Indole

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Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. The participation of the nitrogen lone electron pair in the aromatic ring means that indole is not a base, and it does not behave like a simple amine.

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Indole is solid at room temperature and has an intense fecal smell. At very low concentrations however it has a flowery smell and is a constituent of many flower scents (such as orange blossoms) and perfumes. It also occurs in coal tar.

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The indole structure can be found in many organic compounds like the amino acid tryptophan and in tryptophan containing protein, in alkaloids, or in pigments.

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Indole undergoes electrophilic substitution, mainly at position 3. Substituted indoles are structural elements of (and for some compounds the synthetic precursors for) the tryptophan-derived tryptamine alkaloids like the neurotransmitter serotonin, melatonin, the hallucinogens psilocybin, DMT, 5-MeO-DMT, or the ergolines like LSD. Other indolic compounds include the plant hormone Auxin (indolyl-3-acetic acid, IAA), the anti-inflammatory drug indomethacin, or the betablocker pindolol.

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The name indole is derived from indigo, a blue pigment obtained from some plant species. The indigo molecule comprises two indole units joined together.

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Aromatic: redirect Aromaticity...

Heterocyclic: REDIRECT Heterocyclic compound...

Organic: Organic has several meanings and related topics. Its original meaning is: part of, or derived from, living matter. It can be related to, or derived from living organisms: organic matter. It can mean, relating to, or affecting a bodily organ: an organic disease. Organic has also come to mean simpl...