Methoxyphenethylamines (MPEAs), as well as methoxyamphetamines (MAs) in the case of the

amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...

(α-methylphenethylamine) homologues, are

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 with one or more

methoxy group In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...

s. In some cases, one or more of the methoxy groups may also be extended to form other

alkoxy In chemistry, the alkoxy group is an alkyl group which is Single bond, singularly bonded to oxygen; thus . Denoted usually with apostrophe('). The range of alkoxy groups is vast, the simplest being methoxy (). An ethoxy group () is found in the ...

and related

group A group is a number of persons or things that are located, gathered, or classed together. Groups of people * Cultural group, a group whose members share the same cultural identity * Ethnic group, a group whose members share the same ethnic iden ...

s such as ethoxy or propoxy. Methoxyphenethylamines may have additional substitutions as well. Many methoxyphenethylamines that have multiple methoxy groups in the 2- through 5-positions of the phenyl ring, for instance

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 ...

, 2C-B, TMA, DOM, and

25I-NBOMe 25I-NBOMe, also known as 2C-I-NBOMe, Cimbi-5, and shortened to "25I", is a psychedelic drug of the phenethylamine, 2C, and NBOMe (25-NB) families. Since 2010, it has circulated in the recreational drug scene, often misrepresented as LSD. It is ...

, are

serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...

5-HT_2A receptor

agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...

s and

serotonergic 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 ...

s. Other methoxyphenethylamines, particularly monomethoxyamphetamines like ''para''-methoxyamphetamine (PMA), are

monoamine 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 ...

s of

norepinephrine Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic compound, organic chemical in the catecholamine family that functions in the brain and human body, body as a hormone, neurotransmitter and neuromodulator. The ...

, and/or

dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. It is an amine synthesized ...

, with

stimulant Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, ...

and/or

entactogen 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 ...

-related effects. Compounds closely related to methoxyphenethylamines include

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 3,4-Methylenedioxyamphetamine, MD ...

s (MDxx) like MDA,

MDMA 3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form), is an empathogen–entactogenic drug with stimulant and minor Psychedelic drug, psychedelic properties. In studies, it has been used ...

, and MMDA, in which two adjacent methoxy groups are bridged, and FLY compounds like 2C-B-FLY, in which methoxy groups are cyclized into

furan Furan is a Heterocyclic compound, heterocyclic organic compound, consisting of a five-membered aromatic Ring (chemistry), ring with four carbon Atom, atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as f ...

ring (The) Ring(s) may refer to: * Ring (jewellery), a round band, usually made of metal, worn as ornamental jewelry * To make a sound with a bell, and the sound made by a bell Arts, entertainment, and media Film and TV * ''The Ring'' (franchise), a ...

s to create

benzofuran Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. This colourless liquid is a component of coal tar. Benzofuran is the structural nucleus (parent compound) of many related compounds with more complex stru ...

ring system A ring system is a disc or torus orbiting an astronomical object that is composed of solid material such as dust, meteoroids, planetoids, moonlets, or stellar objects. Ring systems are best known as planetary rings, common components of sate ...

s. Almost all known psychedelic phenethylamines are either methoxyphenethylamines or closely related compounds like MDxx or

s. There are only a few known exceptions, such as

fenfluramine Fenfluramine, sold under the brand name Fintepla, is a serotonergic medication used for the treatment of seizures associated with Dravet syndrome and Lennox–Gastaut syndrome. It was formerly used as an appetite suppressant in the treat ...

and

lorcaserin Lorcaserin, marketed under the brand name Belviq, was a weight-loss drug developed by Arena Pharmaceuticals. It reduces appetite by activating serotonin receptor the 5-HT2C receptor in the hypothalamus, a region of the brain which is known to ...

, which can both produce psychedelic effects at high and supratherapeutic doses. This is in notable contrast to

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 such as DET, which require no specific ring substitutions to be psychedelic.

