Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Phytochem Anal. 2015 May-Jun;26(3):183-8. doi: 10.1002/pca.2548. Epub 2015 Jan
 26.

LC-MS/MS quantitative determination of Tetrapterys mucronata alkaloids, a plant 
occasionally used in ayahuasca preparation.

Queiroz MM(1), Marti G, Queiroz EF, Marcourt L, Castro-Gamboa I, Bolzani VS, 
Wolfender JL.

Author information:
(1)Núcleo de Bioensaios, Biossíntese e Ecofisiologia de Produtos Naturais 
(NuBBE), Instituto de Química, Universidade Estadual Paulista (UNESP), 
Araraquara, São Paulo, Brazil.

INTRODUCTION: Tetrapterys mucronata Cav. (Malpighiaceae) is a plant used in some 
regions of Brazil in the preparation of ayahuasca.
OBJECTIVE: To determine the content of the main tryptamine alkaloids in the stem 
bark of T. mucronata Cav. and assess their possible toxic and hallucinogenic 
properties based on the doses found in a water decoction that mimics the 
ayahuasca preparation.
METHODS: Four alkaloids previously described for their toxic and hallucinogenic 
properties were quantitated by multiple reaction monitoring HPLC combined with 
electrospray ionisation and tandem MS (HPLC-ESI/MS/MS) in the water decoction 
and ethanolic extracts from the bark of T. mucronata.
RESULTS: Exhaustive extraction of the stem barks with ethanol revealed the 
following alkaloid levels: bufotenine (1) 3.26 ± 0.31 mg/g, 
5-methoxy-N-methyltryptamine (2) 0.88 ± 0.08 mg/g, 5-methoxy-bufotenine (3) 3.07 
± 0.22 mg/g and 2-methyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline (4) 0.14 ± 
0.004 mg/g. The water decoction presented slightly lower levels, ranging between 
2.32 ± 0.14, 0.50 ± 0.04, 1.53 ± 0.09 and 0.10 ± 0.01 mg/g for (1), (2), (3) and 
(4) respectively.
CONCLUSIONS: The HPLC-ESI/MS/MS quantitation revealed significant alkaloid 
levels, in particular for bufotenine and 5-methoxy-bufotenine. As such compounds 
are known for their toxic and hallucinogenic properties, these results indicate 
that the consumption of this plant as an ingredient in ayahuasca preparations 
may present a risk to consumers.

Copyright © 2015 John Wiley & Sons, Ltd.

DOI: 10.1002/pca.2548
PMID: 25620461 [Indexed for MEDLINE]


2. Psychiatry Clin Neurosci. 2007 Apr;61(2):196-9. doi: 
10.1111/j.1440-1819.2007.01638.x.

Acute confusional state after designer tryptamine abuse.

Itokawa M(1), Iwata K, Takahashi M, Sugihara G, Sasaki T, Abe Y, Uno M, Hobo M, 
Jitoku D, Inoue K, Arai M, Yasuda I, Shintani M.

Author information:
(1)Schizophrenia Research Project, Tokyo Institute of Psychiatry, Tokyo, Japan. 
mitokawa@prit.go.jp

A 23-year-old Japanese woman was brought to the emergency department about 6.5 h 
after taking liquid and later a half tablet purchased on the street. About 4.5 h 
prior to presentation, she displayed excited and disorganized behavior. On 
examination, she was not alert or oriented, with a Glasgow Coma Scale score of 
13, did not answer any questions from doctors while smirking and looking around 
restlessly, and sometimes exhibited echolalia, imitating the speech of doctors. 
She was given intravenous infusion of fluid for 8 h, then discharged. Gas 
chromatography-mass spectrometry of urine revealed 
5-methoxy-diisopropyltryptamine, 5-methoxy-N-methyltryptamine and an 
unidentified tryptamine. Identifying chemical products based solely on 
information of users is insufficient, and urinalysis is necessary in cases 
potentially involving designer drugs.

DOI: 10.1111/j.1440-1819.2007.01638.x
PMID: 17362440 [Indexed for MEDLINE]


3. Chem Pharm Bull (Tokyo). 2001 Jan;49(1):87-96. doi: 10.1248/cpb.49.87.

The chemistry of indoles. CIII. Simple syntheses of serotonin, 
N-methylserotonin, bufotenine, 5-methoxy-N-methyltryptamine, bufobutanoic acid, 
N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine, and lespedamine based on 
1-hydroxyindole chemistry.

Somei M(1), Yamada F, Kurauchi T, Nagahama Y, Hasegawa M, Yamada K, Teranishi S, 
Sato H, Kaneko C.

