Alphamethyltryptamine
Encyclopedia
α-Methyltryptamine is a psychedelic
, stimulant
, and entactogen drug
of the tryptamine
class. It was originally developed as an antidepressant by workers at Upjohn in the 1960s.
as schedule I controlled substance
s in the Controlled Substances Act
of the United States on April 4, 2003. αMT is still legal in most of the world.
with a methyl substituent
at the alpha carbon
. Its chemical relation to tryptamine is analogous to that of amphetamine
to phenethylamine
, amphetamine being α-methylphenethylamine. αMT is closely related to the neurotransmitter
serotonin
(5-hydroxytryptamine) which partially explains its mechanism of action
.
of serotonin
, norepinephrine
, and dopamine
, and as a non-selective
serotonin receptor agonist
. It also acts as a very weak, non-selective and reversible
inhibitor
of the enzyme
monoamine oxidase
(MAO), but this is unlikely to be very significant if at all with typical doses.
Like many other serotonin releasing agent
s, αMT's analogue αET has been shown to produce long-lasting serotonergic neurotoxicity at very high doses, and the same likely holds true for αMT as well, though no studies have been performed to verify this as of yet. However, based on anecdotal reports, both αMT and αET appear to produce considerably less of a hangover in comparison to MDMA, although this is not necessarily an indication of long-term safety.
Despite some experiential similarities, αMT is fairly different chemically from MDMA, and is part of the tryptamine
family. It can cause strong distortions, delusions and hallucinations, and many other effects similar to those of LSD, psilocin and MDMA.
and produces stimulation
. With 20–30 mg, euphoria
, empathy
, and psychedelic
effects become apparent and can last as long as 12 hours. 40+ mg is generally considered a strong dose, and may in rare cases or extreme doses last for 24 hours or more. αMT in freebase
form can be smoked, and 2–5 mg is typically used.
s including anxiety
, restlessness, muscle tension, jaw tightness, pupil dilation, tachycardia
, headache
s, nausea
, and vomiting
, among others.
in the United States. It is legal in the United Kingdom, however, and does not fall under the tryptamine clause as its substituent
is not on the nitrogen
position. See "2001 Misuse of Drugs Act: Schedule 1, Regulation 3" for more information. Similarly, Canada has no mention of this substance in the Controlled Drugs and Substances Act
.
αMT is reported to be a schedule 8 controlled drug in Australia
, though this is unconfirmed. It is known that 5-MeO-αMT is schedule 9 in Australia however.
, and the second a 22 year old FIU student in Miami. However, further analysis revealed that there was no AMT in the tablet Felicia Staats had taken There are reports of a third death, but there is currently no verifiable media information.
Psychedelic drug
A psychedelic substance is a psychoactive drug whose primary action is to alter cognition and perception. Psychedelics are part of a wider class of psychoactive drugs known as hallucinogens, a class that also includes related substances such as dissociatives and deliriants...
, stimulant
Stimulant
Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...
, and entactogen drug
Drug
A drug, broadly speaking, is any substance that, when absorbed into the body of a living organism, alters normal bodily function. There is no single, precise definition, as there are different meanings in drug control law, government regulations, medicine, and colloquial usage.In pharmacology, a...
of the tryptamine
Tryptamine
Tryptamine is a monoamine alkaloid found in plants, fungi, and animals. It is based around the indole ring structure, and is chemically related to the amino acid tryptophan, from which its name is derived...
class. It was originally developed as an antidepressant by workers at Upjohn in the 1960s.
History
In the 1990s αMT resurfaced as a drug of recreational use via easy access through the internet, leading to its placement along with 5-MeO-DiPT5-MeO-DIPT
5-methoxy-diisopropyltryptamine is a tryptamine psychedelic used as a recreational drug under the street names "foxy" and "foxy methoxy". 5-MeO-DiPT is orally active, and dosages between 6–20 mg are commonly reported. Many users note an unpleasant body load accompanies higher dosages...
as schedule I controlled substance
Controlled substance
A controlled substance is generally a drug or chemical whose manufacture, possession, or use are regulated by a government. This may include illegal drugs and prescription medications ....
s in the Controlled Substances Act
Controlled Substances Act
The Controlled Substances Act was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. The CSA is the federal U.S. drug policy under which the manufacture, importation, possession, use and distribution of certain...
of the United States on April 4, 2003. αMT is still legal in most of the world.
Chemistry
αMT is tryptamineTryptamine
Tryptamine is a monoamine alkaloid found in plants, fungi, and animals. It is based around the indole ring structure, and is chemically related to the amino acid tryptophan, from which its name is derived...
with a methyl substituent
Substituent
In organic chemistry and biochemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon...
at the alpha carbon
Alpha carbon
The alpha carbon in organic chemistry refers to the first carbon that attaches to a functional group . By extension, the second carbon is the beta carbon, and so on....