List of methoxyphenethylamines

Phenethylamines

* Monomethoxyphenethylamines (MPEAs) (e.g., 2-MPEA, 3-MPEA, 4-MPEA) * Dimethoxyphenethylamines (DMPEAs) (e.g., 2,5-DMPEA (2C-H), 3,4-DMPEA, 3,5-DMPEA (DMPEA-6), MEPEA, macromerine) ** 2Cs (4-substituted 2,5-DMPEAs) (e.g., 2C-B,

2C-C 2C-C is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. In his book '' PiHKAL (Phenethylamines i Have Known And Loved)'', Shulgin lists the dosage range as 20–40 mg. 2C- ...

2C-D 2C-D, also known as 2C-M or as 2,5-dimethoxy-4-methylphenethylamine, is a psychedelic drug of the 2C family that is sometimes used as an entheogen. It was first synthesized in 1970 by a team from the Texas Research Institute of Mental Sciences, a ...

2C-E 2C-E is a Psychedelic drug, psychedelic phenethylamines, phenethylamine of the 2C (psychedelics), 2C family. It was first synthesized by Alexander Shulgin and documented in his book ''PiHKAL''. Like the other substances in its family, it produces ...

2C-I 2C-I, also known as 2,5-dimethoxy-4-iodophenethylamine, is a phenethylamine of the 2C family with psychedelic effects. It was first synthesized by Alexander Shulgin, and is described in Shulgin's book ''PiHKAL'' (1991). The substance is con ...

, 2C-T-2) *** TWEETIOs (e.g., 2CD-2-ETO, 2CD-5-ETO, 2CE-5-ETO, 2CT2-5-ETO, ASR-2001 (2CB-5PrO)) ** Scalines (4-substituted 3,5-DMPEAs) (e.g., 4-desoxymescaline (DESOXY; 4-Me-3,5-DMPEA)) * Trimethoxyphenethylamines (TMPEAs) (e.g., 2,4,5-TMPEA (TMPEA-2; 2C-O),

(3,4,5-TMPEA), isomescaline (2,3,4-TMPEA)) ** 2Cs (4-substituted 2,5-DMPEAs) (e.g., 2C-O, 2C-O-2, 2C-O-4) ** Scalines (4-substituted 3,5-DMPEAs) (e.g.,

escaline Escaline (E), also known as 3,5-dimethoxy-4-ethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline. It is the 4- ethoxy analogue of mescaline (3,4,5-trimethoxyphenethylamine) and the pheneth ...

proscaline Proscaline (4-propoxy-3,5-dimethoxyphenethylamine or 4-propoxy-3,5-DMPEA) is a Psychedelic drug, psychedelic and hallucinogenic drug. It has structural properties similar to the drugs mescaline, isoproscaline, and escaline. In ''PiHKAL'', Alexan ...

, allylescaline, methallylescaline) ** Other substitution patterns (e.g., ψ-2C-T-4, isomescaline, CT-5172) * Tetramethoxyphenethylamines (TeMPEAs) (e.g., TeMPEA (2,3,4,5-TeMPEA), TeMPEA-2 (2,3,4,6-TeMPEA), TeMPEA-3 (2,3,5,6-TeMPEA)) * Pentamethoxyphenethylamine (PeMPEA or 2,3,4,5,6-PeMPEA) * 25-NB or NBOMes (''N''-benzyl-MPEAs) (e.g.,

, NBOMe-mescaline) * PEA-NDEPAs (e.g., 3,4-DMPEA-NDEPA, 25D-NM-NDEAOP (25D-NM-NDEPA), M-NDEPA)

Amphetamines

* Monomethoxyamphetamines (MAs) (e.g., OMA (2-MA),

MMA Mixed martial arts (MMA) is a full-contact fighting sport based on striking and grappling; incorporating techniques from various combat sports from around the world. In the early 20th century, various inter-stylistic contests took place t ...

