Phyfochemisrry, 1977, Vol. 16, pp. 9-18. Pergamon Press Printed in England.

REVIEW

PHENETHYLAMINE AND RELATED COMPOUNDS

IN PLANTS
TERENCE A. SMITH
Long Ashton Research Station, University of Bristol, Bristol, BS18 9AF, England

(Revisedreceived 30 July 1976)

Key Word Index-Algae; Fungi; Spermatophyta; food plants; phenethylamine; tyramine; dopamine; mescaline;
adrenaline; ephedrine; derivatives; review.

Abstract-A comprehensive and up-to-date listing is provided of the distribution of phenethylamines in the Plant
Kingdom. Such a listing is of importance because of their considerable physiological activity in higher animals.
Their distribution in plants is also of some taxonomic interest.

Phenethylamine and p-hydroxyphenethylamine (tyra- the Table, see Fig. 1). The biosynthesis of the phenethyl-
mine) are found in many families throughout the plant amines in higher plants has been reviewed recently [6].
kingdom. These amines and their derivatives may occur One reason for the importance of these compounds is
at quite high levels in certain species; for instance due to their physiological activity in higher animals. The
noradrenaline is found in Portulaca oleracea at 13 hormone adrenaline (epinephrine) and the transmitters
pmol/g fr. wt [l]. The range of structures is particularly in the sympathetic nervous system (noradrenaline, dop-
amine) are hydroxylated phenethylamines, collectively
known as the catecholamines. Ingestion of these and
related amines in food, especially by patients using
monoamine oxidase inhibitors as anti-depressants, can
induce significant physiological effects [7]. Potential
food plants are marked + in the Table.
Aegelln [I631 Mescaline, found in several cacti, is a powerful hallu-
cinogen [8], and dietary phenethylamine may precipitate
migraines [9]. Ephedrine is used in medicine for its
Tembamlde [l64,167_l properties as a hypertensive and bronchodilator. Syne-
phrine, which is a stimulant and decongestant occurs in
tangerines at levels which are high enough to be physio-
N-Benzyltyramlne logically effective [lo]. Hordenine is a diuretic and is a
HOOCH* CH, NH io [I 651 remedy for diarrhoea and dysentery [ 111, probably due
to its antiseptic properties [12, 131. Moreover the excre-
tion of some of these amines is important in the diagnosis
MeOoCH-CH NH&) Alatamlde [I691 of certain diseases (e.g. phaeochromocytoma) and know-
ledge of their presence in food is needed for this reason.
No essential metabolic function for the phenethyl-
h’+CH, CH,NH ;a
N-Benzyttyramlne amines in plants is established, though they are the pre-
methyl ether [I691 cursors of a series of tetrahydroisoquinoline alkaloids
found especially in the cacti. Like the uncommon amino
N-Homoveratryl acids [14] the phenethylamines may benefit the plant
twfweratrykwnlne which produces them by acting as deterrents to insect
n [I701 predators and foraging animals and for this reason they
Me -
may be of agriculturalsignificance. Hordenine is a feed-
CH, CH,tb i-C,-, Hwclavln [I721 ing repellent for grasshoppers [15], and the presence of
phenethylamines in Acacia used as herbage may cause
locomotor ataxia in sheep [17]. Moreover resistance of
Fig. 1. Structures of phenethylamine conjugates. sugarbeet to the fungus Cercospora beticola may be re-
lated to the presence of dopamine [ 163.
wide in some plant families, notably in the Cactaceae and The reliability of the methods used in characterizing
in the Leguminosae. It is likely that the distribution of the amines varies considerably. Early workers depended
these amines will be useful in chemotaxonomic studies on elemental analysis and mp of the amines, with or
[2-51. In some cases, especially in the Rutaceae, these without derivatization. Identification now often depends
occur as conjugates with aromatic acids (denoted * in on PC or TLC R, values, using as chromogenic reagent
9
10 TEEENCE A. SMITH

_. .___ __ ~~___ ..~..

