erroneously listed as contain- uzA reocereua s yacuchenis s johns
ing mescaline in the following reports: cocH Frugoni Tyramine (0.135% by dry weight as HCl)
1956(?), cruz sáncHez 1948b, gutiérrez-noriegA & lee et al. 1975 (cultivated in Arizona)
cruz sáncHez 1947, mArini-Bettòlo & cocH Frugoni
1956, mArini-Bettòlo & cocH Frugoni 1958 and, aLmost The genus uzA reocereu s needs analysis.
inCreDiBLy, turner & HeymAn 1960.
der mArderosiAn 1966 indicated that “correspondence aB cek eb rgiam ilitaris (anDot) Bravo ex sanChez
with the original author” verifed that their material had mejoraDa
indeed been misidentifed. While it was not specifcally 3-Methoxytyramine (0.02% dry wt.) PummAngurA & mc-
stated; turner & HeymAn were implied. lAugHlin 1981a [Collected in Michoacan, Mexico] [Also in
All of the above were apparently based on misidentifed PummAngurA et al. 1981b]; (Not identifed by Ferrigni
plants. (Actual identi ty was almost certainly et al. 1984.)
Trichocereus pachanoi.in all instances. It is demonstrably 3,4-Dimethoxyphenethylamine (0.025% dry wt. [as HCl])
t he case in c r u z s á n c H e z 1948 where an mAtA & mclAugHlin 1980b; (Not identifed Ferrigni et
unmistakable T. pachanoi photograph was included. al. 1984.)
This is also discussed in more detail in Part B; San Pedro]
8
Cactus Chemistry: By Species
3,4 - Dimethoxy-N -methylphenethylamine (Detected: N o poP ual r ro an metn a l purpro teyld use d as a n ayahuasca amd itx ure
quantifcation) Ferrigni et al. .4891 a dn aenol as a haul ciegon in c . hT e cal ims ew re id screid te d yb
3 , 4 - Dimethoxy-N , N - dimethylphenethylamine (0 . 0 5 8 8 % stuArt .302
dry wt.) PummAngurA & mclAugHlin a1891 ; rT( ace: See mro e cmo metn s i n the Activity Notes .
Ferrigni et al. ).4891
eM-3[ thyxo pheen thyal mien E( rror . Base d no typ o i n Ferrigni et Browningia candelaris (meyen) Br. & r.
al. ].4891 nI rd ie d aeria l parts:
hP[ een thyal mien E( rror . Base d no misreaid gn fo typ o i n Ferrigni
%850.0 cA-N etyid-4,3-l methyxo pheen thyal mien
et al. ].4891
%5420.0 iD-N,N methyid-4,3-l methyxo pheen thyal mien
slA o ctno aisn smo e isuqo iilon en s S[ ee toN e ;] t( etrahyrd ,o
%7230.0 iD-N,N methym-4-l ethyxo pheen thyal mien
id hyrd o a dn uf yl armo atic:)
%030.0 eM-4 thyxo amphetamien
eH il amien %57.0( rd y tw . a[ s CH )]l aM ta & cM aL uhg il n
ecHeverrí A & neimeyer 2102
;b0891 %20.1 yb rd y tw . a[ s CH )]l PummAngurA & mc-
slA o see the itn eresti gn cejno cture i n ostolAzA 7891
lAugHlin 1981a; (Identifed by ms/ms; but not mentioned
i n epx erimetn a l accuo tn fo isalo tisno : Ferrigni et al. )4891
hT e etn ire eg un s Browningia en esd aan yl sis.
eL maireco ereien %43 0 . 0 ( yb rd y tw . a[ s CH )]l PummAngurA
& mclAugHlin a189 1 slA [ o yb PummAngurA et al. ;] b 1 8 9 1
Cactus grandifora linnAeus See as Selenicereus grandiforus
(Not identifed in ms/ms by Ferrigni et al. )4891
N-Methylheliamine (Identifed by ms/ms; Detected in an Carnegiea euphorbioides (HAw.) BAckeBerg
impure resiud e ) Ferrigni et al. 4891 See as Neobuxbaumia euphorbioides
Dehydroheliamine (Identifed by ms/ms; 0.07% by dry wt.
