3. INDOLE
• Indole is an aromatic, heterocyclic, organic compound with the formula C8H7N. It has
a bicyclic structure, consisting of a six-membered benzene ring fused to a five-
membered pyrrole ring. Indole is widely distributed in the natural environment and
can be produced by a variety of bacteria. As an intercellular signal molecule, indole
regulates various aspects of bacterial physiology,
including spore formation, plasmid stability, resistance to drugs, biofilm formation,
and virulence. The amino acid tryptophan is an indole derivative and the precursor of
4. • Indole is a solid at room temperature. It occurs naturally in human feces and has an intense fecal odor. At very low
concentrations, however, it has a flowery smell, and is a constituent of many perfumes. It also occurs in coal tar.
• The corresponding substituent is called indolyl.
• 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, which includes
the neurotransmitter serotonin and the hormone melatonin, as well as the naturally occurring psychedelic
drugs dimethyltryptamine and psilocybin. Other indolic compounds include the plant hormone auxin (indolyl-3-acetic
acid, IAA), tryptophol, the anti-inflammatory drug indomethacin, and the betablocker pindolol.
• The name indole is a portmanteau of the words indigo and oleum, since indole was first isolated by treatment of the indigo
dye with oleum.
5. TRYPTOPHAN
E
Tryptophan is an α-amino acid that is used in the biosynthesis of proteins.
Tryptophan contains an α-amino group, an α-carboxylic acid group, and a
de chain indole, making it a polar molecule with a non-polar aromatic beta
carbon substituent. Tryptophan is also a precursor to
he neurotransmitter serotonin, the hormone melatonin, and vitamin B3.[4] It
is encoded by the codon UGG.
6. • Amino acids, including tryptophan, are used as building blocks in protein
biosynthesis, and proteins are required to sustain life. Tryptophan is among the less
common amino acids found in proteins, but it plays important structural or functional
roles whenever it occurs. For instance, tryptophan and tyrosine residues play special
roles in "anchoring" membrane proteins within the cell membrane. Tryptophan, along
with other aromatic amino acids, is also important in glycan-protein interactions. In
addition, tryptophan functions as a biochemical precursor for the
following compounds:
• Serotonin (a neurotransmitter), synthesized by tryptophan hydroxylase.
• Melatonin (a neurohormone) is in turn synthesized from serotonin, via N-
7. 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
first one being the heterocyclicnitrogen).The structure of tryptamine is a shared feature of certain
aminergic neuromodulators including melatonin, serotonin, bufotenin and psychedelic derivatives such
as dimethyltryptamine (DMT), psilocybin, psilocin and others.Tryptamine has been shown to activate trace amine-
associated receptors expressed in the mammalian brain, and regulates the activity
of dopaminergic, serotonergic and glutamatergicsystems.In the human gut, symbiotic bacteria convert dietary tryptophan to
tryptamine, which activate- receptors and regulates gastrointestinal motility.Multiple tryptamine-derived drugs have been
developed to treat migraines, while trace amine-associated receptors are being explored as a potential treatment target for
neuropsychiatric disorders.
8. • Tryptamines act predominantly as hallucinogens. Classic hallucinogens (psychedelics) mediate specific serotonin-receptor
activities and produce hallucinations. Substances in these group mimic the effects of traditional drugs such as 2C-B, LSD
and DMT but may also possess residual stimulant activity.
• Reported adverse effect
• Toxicological studies on tryptamines remain limited. Reported adverse effects related to the use of ‘foxy methoxy’ include
restlessness, agitations, gastrointestinal distress, and muscle tension [4]. Rhabdomyolosis after ingestion of ‘Foxy’ has also
been described in a case study . Other fatalities associated with the use of ‘Foxy’ and other tryptamines have also been
described in scientific literature.
9. SERETONIN
• Serotonin, also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter. It also acts as a hormone.
• As a neurotransmitter, serotonin carries messages between nerve cells in your brain (your central nervous system) and throughout
your body (your peripheral nervous system). These chemical messages tell your body how to work.
• Serotonin plays several roles in your body, including influencing learning, memory, happiness as well as regulating body temperature,
sleep, sexual behavior and hunger. Lack of enough serotonin is thought to play a role in depression, anxiety, mania and other health
conditions.
• Most of the serotonin found in your body is in your gut (intestines). About 90% of serotonin is found in the cells lining your
gastrointestinal tract. It’s released into your blood circulation and absorbed by platelets. Only about 10% is produced in your brain.
• Serotonin is made from the essential amino acid tryptophan. An essential amino acid means it can’t be made by your body. It has to
be obtained from the foods you eat.
10. • Serotonin plays a role in many of your body’s functions:
• Digestion: Most of your body’s serotonin is in your GI tract where it helps control your bowel function and plays
a role in protecting your gut. Your gut can increase serotonin release to speed digestion to rid your body of
irritating foods or toxic products. Serotonin also plays a part in reducing your appetite while eating.
• Nausea: Nausea is triggered when serotonin is released into your gut faster than it can be digested. The
chemical message is received by your brain, which you perceive as nausea. Many drugs used to reduce feelings
of nausea and vomiting target specific serotonin receptors in your brain.
• Sleep: Serotonin, together with another neurotransmitter dopamine, plays a role in the quality of your sleep
(how well and how long you sleep). Your brain also needs serotonin to make melatonin, a hormone that
regulates your sleep-wake cycle.
• Wound healing: Serotonin is released by platelets in your blood to help heal wounds. It also causes the tiniest
blood vessels, arterioles, to narrow, which slows blood flow and helps clots to form. This is an important
process in wound healing.
11. SKATOLE
• Skatole or 3-methylindole is an organic compound belonging to the indole family. It
occurs naturally in the feces of mammals and birds and is the primary contributor to
fecal odor. In low concentrations, it has a flowery smell and is found in
several flowers and essential oils, including those of orange blossoms, jasmine,
and Ziziphus mauritiana.
• It is used as a fragrance and fixative in many perfumes and as an aroma
compound. Its name derives from the Greek root skato-, meaning feces. Skatole
12. • Skatole, or 3-methylindole, is a foul-smelling constituent of mammalian feces; it is produced by the
decomposition of tryptophan in the digestive tract. It has a floral aroma at low concentrations, contributing to
the pleasant smell of flowers such as jasmine and orange blossoms. Skatole also occurs naturally in substances
as diverse as beetroot and coal tar.
• Skatole is one of many compounds that are attractive to males of various species of orchid bees, which
apparently gather the chemical to synthesize pheromones; it is commonly used as bait for these bees for
study. It is also known for being an attractant for the Tasmanian grass grub beetle (Aphodius tasmaniae).
• Skatole has been shown to be an attractant to gravid mosquitoes in both field and laboratory conditions.
Because this compound is present in feces, it is found in combined sewage overflows (CSO), as streams and
lakes containing CSO water have untreated human and industrial waste. CSO sites are thus of particular
interest when studying mosquito-borne diseases such as West Nile virus.
