Buy α-Methyltryptamine (AMT) Cas 299-26-3

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α-Methyltryptamine (αMT, AMT) is a psychedelic, stimulant, and entactogen drug of the tryptamine and α-alkyltryptamine families.^[5][6] It was originally developed as an antidepressant at Upjohn in the 1960s, and was used briefly as an antidepressant in the Soviet Union under the brand name Indopan or Indopane before being discontinued. Buy α-Methyltryptamine (AMT) Cas 299-26-3^[4][7][8]

Side effects of αMT include agitation, restlessness, confusion, lethargy, pupil dilation, jaw clenching, and rapid heart rate, among others.^[4][9] αMT acts as a releasing agent of serotonin, norepinephrine, and dopamine, as a serotonin receptor agonist, and as a weak monoamine oxidase inhibitor.^[1] αMT is a substituted tryptamine and is closely related to α-ethyltryptamine (αET) and other α-alkylated tryptamines.^[1][5]

αMT appears to have first been described by at least 1929.^[10][11] It started being more studied in the late 1950s and was briefly used as an antidepressant in the Soviet Union in the 1960s.^{[4][12][9][13][14]} The drug started being used recreationally in the 1960s, with use increasing in the 1990s, and cases of death have been reported.^{[4][13][9][12]} αMT is a controlled substance in various countries, including the United States.^[13][4]

Under the brand name Indopan or Indopane, αMT at doses of 5 to 10 mg was used for an antidepressant effect.^[4][7][8]

At a dose of 20 mg, it produces euphoria, while doses above 30 mg result in strong hallucinogenic effects. At doses over 30 mg, the compound may cause several side effects, including anxiety, muscle tightness, vomiting, and hyperthermia.^[15] A dose exceeding 40 mg is generally considered strong. In rare cases or extreme doses, the duration of effects might exceed 24 h. Users report that αMT may be smoked, with doses between and 2 and 20 mg.^{[2][unreliable source?][5]}

A dose of 20 mg of αMT is said to be equivalent to 50 μg of LSD. However, its onset of action is delayed, with effects appearing after only 3 to 4 hours, and it is longer-lasting. In addition, αMT is described as unpleasant compared to LSD, with symptoms of nervousness, irritability, restlessness, and inability to relax.^[16]

Neurologic side effects of αMT include agitation, restlessness, confusion, and lethargy.^[4][9][16] Physical manifestations including vomiting, mydriasis (pupillary dilation), jaw clenching, tachycardia, salivation, diaphoresis (sweating), and elevations in blood pressure, temperature, and respiratory rate.^[4][9]

Side effects self-reported by recreational users include anxiety, muscle tension, jaw tightness, pupil dilation, tachycardia, headaches, nausea, and vomiting, as well as psychedelic effects including visual hallucinations and an altered state of mind.^[5][17]

αMT is capable of causing life-threatening side effects including hyperthermia, hypertension, and tachycardia.^[9][18] Fatalities have been reported in association with high doses or concomitant use of other drugs.^[19]

Fatalities verified with toxicology and autopsy include those of a 22-year-old man in Miami-Dade County, Florida and a British teenager, both of whom died after consuming 1 g of αMT.^[20][9]

αMT acts as a relatively balanced reuptake inhibitor and releasing agent of the main three monoamines; serotonin, norepinephrine, and dopamine,^[21] and as a non-selective serotonin receptor agonist.^[22] It has relatively weak psychedelic-like effects in animals compared to other psychedelic substituted tryptamines, for instance in terms of the head-twitch response in rodents.

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       alpha-Methyltryptamine

       Catalog No.

       S530641

       CAS No.

       299-26-3

       M.F

       C11H14N2

       M. Wt

       174.24 g/mol

       Availability

       In Stock

       * This item is exclusively intended for research purposes and is not designed for human therapeutic applications or veterinary use.
       

       Content Navigation

       • 1. General Information
       • 2. Description
       • 3. Chemical Reactions
       • 4. Biological Activity
       • 5. Synthesis Methods
       • 6. Interaction Studies

       • 7. Similar Compounds
       • 8.
       • 9. Specification
       • 10. Others
       • 11. Reference

       General Information

       CAS Number

       299-26-3

       Product Name

       alpha-Methyltryptamine

       IUPAC Name

       1-(1H-indol-3-yl)propan-2-amine

       Molecular Formula

       C11H14N2

       Molecular Weight

       174.24 g/mol

       InChI

       InChI=1S/C11H14N2/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8,13H,6,12H2,1H3

       InChI Key

       QSQQQURBVYWZKJ-UHFFFAOYSA-N

       SMILES

       CC(CC1=CNC2=CC=CC=C21)N

       solubility

       Soluble in DMSO

       Synonyms

       alpha-methyltryptamine, indopan, indopan hydrochloride, indopan hydrochloride, (+-)-isomer, indopan mesylate, indopan monoacetate, indopan monoacetate, (S)-isomer, indopan monohydrochloride, indopan monohydrochloride, (+-)-isomer, indopan monohydrochloride, (R)-isomer, indopan monohydrochloride, (S)-isomer, indopan monotosylate, (R)-isomer, indopan monotosylate, (S)-isomer, indopan, (+-)-isomer, indopan, (R)-isomer, indopan, (S)-isomer