Algae Ceramium rubrum Pe

Cystoclonium purpureum Pe
Desmarestia aculeata Pe
Dumontia incrassata Pe
Monostroma fuscum Dop
Phyllophora nervosa (DC.) Grev. Hord
Polyides rotundus Pe
Polysiphonia urceolata Pe
Fungi Boletus edulis Bull. Pe ; Tyr
Boletus luteus L. Pe
Eoletus zelleri Murr. Tyr ; Me-Tyr ; Hord
Clauiceps purpurea (Fr) Tulasne Pe ; Tyr
Coprinus atrumentarius Bull. Pe ; Tyr
Coprinus comatus Gray Tyr
Coprinus micaceus Bull. Pe
Fomes pini (Thore. ex Fr.) Overh. Hord
lnocybe patouillardi Bres. Pe
Marasmius peronatus Fr. Pe
Nematolomafasciculare Pe
Phallus impudicus L. Pe ; Tyr
Phlegmacium ntellloleus Pe
Pholiota mutahilis Pe
Polyporus berkeleyi Fr. Hord
Polyporus sulphureus Bull. ex Fr. Pe
POlY~~S spp. Tyr ; Me-Tyr ; Hord
Amary~lida~ae Amaryllis vittata Ait. Tyr ; Me-Tyr ; Ott ; Syn
C&urn yuc~~~o~rn Sat&b. Tyr
Crinum sp. Tyr
Eucharis grandijlora Pfanch. Syn
Haemanthus katharinae Baker Tyr ; Me-Tyr ; Syn
Hymenocallis americana Roem. Tyr
Pancratium maritimum L. Tyr ; Me-Tyr ; Hord
Ungernia ferganica Vved. Hord
Ungernia trisphaera Bnge. Hord
Vngernia victoris Vved. Hord
Anacardiaceae Schinus terebinthifolius Raddi Tyr
Araceae Arum maculutum L Pe
Colocasia antiquorum Schott. + Tyr
Asclepiadaceae Wncetoxinrm &&ale Pe
Berberidaceae il’an&nti domestica Thunb. Tyr ; Hord
Bignoniaceae ~acaranda a~~t~lia Humb. & Bonpl. Tyr
Pyrost~ia ignea Presl. TYr
Cactaceae Ariocarpus halides (Casta&da) Hord ; 4-OH 3-Me0 diMe-Pe ;
E. F. Anderson 3,4-diMeO Me-Pe
Ariocarpusfissuratus (Eng.) Schumann Me-Tyr ; Hord ; 3,4-diMe0 Me-Pe
Ariocarpus kotschoubeyanus (Lem.)
Schumann
Me-Tyr; Hord E:Z]
Ariocarpus retusus Scheid. Me-Tyr ; Hord ; 3,4-diMe0 Me-Pe : [461
/I-Me0 Me-Pe
Ariocarpus scapharostrus Biideker Me-Tyr ; Hard; 3,4-diMe0 Me-Pe ; [471
3&diMeO diMe-Pe
Ariocarpus trigonus (Web.) Schumann Me-Tyr ; Hord ; 3,4-diMe0 Me-Pe [481
Azureocereus ayacuchensis Johns. Tyr c491
Carnegiea gigantea (Ens.) Br. & R. Dop; 3-Me0 4-OH Pe ; 3.4-diMe0 Pe [SO.511
Cereus aethiops Haworth Tyr ; Hord ; Cand
Cereus alaffiportanus Pfeiff. Hord E::3
Cer~s~rbes~i 0. Tyr
Cereus gfaueus SR. Tyr ; Hord E:.:]
Cereus pe~v~an~ (I,.) Mill. Tyr; Hord
Cereus peruvianus-monstruosus DC. Tyr FC]
Coryphantha bumammo (Ehrenberg) Hord ; 3.4-diMeO Me-Pe : c551
Br. & R. 4-Me0 Me-Pe
