Methylethyltryptamine (MET), also known as ''N''-methyl-''N''-ethyltryptamine (''N'',''N''-MET), is a

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 ...

of the

tryptamine Tryptamine is an indolamine metabolite of the essential amino acid tryptophan. The chemical structure is defined by an indole—a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the firs ...

family. It is closely related to

dimethyltryptamine Dimethyltryptamine (DMT), also known as ''N'',''N''-dimethyltryptamine (''N'',''N''-DMT), is a Psychedelic drug, serotonergic hallucinogen and Investigational New Drug, investigational drug of the substituted tryptamine, tryptamine family tha ...

(DMT) and to

diethyltryptamine DET, also known under its chemical name ''N'',''N''-diethyltryptamine and as T-9, is a psychedelic drug closely related to DMT and 4-HO-DET. DET, alongside DMT, was placed into the UN Schedule 1 list of illegal drugs in the 1970s, and is unco ...

(DET). The drug acts as an

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 ...

of the

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-HT₂ receptors and to a lesser extent as a

serotonin releasing agent A serotonin releasing agent (SRA) is a type of drug that induces the release of serotonin into the neuronal synaptic cleft. A selective serotonin releasing agent (SSRA) is an SRA with less significant or no efficacy in producing neurotransmitter ...

. It was encountered as a novel

designer drug 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. ...

Europe Europe is a continent located entirely in the Northern Hemisphere and mostly in the Eastern Hemisphere. It is bordered by the Arctic Ocean to the north, the Atlantic Ocean to the west, the Mediterranean Sea to the south, and Asia to the east ...

in 2014.

Use and effects

MET has been briefly mentioned 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 ''

TiHKAL ''TiHKAL: The Continuation'' is a 1997 book written by Alexander Shulgin and Ann Shulgin about a family of psychoactive drugs known as tryptamines. A sequel to '' PiHKAL: A Chemical Love Story'', ''TiHKAL'' is an acronym that stands for "Trypt ...

'' (''Tryptamines I Have Known and Loved'') and other publications, where he has stated it to be orally active as a psychedelic at doses of 80 to 100mg. The freebase of MET is active as a psychedelic via

vaporization Vaporization (or vapo(u)risation) of an element or compound is a phase transition from the liquid phase to vapor. There are two types of vaporization: evaporation and boiling. Evaporation is a surface phenomenon, whereas boiling is a bulk phenome ...

at a dose of 15mg per a 2011

Erowid Erowid, also called Erowid Center, is a non-profit educational organization that provides information about psychoactive plants and chemicals. Erowid documents legal and illegal substances, including their intended and adverse effects. Inform ...

trip report."That's okay, you're good" MET trip report
- ''The Vaults of Erowid''

Interactions

Pharmacology

MET is a

5-HT_2A and 5-HT_2C receptor

partial agonist In pharmacology, partial agonists are drugs that bind to and activate a given Receptor (biochemistry), receptor, but have only partial Intrinsic activity, efficacy at the receptor relative to a full agonist. They may also be considered Ligand (bio ...

. It shows very weak activity as an agonist of the serotonin 5-HT_1A and 5-HT_2B receptors. In addition to acting at the serotonin 5-HT₂ receptors, MET is a

with lower

potency Potency may refer to: * Potency (pharmacology), a measure of the activity of a drug in a biological system * Virility * Cell potency, a measure of the differentiation potential of stem cells * In homeopathic dilutions, potency is a measure of ho ...

. It produces the

head-twitch response The head-twitch response (HTR), also sometimes known as wet dog shakes (WDS) in rats, is a rapid side-to-side head movement that occurs in mice and rats in association with serotonin 5-HT2A receptor activation. Serotonergic psychedelics like lys ...

, a behavioral proxy of

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 ...

effects, in animals.

Chemistry

MET, also known as ''N''-methyl''-N''-ethyltryptamine, is a

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 ...

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 ...

. It is closely related to ''N'',''N''-dimethyltryptamine (DMT) and to other ''N'',''N''-di

alkylated Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting al ...

tryptamines. Analogues of MET besides DMT include DET,

DPT DPT may refer to: Science and medicine * Dpt (unit) (dioptre/diopter), most commonly a unit measuring refraction and power in a lens or curved mirror * Dermatopontin, a human extracellular matrix protein * Dipropyltryptamine, a psychedelic tryptam ...

DiPT Diisopropyltryptamine (DiPT), also known as ''N'',''N''-diisopropyltryptamine, is a Psychedelic drug, psychedelic Psychedelics, dissociatives and deliriants, hallucinogenic drug of the substituted tryptamine, tryptamine family that has a unique ...

, DBT, MiPT, MBT, EPT, EiPT, and PiPT, among others.

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 MET include

4-HO-MET 4-HO-MET, also known as 4-hydroxy-''N''-methyl-''N''-ethyltryptamine or as metocin, is a lesser-known psychedelic drug of the tryptamine family related to psilocin. It is a close structural and functional analogue of psilocin (4-HO-DMT) and is ...

, 5-MeO-MET,

5-fluoro-MET Bretisilocin, also known by its developmental code name GM-2505 and as 5-fluoro-''N''-methyl-''N''-ethyltryptamine (5F-MET or 5-fluoro-MET), is a serotonergic psychedelic of the tryptamine family which is under development for the treatment of ...

, and

7-F-5-MeO-MET 7-F-5-MeO-MET (5-MeO-7-F-MET, 5-Methoxy-7-fluoro-''N''-methyl-''N''-ethyltryptamine) is a tryptamine derivative which acts as a serotonin receptor agonist selective for the 5-HT2 subtypes, with a EC50#Calculation of EC50, pEC50 of 8.71 at 5-HT2A ...

. The

lysergamide Lysergamides, also known as ergoamides or as lysergic acid amides, are amides of lysergic acid (LA). They are ergolines, with some lysergamides being found naturally in ergot as well as other fungi. Lysergamides are notable in containing embedd ...

counterpart of MET is

ETH-LAD ETH-LAD, or ETHLAD, also known as 6-ethyl-6-nor-lysergic acid diethylamide (6-ethyl-6-nor-LSD), is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD; also known as METH-LAD). It is slightly more potent than ...

, an analogue of

LSD Lysergic acid diethylamide, commonly known as LSD (from German ; often referred to as acid or lucy), is a semisynthetic, hallucinogenic compound derived from ergot, known for its powerful psychological effects and serotonergic activity. I ...

that was first developed and characterized by

History

MET appears to have first been described in the literature by 1981. It was specifically mentioned in Michael Valentine Smith's ''Psychedelic Chemistry''. Subsequently, MET was briefly described in

's ''

'' (''Tryptamines I Have Known and Loved'') in 1997. MET was encountered as a novel

in 2014.

References

External links

MET - Isomer Design

MET - Psychonaut Wiki

MET - Erowid

The Big & Dandy MET Thread - Bluelight

MET scraps - Bluelight
{{Tryptamines 5-HT2A agonists 5-HT2C agonists Designer drugs N,N-Dialkyltryptamines Entheogens Psychedelic tryptamines Serotonin releasing agents