. Its chemical relation to tryptamine is analogous to that of amphetamine
Amphetamine
Amphetamine or amfetamine is a psychostimulant drug of the phenethylamine class which produces increased wakefulness and focus in association with decreased fatigue and appetite.Brand names of medications that contain, or metabolize into, amphetamine include Adderall, Dexedrine, Dextrostat,...
to phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...
, amphetamine being α-methylphenethylamine. αMT is closely related to the neurotransmitter
Neurotransmitter
Neurotransmitters are endogenous chemicals that transmit signals from a neuron to a target cell across a synapse. Neurotransmitters are packaged into synaptic vesicles clustered beneath the membrane on the presynaptic side of a synapse, and are released into the synaptic cleft, where they bind to...
serotonin
Serotonin
Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract, platelets, and in the central nervous system of animals including humans...
(5-hydroxytryptamine) which partially explains its mechanism of action
Mechanism of action
In pharmacology, the term mechanism of action refers to the specific biochemical interaction through which a drug substance produces its pharmacological effect...
.
Pharmacology
αMT acts as relatively balanced releasing agentReleasing agent
A releasing agent , or simply releaser, is a drug that induces the release of a neurotransmitter from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrations of the neurotransmitter. Many drugs use neurotransmitter release to exert their psychological and...
of serotonin
Serotonin
Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract, platelets, and in the central nervous system of animals including humans...
, norepinephrine
Norepinephrine
Norepinephrine is the US name for noradrenaline , a catecholamine with multiple roles including as a hormone and a neurotransmitter...
, and dopamine
Dopamine
Dopamine is a catecholamine neurotransmitter present in a wide variety of animals, including both vertebrates and invertebrates. In the brain, this substituted phenethylamine functions as a neurotransmitter, activating the five known types of dopamine receptors—D1, D2, D3, D4, and D5—and their...
, and as a non-selective
Binding selectivity
Binding selectivity refers to the differing affinities with which different ligands bind to a substrate forming a complex. A selectivity coefficient is the equilibrium constant for the reaction of displacement by one ligand of another ligand in a complex with the substrate...
serotonin receptor agonist
Agonist
An agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...
. It also acts as a very weak, non-selective and reversible
Reversible reaction
A reversible reaction is a chemical reaction that results in an equilibrium mixture of reactants and products. For a reaction involving two reactants and two products this can be expressed symbolically as...
inhibitor
Enzyme inhibitor
An enzyme inhibitor is a molecule that binds to enzymes and decreases their activity. Since blocking an enzyme's activity can kill a pathogen or correct a metabolic imbalance, many drugs are enzyme inhibitors. They are also used as herbicides and pesticides...
of the enzyme
Enzyme
Enzymes are proteins that catalyze chemical reactions. In enzymatic reactions, the molecules at the beginning of the process, called substrates, are converted into different molecules, called products. Almost all chemical reactions in a biological cell need enzymes in order to occur at rates...
monoamine oxidase
Monoamine oxidase
L-Monoamine oxidases are a family of enzymes that catalyze the oxidation of monoamines. They are found bound to the outer membrane of mitochondria in most cell types in the body. The enzyme was originally discovered by Mary Bernheim in the liver and was named tyramine oxidase...
(MAO), but this is unlikely to be very significant if at all with typical doses.
Like many other serotonin releasing agent
Serotonin releasing agent
A serotonin releasing agent is a type of drug which induces the release of serotonin from the pre-synaptic neuron into the synapse...
s, αMT's analogue αET has been shown to produce long-lasting serotonergic neurotoxicity at very high doses, and the same likely holds true for αMT as well, though no studies have been performed to verify this as of yet. However, based on anecdotal reports, both αMT and αET appear to produce considerably less of a hangover in comparison to MDMA, although this is not necessarily an indication of long-term safety.
Despite some experiential similarities, αMT is fairly different chemically from MDMA, and is part of the tryptamine
Tryptamine
Tryptamine is a monoamine alkaloid found in plants, fungi, and animals. It is based around the indole ring structure, and is chemically related to the amino acid tryptophan, from which its name is derived...
family. It can cause strong distortions, delusions and hallucinations, and many other effects similar to those of LSD, psilocin and MDMA.
Dosage and effects
αMT was used as an antidepressant at doses of 5–10 mg. At these levels it improves moodMood (psychology)
A mood is a relatively long lasting emotional state. Moods differ from emotions in that they are less specific, less intense, and less likely to be triggered by a particular stimulus or event....
and produces stimulation
Stimulant
Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...
. With 20–30 mg, euphoria
Euphoria
Euphoria is an emotional and mental state defined as a sense of great elation and well being.Euphoria may also refer to:* Euphoria , a genus of scarab beetles* Euphoria, a genus name previously used for the longan and other trees...