Coryphantha calipensis H. Bravo Me-Tyr ; Word : Normac : c551
3,4-diMeO Me Pe ;
3,4-diMe0 b-Me0 Me-Pe:
3,4diMeO @-Me0 diMe-Pe
Coryphantha cornijera (DC) Lem. Me-Tyr ; Hord ; Syn : C561
4-Me0 Pe ;
4-Me0 B-OH Pe ;
3,4-diMeO Me-Pe
~oryphantha cornifea (DC.) Br. & R. Me-Tyr ; Word ; Syn ; [5bl
var echinus (Engelm.) Br. t R. @-Me0 Syn : 4-Me0 Me-Pe :
 Phenethylamine and related compounds in plants

Cactaceae (continued) 3,4-diMe0 Me-Pe; Macrom;

4Me0 &OH Pe
corypkuntha durang~s~s {Riinge) Me-Tyr ; Hord ; Syn:
Br. & R. 3PdiMeO Me-Pe
Cory~~~~~~ e~epk~tidens Lem. Me-Tyr ; Hord ; Syn ;
3.4-diMeO Me-Pe;
Macrom ; 4MeO b-OH Pe
Coryphantka greenwoodii H. Bravo Hord ; Normac;
&Me0 Syn ;
3,4-diMe0 &Me0 MePe;
3.4diMe0 Me-Pe ;
3,4-diMeO diMe-Pe ;
3,4diMeO &Me0 diMe-Pe
~orypka~tka macrameris var runyoniS Me-Tyr ; Tyr ; Hord ;
(Br. & R.) L. Benson Syn ; Metaneph ;
Me-Metaneph ;
4-Me0 Me-Pe ;
3,4-diMe0 M&Pe;
Macrom; Normac;
N-Formyl Normac
Corypkantka ottonis (Pfeif.) Lem. Me-Tyr ; Hord ; Syn ;
4-Me0 Pe
Corypkantha pectinata (Engelm.) Me-Tyr ; Hord ; Syn : b-Me0 Syn ;
B.&R. 4-Me0 Me-Pe ;
3,4-diMeO Me-Pe ; Macrom ;
4MeO B-OH Pe
Coryph~tka poseig~~~a (Dietr.) Me-Tyr ; Hard ; Syn ;
Br. & R. 4-Me0 Pe
Corypkantka radians (DC.) Br. & R. Me-Tyr; Hord
Coryp~ntku r~~~~osa Cutak Me-Tyr ; Hord ; Syn ;
&Me0 Syn ;
4MeO Me-Pe
Corypkantka vivipera (Nutt.) Eng. Hord
~ofi~otkeIe ~~im~~a (DC.) Br. t R. PMeO B-OH Me-Pe
Dolickotkele spkaerica (Dietrich) Br. & R. Me-Pe ; Me-Tyr ; Syn ;
j&Me0 Syn ; /?-Et0 Syn
~oli~otkele surculosa (Boed.) F. Buxb. Me-Pe ; Me-Tyr ; Hord ; Syn
Echinocereus merkeri Hildm. Hord; 3-Me0 4-OH Pe;
3,4-diMe0 Pe;
3&diMeO Me-Pe ;
3&diMeO diMe-Pe
~cki~ps~s eyriesii G. (Turpin) Zucc. Hord
E~i~~sis rk~o~icka Schuma~ Tyr ; Hord
Gymnocactus lyltrirreauus Glass & Foster Me-Pe ; Me-Tyr ; Hord
G~~ocac~s b~ga~~~i(Web.) Backbg Me-Pe : Me-Tvr : Hord
Gvmnocactus kor~Ri1~ (Lem.) Backbg. Me-Pe ; Hord _
G;mnocactus knutkianus (Boed.) Backbg. Me-Pe
Gymnocacrus mandragora (Fric.) Backbg. Me-Pe ; Me-Tyr
G~rn~~ac~s roseanus (Boed.) Me-Pe ; Me-Tyr ; Hord
-Glass & Foster
GQ~~~c~ uicreckii {Werd.) Backbg. Me-Pe
G~mno~aly~um ~~~bo~rn (Haw.) Pfeiff Mesc
Gymnacalycium leeanum (Hook.) Br. & R. Tyr ; Me-Tyr ; Hord
Gymnocalycium sckiekendantzii Hord ; Cand
( Weber) Br. & R.
