chemistry

Substituted methoxyphenethylamine

Substituted methoxyphenethylamine is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Substituted methoxyphenethylamine rather than just read about it. In short: 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 groups may also be extended to form other alkoxy and related groups such as ethoxy or propoxy.

Key takeaways

Substituted methoxyphenethylamine belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Substituted methoxyphenethylamine to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Substituted methoxyphenethylamine from memory before moving on to harder problems.

Reference excerpt

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 groups may also be extended to form other alkoxy and related groups 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, 2C-B, TMA, DOM, and 25I-NBOMe, are serotonin 5-HT2A receptor agonists and serotonergic psychedelics. Other methoxyphenethylamines, particularly monomethoxyamphetamines like para-methoxyamphetamine (PMA), are monoamine releasing agents of serotonin, norepinephrine, and/or dopamine, with stimulant and/or entactogen-related effects. Compounds closely related to methoxyphenethylamines include methylenedioxyphenethylamines (MDxx) like MDA, MDMA, 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 rings to create benzofuran ring systems. Almost all known psychedelic phenethylamines are either methoxyphenethylamines or closely related compounds like MDxx or benzofurans. There are only a few known exceptions, such as fenfluramine and lorcaserin, which can both produce psychedelic effects at high and supratherapeutic doses. This is in notable contrast to tryptamines such as dimethyltryptamine (DMT), 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-D, 2C-E, 2C-I, 2C-T-2) TWEETIOs (e.g., 2CB-2-EtO, 2CD-5-EtO, 2CT2-2-EtO, ASR-2001 (2CB-5PrO)) Scalines (4-substituted 3,5-DMPEAs) (e.g., 4-desoxymescaline (DESOXY; 4-Me-3,5-DMPEA)) Ψ-PEAs (4-substituted 2,6-DMPEAs) (e.g., Ψ-2C-T-4) Trimethoxyphenethylamines (TMPEAs) (e.g., 2,4,5-TMPEA (2C-O; TMPEA-2), mescaline (3,4,5-TMPEA; TMPEA-1), isomescaline (2,3,4-TMPEA; TMPEA-3), ψ-2C-O (2,4,6-TMPEA), 2,3,5-TMPEA (TMPEA-4), 2,3,6-TMPEA (TMPEA-5)) 2Cs (4-substituted 2,5-DMPEAs) (e.g., 2C-O, 2C-O-4, 2C-O-22) Scalines (4-substituted 3,5-DMPEAs) (e.g., mescaline, escaline, proscaline, allylescaline, methallylescaline) Ψ-PEAs (4-substituted 2,6-DMPEAs) (e.g., Ψ-2C-O (TMPEA-6), Ψ-2C-DFMO (ψ-2C-O-35)) Other substitution patterns (e.g., 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., 25I-NBOMe, NBOMe-mescaline) PEA-NDEPAs (e.g., PEA-NM-NDEPA, 3,4-DMPEA-NDEPA, 25D-NM-NDEAOP (25D-NM-NDEPA), M-NDEPA)

Amphetamines

Monomethoxyamphetamines (MAs) (e.g., OMA (2-MA), MMA (3-MA), PMA (4-MA), 3-methoxy-4-methylamphetamine (MMA), 4-ETA, 2-TOM, 5-TOM, 2-TOET, 5-TOET, TOMSO) N-Alkyl-MAs (e.g., methoxyphenamine (OMMA), MMMA, PMMA, PMEA) Dimethoxyamphetamines (DMAs) (e.g., 2,4-DMA (DMA-3), 2,5-DMA (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, DOC, DOET, DOI, DOM, Aleph (DOT)) N-Alkyl-DOx (e.g., Beatrice (methyl-DOM; MDOM), N-methyl-DOET, methyl-DOB (MDOB), N-methyl-DOI, IDNNA (N,N-dimethyl-DOI), N-methyl-TMA-2) 3Cs (4-substituted 3,5-DMAs) (e.g., 4-Br-3,5-DMA, 4-PhPr-3,5-DMA) Ψ-PEAs (4-substituted 2,6-DMAs) (e.g., Ψ-DOM, Ψ-DODFMO, TMA-6 (Ψ-TMA-2; 2,4,6-TMA)) 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; Ψ-TMA-2)) N-Alkyl-TMAs (e.g., N-methyl-TMA, N-methyl-TMA-2) DOx (4-substituted 2,5-DMAs) (e.g., TMA-2, MEM, MPM, MALM, MMALM, MTFEM) 3Cs (4-substituted 3,5-DMAs) (e.g., TMA (3C-M), 3C-E, 3C-P, 3C-AL, 3C-MAL, 3C-DFE, 3C-TFE, 3C-BZ) Ψ-PEAs (4-substituted 2,6-DMAs) (e.g., TMA-6 (Ψ-TMA-2)) Tetramethoxyamphetamines (TeMAs) (e.g., TeMA (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 (4C-D), 4C-B, 4C-I, 4C-P, 4C-T-2, 4C-TFM) Others (e.g., α-ethylmescaline (AEM))

α-Propylphenethylamines

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

Others and related compounds

Ring-extended phenethylamines

Methylenedioxyphenethylamines (MDxx) (e.g., MDPEA (homopiperonylamine), MDMPEA (homarylamine), MDA (tenamfetamine), MDMA (midomafetamine), MDEA, BDB (J), MBDB (methyl-J), BDP (K), MPAP (PBDP; propyl-K), methylone (MDMC)) Monomethoxymethylenedioxyphenethylamines (MMPEAs) (e.g., lophophine (MMDPEA; 2C-MMDA-1), 2C-MMDA-2 (MMDPEA-2; 2C-2), 2C-MMDA-3a (MMDPEA-3a; 2C-3a), 2C-MMDA-4, MMDA, MMDA-2, MMDA-3a, MMDA-3b, MMDA-4, MMDA-5, EMDA-2) 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, EDMC, MEDA) Benzofurans (e.g., 5-APB, 5-MAPB, 6-APB, 5-APDB, 6-APDB, F (F-1), F-2, F-22, DOH-5-hemiFLY (semi-fly), DOB-5-hemiFLY (bromo-semi-fly)) FLY compounds (benzodifurans) (e.g., 2C-B-FLY, DOB-FLY, Bromo-DragonFLY (DOB-DFLY), TFMFly) Methylenethiooxyphenethylamines (e.g., SDA (3T-MDA), SDMA (3T-MDMA), 4T-MMDA-2) Others (e.g., MTDA)

Rigid/constrained phenethylamines

… excerpt ends here. Continue reading the full article.

Illustrations

Worked examples

Example 1 — a first encounter with Substituted methoxyphenethylamine

Start with the simplest possible case. Write down what Substituted methoxyphenethylamine claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Substituted methoxyphenethylamine before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Substituted methoxyphenethylamine ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Substituted methoxyphenethylamine

In research: Substituted methoxyphenethylamine appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Substituted methoxyphenethylamine in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Substituted methoxyphenethylamine is common in secondary-school and first-year university syllabi. It links to neighbouring topics Alexander Shulgin, Chemical classes of psychoactive drugs, Methoxyphenethylamines, so understanding it makes those chapters shorter.
In everyday life: Look for Substituted methoxyphenethylamine outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Substituted methoxyphenethylamine in 20 minutes

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Frequently asked questions

What is Substituted methoxyphenethylamine in simple terms?

Why does Substituted methoxyphenethylamine matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Substituted methoxyphenethylamine?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Substituted methoxyphenethylamine.