ACS Omega
May 13, 2026
Darío Martínez-afani, Breno A. Soares, Jaime Mella-Raipán et al.
1 citation
High Resolution Image Download MS PowerPoint Slide Serotonin 5-HT 2 receptor ligands have attracted the attention of medicinal chemists for the last half-century, first as hallucinogens and later for their antipsychotic, appetite suppressant, antiaddictive and antidepressant potential. Unlike the very potent N -benzylphenethylamine derivatives that include the abundantly studied NBOMe drugs, N...
Natural Product Communications
April 20, 2026
Bruce K. Cassels
11 citations
Alkaloids of the Cactaceae have been studied for the last 120 years. The first half of that period provided the “classic” compounds, after which a large number of usually very similar analogs were isolated or determined with modern methods. Although some unusual synthetic approaches have been developed, their preparation is generally quite straightforward. Their biosynthesis has been studied...
ACS Chemical Neuroscience
March 20, 2026
E. Pottie, Emma Vertriest, Darío Martínez-afani et al.
N-Benzyl-derived phenethylamines are highly active (psychedelic) 5-HT2AR (serotonin 2A receptor) agonists used as biochemical tools and on the drug market. The impact of adding an N-benzyl substituent to the tryptamine core structure has scarcely been studied. A recent systematic exploration of N-benzyl-substituted (5-MeO-)tryptamines revealed a surprisingly low activity in a Ca2+ mobilization...
Frontiers in Pharmacology
2026
Patricio Sáez-briones, Amanda Silva-Rodríguez, Michelle Morales-Vidal et al.
In humans, empathy is expressed through various prosocial behaviours between individuals that may be enhanced after intake of the synthetic entactogen MDMA (3,4-methylenedioxymethamphetamine, "Ecstasy") as the behavioural expression of the so-called entactogenic syndrome. Rodents may also exhibit empathy-like behaviours, such as social interaction and helping behaviour. In this regard, while...
ACS Chemical Neuroscience
February 7, 2024
Breno A. Soares, Thirumal Yempala, Darío Martínez-afani et al.
4 citations
The introduction of arylmethyl substituents on the amine nitrogen atom of phenethylamines and tryptamines often results in profound increases in their affinity and functional activity at 5-HT2 serotonin receptors. To probe the sensitivity of this effect to substantially larger N-substituents, ten derivatives of the well-characterized psychedelic phenethylamine 2C-B were prepared by appending...
Front Pharmacol
February 28, 2019
Patricio Sáez-briones, Vicente Castro-Castillo, Gabriela Díaz-véliz et al.
4 citations
Aromatic Bromination Abolishes the Psychomotor Features and Pro-social Responses of MDMA ("Ecstasy") in Rats and Preserves Affinity for the Serotonin Transporter (SERT).
ACS Chemical Neuroscience
May 30, 2018
Bruce K. Cassels, Patricio Sáez-briones
84 citations
Archeological studies in the United States, Mexico, and Peru suggest that mescaline, as a cactus constituent, has been used for more than 6000 years. Although it is a widespread cactus alkaloid, it is present in high concentrations in few species, notably the North American peyote ( Lophophora williamsii) and the South American wachuma ( Trichocereus pachanoi, T. peruvianus, and T. bridgesii)....
Journal of Chromatographic Science
July 12, 2016
B. Duffau, Cristian Camargo, M. Kogan et al.
Use of unauthorized synthetic drugs is a serious, forensic, regulatory and public health issue. In this scenario, consumption of drug-impregnated blotters is very frequent. For decades, blotters have been generally impregnated with the potent hallucinogen known as lysergic acid diethylamide (LSD); however, since 2013 blotter stamps with N-2 methoxybenzyl-substituted phenylethylamine...
Jpc-journal of Planar Chromatography-modern Tlc
September 30, 2015
B. Duffau, Cristian Camargo, Bruce K. Cassels et al.
All over the world, hallucinogens have long been abused to experience their effects; in this context, abuse of drugs is a serious public health issue. Because the consumption of blotters impregnated with drug is very frequent, hallucinogens are the most common drugs found in blotters [1]. Since decades, blotters have been generally impregnated with the potent hallucinogen known as lysergic acid...