Author information:
(1)Faculty of Pharmaceutical Sciences, Kanazawa University, Japan. 
somei@dbs.p.kanazawa-u.ac.jp

Application of regioselective nucleophilic substitution reactions of 
1-hydroxytryptamines to novel and simple syntheses of serotonin (1a), 
N-methylserotonin (1b), bufotenine (1c), 5-methoxy-N-methyltryptamine (2a), 
bufobutanoic acid (3a), N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine (4), 
and lespedamine (5) are described. Effective syntheses of 5-benzyloxytryptamine 
and 1-methoxy-2-oxindoles are also reported.

DOI: 10.1248/cpb.49.87
PMID: 11201232 [Indexed for MEDLINE]


4. Plant Physiol. 1988 Oct;88(2):315-20. doi: 10.1104/pp.88.2.315.

N,N-Dimethyltryptamine Production in Phalaris aquatica Seedlings: A Mathematical 
Model for its Synthesis.

Mack JP(1), Mulvena DP, Slaytor M.

Author information:
(1)Chemistry Department, University of Maryland Baltimore County, Catonsville, 
Maryland 21228.

The activities of three enzymes and the concentration of intermediates involved 
in the synthesis of N,N-dimethyltryptamine (DMT) from endogenous tryptophan 
(TRP) have been measured in vitro in seedlings of Phalaris aquatica L. cv 
Australian Commercial over 16 days after planting. The activities of tryptophan 
decarboxylase and the two N-methyl-transferases increased rapidly to maximal 
rates of substrate conversion at day 5 of 95, 1000, and 2200 micromoles per hour 
per milliliter, respectively. After these maximal rates, the activities 
decreased rapidly. The concentration of intermediates increased rapidly from 
zero in the seeds to maximal values of 25 and 53 micromolar at day 5 for 
tryptamine (T) and N-methyltryptamine (MT), respectively, 1000 micromolar at day 
6 for TRP, and 650 micromolar at day 8 for DMT. The concentration of DMT and of 
all the intermediates in its synthesis declined rapidly after the maximal value 
had been reached. A mathematical model of the pathway from TRP to DMT using 
these enzymes correctly predicts the concentrations of T and MT, intermediates 
whose concentration is determined only by the pathway, and confirms that these 
three enzymes are responsible for the in vivo synthesis of DMT. Kinetic studies 
are reported for these enzymes. Tryptophan decarboxylase uses pyridoxal 
phosphate (PALP) as a coenzyme and has the following kinetic constants: K(m) 
(PALP) = 2.5 micromolar, K(m) (TRP) = 200 micromolar, K(i) (MT) = 5 millimolar, 
and K(i) (DMT) = 4 millimolar. The N-methyltransferases use S-adenosylmethionine 
(SAM) as substrate; S-adenosylhomocysteine (SAH) is assumed to be the product. 
The mechanism of secondary indolethylamine-N-methyltransferase, determined by 
initial velocity studies, is rapid equilibrium random with formation of both 
dead end complexes. Secondary indolethylamine-N-methyltransferase methylates 
both MT and 5-methoxy-N-methyltryptamine (5MeOMT). The kinetic constants for the 
methylation of MT are: K(MT) = 40 +/- 6, K(SAM) = 55 +/- 15, K(DMT) = 60, K(SAH) 
= 4.3 +/- 0.4 micromolar with unity interaction factors. The kinetic constants 
for the conversion of 5MeOMT to 5-methoxy-N,N-dimethyltryptamine (5MeODMT) are 
K(5MeOMT) = 40 +/- 10, K(SAM) = 90 +/- 40, and K(SAH) = 2.9 +/- 0.3 micromolar 
with unity interaction factors, except for SAM-5MeODMT = 2.0 +/- 0.9 and 
SAH-5MeOMT = 0.45 +/- 0.25. The kinetic constants for primary indolethylamine 
N-methyltransferase are K(m) (T) = 20, K(m) (SAM) = 40, K(i) (DMT) = 450 
micromolar with the substrates binding independently.

DOI: 10.1104/pp.88.2.315
PMCID: PMC1055574
PMID: 16666301


5. Biochem Pharmacol. 1964 Mar;13:531-4. doi: 10.1016/0006-2952(64)90174-1.

THE RELATIONSHIP BETWEEN THE METABOLIC FATE AND PHARMACOLOGICAL ACTION OF 
5-METHOXY-N-METHYLTRYPTAMINE.

TABORSKY RG, MCISAAC WM.

DOI: 10.1016/0006-2952(64)90174-1
PMID: 14157616 [Indexed for MEDLINE]