Substituted Methylenedioxyphenethylamines
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The substituted methylenedioxyphenethylamines (abbreviated as MDxx) represent a diverse chemical class of compounds derived from
phenethylamines Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative (chemistry), derivative compounds of phenethylamine ...
. This category encompasses numerous psychoactive substances with
entactogenic Entactogens, also known as empathogens or connectogens, are a class of psychoactive drugs that induce the production of experiences of emotional communion, oneness, connectedness, emotional openness—that is, empathy—as particularly observe ...
,
psychedelic 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 halluci ...
, and/or stimulant properties, in addition to entheogens. These compounds find application as
research chemicals Research chemicals are chemical substances which scientists use for medical and scientific research purposes. One characteristic of a research chemical is that it is for laboratory research use only; a research chemical is not intended for human ...
,
designer drugs A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. ...
, and recreational substances. The base
compound Compound may refer to: Architecture and built environments * Compound (enclosure), a cluster of buildings having a shared purpose, usually inside a fence or wall ** Compound (fortification), a version of the above fortified with defensive struc ...
of the MDxx class is
3,4-methylenedioxyphenethylamine 3,4-Methylenedioxyphenethylamine, also known as 3,4-MDPEA, MDPEA, and homopiperonylamine, is a substituted phenethylamine formed by adding a methylenedioxy group to phenethylamine. It is structurally similar to MDA, but without the methyl gro ...
(MDPEA), and the prototypical agent of this class is 3,4-methylenedioxy-''N''-methylamphetamine (MDMA; "ecstasy"). Other notable MDxx class substances include 3,4-methylenedioxyamphetamine (MDA), 3,4-methylenedioxy-''N''-ethylamphetamine (MDEA; "Eve"), ''N''-methyl-1,3-benzodioxolylbutanamine (MBDB; "Eden"), and 3,4-methylenedioxy-''N''-methylcathinone (βk-MDMA; "Methylone").


List of substituted methylenedioxyphenethylamines

The compounds most commonly regarded as comprising the family of MDxx derivatives include:


Related compounds

In addition, there are a number of other compounds that have some structural and pharmacological similarities to the methylenedioxyphenethylamines, and are useful for comparison. These can be broadly divided into (i) compounds where the methylenedioxyphenyl ring is retained but the phenethyl portion is modified, or (ii) compounds which retain the 3,4-cyclised amphetamine core common to the MDxx compounds, but have the 1,3- benzodioxole ring replaced by related heterocycles. In addition to the (i) and (ii) compounds, MDxx compounds are closely related to the other two main phenylethylamine classes, those being
substituted amphetamines Substituted amphetamines, or simply amphetamines, are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetam ...
and substituted cathinones. Like amphetamines and cathinones, MDxx compounds derive most if not all of their stimulant effects from the
phenylethylamine 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 ...
core, in fact most MDxx compounds can also be grouped with cathinones and or amphetamines due to having similar functional groups, but in most cases any compound with a
methylenedioxy Methylenedioxy is the term used in the field of chemistry, particularly in organic chemistry, for a functional group with the structural formula which is connected to the rest of a molecule by two chemical bonds. The methylenedioxy group consist ...
group attached will be grouped as an MDxx compound due to the unique hallucinogenic and empathogenic/entactogenic effects that are not present in most other amphetamines and present to a lesser extent in most cathinones.


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 ...
* 2Cs,
DOx 4-Substituted-2,5-dimethoxyamphetamines (DO''x'') is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- positio ...
, 4Cs,
25-NB The 25-NB (25''x''-NB''x'') series, or NBOMe series, also known as the ''N''-benzylphenethylamines, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C family. The most commonly encountere ...
*
Substituted amphetamine Substituted amphetamines, or simply amphetamines, are a chemical class, class of compounds based upon the amphetamine structure; it includes all derivative (chemistry), derivative compounds which are formed by replacing, or substitution reacti ...
s *
Substituted benzofuran The substituted benzofurans are a class of chemical compounds based on the heterocyclic compound, heterocyclic and polycyclic compound, polycyclic compound benzofuran. Many medicines use the benzofuran core as a scaffold, but most commonly the t ...
s *
Substituted cathinone Substituted cathinones, or simply cathinones, which include some stimulants and Empathogen-entactogen, entactogens, are chemical derivative, derivatives of cathinone. They feature a substituted phenethylamine, phenethylamine core with an alkyl ...
s *
Substituted phenethylamine Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative (chemistry), derivative compounds of phenethylamine ...
s * Substituted phenmetrazines *
Substituted tryptamine Substituted tryptamines, or simply tryptamines, also known as serotonin analogues (i.e., 5-hydroxytryptamine analogues), are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all trypt ...
s * ''
PiHKAL ''PiHKAL: A Chemical Love Story'' is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is Psychoactive drug, psychoactive phenethylamine Derivative (chemistry), chemical derivatives, notably those that act ...
'' * ''
The Shulgin Index ''The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds'' is a 2011 book written by Alexander Shulgin, Tania Manning, and Paul F. Daley and published by Transform Press. It followed the earlier books ''PiHKAL, PiHKAL: A ...
''


References


External links


PiHKAL ("Phenethylamines i Have Known And Loved")
by Alexander "Sasha" Shulgin (1991)
Psychotomimetic Drugs: Structure-Activity Relationships
by Alexander "Sasha" Shulgin (1978)
Mescaline: The Chemistry and Pharmacology of its Analogues
by Alexander "Sasha" Shulgin (1972) {{DEFAULTSORT:Substituted Methylenedioxyphenethylamines Alexander Shulgin Chemical classes of psychoactive drugs Methylenedioxyphenethylamines