Phenethylamine alkaloids

Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a naturally occurring classical psychedelic protoalkaloid of the substituted phenethylamine class, found in cacti like peyote (Lophophora williamsii) and San Pedro (certain species of the genus Echinopsis).

Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace amine-associated receptor 1 (TAAR1) and inhibiting vesicular monoamine transporter 2 (VMAT2) in monoamine neurons. To a lesser extent, it also acts as a neurotransmitter in the human central nervous system. In mammals, phenethylamine is produced from the amino acid L-phenylalanine by the enzyme aromatic L-amino acid decarboxylase via enzymatic decarboxylation.

Tyramine ( ) (also spelled tyramin), also known under several other names, is a naturally occurring trace amine derived from the amino acid tyrosine. Tyramine acts as a catecholamine releasing agent. Notably, it is unable to cross the blood-brain barrier, resulting in only non-psychoactive peripheral sympathomimetic effects following ingestion. A hypertensive crisis can result, however, from ingestion of tyramine-rich foods in conjunction with the use of monoamine oxidase inhibitors (MAOIs).

Trabectedin, sold under the brand name Yondelis, is an antitumor chemotherapy medication for the treatment of advanced soft-tissue sarcoma and ovarian cancer.

Hordenine, also known as '''N,N-dimethyltyramine or as 4-hydroxy-N,N-dimethylphenethylamine', is an alkaloid of the phenethylamine class that occurs naturally in a variety of plants, taking its name from one of the most common, barley (Hordeum species). Chemically, hordenine is the N-methyl derivative of N-methyltyramine, and the N,N''-dimethyl derivative of the well-known biogenic amine tyramine, from which it is biosynthetically derived and with which it shares some pharmacological properties (see below). , hordenine is widely sold as an ingredient of nutritional supplements, with sellers cl

3-Methoxytyramine (3-MT), also known as 3-methoxy-4-hydroxyphenethylamine, is a human trace amine and the major metabolite of the monoamine neurotransmitter dopamine. It is formed by the introduction of a methyl group to dopamine by the enzyme catechol-O-methyltransferase (COMT). 3-MT can be further metabolized by the enzyme monoamine oxidase (MAO) to form homovanillic acid (HVA), which is then typically excreted in the urine.

'''N-Methylphenethylamine (NMPEA''') is a naturally occurring trace amine neuromodulator in humans that is derived from the trace amine, phenethylamine (PEA). It has been detected in human urine (<1&nbsp;μg over 24&nbsp;hours) and is produced by phenylethanolamine N-methyltransferase with phenethylamine as a substrate, which significantly increases PEA's effects. PEA breaks down into phenylacetaldehyde which is further broken down into phenylacetic acid by monoamine oxidase. When this is inhibited by monoamine oxidase inhibitors, it allows more of the PEA to remain present and produce psychoac

Varacin is a bicyclic organosulfur compound originally found in marine Ascidiacea from the Polycitor genus. It contains an unusual 1,2,3,4,5-benzopentathiepine ring system.

3,4-Dimethoxyphenethylamine (DMPEA or 3,4-DMPEA), also known as homoveratrylamine, 3-desmethoxymescaline, or '''O,O-dimethyldopamine''', is a chemical compound of the phenethylamine family. It is an analogue of the major human neurotransmitter dopamine where the 3- and 4-position hydroxy groups have been replaced with methoxy groups. It is also closely related to mescaline (3,4,5-trimethoxyphenethylamine; 3,4,5-TMPEA) and to 3,4-dimethoxyamphetamine (3,4-DMA).

Macromerine, also known as 'β-hydroxy-3,4-dimethoxy-N,N-dimethylphenethylamine', is a phenethylamine derivative. It was first identified from the cactus Coryphantha macromeris. It can also be found in C. runyonii, C. elephantidens, and other related members of the family Cactaceae.

Lophophorine, also known as '''N-methylanhalonine', is a tetrahydroisoquinoline alkaloid made by various cacti in the Lophophora'' family. It has been found to lack hallucinogenic effects in humans. Arthur Heffter tried lophophorine at a dose of 20mg resulted in vasodilation, an immediate headache, and a warm flushed feeling, effects which dissipated within an hour. It has also been said to produce nausea in humans. Lophophorine is described as highly toxic and produces strychnine-like convulsions in animals.

Lophophine, also known as 2C-MMDA-1, 5-methoxy-MDPEA, or 3-methoxy-4,5-methylenedioxyphenethylamine (MMDPEA or MMDPEA-1), is a psychedelic drug of the methylenedioxyphenethylamine family. It is the α-demethylated homologue of MMDA, and is also closely related to mescaline (3,4,5-trimethoxyphenethylamine) and MDPEA. Lophophine has been encountered as a novel designer drug.

Aspidophytine is an indole alkaloid that has attracted significant attention from synthetic chemists. An extract of the cockroach plant, aspidophytine is an insecticidal substance particularly effective against cockroaches. It is one of the two components of the dimer haplophytine.