Alpha-Methyltryptamine

Alpha-Methyltryptamine (AMT) is a potent stimulant and psychedelic drug of the tryptamine family. As a pharmaceutical drug this compound was sold under the name Indopan in the Soviet Union. The effects typically last 8-12 hours, but in some cases can last 24 hours or longer at higher doses. AMT acts as a monoamine oxidase inhibitor and therefore combinations with some drugs or types of food can be dangerous.

Contents

1Introduction to Alpha-Methyltryptamine

2Using Alpha-Methyltryptamine

2.1Ways of administration

2.2Effects of Alpha-Methyltryptamine

2.3Combinations with Alpha-Methyltryptamine

2.4Different Uses for Alpha-Methyltryptamine

3Pharmacology of Alpha-Methyltryptamine

4Chemistry of Alpha-Methyltryptamine

5The dangers of Alpha-Methyltryptamine

6Producing Alpha-Methyltryptamine

7Forms of Alpha-Methyltryptamine

8Legal status of Alpha-Methyltryptamine

8.1United Nations

8.2USA

8.3EU

8.4Other Countries

9History of Alpha-Methyltryptamine

10More Alpha-Methyltryptamine Sections

11The latest Alpha-Methyltryptamine threads

12References

Introduction to Alpha-Methyltryptamine

Using Alpha-Methyltryptamine

Vendors and online reports stress the fact that aMT is active from very small doses as low as 10mg oral or even 2mg when smoked so caution should be taken to correctly measure doses especially when smoking.

aMT is well known for its long duration of action typically in the 10-12 hour range, although 24 hour+ experiences are not unheard of. Users should take the long duration into account when scheduling such an experience

Ways of administration

aMT can be taken:

orally with dosage ranging from 10mg (threshold dose) to 100mg (extremely strong experience)

Smoked with dosage ranging from 2-4mg to 20mg. Onset is much faster than oral administration

It has been reported that insufflation of aMT produces much weaker effects and that this method of administration is fairly painful.
It has also been suggested that this route of administration is ineffective due to aMT freebass, the commonly available form, is insoluable in water, making absorbtion VIA mucus membranes ineffective.

Effects of Alpha-Methyltryptamine

The effects of aMT vary considerably depending on dosage and route of administration.
Reports suggest weak doses (below 50-60mg) taken orally produce a stimulating 'speedy' effect with a noticable body load.
Higher doses (60mg+) have been reported to produce varying degrees of psychadelic visuals.
Reports state that doses of 100mg+ are too strong and overwhelming for inexperienced users without tollerance. These reports speak of considerable side effects. The onset of orally administered aMT can take as long as two hours so users should avoid redosing until sufficient time has passed to fully judge their level of intoxication.

Smoking aMT is reported to produce less psychadelic effects and more stimulant style effects with both a faster onset and a shorter duration. Care should be taken with measuring doses as aMT is considerably more potent by weight when smoked.

Combinations with Alpha-Methyltryptamine

Anecdotal reports suggest cannabis can potentiate the psychadelic effects of aMT

Different Uses for Alpha-Methyltryptamine

Alpha-methyltryptamine was originaly used as an anti-depressant in the 1960's.

Annecdotal reports suggest aMT functions well as an anti-depressant at doses of around 5mg daily

Pharmacology of Alpha-Methyltryptamine

From Wikipedia:

αMT acts as relatively balanced releasing agent of serotonin, norepinephrine, and dopamine, [5] and as a non-selective serotonin receptor agonist. [6] 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. [citation needed]

Like many other serotonin releasing agents, αMT's analogue αET has been shown to produce long-lasting serotonergic neurotoxicity at very high doses, [7] 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. [8][9]

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.
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Chemistry of Alpha-Methyltryptamine

From Wikipedia:

αMT is tryptamine 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.
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Column 1 Column 2

Systematic(IUPAC) name: 2-(1H-Indol-3-yl)-1-methyl-ethylamine

Synonyms: -methyl-1H-indole-3-ethanamine, 3-(2-aminopropyl)indole, 1-(1H-Indol-3-yl)propan-2-amine, AMT, Indopan, IT-290, IT-403, U-14,164E, 3-IT

Molecular Formula: C₁₁H₁₄N₁₈

Molar mass: 174.24 g/mol [2]