Heliantkocereus huascha (Weber) Br. & R. Hord
~eii~t~c~e~ p~a~ana (Weber) Hord
Backbg.
~el~antkoe~e~ poco Backbg. Hord
!
Lopkopkora di&sa (Croizat) Bravo. Mesc
~o~kopk~a wil~i~i~ (Lem.) Coult. Tyr ; Me-Tyr ; Hord ;
= Ankalonium lewinii Hennings Cand ; Dop ; Epinine ;
3,4-diMe0 Pe ;
4-OH 3-Me0 Pe;
3,4diOH 5-Me0 Pe ;
3-Me0 4-OH Me-Pe;
.%OH 3,4-diMe0 Pe ;
4-08 3,5-diMe0 Pe ;
3..OH 4,SdiMeO Me-Pe ;
3-OH 4,5-diMe0 diMe-Pe;
Mesc ; N-Me-Mesc ;
N-Formyl Mesc :
N-Acetyl Mesc
12 TEKIZ~XA. ShllTlI

Cactaceae (continued)
~ummi~iuria elongara DC. Tyr ; Me-Tyr ; Word ;
-Syn; /GleO Syn
Mammillaria heyderi Muehl. 3.4diMe0 Me-Pe
Notocuefus ottonis (Lehm.) Berg. ex fiord
Rackbg. & Knutb
~bregonja de~egrii FriC Tyr; Me-Tyr; Hord
Opuntia aur~t~ca Lindley Hard
Opuntia clavata Eng. Tyr ; Me-Tyr ; Hard
Opuntia maidon~ensis Are&. Hord
~pun&ia allures Mill. Hord
Pachycff~s ~ecten~or~~num (Eng.) 3-OH &Me0 Pe
Br. & R.
Pelecyphoru asellzj%rmisEhrenberg Hord ; 3,4-diMeO Pe ;
Me .Mesc ; 3,4-diMe0 Me--Pe :
3-OH 4,5-diMe0
diMe--Pe ; Mew
Pelecyphora pseudopectinata Backbg. Hard
Sohsia pectinata Br. & R. Me Tyr ; Hord
Stetsonia coryne (SD.) Br. & R. Tyr ; T≻ Me-Tyr ;
Coryn; 3-Me0 4-OH Pe;
3&diMeO Pe
~i&ho~~~s bridgesii (SD.) Br. & R. Tyr ; 3,4-diMe0 Pe ;
3-Me0 4-OH Pe: Mesc
Trichocereus camarguensis Card. Me-Tyr ;
Tyr :,Q,&diMeO Pe ;
3-Me0 4-OH Pe:
~~~hoc~r~s ca~ic~s (Gill) Br. & R. Hard ; Cand
T%hocereus chilensis (Colla) Br. & R. Cand
‘Bichocereus couruntii (Schu.) Backbg. Tyr ; Me-Tyr ;
3-Me0 4-OH Pe;
3-Me0 4-OH Me- Pe;
3,4-diMe0 Pe
TPichocereus cuzcoensis Br. & R. Tyr ; 3-Me0 4-OH Pe:
3-OH 4,5-diMe0 pe ;
S-OH 3,4-diMe0 Pe ;
Mesc
~ichocer~s~lvi~~us R&L Tyr ; Me-Tyr ; Mesc
~icho~er~s knuth~~~ Badkbg. Tyr; 3-Me0 4-OH Pe
TPichocereus lamprochlorus (Lem.) Hord ; Cand
Backbg.
~~~o~e~~s ma~ogon~ (SD.) Rice. Tyr ; Mesc ;
3,4-diMe0 Pe;
3-Me0 4-OH Pe
Tfichocereus manguinii Backby. Tyr ; Me-Tyr ; Hord ;
3-Me0 4-OH Pe
~iebo~er~s pach~oi Br. & R. Tyr ; Hord;
S-OH 3,4-diMe0 Pe ;
4-OH 3,QliMeO Pe;
3,4-diMe0 Pe :
3-Me0 4-OH Pe; Mesc
Trichocereus peruvianus Br. & R. Tvr; 3-Me0 4-OH Pe
~i~hocer~s ~~~reo~~ios~ Wgt. G&Tyr ; Tyr
~ic~oc~~s san~iaguens~s(Speg.) Backbg. Tyr; Hord
Tfichocereus sch~~kend~t~i~ (Web.) Me-Tyr ; Hord
Br. & R.