       Canonical SMILES

       CC(CC1=CNC2=CC=CC=C21)N

       The exact mass of the compound alpha-Methyltryptamine is 174.1157 and the complexity rating of the compound is unknown. The solubility of this chemical has been described as Soluble in DMSO. The compound has been submitted to the National Cancer Institute (NCI) for testing and evaluation and the Cancer Chemotherapy National Service Center (NSC) number is 97069. Its Medical Subject Headings (MeSH) category is Chemicals and Drugs Category – Organic Chemicals – Amines – Biogenic Amines – Biogenic Monoamines – Tryptamines – Supplementary Records. It belongs to the ontological category of tryptamines in the ChEBI Ontology tree. The United Nations designated GHS hazard class pictogram is Acute Toxic, and the GHS signal word is DangerThe storage condition is described as Dry, dark and at 0 – 4 C for short term (days to weeks) or -20 C for long term (months to years)..

       Description

       Alpha-Methyltryptamine is a synthetic compound belonging to the tryptamine class, closely related to the neurotransmitter serotonin. It is characterized by a methyl group attached to the alpha carbon of the tryptamine backbone, which distinguishes it from other tryptamines. This structural modification allows alpha-methyltryptamine to act as a monoamine oxidase inhibitor and a stimulant, with psychoactive effects that can include hallucinations and euphoria. Originally developed in the 1960s as an antidepressant under the trade name “Indopan,” it is now recognized for its psychedelic properties at higher doses, with effects lasting up to 24 hours   .

       Chemical Reactions

       Alpha-methyltryptamine undergoes various chemical transformations, primarily involving oxidation, reduction, and conjugation reactions. Key reactions include:

       • Oxidation: Alpha-methyltryptamine can be oxidized to form various metabolites, including N-acetylated and sulfated derivatives.
       • Reduction: The compound can be reduced using agents like lithium aluminum hydride or copper(II) chloride, which can convert ketoximes derived from its precursors into active forms  .
       • Conjugation: Phase II metabolic reactions may include glucuronidation and sulfation, which modify the compound for excretion .

       Biological Activity

       Alpha-methyltryptamine exhibits significant biological activity due to its interaction with serotonin receptors. It acts as a releasing agent of serotonin, norepinephrine, and dopamine while also functioning as a non-selective agonist at serotonin receptors, particularly 5-HT2A. Its monoamine oxidase inhibition contributes to prolonged effects in the central nervous system. Side effects may include agitation, pupil dilation, and rapid heart rate, along with potential neurotoxicity at high doses   .

       Synthesis Methods

       The synthesis of alpha-methyltryptamine can be achieved through several methods:

       • Nitroaldol Condensation: This involves the reaction between indole-3-carboxaldehyde and nitroethane in the presence of ammonium acetate, yielding 1-(3-indolyl)-2-nitropropene-1. This intermediate can then be reduced to alpha-methyltryptamine using lithium aluminum hydride.
       • Condensation with Hydroxylamine: Another method involves condensing indole-3-acetone with hydroxylamine followed by reduction with lithium aluminum hydride  .

       These methods highlight the versatility in producing alpha-methyltryptamine from readily available precursors.

       Interaction Studies

       Alpha-methyltryptamine interacts with various substances due to its pharmacological profile. Notably:

       • Monoamine Oxidase Inhibitors: Caution is advised when combining alpha-methyltryptamine with other monoamine oxidase inhibitors due to the risk of serotonin syndrome.
       • Stimulants: Co-administration with stimulants can lead to increased cardiovascular risks.
       • Psychoactive Substances: Its effects may be potentiated when taken alongside other psychedelics or entactogens  .

       Research into these interactions is crucial for understanding safe usage parameters.

       Similar Compounds

       Alpha-methyltryptamine shares structural similarities with several other compounds in the tryptamine class. Here are some notable comparisons:

       Compound Name	Structural Features	Unique Properties
       Alpha-Ethyltryptamine	Ethyl group at alpha carbon	Associated with long-lasting serotonergic neurotoxicity at high doses
       N,N-Dimethyltryptamine	Two methyl groups on nitrogen	Known for strong psychedelic effects and rapid onset
       Alpha-Methylserotonin	Methyl group on serotonin backbone	Acts as a more potent serotonin receptor agonist
       Indolylpropylaminopentane	Longer alkyl chain compared to alpha-methyltryptamine	Exhibits unique psychedelic properties distinct from shorter analogs

       Alpha-methyltryptamine’s unique methyl substitution allows it to exhibit both stimulant and hallucinogenic properties while maintaining a distinct pharmacological profile compared to its analogs.

       Structure and Nomenclature

       AMT’s systematic name is 3-(2-aminopropyl)indole, with a molecular formula of C₁₁H₁₄N₂ (molecular weight: 174.24 g/mol). Its structure comprises an indole moiety—a bicyclic aromatic system—with a methyl group attached to the alpha carbon of the ethylamine side chain. This substitution confers resistance to monoamine oxidase A (MAO-A) degradation, prolonging its pharmacokinetic profile.

