Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. J Psychopharmacol. 2022 Jul;36(7):836-848. doi: 10.1177/02698811221104050.
Epub  2022 Jun 20.

β-carboline-independent antidepressant-like effect of the standardized extract 
of the barks of Mimosa tenuiflora (Willd) Poir. occurs via 5-HT(2A/2C) receptors 
in mice.

Duarte-Filho LAMS(1), Amariz IA(2)(3), Nishimura RHV(3), Massaranduba 
ABR(4)(5)(6), Menezes PMN(2), Damasceno TA(1), Brys I(4)(5), Rolim 
LA(1)(2)(3)(7), Silva FS(1)(7), Ribeiro LAA(1)(7).

Author information:
(1)Pós-Graduação em Biociências (PGB) UNIVASF, Pernambuco, Brazil.
(2)Rede Nordeste de Biotecnologia (RENORBIO), Universidade Federal Rural de 
Pernambuco, Recife, Pernambuco, Brazil.
(3)Central de Análise de Fármacos, Medicamentos e Alimentos (CAFMA) UNIVASF, 
Petrolina, Pernambuco, Brazil.
(4)Pós-Graduação em Ciências da Saúde e Biológicas (PGCSB) UNIVASF, Petrolina, 
Pernambuco, Brazil.
(5)Grupo de Pesquisa em Neurociências e Psicologia Experimental (Neurovale) 
UNIVASF, Petrolina, Pernambuco, Brazil.
(6)Grupo de Pesquisa em Processamento de Sinais e Visão Computacional (SigProCV) 
UNIVASF, Petrolina, Pernambuco, Brazil.
(7)Universidade Federal do Vale do São Francisco (UNIVASF), Petrolina, 
Pernambuco, Brazil.

BACKGROUND: Depression is a psychiatric disorder with limited therapy options. 
Psychedelics are new antidepressant candidates, being the ayahuasca one of the 
most promising ones. A synergistic combination of N,N-dimethyltryptamine (DMT) 
and β-carbolines allows ayahuasca antidepressant properties. Another psychedelic 
and DMT-containing beverage is the jurema wine used religiously by indigenous 
people from Northeastern Brazil.
AIMS: To evaluate the antidepressant-like effect of standardized extract of 
Mimosa tenuiflora (SEMT), associated or not with harmine (β-carboline), in 
behavioral models of depression.
METHODS: The SEMT was submitted to (+) ESI-IT-LC/MS analysis for DMT 
quantification. To assess the antidepressant-like effect of SEMT, the open field 
(OFT), tail suspension (TST), and forced swim (FST) tests were performed. To 
verify the participation of serotonergic systems, the 5-hydroxytryptophan 
(5-HTP)-induced head twitch test was performed.
RESULTS: The content of DMT found in SEMT was 24.74 ± 0.8 mg/g. Yuremamine was 
also identified. SEMT presented an antidepressant-like effect in mice submitted 
to the TST and FST, independent from harmine, with no significant alterations on 
the OFT. The sub-dose interaction between SEMT and ketamine also produced an 
anti-immobility effect in the TST, with no changes in the OFT. SEMT potentiated 
the head twitch behavior induced by 5-HTP and ketanserin prevented its 
antidepressant-like effect in the TST (p < 0.05).
CONCLUSIONS: SEMT presented a harmine-independent antidepressant-like effect in 
mice submitted to the TST and FST. This effect occurs possibly via activation of 
serotonergic systems, particularly the 5-HT2A/2C receptors.

DOI: 10.1177/02698811221104050
PMID: 35723216 [Indexed for MEDLINE]


2. J Psychoactive Drugs. 2021 Jan-Mar;53(1):65-75. doi: 
10.1080/02791072.2020.1815911. Epub 2020 Sep 8.

Chemical Composition of Traditional and Analog Ayahuasca.

Kaasik H(1), Souza RCZ(2), Zandonadi FS(2), Tófoli LF(3), Sussulini A(2).

Author information:
(1)School of Theology and Religious Studies; and Institute of Physics, 
University of Tartu, Tartu, Estonia.
(2)Laboratory of Bioanalytics and Integrated Omics (LaBIOmics), Institute of 
Chemistry, University of Campinas (UNICAMP), Campinas, SP, Brazil.
(3)Interdisciplinary Cooperation for Ayahuasca Research and Outreach (ICARO), 
School of Medical Sciences, University of Campinas (UNICAMP), Campinas, Brazil.

Traditional ayahuasca can be defined as a brew made from Amazonian vine 
Banisteriopsis caapi and Amazonian admixture plants. Ayahuasca is used by 
indigenous groups in Amazonia, as a sacrament in syncretic Brazilian religions, 
and in healing and spiritual ceremonies internationally. The study aimed to 
determine concentrations of the main bio- and psychoactive components of 
ayahuasca used in different locations and traditions. We collected 102 samples 
of brews from ayahuasca-using communities. Concentrations of 
N,N-dimethyltryptamine (DMT), tetrahydroharmine, harmine, and harmaline were 
determined by ultra-high performance liquid chromatography coupled to tandem 
mass spectrometry (UHPLC-MS/MS). Qualitative analyses for non-traditional 
additives (moclobemide, psilocin, yuremamine) were performed by high resolution 
mass spectrometry. Higher and more variable concentrations of DMT in neoshamanic 
ayahuasca samples compared to indigenous samples may indicate use of higher and 
more variable proportions of DMT-containing admixture plants. From European 
samples, we found two related samples of analog ayahuasca containing 
moclobemide, psilocin, DMT, yuremamine, and very low concentrations of B. caapi 
alkaloids. Some analogs of ayahuasca (Peganum harmala, Mimosa tenuiflora) were 
used in Europe. No analogs were found from Brazil or Santo Daime ceremonies in 
Europe. We recommend awareness about the constituents of the brew and ethical 
self-regulation among practitioners of ayahuasca ceremonies.