Trichocereus skottsberg~i Backbg. Me-Tyr : Hard
~ic~oeereus spa&h~~us &em.) Rice. Hord : Cand
~ic~~~reus strigosus (SD.) Br. & R. Hord
~ichocmeus taquimbaiensis Card. Hord; 3-Me0 4-OfI Pe;
3,4-diMe0 Pe ; Mesc
~~~~o~er~s terscheckit (Parm.) Er. & R. Mesc ; Trich
~icho~er~s the~egonoides (Speg.) Br. & R. Hord
Pichocereus thelegonus (Web.) Br. B( R. Me-Tyr; Hord
Trichocereus tunariensis Card. Tvr : Hord
Pichocereus validus (Maw.) Backbg. lbiesc
Echocereus werdermannianus Backbg. Tyr ; 3,4-diMe0 Pe ;
3-Me0 4-OH Pe;
3,S-diMeO 4-OH Pe;
Mesc
Tirbinocurpus pseudomacrochete Hord
(Backbg.) F. Buxb. & Backbg.
 Phenethylamine and related compounds in plants 13

Cactaceae (continued)
Wgginsia erinacea (Haw.) D. M. Porter Hord c541
Wgginsia macrocantha (Arech.) D. M. Hord c541
Porter
u5gginsia tephracantha (Link & Otto) Hord 1541
D. M. Porter
Cannabinaceae Cannabis sativa L. Hord
Caprifoliaceae Lonicera maackii Maxim. Pe [:I
Sambucus canadensis L. Tyr [51
Wrburnum lantana L. Pe c421
Wburnum odoratissimum Ker. Tyr [51
Celastraceae Catha edulis Forsk. Eph ; Nor$Eph C811
Chenopodiaceae Anabasis iaxartica (Bge.) Benth. MeTvr
Arthrophytum leptocladum M. Pop. Me-Pi t::j
Beta vulgaris L. + Dop
Halostachys caspica Halos Ki”“’
Haloxylon salicornicum (Moq-Tand.) Tyr ; Me-Tyr ; Syn [861
Boiss.
Spinacia oleracea L. + Dop ; Tyr
Compositae Aster linmii$olius L. Tyr R 881
Silybum marianum (L.) Gaertn. Tyr
Comaceae Cornus alba L. ssp tatarica Pe E29j901
Cornus sanguinea L. Pe [321
Cmciferae Capsella bursapastoris (L.) Medic. Tyr
Cyperaceae Cyperus papyrus L. Tyr ; Ott Ez;’
Cyperus rotundus L. Ott
Mariscus jamaicensis Crantz. Tyr ‘c:j
Ericaceae Erica lusitanica Rud. 4-Me0 Pe [921
Euphorbiaceae Croton humilis L. MeTyr ; Me-Homotyr
Securinega virosa Baill. Hord E:j
Geraniaceae Erodium cicutarium L. Tyr [951
Gnetaceae Ephedra alata Decne Eph ; +Eph
Ephedra alenda (Stapf.) Andreanszky Wph K981
Ephedra altissima Desf. Eph; v=ph
Ephedra americana Humb. Sz Bonpl. Eph EZ:3
Ephedra andina Poepp. W [981
Ephedra calgornica S. Wats. W ; JlW c971
Ephedra distachya L. W ; *J-W [97-993
Ephedra equisetina Bunge W ; @ph c971
Ephedrafragilis Desf. Eph; Wph [97, mO1
Ephedra gerardiana Wall. Eph; Wph B:j 1~,1011
Eihedra jracilis R. Phil. W ; SEph
Evhedra helvetica C. A. Mev. W ; Wph [971
Ebhedra intermedia S&e& 19,C. A. Mey W ; JlEph F;$‘“, 1011
Ephedra monosperma S. G. Gmel. Eph; Wph
Ephedra monostachya L. W ; Wph [971
Ephedra nebrodensis Tineo Eph; Wh [97, 101, 1023