       Synonyms and Stereoisomers

       AMT is known by multiple identifiers:

       • Indopan (historical brand name in the Soviet Union)
       • IT-290 (Sandoz developmental code)
       • Ro 3-0926 (Upjohn designation)
       • U-14,164E (Upjohn reference)

       The compound exists as two enantiomers:

       • (S)-(+)-alpha-Methyltryptamine (CAS 7795-52-0)
       • (R)-(-)-alpha-Methyltryptamine (CAS 299-26-3)

       Key Structural Features

       Feature	Description
       Indole Core	Bicyclic aromatic system (pyrrole ring fused to benzene)
       Ethylamine Side Chain	Methyl group at alpha carbon (C1 of the propan-2-amine chain)
       Amino Group	Primary amine (-NH₂) attached to the beta carbon of the side chain

       Historical Development and Initial Pharmacological Characterization

       Origins and Early Clinical Trials

       AMT was synthesized in the 1960s by Upjohn as part of a broader effort to develop tryptamine-based antidepressants. Initial animal studies indicated potential as a monoamine oxidase inhibitor (MAOI), prompting clinical trials in the Soviet Union under the brand name Indopan. The compound was administered in 5–10 mg doses for depression, but its use was discontinued due to reports of psychosis and toxicity.

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       Pharmacological Mechanisms

       Early studies revealed AMT’s dual action:

       • Monoamine Reuptake Inhibition:
         • Blocks serotonin (5-HT), norepinephrine, and dopamine transporters (SERT, NET, DAT).
         • EC₅₀ values for serotonin reuptake inhibition range from 22–68 nM, comparable to MDMA.
       • Monoamine Release:
         • Releases stored serotonin, norepinephrine, and dopamine from presynaptic terminals.
       • Serotonin Receptor Agonism:
         • Activates 5-HT₂A receptors (EC₅₀: 23 nM), contributing to hallucinogenic effects.

       These mechanisms align with those of other α-alkylated tryptamines but differ from non-α-alkylated analogs (e.g., DMT) in MAO-A resistance

       AMT/ alpha -Methyltryptamine

       aMT, also known as alpha-methyltryptamine, is a chemical compound belonging to the tryptamine class. It is a derivative of tryptamine and shares structural similarities with other psychedelic substances.  It is known for its hallucinogenic and stimulant effects. Here is some information about this product.

       • This product is typically found as a white or off-white crystalline powder.
       • It is sparingly soluble in water but dissolves readily in polar organic solvents like ethanol or methanol.

       Key Features and Benefits of AMT/ alpha -Methyltryptamine

       • Research Purposes: This product is commonly used by researchers and scientists to study its chemical properties, pharmacological effects, and potential therapeutic applications. It can be utilized in various fields such as neuroscience, pharmacology, and medicinal chemistry.
       • Psychoactive Properties: aMT is known to exhibit psychoactive effects, similar to other tryptamine derivatives. It is often described as a psychedelic substance, capable of inducing altered states of consciousness, changes in perception, mood elevation, and sensory enhancement. However, it is important to note that the subjective experiences and effects of aMT may vary among individuals.
       • Limited Availability: This product is a rare compound and may not be readily available in the market. Its production and distribution are strictly regulated, and it is primarily obtained through reputable research chemical suppliers.
       • Safety Precautions: As with any research chemical, it is crucial to handle aMT with caution. Researchers should follow proper laboratory protocols, including wearing appropriate protective equipment and working in a well-ventilated area. It is advised to consult with a qualified professional before conducting any experiments involving this product.
       • Psychoactive Effects: aMT is renowned for its potential psychoactive effects, which can vary depending on the dosage and individual sensitivity. Researchers have reported altered states of consciousness, enhanced mood, and changes in perception when studying this compound.
       • Molecular Structure: This product has a molecular formula of C11H14N2 and a molar mass of 174.24 g/mol. It features a tryptamine backbone with a methyl group attached to the alpha position.
       • Dosage and Administration: It is crucial to handle aMT with care and adhere to proper safety protocols, as with any research chemical. Dosage recommendations can vary, but researchers typically start with low doses (10-20 mg) to assess individual sensitivity and gradually increase if necessary. It is essential to consult relevant literature and follow ethical guidelines when conducting research involving this product.

       Pharmacology and Effects:

       • This product acts primarily as a non-selective serotonin receptor agonist, affecting various serotonin receptors in the brain.
       • The effects of this product can vary depending on the dosage and individual factors. Common effects may include:
         • Altered perception and enhanced sensory experiences
         • Changes in thought patterns and introspection
         • Euphoria and mood enhancement
         • Increased energy and stimulation
         • Visual and auditory hallucinations
         • Time distortion
         • Increased heart rate and blood pressure

       Safety and Legality:

       • AMT is a potent psychoactive substance and should be handled with caution. It is important to use proper safety precautions and conduct research in a controlled environment.
       • The legal status of AMT varies by country. It is important to be aware of the laws and regulations regarding its purchase, possession, and use in your jurisdiction.

       Ordering Information:

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