(3-MA), PMA (4-MA), 3-methoxy-4-methylamphetamine (MMA), 4-ETA, 2-TOM, 5-TOM, 2-TOET, 5-TOET, TOMSO) ** ''N''-

Alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl group is derived from a cy ...

MAs (e.g., methoxyphenamine (OMMA), MMMA, PMMA, PMEA) * Dimethoxyamphetamines (DMAs) (e.g., 2,4-DMA (DMA-3),

2,5-DMA 2,5-Dimethoxyamphetamine (2,5-DMA), also known as DMA-4 or as DOH, is a drug of the substituted phenethylamine, phenethylamine and substituted amphetamine, amphetamine families. It is one of the dimethoxyamphetamine (DMA) series of positional iso ...

(DMA-4; DOH), 3,4-DMA, 3,5-DMA (DMA-6), 3,4-DMMA, methoxamine (β-OH-2,6-DMA)) ** DOx (4-substituted 2,5-DMAs) (e.g.,

DOB DOB or Dob often refers to date of birth. DOB or Dob may also refer to: Biochemistry * 2,5-dimethoxy-4-bromoamphetamine, Bromo-DMA, a psychedelic drug ** Meta-DOB, related substance ** Methyl-DOB, related substance * HLA-DOB, human gene Organiz ...

DOC DOC, Doc, doc or DoC may refer to: People and characters * Doc, an abbreviation of doctor * Doc (nickname) * Doc (mascot), the Towson University mascot Persons * The D.O.C., American rapper (born 1968) * Doc Gallows (born 1983), ring nam ...

, DOET, DOI, DOM,

Aleph Aleph (or alef or alif, transliterated ʾ) is the first Letter (alphabet), letter of the Semitic abjads, including Phoenician alphabet, Phoenician ''ʾālep'' 𐤀, Hebrew alphabet, Hebrew ''ʾālef'' , Aramaic alphabet, Aramaic ''ʾālap'' � ...

(DOT)) *** ''N''-Alkyl DOx (e.g., Beatrice (methyl-DOM; MDOM), methyl-DOB (MDOB), ''N''-methyl-DOI, IDNNA (''N'',''N''-dimethyl-DOI)) ** 3Cs (4-substituted 3,5-DMAs) (e.g., 4-Br-3,5-DMA, 4-I-3,5-DMA,

4-PhPr-3,5-DMA 4-PhPr-3,5-DMA, also known as 4-(3-phenylpropyl)-3,5-dimethoxyamphetamine, is a serotonin receptor modulator of the phenethylamine and amphetamine families. It is structurally related to the DOx drugs but has one of its methoxy groups in the 3 ...

) ** Other substitution patterns (e.g., ψ-DOM) * Trimethoxyamphetamines (TMAs) (e.g., TMA (3,4,5-TMA), TMA-2 (2,4,5-TMA), TMA-3 (2,3,4-TMA), TMA-4 (2,3,5-TMA), TMA-5 (2,3,6-TMA), TMA-6 (2,4,6-TMA)) ** DOx (4-substituted 2,5-DMAs) (e.g., TMA-2, MEM, MPM, MIPM,

MALM is a village in Steinkjer Municipality in Trøndelag county, Norway. The village of Malm is located along the Beitstadsundet strait which flows into the Trondheimsfjorden. The village of Bartnes lies across the strait from Malm. The village li ...

, MFEM) ** 3Cs (4-substituted 3,5-DMAs) (e.g., TMA,

3C-E 3C-E (3,5-Dimethoxy-4-ethoxyamphetamine) is a psychedelic of the amphetamine class. It was first synthesized by Alexander Shulgin. In his book ''PiHKAL'', Shulgin lists the dosage range as 30 to 60 mg, consumed orally. The duration of act ...

3C-P 3C-P, also known as 4-propoxy-3,5-dimethoxyamphetamine, is a psychedelic phenethylamine. It has structural and pharmacodynamic properties similar to the drugs mescaline, proscaline, and amphetamine. Little information exists on the human pharma ...