CAS Registry Number: 299-26-3 (freebase), 7795-51-9 ((S)-form), 7795-52-0 ((R)-form), 21463-31-0 (hydrochloride)

Melting Point: 101-102°C, also reported 98-99°C; 125-126°C ((S)-form), 126-127°C ((R)-form)

Boiling Point: no data

Flash Point: no data

Solubility: no data

Additionnal data: none

Notes: Racemate aspect : white powder; crystallized from diethyl ether. (S)-form crystallized from ethyl acetate/hexane

[1]

Column 1	Column 2
Systematic(IUPAC) name:	2-(1H-Indol-3-yl)-1-methyl-ethylamine
Synonyms:	-methyl-1H-indole-3-ethanamine, 3-(2-aminopropyl)indole, 1-(1H-Indol-3-yl)propan-2-amine, AMT, Indopan, IT-290, IT-403, U-14,164E, 3-IT
Molecular Formula:	C₁₁H₁₄N₁₈
Molar mass:	174.24 g/mol [2]
CAS Registry Number:	299-26-3 (freebase), 7795-51-9 ((S)-form), 7795-52-0 ((R)-form), 21463-31-0 (hydrochloride)
Melting Point:	101-102°C, also reported 98-99°C; 125-126°C ((S)-form), 126-127°C ((R)-form)
Boiling Point:	no data
Flash Point:	no data
Solubility:	no data
Additionnal data:	none
Notes:	Racemate aspect : white powder; crystallized from diethyl ether. (S)-form crystallized from ethyl acetate/hexane

The dangers of Alpha-Methyltryptamine

From Wikipedia:

αMT can produce side effects including anxiety, restlessness, muscle tension, jaw tightness, pupil dilation, tachycardia, headaches, nausea, and vomiting, among others.
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aMT in conjunction with SSRI/SNRI medication can precipitate serotonin syndrome. The initial symptoms of which are easily confused with normal aMT effects and side effects. Overdose can be fatal if serotonin shock is induced and not recognised and dealt with both quickly and effectively.

The muscle tensions induced can lead to rhabdomyolysis.

From Wikipedia:

...is a condition in which damaged skeletal muscle tissue breaks down rapidly.
Breakdown products of damaged muscle cells are released into the bloodstream; some of these, such as the protein myoglobin, are harmful to the kidneys and may lead to kidney failure.
The severity of the symptoms, which may include muscle pains, vomiting and confusion, depends on the extent of muscle damage and whether kidney failure develops.
The muscle damage may be caused by physical factors (e.g. crush injury, strenuous exercise), medications, drug abuse, and infections. Some people have a hereditary muscle condition that increases the risk of rhabdomyolysis.
The diagnosis is usually made with blood tests and urinalysis. The mainstay of treatment is generous quantities of intravenous fluids, but may include dialysis or hemofiltration in more severe cases.

These are the dangers common to all psychedelic drugs:

Accidental injury. When on a psychedelic drug, it is easier to accidentally injure yourself. Also because of the disorientating and potentially delusion inspiring nature of the experience, you could be lead to inflict harm on others or yourself. People have fallen off rooftops, run into traffic, attempted to throw people off rooftops as 'sacrifices', drowned, and so on. The best way of protecting against this is to have a friend with you who is sober to look after you and handle any negative situation that might arise.

Bad trips. A bad trip is a negative psychedelic experience. It can range from a mildly negative feeling of anxiety/discomfort, to full-blown psychosis. Bad trips usually ruin a psychedelic experience for the tripper and everyone else. Most bad trips are manageable, just very uncomfortable and difficult. Some are extreme and unmanageable though. It's not uncommon for a bad trip to result in lingering psychological issues. Usually just a few days of negative emotions and anxiety. Sometimes, however, a week or so of serious anxiety, destabilized mental state and impaired functioning is possible. On very rare occasions, a month or two of severely diminished functioning, traumatized mental state, depression & crippling anxiety can occur. More information on bad trips can be found here. The best way of avoiding a bad trip is having the correct set and setting.

Permanent psychosis. Psychedelics are believed by researchers not to cause permanent psychosis, however they could trigger a latent mental illness in someone who was already predisposed to it, or make existing mental illnesses worse. If there is a history of mental illness in your family, you are more likely to be predisposed. Everyone is at some risk, however.

