5-(2-Aminopropyl)indole
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5-(2-Aminopropyl)indole
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| Systematic (IUPAC) name | |
| 2-(1H-indol-5-yl)-1-methyl-ethylamine | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | Uncontrolled (but covered under the Federal Analogue Act in the United States and Australia and likely under similar bills in other countries) |
| Routes | Oral |
| Identifiers | |
| CAS number | 3784-30-3 |
| ATC code | None |
| ChemSpider | 25991467  |
| Chemical data | |
| Formula | C11H14N2 |
| Mol. mass | 174.24 g/mol |
| SMILES | eMolecules & PubChem |
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5-(2-Aminopropyl)indole (5-API, 5-IT) is an indole derivative with stimulant effects. It has been sold as a research chemical by online vendors. Hence, it is a designer drug.
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Contents
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Chemistry
Although 5-IT is a positional isomer of the tryptamine drug αMT, the compound is not itself a tryptamine as the indole ring is substitued at the 5 position rather than at the 3 position. The compound is closer chemically to phenethylamine derivatives such as 5-APB. This is reflected in the compound's effects when used as a drug, which are reportedly stimulating rather than psychedelic.
Dosage and effects
Alexander Shulgin wrote briefly about 5-API in TiHKAL saying: "at 20 milligrams orally, [it] is a long-lived stimulant producing increased heart-rate, anorexia, diuresis, and slight hyperthermia for about twelve hours."[1] 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.
Legality
- 5-API is a positional isomer of αMT, and as such is covered by the analogue act in the USA.
- 5-API is legal in the UK, as it is a homolog of tryptamine (structurally related more towards a phenethylamine in spite of being an idole) which is not substituted on the ring with "alkoxy, alkylenedioxy or halide substituents", nor explicitly named in the Misuse of Drugs Act
- 5-API is covered by the Australian analogue act as an analogue of MDA "by the replacement of up to 2 carbocyclic or heterocyclic ring structures with different carbocyclic or heterocyclic ring structures"[2]
See also
References
- ^ Shulgin, Alexander (December 1997). Tihkal: A Continuation [Paperback]. Transform Press. ISBN 978-0-9630096-9-2. http://www.erowid.org/library/books_online/tihkal/tihkal48.shtml. Retrieved 2012-02-08.
- ^ "Criminal Code Act 1995" (PDF). Australian Government. 2009-08-05. http://www.comlaw.gov.au/ComLaw/Legislation/ActCompilation1.nsf/0/1B4A2DD73EF9A4BBCA2576040024B600/$file/CriminalCode1995_WD02.pdf. Retrieved 2012-02-08. "PAGE 503"
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