2,6-Dimethoxyphenethylamine
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2,6-Dimethoxyphenethylamine (2,6-DMPEA), also known as DMPEA-5, is a
drug A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via insufflation (medicine), inhalation, drug i ...
of the
phenethylamine 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 ami ...
family related to the
psychedelic drug Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluc ...
mescaline Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a natural product, naturally occurring psychedelic drug, psychedelic alkaloid, protoalkaloid of the substituted phenethylamine class, found ...
(3,4,5-trimethoxyphenethylamine). It is one of the
positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...
s of
dimethoxyphenethylamine Dimethoxyphenethylamine may refer to: * 2,3-Dimethoxyphenethylamine (2,3-DMPEA; DMPEA-2) * 2,4-Dimethoxyphenethylamine (2,4-DMPEA; DMPEA-3) * 2,5-Dimethoxyphenethylamine (2C-H; 2,5-DMPEA; DMPEA-4) * 2,6-Dimethoxyphenethylamine (2,6-DMPEA; DMPEA ...
. Its ''
in-vitro ''In vitro'' (meaning ''in glass'', or ''in the glass'') studies are performed with cells or biological molecules outside their normal biological context. Colloquially called " test-tube experiments", these studies in biology and its subdis ...
''
metabolism Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the co ...
and effects on cat behavior have been described. The drug showed no activity as a
norepinephrine reuptake inhibitor A norepinephrine reuptake inhibitor (NRI, NERI) or noradrenaline reuptake inhibitor or adrenergic reuptake inhibitor (ARI), is a type of drug that acts as a reuptake inhibitor for the neurotransmitters norepinephrine (noradrenaline) and epinep ...
or
releasing agent A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the release of one or more monoamine neurotransmitters from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrati ...
''in vitro''. It is relatively unaffected by
monoamine oxidase Monoamine oxidases (MAO) () are a family of enzymes that catalyze the oxidation of monoamines, employing oxygen to clip off their amine group. They are found bound to the outer membrane of mitochondria in most cell types of the body. The fi ...
(MAO) and is said to be behaviorally inactive in animals. The effects of 2,6-DMPEA in humans have not been reported and are unknown. 2,6-DMPEA was first described in the
scientific literature Scientific literature encompasses a vast body of academic papers that spans various disciplines within the natural and social sciences. It primarily consists of academic papers that present original empirical research and theoretical ...
by at least 1962. It was included as an entry in
Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...
's 2011 book '' The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds''. Notable
derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...
s of 2,6-DMPEA include the psychedelic and related drugs
Ψ-2C-T-4 2C-T-4, also known as 4-isopropylthio-2,5-dimethoxyphenethylamine, is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and is used as entheogenic recreational drug. Effects 2C-T-4 produces psychedelic ...
(psi-2C-T-4),
ψ-DOM ψ-DOM, or psi-DOM, also known as 2,6-dimethoxy-4-methylamphetamine, is a hallucinogenic, psychedelic drug of the Ψ-PEA family and a structural isomer of the better-known hallucinogen DOM. ψ-DOM was first reported by Alexander Shulgin in his ...
(psi-DOM), and
CT-5172 CT-5172, also known as 2,6-dimethoxy-3,5-dichlorophenethylamine, is a claimed hallucinogen of the phenethylamine family. It is an analogue of the serotonergic psychedelics mescaline and the 2C series but with an unusual substitution pattern on t ...
.


See also

*
Substituted methoxyphenethylamine Methoxyphenethylamines (MPEAs), as well as methoxyamphetamines (MAs) in the case of the amphetamine (α-methylphenethylamine) homologues, are substituted phenethylamines with one or more methoxy groups. In some cases, one or more of the methoxy ...
*
Dimethoxyphenethylamine Dimethoxyphenethylamine may refer to: * 2,3-Dimethoxyphenethylamine (2,3-DMPEA; DMPEA-2) * 2,4-Dimethoxyphenethylamine (2,4-DMPEA; DMPEA-3) * 2,5-Dimethoxyphenethylamine (2C-H; 2,5-DMPEA; DMPEA-4) * 2,6-Dimethoxyphenethylamine (2,6-DMPEA; DMPEA ...
* 2,6-Dimethoxyamphetamine * TMA-6 (2,4,6-trimethoxyamphetamine)


References


External links


2,6-DMPEA - Isomer Design
{{DEFAULTSORT:Dimethoxyphenethylamine, 2,6- Methoxyphenethylamines