Alpha-methyltryptamine

Structural formula
	Structural formula without stereochemistry
General
Surname	Alpha-methyltryptamine
other names	AMT; α-MT; 1- (Indol-3-yl) propan-2-amine ( IUPAC ) ; DL -3- (2-aminopropyl) indoles; Indopan;
Molecular formula	C 11 H 14 N 2
Brief description	colorless crystals (acetate)
External identifiers / databases
EC number	206-073-7
ECHA InfoCard	100.005.522
PubChem	9287
DrugBank	DB01446
Wikidata	Q421163
Drug information
Drug class	Tryptamines
properties
Molar mass	174.24 g · mol -1
Physical state	firmly
Melting point	98-100 ° C ; 143-144 ° C ( acetate ); 200–203 ° C ( fumarate );
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 300-310-330
	P: 260-264-280-284-302 + 350-310
Toxicological data	50 mg kg −1 ( LD 50 , rat , sc )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

α-Methyltryptamine , also known as α-MT , AMT or IT-290, is a synthetically produced psychoactive drug belonging to the tryptamine family. It was first marketed as an antidepressant in the Soviet Union in the 1960s under the name Indopan . 5-mg and 10-mg pills were available. As with many other tryptamines, psychedelic effects can be achieved in increased doses . The effect sets in after about two to three hours and can last for 18 to 24 hours. Alpha-methyltryptamine is also a MAOI (monoamine oxidase inhibitor) and a stimulant .

chemistry

AMT is structurally closely related to the neurotransmitter serotonin and mediates its effect on the 5-HT ₂ receptors as well as on the 5-HT _1B receptor . In addition, as a MAOI, AMT inhibits the reuptake of serotonin and its breakdown process.

dosage

Oral ingestion of 5 to 20 mg shows the stimulating effect. From 20 to 30 mg, hallucinogenic effects are noticed that can last up to 24 hours. It has been reported that up to 150 mg has been taken, although 60 to 80 mg is considered a strong dose . The free base (“freebase”) can also be smoked at a dosage of 5 to 20 mg.

effect

AMT is a long-lasting, euphoric psychedelic . Many users experience nausea and vomiting . Erowid lists the following symptoms:

Positive effects

Increase in performance
Mood lightening
Patterns and hallucinations with eyes closed
Increased noticing and appreciation of music
Feeling connected with other people
Color intensification

Neutral effects

General change in consciousness
Blurred vision
restlessness
yawning
Mydriasis (dilation of the pupils )

negative

Anxiety , tension
Nausea and vomiting
Disorientation or difficulty finding your way
Muscle aches
a headache
involuntary clenching of the jaw ( bruxism )

Deaths

Between April and August 2012 alone, four EU countries, including Germany, reported 24 deaths in which the synthetic substance 5-IT (an isomer of AMT) played a role with stimulating and hallucinogenic effects.

Legal status

Germany

In the Federal Republic of Germany, AMT is a non-marketable narcotic due to its listing in Appendix 1 BtMG . Handling without permission is generally a criminal offense. Further information can be found in the main article Narcotics Law in Germany .

United States

In the US, AMT is a Schedule I drug and falls under the Controlled Substance Act.

Web links

TiHKAL: AMT (English)
AMT . In: Erowid . (English)
isomerdesign.com: AMT (English)

Individual evidence

↑ ^a ^b ^c TiHKAL: AMT
↑ ^a ^b ^c ^d data sheet α-Methyltryptamine from Sigma-Aldrich , accessed on May 29, 2012 ( PDF ).
↑ ME GREIG, RA WALK, AJ GIBBONS: The effect of three tryptamine derivatives on serotonin metabolism in vitro and in vivo. In: The Journal of pharmacology and experimental therapeutics. Volume 127, October 1959, pp. 110-115, ISSN 0022-3565 . PMID 13851725 .
↑ DJ Mckenna, DB Repke u. a .: Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. In: Neuropharmacology. 29, 1990, pp. 193-198, doi : 10.1016 / 0028-3908 (90) 90001-8 .
↑ David E. Nichols, David H. Lloyd et al. a .: Synthesis and serotonin receptor affinities of a series of enantiomers of α-methyltryptamines: evidence for the binding conformation of tryptamines at serotonin 5-HT1B receptors. In: Journal of Medicinal Chemistry. 31, 1988, pp. 1406-1412, doi : 10.1021 / jm00402a026 .
↑ Erowid: AMT Dosage . Retrieved March 1, 2014.
^ Erowid: AMT Effects . Retrieved November 8, 2010.
↑ EU Commission: International Day Against Drug Abuse and Drug Trafficking: European Commission calls for an EU-wide ban on the synthetic drug "5-IT" , press release from June 25, 2013.

[tihkal-1] TiHKAL: AMT

[Sigma-2] ta sheet α-Methyltryptamine from Sigma-Aldrich , accessed on May 29, 2012 ( PDF ).

[PMID13851725-3] ME GREIG, RA WALK, AJ GIBBONS: The effect of three tryptamine derivatives on serotonin metabolism in vitro and in vivo. In: The Journal of pharmacology and experimental therapeutics. Volume 127, October 1959, pp. 110-115, ISSN 0022-3565 . PMID 13851725 .

[DOI10.1016/0028-3908(90)90001-8-4] DJ Mckenna, DB Repke u. a .: Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. In: Neuropharmacology. 29, 1990, pp. 193-198, doi : 10.1016 / 0028-3908 (90) 90001-8 .

[DOI10.1021/jm00402a026-5] David E. Nichols, David H. Lloyd et al. a .: Synthesis and serotonin receptor affinities of a series of enantiomers of α-methyltryptamines: evidence for the binding conformation of tryptamines at serotonin 5-HT1B receptors. In: Journal of Medicinal Chemistry. 31, 1988, pp. 1406-1412, doi : 10.1021 / jm00402a026 .

[6] Erowid: AMT Dosage . Retrieved March 1, 2014.

[7] Erowid: AMT Effects . Retrieved November 8, 2010.

[8] EU Commission: International Day Against Drug Abuse and Drug Trafficking: European Commission calls for an EU-wide ban on the synthetic drug "5-IT" , press release from June 25, 2013.