5-(2-Aminopropyl)indole (5-API, 5-IT, PAL-571) is an

indole Indole is an aromatic heterocyclic organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other c ...

and phenethylamine derivative with empathogenic effects. Its preparation was first reported by

Albert Hofmann Albert Hofmann (11 January 1906 – 29 April 2008) was a Swiss chemist known for being the first to synthesize, ingest, and learn of the psychedelic effects of lysergic acid diethylamide (LSD). Hofmann's team also isolated, named and synthesi ...

in 1962. It is a

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. D ...

that has been openly sold as a recreational drug by online vendors since 2011.

Chemistry

Although 5-IT is a

positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is another compound whose molecule has the same number of atoms of each element, but with logically distinct bonds between them. The term meta ...

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 f ...

drug αMT, the compound is not itself a tryptamine as the indole ring is substituted at the 5 position rather than at the 3 position. The compound is closer chemically to phenethylamine derivatives such as

5-APB 5-APB (abbreviation of "5-(2-aminopropyl)benzofuran"; see infobox for the correct IUPAC name) is an empathogenic psychoactive compound of the substituted benzofuran, substituted amphetamine and substituted phenethylamine classes. 5-APB and ot ...

. This is reflected in the compound's effects when used as a drug, which are reportedly stimulating rather than psychedelic.

Pharmacology

5-IT acts as a triple monoamine releasing agent with EC₅₀ values of 12.9 nM for dopamine, 13.3 nM for

norepinephrine Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic chemical in the catecholamine family that functions in the brain and body as both a hormone and neurotransmitter. The name "noradrenaline" (from Latin '' ad' ...

and 104.8 nM for serotonin and also as MAO-A inhibitor.

Dosage and effects

Alexander Shulgin wrote briefly about 5-IT in ''

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 ...

'' saying: "at 20 milligrams orally, tis a long-lived stimulant producing increased heart-rate, anorexia, diuresis, and slight hyperthermia for about twelve hours." As 5-IT is not a tryptamine and thus not within the scope of the book, it is not discussed in any more detail than this. The following symptoms can indicate 5-IT has been ingested:

hyperthermia Hyperthermia, also known simply as overheating, is a condition in which an individual's body temperature is elevated beyond normal due to failed thermoregulation. The person's body produces or absorbs more heat than it dissipates. When extreme ...

tachycardia Tachycardia, also called tachyarrhythmia, is a heart rate that exceeds the normal resting rate. In general, a resting heart rate over 100 beats per minute is accepted as tachycardia in adults. Heart rates above the resting rate may be normal ( ...

increased blood pressure Hypertension (HTN or HT), also known as high blood pressure (HBP), is a long-term medical condition in which the blood pressure in the arteries is persistently elevated. High blood pressure usually does not cause symptoms. Long-term high bl ...

dilated pupils Mydriasis is the dilation of the pupil, usually having a non-physiological cause, or sometimes a physiological pupillary response. Non-physiological causes of mydriasis include disease, trauma, or the use of certain types of drugs. Normally, as ...

(mydriasis), agitation, excessive

sweat Perspiration, also known as sweating, is the production of fluids secreted by the sweat glands in the skin of mammals. Two types of sweat glands can be found in humans: eccrine glands and apocrine glands. The eccrine sweat glands are distrib ...

ing, jaw clenching,

insomnia Insomnia, also known as sleeplessness, is a sleep disorder in which people have trouble sleeping. They may have difficulty falling asleep, or staying asleep as long as desired. Insomnia is typically followed by daytime sleepiness, low energy, ...

, disorientation, restlessness,

anxiety Anxiety is an emotion which is characterized by an unpleasant state of inner turmoil and includes feelings of dread over anticipated events. Anxiety is different than fear in that the former is defined as the anticipation of a future threat wh ...

, and tremor. It is a MAOI, and when combined with a contraindicated substance, it can lead to death.

Deaths

5-IT has been attributed to 14 deaths of people in Sweden since its discovery. 5-IT was listed as the sole intoxicant in two cases but other drugs were also found in the twelve other

post mortem An autopsy (post-mortem examination, obduction, necropsy, or autopsia cadaverum) is a surgical procedure that consists of a thorough Physical examination, examination of a Cadaver, corpse by dissection to determine the cause, mode, and manner o ...

examinations. The 14 deaths occurred between April and July 2012, but a definitive identification of 5-IT in the post-mortem samples was not made until July. All of the dead were young men aged between 20-30. Eleven non-fatal poisonings due to 5-IT also reportedly occurred during the same time period.

Legality

* 5-IT is a positional isomer of αMT, and as such is considered legally the same as αMT under the

Controlled Substance Act The Controlled Substances Act (CSA) is the statute establishing federal U.S. drug policy under which the manufacture, importation, possession, use, and distribution of certain substances is regulated. It was passed by the 91st United States ...

in the USA. (The Federal Analog Act includes a clause concerning the effects of the substance as well.) * 5-IT was banned as a

temporary class drug A temporary class drug is a relatively new status for controlled drugs, which has been adopted in some jurisdictions, notably New Zealand and the United Kingdom, to attempt to bring newly synthesised designer drugs under legal control. The control ...

in June 2013, along with 9 other related compounds. On March 5, 2014 the UK Home Office announced that 5-API would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs. * 5-IT is covered by the Australian analogue act as an analogue of

MDA MDA, mda, or ''variation'', may refer to: Places * Moldova, a country in Europe with the ISO 3166-1 country code MDA Politics * Meghalaya Democratic Alliance (2018), ruling coalition government in the Indian State of Meghalaya led by National Pe ...

"by the replacement of up to 2 carbocyclic or heterocyclic ring structures with different carbocyclic or heterocyclic ring structures". * A formal application for 5-IT to be made illegal in Sweden was made on July 26, 2012, but did not come into effect immediately. * 5-IT was made illegal in Denmark on 30 September 2012. * 5-IT is an Anlage I controlled drug in Germany. * The European Commission published a proposal for a decision calling upon its member states to take measures to control 5-(2-aminopropyl)indole. It asked member states to introduce control measures and criminal penalties as provided under their national legislation covering psychotropic substances.

References