Ephedra nevadensis Wats. W Cl@Xi
Ephedra pachyclada Boiss. W ; SW [% 1001
Ephedra procera C. A. Mey. W ; SW FL’,;] 1031
Ephedra sinica Stapf. Eph ; $Eph ; Me-Eph ;
Me-SEph
Ephdra triandra Tul. Eph - r971
Ephedra trifirca Torr. Eph; @ph
Ephdra tweediana C. A. Mey. Eph 8;j
Eihedra viridis Coville Eph ; $Eph
Evhedra vulaaris L. C. Rich. Eph ; JlEph ; Noreph ; Me- -Eph E;j
Gramineae iordeum mkinum L. Hord [W
Hordeum vulgare L. + Tyr ; MeTyr ; Hord ; Cand [105, 1063
Lulium multiforum Lam. Annuloline* ; Ckt [107, 1081
Pan&m miliaceum L. + Tyr ; Me+Tyr ; Hord ppr’ ‘21
Phalaris arundinacea L. Hord
Sorghum vulgare Pers. + Hord [109, 1143
ZWicum vulgare Vill. + Me-Tyr; Hord yy41
Zea mays L. + Tyr
Juglandaceae Juglans nigra L. + Tyr [51
Labiatae Lamium album L. Tyr Cl161
Lauraceae Ocolea pretiosa Pe [1171
Persea americana Mill. + Tyr ; Dop C881
Leguminosae Acacia accola Maiden & Betche Pe ; Me-Pe Cl181
Acacia acinacea Lindl Pe Cl191
Acacia adunca Me-Pe
Acacia augusrissima Me-Pe
14 TERENCEA. SMITH

Leguminosae (continued)
Acacia berlandieri MePe ; ‘W ; Me-Tyr ‘; Hord [121, 1221
Acacia buxifolia Cunn. Pe Cl191
Acacia cardiophylla Pe t1181
Acacia constricta Me-Pe r171
Acacia cultriformis Cunn. Pe
AcaciafIoribunda Sieb. Pe [:::j
Acacia greggii Me-Pe ; Tyr 1171
Acacia harpophylla Pe : Hord t1201
Acacia holoserica Hard t1201
Acacia kettlewelliae Maiden Pe: Me- Pe F::3 1201
Acacia longifolia Willd. Pe
Acacia lunata Sieb. Pe r1231
Acacia podalyriaefolia Cunn. Pe y;l~231
Acacia praetervisa Domin. Pe; Me-Pe
Acacia pravissima F.v.M. Pe r1231
Acacia prommens Cum. Pe ; Me-Pe [123,1241
Acacia prurnosa Cum. Pe
Acacia rigidula Me-Pe ; Me-Tyr t::;’
Acacia roemeriana Me Pe ; Tyr ; Me-Tyr 1171
Acacia schottii Me-Pe 1’71
Acacia spectabilis Cunn. Pe [I181
Acactu spriorbi\ Labill. Hord Ff::j 1251
Acacta suaueolens Willd. Pe
Acaciu texensis Me- Pe ; Tyr t-171
Acacia uerticillata Willd. Pe El’91
Albizzia adianthifolia (Schumack)
W. F. Wight Pe
Albizzia julibrissin Durazz. Noradr [Kj
Alhagi pseudalhagi (Bieb.) Desv. Pe ; Me-Pe ; Me-Tyr ; [2. 1281
Hord, Me-Mesc ; Coryn ;
3-Me0 4-OH triMe-Pe
Calliandra haematocephala Hassk. Tyr I51
Cassia alata L. Tyr t51
Cassia marilandica L. Me-Pe Cl71
Cytisus scoparius (L.) Link. Tyr ; Dop ; Me-Dop ; Epinine r1291
Daleafiutescens MeePe 1171
Desmodium cephalotes Wall. Pe ; Tyr ; Hord ; Cand L1301
Desmodium gangeticum DC. Me-Tyr : Pe ; Hord ; Cand ~1::j”21
Desmodium gyrans DC. Pe