PTSD, anxiety disorder, depression & depersonalization. There are anecdotal reports of the trauma inflicted by some bad trips leading to depression and anxiety which while usually temporary, could potentially develop into lasting disorders. While no different to the potential of any traumatic event to cause lasting disorders, nonetheless this is a danger of psychedelic drug use.
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Producing Alpha-Methyltryptamine

Information provided by Iggypoop in the aMT info thread

SYNTHESIS: There was prepared a solution of 25.75 g indole in 100 mL DMF. A second solution was also prepared by cooling 80 mL DMF in an external ice bath (internal temperature about 12 °C), stirring well, and adding 20 mL POCl3 dropwise over the course of 30 min. This was then warmed to 25 °C and the first solution of indole in DMF was added dropwise (with continued stirring) over an additional 30 min. Stirring was continued for yet another 45 min, during which time the temperature was raised to 40 °C. Yellow solids formed during this period. The reaction mixture was poured onto chipped ice which produced a clear red solution. This was made basic with the addition of 200 mL 5 N NaOH which allowed the separation of a yellow solid. This was diluted by the addition of 200 mL hot H2O and, after cooling again, the product was removed by filtration and washed with cold H2O. This can be recrystallized from aqueous DMF to yield, after air drying, 24.5 g (84%) of indole-3-carboxaldehyde as faint orange needles.

A solution of 4.35 g indole-3-carboxaldehyde in 17.2 mL nitroethane was treated with 0.77 g ammonium acetate and heated, with occasional swirling, on the steam bath for 2.5 h. The excess reagent was removed under vacuum and the resulting yellow solids washed with H2O and air dried. Trituration under 25 mL dry MeOH, filtration, and air-drying gave 5.22 g (86%) 1-(3-indolyl)-2-nitropropene-1 as a yellow powder with mp 190-192 °C.

A suspension of 10.7 g LAH in 100 mL anhydrous THF was placed under an inert atmosphere, stirred, and treated dropwise with a solution of 10 g 1-(3-indolyl)-2-nitropropene-1 in anhydrous THF over the course of 2.5 h. The reaction mixture was brought to reflux temperature, held there for 2 h, and then returned to room temperature. The excess hydride was destroyed with an aqueous THF solution (80 mL of 25% solution) and there was then added 10 mL of 50% NaOH. There was added 150 mL Et2O, and the stirring was continued until no more solids formed. The reaction mixture was filtered and the filter cake washed with 150 mL Et2O. The filtrates and washings were combined, dried over K2CO3, and the solvent removed undervacuum.Theresidueweighed 9.2 g and wasdistilled at130-140 °Cat1 mm/Hg to give a white oil that crystallized and had a mp of 96-98 °C. This was recrystallized from an ethyl acetate/petroleum ether mixture, and had a mp of 97-100 °C. The yield was 6.3 g (73%). IR (in cm-1): 750, 818, 911, 933, 1093, 1111. MS (in m/z): C2H6N+ 44 (100%); indolemethylene+ 130, 131 (44%, 43%); parent ion 174 (2%). A sample dissolved in 10 volumes of methanol, treated with one equivalent of glacial acetic acid, and taken to dryness under vacuum gave the acetate salt which, on recrystallization from ethyl acetate and air drying to constant weight yielded the product a-methyltryptamine (a-MT) as fine white crystals with a mp of 143-144 °C. The fumarate salt, formed by the addition of ethyl acetate to a hot solution of free base a-MT in methanol which had been neutralized with fumaric acid, was isolated as fine white needles with a mp of 200-203 °C. SYNTHESIS: There was prepared a solution of 25.75 g indole in 100 mL DMF. A second solution was also prepared by cooling 80 mL DMF in an external ice bath (internal temperature about 12 °C), stirring well, and adding 20 mL POCl3 dropwise over the course of 30 min. This was then warmed to 25 °C and the first solution of indole in DMF was added dropwise (with continued stirring) over an additional 30 min. Stirring was continued for yet another 45 min, during which time the temperature was raised to 40 °C. Yellow solids formed during this period. The reaction mixture was poured onto chipped ice which produced a clear red solution. This was made basic with the addition of 200 mL 5 N NaOH which allowed the separation of a yellow solid. This was diluted by the addition of 200 mL hot H2O and, after cooling again, the product was removed by filtration and washed with cold H2O. This can be recrystallized from aqueous DMF to yield, after air drying, 24.5 g (84%) of indole-3-carboxaldehyde as faint orange needles.