Journal of the Chilean Chemical Society
September 1, 2014
Cristián Tirapegui, Miguel A Toro-Sazo, Bruce K. Cassels
1 citation
In the last four years a group of extremely potent designer drugs, the N-benzylated phenylethylamines known as the NBOMe series, has surfaced on the street and in the news media. Although data documenting their high affinity and preference for 5-HT2 serotonin receptors abound (5-HT2A receptor activation is generally associated with the action of the "classical" hallucinogens), relatively little...
Behavioral Neuroscience
October 1, 2010
David Quinteros-Muñoz, Patricio Sáez-briones, Gabriela Díaz-véliz et al.
12 citations
3,4-methylenedioxymethamphetamine (MDMA; "ecstasy") is a psychoactive drug structurally related to other phenylisopropylamines acting as stimulants or hallucinogens in humans. Although MDMA has a pharmacological identity of its own, the distinction of its acute effects from those of stimulants or even hallucinogens is controversial. In this work, dose-response curves (0.25, 0.5, 1, 3, 5, and 10...
The Journal of pharmacology and experimental therapeutics
June 2007
Pablo R Moya, Kelly A Berg, Manuel A Gutiérrez-Hernandez et al.
2,5-Dimethoxy-4-substituted phenylisopropylamines and phenethylamines are 5-hydroxytryptamine (serotonin) (5-HT)(2A/2C) agonists. The former are partial to full agonists, whereas the latter are partial to weak agonists. However, most data come from studies analyzing phospholipase C (PLC)-mediated responses, although additional effectors [e.g., phospholipase A(2) (PLA(2))] are associated with...
British Journal of Pharmacology
April 1, 2004
Claudio A Villalobos, Paulina Bull, Patricio Sáez et al.
50 citations
1. We recently described that several 2-(2,5-dimethoxy-4-substituted phenyl)ethylamines (PEAs), including 4-I=2C-I, 4-Br=2C-B, and 4-CH(3)=2C-D analogs, are partial agonists at 5-HT(2C) receptors, and show low or even negligible intrinsic efficacy at 5-HT(2A) receptors. These results raised the proposal that these drugs may act as 5-HT(2) antagonists. 2. To test this hypothesis, Xenopus laevis...
British Journal of Pharmacology
June 1, 2002
Claudio Acuña-Castillo, Claudio A Villalobos, Pablo R Moya et al.
The pharmacological profile of a series of (+/-)-2,5-dimethoxy-4-(X)-phenylisopropylamines (X=I, Br, NO(2), CH(3), or H) and corresponding phenylethylamines, was determined in Xenopus laevis oocytes injected with cRNA coding for rat 5-HT(2A) or 5-HT(2C) receptors. The efficacy and relative potency of these drugs were determined and compared to classical 5-HT(2) receptor agonists and...
Life Sciences
November 17, 2000
Claudio Acuña-Castillo, C Scorza, M Reyes-Parada et al.
3 citations
To assess the pharmacodynamic profile of ALEPH-2, a phenylisopropylamine derivative with alleged anxiolytic and hallucinogenic properties, Xenopus laevis oocytes were microinjected with either of the rat cRNA for the 5-HT2A or the 5-HT2C receptor. Concentration-response curves were obtained following the exposure of the oocytes to varying concentrations of either ALEPH-2 or 5-hydroxytryptamine...
Naunyn-Schmiedeberg's archives of pharmacology
November 1, 1996
M Reyes-Parada, C Scorza, V Romero et al.
6 citations
Serotonergic behavioral responses, effects on motor activity and core temperature, and binding properties of the novel putative anxiolytic amphetamine derivative (+/-)1-(2,5-dimethoxy-4-ethylthio-phenyl)-2-aminopropane (ALEPH-2), were examined in rodents in order to elucidate the mechanism underlying its anxiolytic-like effect. After peripheral administration in rats, ALEPH-2 induced some...
General pharmacology
1994
Patricio Sáez, Y Borges, E Gonzalez et al.
21 citations
1. 2C-H [2-(2,5-dimethoxyphenyl)ethylamine] (pD2 = 6.74), TMPEA [2,(2,4,5-trimethoxyphenyl)ethylamine] (pD2 = 5.83), 2C-D [2-(2,5-dimethoxy-4-methylphenyl)ethylamine] (pD2 = 5.06), homoveratrylamine [DMPEA, 2-(4,5-dimethoxyphenyl)ethylamine] (pD2 = 4.46) and homopiperonylamine [MDPEA, 2-(3,4-methylenedioxyphenyl)ethylamine] (pD2 = 4.19), elicit concentration-dependent contraction of the...