isalo te )d Ferrigni et al. 4891 Carnegiea gigantea (engeLmann) Britton & rose
Dehydrolemaireocereine (Identifed by ms/ms; 0.006% by AKA s“ aguaro ,” s“ ahuaro ,” s“ uwarrow ,” s“ uwarro ,”
rd y tw . isalo te )d Ferrigni et al. 4891 s“ uaharo ,” s“ uguaro ” stAndley :4291 909
Backebergine (Identifed by ms/ms; 0.0126% by dry wt. %8-78 aw ter yb ew ihg t kircHer 2891
isalo te )d Ferrigni et al. 4891 iD-4,3 methyxo pheen thyal mien l“( ess than ” )%5410.0 BruHn
Isobackebergine (Identifed by ms/ms; 0.022% by dry wt. & lundström b6791 S( ee toN e )A & t( race ) BruHn et al. 0791
isalo te )d Ferrigni et al. 4891 eM-3 thyxo tyramien t( race ) Bruh n et al. 079 1 & s( ma l amuo tn s )
eM-N thyell maireco ereien p( so sielb presecn e ; en ither prevo n BruHn & lundström b6791
ron id smisse )d Ferrigni et al. 4891 D opamine (0 . 2 6 % , as HCl, reported from young cultivat-

[ iD- 8 , 7 methyxo id- 4 , 3 - hyrd yxo isuqo iilo n en is a typrgo aphica l error ed plants [ Raised in the Netherlands ]; not observed in their
itn eidn gn iD- 8 , 7 methyxo id- 4 , 3 - hyrd io suqo iilo n en i( e. . eD hyrd lo - aan yl sis fo iw c-dl elo cte d materia l [ Celo cte d i n rA ianoz )] BruHn
emaireco ereien ) Ferrigni et al. 4891 aw s cite d as the reef recn e]
& lundström 1976b. [Reported in cortical tissue (pulp) at
unger et al. 0891 eav ul ate d this species usi gn SEKIM a dn repro te d
1%; Calus tissue and adjacent areas had higher dopamine
ed tecti gn 3 aakl iol sd ub t it is ucn el ar eax ctyl hw ich ismo ers they
ccno etn ratisno tha n heatl hy tissue S( ee toN e B:) steelink et
sbo erev .d enO appeare d t o eb eM-N thyhl eil amien .
al. 7691 [ Celo cte d i n rA ianoz ]
tcl eax mian ti no shewo d the presecn e fo aakl iol sd a dn the
yT[ ramien , iD-4,3 eM AEP-HO-5-O a dn iD-5,3 eM AEP-HO-4-O haev
asb ecn e fo triterpeen ylg cso ied s: kircHer 2891
asl o eb e n erroneously il ste d rof this species ub t the cal ims are ton
iK rcher repro te d the same sterslo as they ha d ecn uo tn ere d
suppro te d yb Agurell b9691 t( he reef recn e that aw s cite].)d
i n L . schottii a dn asl o hw at they thuo hg t aw s aL uric aci.d [ eM scail en has eb e n erroneously il ste d rof this species . hT e cal im is ton
iL pi d ctno etn ed termien d t o eb %7 yb rd y ew ihg t: kircHer suppro te d yb ayn fo the reef recn es that ew re ig ev .n i[ e. . Agurell ,b9691
2891 kAPAdiA & FAyez 0791 S[ ee toN e C ] a dn mAtA & mclAugHlin ].6791
Backebergia Note: One other partialy saturated TH I Q was Carn
egine Isolated (0.7 % dry wt) & named by Heyl .8291
ed picte d i n eF rriing s’ il en id arg am ek y ub t appears t o haev eb e n
( 0 . 5 7 5 % yiel d by dry weight (as HCl ) in ordAz et al.
use d as a sytn hetic itn ermeid ary a dn ton isalo te d rf mo the pal tn . tI
1 9 8 3 . ) I dentified in Brown et al. 1 9 6 8 ; Reported pres-
shuo dl eb ton e d that eb sied s haiv gn at el ast eno typ o i n their ek y ,
ent in decent amounts (7 0 % o f total alkaloid content) i n
the frst two generic line diagrams are switched. [PEA  ]QIHT
Brown et al. 1972b . [Presence also noted in Hodgekins et
al. 1967 ] Also by BruHn et al. ,0791 hw ,o uiln ek Brown ,
Borzicactus sepium (hBk) Britton & rose sug gested presence i n youn g plants but n ot i n larger
ewolF r ctno aisn Betain ,n hP ycol acti ,n sI po hycol acti n s p e c i m e n s . I a m u n a b l e t o d e t e r m i n e
a dn traces fo sI ebo tain n PiAttelli & imPerAto 9691 d e t a i l s d u e t o p r o c e d u r a l d i f f e r e n c e s .