A solution of 4.35 g indole-3-carboxaldehyde in 17.2 mL nitroethane was treated with 0.77 g ammonium acetate and heated, with occasional swirling, on the steam bath for 2.5 h. The excess reagent was removed under vacuum and the resulting yellow solids washed with H2O and air dried. Trituration under 25 mL dry MeOH, filtration, and air-drying gave 5.22 g (86%) 1-(3-indolyl)-2-nitropropene-1 as a yellow powder with mp 190-192 °C.

A suspension of 10.7 g LAH in 100 mL anhydrous THF was placed under an inert atmosphere, stirred, and treated dropwise with a solution of 10 g 1-(3-indolyl)-2-nitropropene-1 in anhydrous THF over the course of 2.5 h. The reaction mixture was brought to reflux temperature, held there for 2 h, and then returned to room temperature. The excess hydride was destroyed with an aqueous THF solution (80 mL of 25% solution) and there was then added 10 mL of 50% NaOH. There was added 150 mL Et2O, and the stirring was continued until no more solids formed. The reaction mixture was filtered and the filter cake washed with 150 mL Et2O. The filtrates and washings were combined, dried over K2CO3, and the solvent removed undervacuum.Theresidueweighed 9.2 g and wasdistilled at130-140 °Cat1 mm/Hg to give a white oil that crystallized and had a mp of 96-98 °C. This was recrystallized from an ethyl acetate/petroleum ether mixture, and had a mp of 97-100 °C. The yield was 6.3 g (73%). IR (in cm-1): 750, 818, 911, 933, 1093, 1111. MS (in m/z): C2H6N+ 44 (100%); indolemethylene+ 130, 131 (44%, 43%); parent ion 174 (2%). A sample dissolved in 10 volumes of methanol, treated with one equivalent of glacial acetic acid, and taken to dryness under vacuum gave the acetate salt which, on recrystallization from ethyl acetate and air drying to constant weight yielded the product a-methyltryptamine (a-MT) as fine white crystals with a mp of 143-144 °C. The fumarate salt, formed by the addition of ethyl acetate to a hot solution of free base a-MT in methanol which had been neutralized with fumaric acid, was isolated as fine white needles with a mp of 200-203 °C.
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Forms of Alpha-Methyltryptamine

Alpha-methyltryptamine freebase is available in:

powder form: it is a fine powder Orange in colour

'Pellet' form, typically 30mg aMT freebase: small blue pellet.

Legal status of Alpha-Methyltryptamine

United Nations

USA

αMT is a Schedule I controlled substance in the Controlled Substances Act of the United States. On Jan 28th, 2003, the DEA announced its intent to emergency schedule AMT. On April 4, 2003, they issued their final order to temporarily place AMT in Schedule I. The temporary scheduling lasted 18 months and on Sep 29, 2004, AMT was placed formally into Schedule I.

EU

Alpha-methyltryptamine was banned in the United Kingdom in early 2015 under new legislation that also banned 5-MeO-DALT. It is also prohibited in Ireland.

Other Countries

AUSTRALIA:

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.

History of Alpha-Methyltryptamine

From wikipedia:

was originally developed as an antidepressant by workers at Upjohn in the 1960s.

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-DiPT as schedule I controlled substances in the Controlled Substances Act of the United States on April 4, 2003. αMT is still legal in most of the world.
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More Alpha-Methyltryptamine Sections

AMT Experiences

The latest Alpha-Methyltryptamine threads

References

[1]Merck Index, fifteenth edition (2013)
[2]Calculated from Atomic Weights of the Elements, 2007

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Introduction to Alpha-Methyltryptamine

Using Alpha-Methyltryptamine

Ways of administration

Effects of Alpha-Methyltryptamine

Combinations with Alpha-Methyltryptamine

Different Uses for Alpha-Methyltryptamine

Pharmacology of Alpha-Methyltryptamine

Chemistry of Alpha-Methyltryptamine

The dangers of Alpha-Methyltryptamine

Producing Alpha-Methyltryptamine

Forms of Alpha-Methyltryptamine

Legal status of Alpha-Methyltryptamine

United Nations

USA

EU

Other Countries

History of Alpha-Methyltryptamine

More Alpha-Methyltryptamine Sections

The latest Alpha-Methyltryptamine threads

References