DOI: 10.1080/02791072.2020.1815911
PMID: 32896230 [Indexed for MEDLINE]


3. Org Lett. 2017 Oct 6;19(19):5022-5025. doi: 10.1021/acs.orglett.7b02005. Epub 
2017 Sep 13.

Cascade Radical Cyclization of N-Propargylindoles: Substituents Dictate 
Stereoselective Formation of N-Fused Indolines versus Indoles.

Gharpure SJ(1), Shelke YG(1).

Author information:
(1)Department of Chemistry, Indian Institute of Technology Bombay , Powai, 
Mumbai 400076, India.

An efficient protocol for the synthesis of pyrrolo[1,2-a]indole derivatives 
having sulfide functionality using cascade radical cyclization on 
propargylindole is described. The nature of the substituents at the propargylic 
carbon bearing nitrogen of the indole has a profound effect on the rate, yield, 
and nature of the product obtained by the cascade radical cyclization. An 
expeditious one-pot route for cascade radical cyclization-desulfurization is 
also presented. Products obtained were elaborated to the core of the putative 
structure of the yuremamine and indoline derivative with five contiguous 
stereocenters.

DOI: 10.1021/acs.orglett.7b02005
PMID: 28902520


4. J Org Chem. 2016 Sep 2;81(17):7945-51. doi: 10.1021/acs.joc.6b01730. Epub 2016
 Aug 24.

Enantioselective Model Synthesis and Progress toward the Putative Structure of 
Yuremamine.

Ghosh A(1), Bainbridge DT(1), Stanley LM(1).

Author information:
(1)Department of Chemistry, Iowa State University , Ames, Iowa 50011, United 
States.

An enantioselective model synthesis of the 2,3-dihydro-1H-pyrrolo[1,2-a]indole 
core of the putative structure of yuremamine is reported in 39% overall yield 
and 96% ee over five steps. The model synthesis leverages enantioselective, 
rhodium-catalyzed hydroacylation of an N-vinylindole-2-carboxaldehyde as the key 
step in the installation of the stereochemical triad. An enantioselective 
synthesis of a densely functionalized dihydropyrroloindolone that maps onto the 
putative structure of yuremamine is demonstrated in 26% yield and 97% ee over 
eight steps.

DOI: 10.1021/acs.joc.6b01730
PMID: 27494137 [Indexed for MEDLINE]


5. Org Biomol Chem. 2016 Jun 28;14(24):5728-43. doi: 10.1039/c6ob00110f. Epub
2016  Feb 18.

Synthetic studies towards putative yuremamine using an iterative C(sp(3))-H 
arylation strategy.

Calvert MB(1), Sperry J.

Author information:
(1)School of Chemical Sciences, University of Auckland, 23 Symonds Street, 
Auckland, New Zealand. j.sperry@auckland.ac.nz.

An overview of an iterative, 8-aminoquinoline (AQ)-directed C(sp(3))-H arylation 
strategy towards the pyrroloindole structure initially assigned to the alkaloid 
yuremamine is described. During initial efforts using a model indane system, it 
was discovered that the iodoresorcinol unit was not a viable C(sp(3))-H 
arylation partner when masked as its dimethyl ether but upon switching to a MOM 
group, the ether oxygen served to stabilise the high valent Pd intermediate 
during the reaction, thus promoting reductive elimination and leading to 
acceptable yields of the C(sp(3))-H arylation product. The second C(sp(3))-H 
arylation with an iodopyrogallol gave a 1,3-diarylated model yuremamine system 
possessing the desired 1,3-cis relationship. When the successful model studies 
were applied to a pyrroloindole system in pursuit of yuremamine, it became 
apparent that C9 underwent competing C(sp(2))-H arylation if left vacant, but 
installing a tryptamine side chain at this site prevented the desired C(sp(3))-H 
arylation from occurring altogether. However, a C9-methyl pyrroloindole 
underwent iterative C(sp(3))-H arylation at C1 with an iodoresorcinol followed 
by C3 with an iodopyrogallol to give a diarylated product with the aryl groups 
in the undesired 1,3-trans-relationship, arising from epimerisation at C1 during 
the second C(sp(3))-H arylation event. Although the synthesis of putative 
yuremamine was not accomplished, several findings are disclosed that will serve 
as useful additions to the burgeoning field of directed C(sp(3))-H arylations 
and related C-H functionalization reactions.

DOI: 10.1039/c6ob00110f
PMID: 26891188 [Indexed for MEDLINE]