slA ;o %910.0 yb rf esh ew ihg t 9.2( rg ams fo ab se rf mo 51 gk
Brasiliopuntia brasiliensis (wiLLDenow) Berger rf esh) BruHn & lundström b6791 [ Agurell et al. a1791 is asl o
Positively identifed in stuArt 302 as t“ chai .” cite d ub t is ton presetn yl aav ial elb ]. slA o isalo te d i n sPätH .9291
Mucilage comprised of Arabin ose (2 6 . 2 % ) , Galactose iG ag tn ien 5( -Hydroxycarnegine) (Identifed) Brown et al. 8691
,)%8.94( aG al cturino c aci d ,)%1.6( hR amson e )%4.9( & S[ ee toN e ;]D ylnO repro te d i n susb tatn ia l amuo tn s ud ri gn
yX sol e .)%6.8( moynA & diFABio 8791 M( AM 1308) aan yl sis fo wild celo cte d adult cacti a dn uof dn t o eb hihg er
i n rg iwo gn tips s( ee asl o Brown et al. b2791 hw o uof dn it
9
http://www.largelyaccurateinformationmedia.com
composed 25- 3 0 % of the total alkaloid content in the Carnegiea Notes:
wholep lantub ti %05 nt heg rowingt ip.) aS[ idt oc ompries A:oC ncerningm ym athw- orf k or Bruhn & LunDström 1976b:
51gk of frehs cactu syielded 23gram sof alak loid.s %08wa s
%03of total alak loid content in Hodgekins et al. ]7691
nonphenolica ndw %02 ap s henolic.hW enp urifyingt hees f ractions
BruHn & lundström b6791 reported .0 %610 yb frehs
they only ues d 1 gram of the nonphenolic and .0 5 gram s of the
wt. .182( 6mg ab es from 51ik lo sof frehs material )oN t
phenolicf raction.s hT ea mountl s its edi nt heira ccounti w s hatw a s
reportedi ng reenhoues g rownp lant( s BruHn & lundström
otb ainedf romt hees a liuq otr s athert hant otal.s
;)b6791nor in young plant sgrown outdoor s in rA ioz na oF ra llc ompounde s cx eptd opaminet hey ieldw s erec alculatedyb ,
( BruHn et al. .)0791 tk ,a sif they had ues d all of their product and then recalculated
aS los lidine oN( rcarnegine ) BruHn et al. 0791 & BruHn themi nt ermo s ft heirf reeab es lA( s ak loidw s ereo tb aineda t s he
hydrochlorideas lti s na llc aes e s cx eptf orrA ioz nine)
& lundströmr b6791 eportedas los lidinet oeb t hem aoj r
B:oD paminec oncentrationw s erer eportedt oi ncreaes w ithe px o-
alak loid .0( %20frehs wt.: .3 2gram sof ab es from 51gk
us ret oa iro rt o acs orib ca cidos lution.s
frehs w ,) herea s Brown et al. 1972b did not fnd salsolidine
nI one caes ; a as mple with .1 %4 dopamine wa s taek n. fA ter 1
ina nyas mplet s heyt ets ed..0 y %74 ieldyb d ryw eighta( s
houra , es condas mplet , hatw at s aek ni mmediatelyn etx t ot heis te
lCH w ) ar s eportedi n ordAz et al. .3891 eS[ ea los Agurell of the frst, showed 2.1%.
et al. a1791 eS ; en otea ob ev ] hT eya los n oteda a h ighd opaminec ontenti nas mplet s aek nn ear
rA ioz nine .0( %630yb frehs wt. ; .1 1gram sof ab es from theab es w( hicha lwayh s aa s h eayv c allul s ayer.)
gk 51 f rehs ) BruHn & lundström b6791 eS[ ea los Agurell C: tI hs ould eb noted that while lits ing kAPAdiA & FAyez ,0791
theyu es dt heov lumea , nda p agen umeb ri , n kAPAdiAe t al. .9691
et al. a1791 eS ; en otea ob ev ]
D: hT eu nuus alus tsb itutiona tt hep 5 ois tionh aa s los eb eno esb rev d
eD hydroas los lidine )?% ( lundstromc 3891 ited PummAngu-
in several other alkaloids found in Pachycereus pringlei , and
rA et al. )3891( J. Nat. Prod.nI( p re.S[ )s uP mmangura ,
Pachycereus weberia , w s ella i s n Pachycereus tehuantepecanas.