, 3C-IP, 3C-AL, 3C-MAL, 3C-FE) * Tetramethoxyamphetamines (TeMAs) (e.g.,

TeMA Tema is a city on the Bight of Benin and Atlantic coast of Ghana. It is located east of the capital city; Accra, in the region of Greater Accra, and is the capital of the Tema Metropolitan District. As of 2013, Tema is the eleventh most p ...

(2,3,4,5-TeMA), TeMA-2 (2,3,4,6-TeMA), TeMA-3 (2,3,5,6-TeMA)) * Pentamethoxyamphetamine (PeMPA or 2,3,4,5,6-PeMPA) * 25-NB or NBOMes (''N''-benzyl-MAs) (e.g., DOM-NBOMe, DOB-NBOMe, DOI-NBOMe) * AMPH-NDEPAs (e.g., DOB-NDEPA, DOI-NDEPA, DOM-NDEPA, DOTFM-NDEPA, TMA-2-NDEPA)

Phenylisobutylamines

* 4Cs (4-substituted 2,5-dimethoxyphenylisobutylamines) (e.g.,

Ariadne In Greek mythology, Ariadne (; ; ) was a Cretan princess, the daughter of King Minos of Crete. There are variations of Ariadne's myth, but she is known for helping Theseus escape from the Minotaur and being abandoned by him on the island of N ...

(4C-D), 4C-B, 4C-C, 4C-E, 4C-I, 4C-T-2)

α-Propylphenethylamines

* 5Cs (4-substituted 2,5-dimethoxy-α-propylphenethylamines) (e.g., 5C-D)

Others and related compounds

Ring-extended phenethylamines

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 3,4-Methylenedioxyamphetamine, MD ...

s (MDxx) (e.g., MDPEA, MDMPEA, MDA,

MDEA MDEA may refer to: * Methyl diethanolamine (''N''-methyl-diethanolamine), CH3N(C2H4OH)2, a chemical used for amine gas treating, also known as gas sweetening or acid gas removal, the removal of hydrogen sulfide and carbon dioxide from gasses in the ...

, BDB (J), MBDB (methyl-J), BDP (K), MPAP (propyl-K),

methylone Methylone, also known as 3,4-methylenedioxy-''N''-methylcathinone (MDMC), is an entactogen and stimulant drug of the amphetamine, cathinone, and benzodioxole families related to 3,4-methylenedioxymethamphetamine (MDMA; "ecstasy"). It is th ...

(MDMC)) ** Monomethoxymethylenedioxyphenethylamines (MMPEAs) (e.g.,

lophophine Lophophine, also known as 3-methoxy-4,5-methylenedioxyphenethylamine (MMDPEA), is a putative psychedelic and entactogen drug of the methylenedioxyphenethylamine family. It is the α-demethylated homologue of MMDA, and is also closely related t ...

(MMDPEA), 2C-MMDA-2, 2C-MMDA-3a, 2C-MMDA-4, MMDA, MMDA-2, MMDA-3a, MMDA-3b, MMDA-4, MMDA-5) ** Dimethoxymethylenedioxyphenethylamines (DMMPEAs) (e.g., 2C-DMMDA, 2C-DMMDA-2, DMMDA, DMMDA-2, DMMDA-3, DMMDA-4, DMMDA-5, DMMDA-6) * Ethylenedioxyphenethylamines (EDxx) (e.g., EDA,

EDMA 3,4-Ethylenedioxy-''N''-methylamphetamine (EDMA) is an entactogen drug of the substituted amphetamine, methamphetamine class. It is an structural analog, analogue of 3,4-methylenedioxy-N-methylamphetamine, MDMA where the methylenedioxy functiona ...