Desmodium tiliaefolium (G.) Don. Tyr ; di-Me0 Pe ; [134]
3,4-diMe0 diMe-Pe ;
3,4diMeO B OH Me-Pe
Desmodium trijlorum DC. Pe : Tyr ; Hord ; Coryn II 11
Entadu pursaetha DC. Dop 3-O-glucoside II1351
Erythrina cristagalli L. Tyr r51
Gleditsin triacanthos L. Me-Pe ; Tyr I.171
Mimosa pudica L. Noradr cl271
Phaseolus multiflorus Lam. + Noradr
Phaseolus radiatus L. + Tyr [1Zj
Pisum satioum L. + Tyr ; Noradr t127.1371
Prosopts alba Grts. Tyr ; Pe
Prosopis glanduloso Tyr ; Me-Tyr t:-:y
Samanea sannan Merr. Noradr
Trifolium alexandrinum L. Tyr [::j
Mcia fuba L. + Epinine
Liliaceae Chlorophytum capense Kuntze. Tyr [:l”’
Cordyline terminalis Kunth. Tyr t51
Eremurus regelii Vved. Hord
Liriope spicata Lour. Tyr ; Ckt K”
Loranthaceae Phoradendron sp. Tyr t:1
Phoradendron argentinum Urb. Tyr 11421
Phoradendronflavescens Nutt. Pe ; Tyr ; Hord [143.1441
Phoradendron hieronymi Trel. Tyr cl421
Phoradendron wattii Kr. & Urb. Tyr [I451
Phoradendron liga (Gill.) Etchl. Tyr cl421
Phoradendron villosum Tyr
Phyrgilanthusflagellaris (Cham. & Tyr [Ej
Schlecht) Eichl.
Psittacanthus cuneifolius (Ruiz & Pav.) Tyr 11421
Blume.
Mscum album L Pe : Tyr (?) [144.146,1471
 Phenethylamine and related compounds in plants

Magnoliaceae Magnolia spp. Tyr ; Sal ; Cand

Michelia alba Sal
Matvaceae Sida sp. Eph
Sida ~rd~olia L. Pe ; Eph ; +Ep&
Maraceae Fiats bengalensis L. Syn
Musaceae Musa paradisiaca L. + Pe ; Tyr ; Noradr ; Dop
Nyctaginaceae Hermidium alipes S. Watson Dop
Orchidaceae Cattleya spp. TYr
Papaveraceae Cheljdoni~ ma&s L. Tyr
Roemeria refracta DC. Eph ; JlEph
Passifloraceae Passiflora quodrangukwis L. + Noradr
Piperaceae Piper amalago L. Dop
Plumbaginaceae Limonium v&are Mill. Tyr
Porttdacaceaa Portulaca oleracea L. + Dop ; Noradr
Rosaceae Crataegus (3 spp.) Pe
Crataegus (8 spp.) Pe
1Wulussp. + Pe
Prunus amygdalus Batsch. + Pe
Pnrnus domestica L. + Tyr ; Noradr
Prunus padus L. + Pe
Pyrus communis L. + Pe
Rubus idaeus I.. -I- TYr
Sorbaria sorbijolia A. Br. Pe
Sorbus aucuparia L. Pe
Spiraea bracteata Zabel Pe
Rutaceae Aegle mmmelos Corn. Aegelin* ; Tembamide*
Casimiroa edulis Llave Br Lex. f N-Benzyltyramine*
Citrus limon Burm. f Tyr ; Me-Tyr ; Syn ; Ott
Citrus medica L. x sine&s Osbeck. Tyr;Syn;Oct
Cirrus reshni Hort. ex. Tan. + Tyr; MpTyr; Syn; Ott
Citrus reticulata Blanco + Tyr ; Me-Tyr ; Hord ; Ott ; Syn
Citrus reticulara Blanco x Tyr ; Ott ; Syn
sinensis Osbeck f
Citrus sinensis Osbeck + Tyr ; Me-Tyr ; Syn ; Noradr
Fagara spp,
Phel~~~ron amurense Rupr.