.J .L cM aL ughlin.D ,.VaD iv e.R & s .G oC ooN ]sk ti n 3891
iG( gantinei a s los f oundi n Pachycereus pecten-aboriginum.)
ora 4891 uthori nde.x hT e uq ets ion of whether any of the Pachycereus alak loid s are
eH liamine )?%( lundstromc 3891 ited PummAngurA et al. actiev a siv is onary compound si san area oev rdue for eav luation.
.3891 eS[ ea los Agurelle t al. a1791 eS ; en otea ob ev ] Preliminary evaluations depict them as rough and with a heavy
eD hydroheliamine .0[ %80yield yb dry weight a( slCH ) ob dy load yet os me few people appear to liek them. oM re ts udy
ic s learlyn eeded.
war s eportedi n ordAze t al. .3891 ]
eS ea los c ommenti s nt he Activity Notes.
unger et al. e 0891 av luatedt hips s ecieu s is nga SEKIM nd
reportedd etectingo( 4 ruq )?5 inoline.s nO ew ar s eported
Cephalocereus chrysacanthus ( weBer) Britton & rose.
to eb aS los lidine ; another wa s either aC rnegine or eles
eS ea P s ilocereus chrysacanthus
ios meric with it.hT e eax ct ios meric identitie sof the rets
Cephalocereus columna-trajani ( kArw.) k.scHumAnn
wan s otc leart ou .s wT oa ppearedt oeb t rimethoyx lated. eS ea C s ephalocereus hoppenstedtii
.1-1 a %7 lak loid( aC rneginea nd iG gantine ) kircHer 2891 Cephalocereus euphorbioides (HAw.) Br & r.
lG ucarica cidt( lcyb kringstAd & nordAl)5791 eS ea s Neobuxbaumia euphorbioides
osI citrica cidt( lcg & lcyb kringstAd & nordAl)5791 Cephalocereus gaumeri Britton & rosei N s OTys nonymou s
withP terocereus (?) gaumeri
uQ inica cidt( lcg & lcyb kringstAd & nordAl)5791
aV nillin , S yringaldehyde & p - H ydro xy ben zalde -
Cephalocereus glaucescens (LaBouret) Borg
hyde were found to eb higher in healthy tius e than in
hT ips s eciew s ar s eportedt ohs ow nod etectalb ea lak loid s
callu stius e. gA lycois de of yH-4 droyx eb noz ic acid and
int hea lak loidcs reeningo s f smolenskie t al. .3791
eF rulic acid were reported a sminor &trace component s
rF uitc ontain s eB taninm( aoj r ,) hP yllocactina ndt race s
reps ectiev ly.
ofosI phyllocactin & osI eb tanin. PiAttelli & imPerAto
3,4 - Dihydroxybenzoic acid, aV nillic acid & p -Hydroxy-
9691
eb noz ic acid were found in callu stius e along with trace
amount s of poC- umaric acid & eF rulic acid. uQ ercetin
Cephalocereus guerronis (BAck.) BuxB.eS ea P s ilocereus
waa s los o esb rev da t.0 o %1 ft het otalc alluub s tw aa s esb nt
guerreronis
fromt her it sb hemes lev .s
steelink et al. 7691
Cephalocereus hoppenstedtii (A.weB.) k.
tlc e xamination showed the pre sence of al kaloid s
sChumann
andt hea esb nceo ft riterpeneg lycois de:s kircHer2891
oN d etectalb ea lak loid.s
iL pidc ontentd eterminedt oeb .2 yb %5 d ryw eight.
cHAleta0891 c ited domingueze t al . 9691
.0 ts %1 erol:s aC mpets erol , iS tots erola ndu 1 nnk own ts erol.
nU alb et od etecta nyts erolo rt riterpeneg lycois de.s kircHer
Cephalocereus leucocephalus (poseLger) Britton
2891
& rose
aC rob hydratei s nh ealthyc orticalt ius ew erer eportedt oeb
n“ apisora( ” Pennington:3691 )51
compoes d of lG ucoes , aG lactoes %13(of all as ccharide
oN d etectalb ea lak loidi s nt hea lak loidcs reeningo s f
conts ituent ,)s yX loes & rA aib noes .
smolenskie t al. .3791
G a lacto se wa s lac k ing from the wound ti s sue.
steelinke t al. 8691
10