, EDMC) *

Benzofuran Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. This colourless liquid is a component of coal tar. Benzofuran is the structural nucleus (parent compound) of many related compounds with more complex stru ...

s and FLY compounds (e.g.,

5-APB 5-APB (abbreviation of "5-(2-aminopropyl)benzofuran") is an empathogenic psychoactive compound of the phenethylamine, amphetamine, and benzofuran families. The drug and other compounds have sometimes been informally called "Benzofury". 5-APB ha ...

, 6-APB, 5-APDB, 6-APDB, 2C-B-FLY, DOB-FLY, Bromo-DragonFLY, TFMFly, F-2, F-22)

Rigid/constrained phenethylamines

Tetrahydroisoquinoline Tetrahydroisoquinoline (TIQ or THIQ), also known as AMPH-CR, is an organic compound with the chemical formula C9H11N. Classified as a secondary amine, it is derived from isoquinoline by hydrogenation. It is a colorless viscous liquid that is mis ...

s (e.g., anhalinine, pellotine, lophophorine, DOM-CR) *

Phenylcyclopropylamine Phenylcyclopropylamines, or 2-phenylcyclopropylamines, also known as phenylcypromines, are phenethylamine and amphetamine derivatives in which the alkyl side chain has been cyclized into a cyclopropyl ring. Examples include the monoamine oxidase ...

s (e.g., DMCPA, TMT) * 1-Aminomethylindanes (1-AMIs) (e.g.,

2CB-Ind 2CB-Ind is a conformationally-restricted derivative of the phenethylamine hallucinogen 2C-B, discovered in 1974 by Alexander Shulgin. It acts as a moderately potent and selective agonist for the 5-HT2A and 5-HT2C receptors, but unlike the co ...

, AMMI,

jimscaline Jimscaline (C-(4,5,6-trimethoxyindan-1-yl)methanamine) is a conformationally-restricted derivative of the cactus-derived hallucinogen mescaline, which was reported in 2006 by a team at Purdue University led by David E. Nichols. It acts as a po ...

) * 2-Aminoindanes (2-AIs) (e.g., DOM-AI, MDAI, MDMAI, MEAI, MMAI) *

2-Aminotetralin 2-Aminotetralin (2-AT), also known as 1,2,3,4-tetrahydronaphthalen-2-amine (THN), is a stimulant drug with a chemical structure consisting of a tetralin core with an amine as substituent. 2-AT is a rigid analogue of phenylisobutylamine and ful ...

s (2-ATs) (e.g., DOM-AT, MDAT, MDMAT) * Benzocyclobutenes (e.g., 2CBCB-NBOMe,

TCB-2 TCB-2 is a hallucinogen discovered in 2006 by Thomas McLean working in the lab of David Nichols at Purdue University. It is a conformationally-restricted derivative of the phenethylamine 2C-B, also a hallucinogen, and acts as a potent agonis ...

, tomscaline) * Tetrahydrobenzopyrans (e.g., CT-5126) * Benzoxepins (e.g., TFMBOX) * Others (e.g., 2C-B-aminorex, 2C-B-morpholine, DMBMPP (juncosamine), LPH-5, LPH-48, Z3517967757, ZC-B)

Other psychedelic phenethylamines

There are few known

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 ...

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 ...

s that are not methoxyphenethylamines or related compounds like

s or

s. Those that are known include the 3-

trifluoromethyl The trifluoromethyl group is a functional group that has the formula . The naming of is group is derived from the methyl group (which has the formula ), by replacing each hydrogen atom by a fluorine atom. Some common examples are trifluoromethane ...

phenethylamine

, the rigid 4- chloro phenethylamine

, and the

benzothiophene Benzothiophene is an aromatic organic compound with a molecular formula C8H6S and an odor similar to naphthalene (mothballs). It occurs naturally as a constituent of petroleum-related deposits such as lignite tar. Benzothiophene has no househol ...

s 5-APBT and 6-APBT. Certain other phenethylamines, like naphthylaminopropane (NAP; PAL-287), are also known to act as