Cand ; Coryn ; Tembam~de*
Cand
~6~~~
Pleiospermium alatum (Wight & Am.) Alatamide* ; [ 169,170)
Swingle N-benzyl4-Me0 Tyr* ;
N-Homoveratroyl-
homove~try~amine*
Teclea s~rnpijc~olia 4-Me0 diMe-Pe
Zanthoxylum clava-her&is L. HercIavin* ; Cand
Saxifragaceae Philadelphw delavayi Pe
Solanaceae Aeonitum napellus L. Eph ; Tyr ; Dop ; Noradr
Aconitum nasuhcm N-Me-Adr
Aconitum pan~~la~m Lam. Noradr
Atropa belladonna L. Pe
Capsicumfrartescens L. Oct.
Nicotiaua tabacum L. Pe; Tyr
Lywp~siwn es~lenrum Miii. -I- TYr
Solanum melongena L. + Tyr
Solanum tuberosum L. + Dop; Noradr; Tyr
Taxaceae Tawus baccata L. Eph
Theaceae Thea sinensis L. + Pe
Verbenaceae Stachytarpheta jamaicensis Vahl. DoP

ninhydrin, fkorescamine or dausyl chloride for the free without prior derivatization and R, may be used as a
amino groups, ~agendo~s reagent for methylat~ means of identification. The most reliable structural
amino groups, and o-dianidisine, tetra-azotized beuzi- assignments are based on additional physical data, in-
dine, Pauly’s, Gibb’s or Folk’s reagent for the hydroxy- eluding MS, IR and PMR.
lated amines. The amines may be separated by GC even

$” P
CH-CH-AmitW WWP

Structuresand abbreviations for the amines cited in the Table.

Pm “OL. 16 NC, 1-s
16 TIXENCE A. SMITH

3 4 5 B a Group

Phenethylamine Pe H H H H H -NH,
Me Pheiethylamine Me-Pe H H H H H -NHMe
DiMePhenethvlamine diMe-Pe H H H H H - N(Me),
Phenethylamiie triMe-Pe H H H H H -N(Me)l
trimethylammonium
hydroxide
Tyramine ‘W H OH H H H -NH,
Me Tyramine Me-Tyr H OH H H H -NHMe
Hordenine (anhaline) Hord H OH H H H - N(Me),
Candicine Cand H OH H H H - N(Me):
Dopamine DoP OH OH H H H -NH,
Epinine Epinine OH OH H H H -NHMe
Cbryneine Coryn OH OH H H H - N(Me)i
Salicifoline Sal OH OMe H H H - N(Me):
Mescaline Mesc OMe OMe OMi: H H -NH,
Me Mescaline Me-Mesc OMe OMe OMe H H -NHMe
Trichocereine Trich OMe OMe OMe H H - N(Me),
Halostachine Halos H H H OH H - NHMe
Octopamine Ott H OH H OH H -NH,
Synephrine (oxedrine) Syn H OH H OH H -NHMe
p-O-Methylsynephrine fiMe-Syn H OH H OMe H - NHMe
Noradrenaline Noradr OH OH H OH H -NH,
(norepinephrine)
Adrenaline Adr OH OH OH H - NHMe
(epinephrine)
Metanephrine Metaneph OMe OH OH H -NHMe
N-Methylmetanephrine Me-Metaneph OMe OH OH H - N(Me),
Normacromerine Normac OMe OMe OH H - NHMe
Macromerine Macrom OMe OMe OH H - N(Me),
Morephedrine Noreph
H H OH Me -NH,
Norpseudoephedrine* Nor$Eph 1
(cathine)
Ephedrine Eph H H OH Me -NHMe
Pseudoephedrine* +Eph 1
Methylephedrine Me-Eph
H H OH Me -N(Me),
Methylpseudoephedrine’ Me-+Eph

* Stereoisomers.

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