, empathy
Empathy
Empathy is the capacity to recognize and, to some extent, share feelings that are being experienced by another sapient or semi-sapient being. Someone may need to have a certain amount of empathy before they are able to feel compassion. The English word was coined in 1909 by E.B...
, and psychedelic
Psychedelic
The term psychedelic is derived from the Greek words ψυχή and δηλοῦν , translating to "soul-manifesting". A psychedelic experience is characterized by the striking perception of aspects of one's mind previously unknown, or by the creative exuberance of the mind liberated from its ostensibly...
effects become apparent and can last as long as 12 hours. 40+ mg is generally considered a strong dose, and may in rare cases or extreme doses last for 24 hours or more. αMT in freebase
Freebase (chemistry)
Freebase or free base refers to the pure basic form of an amine, as opposed to its salt form. The amine is usually an alkaloid natural product. Free base is commonly used in organic chemistry and pharmaceuticals to describe the unprotonated amine form of a compound.Most alkaloids are unstable in...
form can be smoked, and 2–5 mg is typically used.
Side effects
αMT can produce side effectSide effect
In medicine, a side effect is an effect, whether therapeutic or adverse, that is secondary to the one intended; although the term is predominantly employed to describe adverse effects, it can also apply to beneficial, but unintended, consequences of the use of a drug.Occasionally, drugs are...
s including anxiety
Anxiety
Anxiety is a psychological and physiological state characterized by somatic, emotional, cognitive, and behavioral components. The root meaning of the word anxiety is 'to vex or trouble'; in either presence or absence of psychological stress, anxiety can create feelings of fear, worry, uneasiness,...
, restlessness, muscle tension, jaw tightness, pupil dilation, tachycardia
Tachycardia
Tachycardia comes from the Greek words tachys and kardia . Tachycardia typically refers to a heart rate that exceeds the normal range for a resting heart rate...
, headache
Headache
A headache or cephalalgia is pain anywhere in the region of the head or neck. It can be a symptom of a number of different conditions of the head and neck. The brain tissue itself is not sensitive to pain because it lacks pain receptors. Rather, the pain is caused by disturbance of the...
s, nausea
Nausea
Nausea , is a sensation of unease and discomfort in the upper stomach with an involuntary urge to vomit. It often, but not always, precedes vomiting...
, and vomiting
Vomiting
Vomiting is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose...
, among others.
Legality
αMT is a schedule I controlled substanceControlled substance
A controlled substance is generally a drug or chemical whose manufacture, possession, or use are regulated by a government. This may include illegal drugs and prescription medications ....
in the United States. It is legal in the United Kingdom, however, and does not fall under the tryptamine clause as its substituent
Substituent
In organic chemistry and biochemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon...
is not on the nitrogen
Nitrogen
Nitrogen is a chemical element that has the symbol N, atomic number of 7 and atomic mass 14.00674 u. Elemental nitrogen is a colorless, odorless, tasteless, and mostly inert diatomic gas at standard conditions, constituting 78.08% by volume of Earth's atmosphere...
position. See "2001 Misuse of Drugs Act: Schedule 1, Regulation 3" for more information. Similarly, Canada has no mention of this substance in the Controlled Drugs and Substances Act
Controlled Drugs and Substances Act
The Controlled Drugs and Substances Act is Canada's federal drug control statute. Passed in 1996 by the Chrétien government, it repeals the Narcotic Control Act and Parts III and IV of the Food and Drug Act and establishes eight Schedules of controlled substances and two Classes of precursors...
.
αMT is reported to be a schedule 8 controlled drug in Australia
Australia
Australia , officially the Commonwealth of Australia, is a country in the Southern Hemisphere comprising the mainland of the Australian continent, the island of Tasmania, and numerous smaller islands in the Indian and Pacific Oceans. It is the world's sixth-largest country by total area...
, though this is unconfirmed. It is known that 5-MeO-αMT is schedule 9 in Australia however.
Deaths
There have been at least two reported deaths due to αMT use. The first was a 21 year old in AlabamaAlabama
Alabama is a state located in the southeastern region of the United States. It is bordered by Tennessee to the north, Georgia to the east, Florida and the Gulf of Mexico to the south, and Mississippi to the west. Alabama ranks 30th in total land area and ranks second in the size of its inland...
, and the second a 22 year old FIU student in Miami. However, further analysis revealed that there was no AMT in the tablet Felicia Staats had taken There are reports of a third death, but there is currently no verifiable media information.
External links
- TiHKALTiHKALTiHKAL: 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 Tryptamines I Have Known and Loved.-Content:TiHKAL, much like its...
entry - αMT Entry in TiHKAL • info
- Erowid page on αMT
- Lycaeum page on αMT