Indoles and Indole Derivatives

Indoles

Indole chemistry is a fascinating and complex area. The foul-smelling indole molecule is the building block for a great variety of chemicals. Moreover, some indole derivatives are vital pharmaceuticals or intermediates.
The amino acid tryptophan along with its derivatives L-5-hydroxytryptophan and N-acetyl-DL-tryptophan are important indole derivatives while serotonin and melatonin are biochemically active indole molecules. There are, in fact, literally hundreds of alkaloid derivatives of indole, many of which are found in nature.
Indoles are important plant growth regulators. Indole-acetic acid, for instance, is a plant hormone which causes growth of plant leaves and stems while indole-butyric acid is a plant hormone that stimulates the growth of plant roots. In addition, indole derivatives play a critical role in microbiology and clinical diagnostics.

Tryptamines

The indole derivative tryptamine (3-(2-aminoethyl)indole) is a monoamine compound that is widespread in nature. Tryptamines are important metabolites derived from the amino acid tryptophan. They play a major role in the biosynthesis of many natural products such as ergoline alkaloids and plant hormones (i.e. auxins).
Tryptamines include melatonin, which is a hormone involved in regulating the sleep-wake cycle, and serotonin, a key metabolite in neural signal transduction. Serotonin (5-hydroxytryptamine, or 5-HT) is a monoamine neurotransmitter, which is synthesized in serotonergic neurons in the central nervous system and in the enterochromaffin cells in the gastrointestinal tract. It is thought that serotonin plays an important role in the biochemistry of depression, bipolar disorder and anxiety.

NOTE: SOME TRYPTAMINES ARE CONTROLLED SUBSTANCES. THESE COMPOUNDS ARE SOLD UNDER THE RESPECTIVE COUNTRY'S REGULATION ONLY. COMPANIES THAT ARE NOT REGISTERED TO OBTAIN THESE COMPOUNDS AND THAT PLACE A REQUEST FOR QUOTATION AT BIOSYNTH WILL BE REPORTED.

List of Serotonins
Cat. No. - Product Name
A-1300 - N-Acetyl-5-hydroxytryptamine
H-8000 - 5-Hydroxytryptamine, free base
H-8050 - 5-Hydroxytryptamine, adipate salt
H-8100 - 5-Hydroxytryptamine creatinine sulfate (salt) monohydrate
H-8105 - 5-Hydroxytryptamine creatinine sulfate (salt) monohydrate, micronized
H-8140 - 5-Hydroxytryptamine hydrochloride
H-8180 - 5-Hydroxytryptamine, maleate salt
H-8220 - 5-Hydroxytryptamine, oxalate salt
M-3550 - 5-Methoxytryptamine, free base ultra pure
M-3554 - 5-Methoxytryptamine hydrochloride



Names and Abbreviations of substituted Tryptamines:

Short NameRalphaR4R5RN1RN2Full Name
Serotonin     OH     5-Hydroxytryptamine
Melatonin     OCH3 O=CH-CH3   5-Methoxy-N-acetyltryptamine
Sumatriptan   SO2NHCH3   CH3 CH3 4-Methylaminosulfonyl-N,N-dimethyltryptamine
DMT       CH3 CH3 N,N-Dimethyltryptamine
DET       CH2CH3 CH2CH3 N,N-Diethyltryptamine
DPT       CH2CH2CH3 CH2CH2CH3 N,N-Dipropyltryptamine
DiPT       CH(CH3)2 CH(CH3)2 N,N-Diisopropyltryptamine
Bufotenine     OH CH3 CH3 5-Hydroxy-N,N-dimethyltryptamine
5-MeO-DMT     OCH3 CH3 CH3 5-Methoxy-N,N-dimethyltryptamine
5-MeO-DIPT     OCH3 CH(CH3)2 CH(CH3)2 5-Methoxy-N,N-diisopropyltryptamine
Psilocin   OH   CH3 CH3 4-Hydroxy-N,N-dimethyltryptamine
Psilocybin   OPO3H2   CH3 CH3 4-Phosphoryloxy-N,N-dimethyltryptamine
Ethocin   OH   CH2CH3 CH2CH3 4-Hydroxy-N,N-diethyltryptamine
Iprocin   OH   CH(CH3)2 CH(CH3)2 4-Hydroxy-N,N-diisopropyltryptamine
Miprocin   OH   CH(CH3)2 CH3 4-Hydroxy-N-isopropyl-N-methyltryptamine
AMT CH3         alpha-Methyltryptamine
AET CH2CH3         alpha-Ethyltryptamine
5-MeO-AMT CH3   OCH     3 5-Methoxy-alpha-methyltryptamine



List of Tryptamines
Cat.No. - Product Name
A-0100 - L-Abrine
A-0400 - N-Acetyl-5-acetoxytryptamine
A-0510 - N-Acetyl-5-benzyloxytryptamine
A-1300 - N-Acetyl-5-hydroxytryptamine
A-1474 - N-Acetyl-6-methoxytryptamine
A-1810 - N-Acetyl-DL-tryptophan Ph. Eur.
B-2150 - 5-Benzyloxytryptamine hydrochloride
B-2154 - 6-Benzyloxytryptamine, free base
B-2160 - 7-Benzyloxytryptamine, free base
C-5165 - 5-Chloro-1-methyltryptamine, free base
C-5535 - 6-Chlorotryptamine, free base
F-6600 - 6-Fluorotryptamine, free base
H-8000 - 5-Hydroxytryptamine, free base
H-8260 - 6-Hydroxytryptamine creatinine sulfate (salt)
M-1250 - Melatonin (synth.) standard-grade
M-3554 - 5-Methoxytryptamine hydrochloride
M-3563 - 6-Methoxytryptamine hydrochloride
M-4662 - 6-Methyltryptamine hydrochloride
M-4665 - 7-Methyltryptamine, free base
M-4667 - 7-Methyltryptamine hydrochloride
N-8150 - 5-Nitrotryptamine, free base
T-8100 - Tryptamine, free base
T-8150 - Tryptamine hydrochloride


Indoxyl Substrates

Indoles play an important role in microbiology and clinical diagnostics by serving as chromogens of enzyme substrates such as X-gal (B-7150). The method is based on the indigo reaction. Indigo is formed by oxidative dimerization of two 3-hydroxyindole (3-indoxyl) molecules. The reaction can only proceed via the phenolate and cannot proceed if the hydroxyl group is linked to another structure.
For example, X-gal (5-bromo-4-chloro-3-indoxyl-beta-D-galactopyranoside) mimics the natural substrate, lactose, of the enzyme beta-galactosidase. X-gal is hydrolyzed by the enzyme, causing a color change. The glycosidic linkage protects the indoxyl from oxidation. Upon removal by the enzyme, the indigo reaction produces the precipitating indigo dye, indicating the enzyme's activity.

Selection of Biosynth's X-Substrates
Cat.No. - Product Name
B-6950 - 5-Bromo-4-chloro-3-indoxyl-N-acetyl-beta-D-galactosaminide
B-7050 - 5-Bromo-4-chloro-3-indoxyl butyrate
B-7100 - 5-Bromo-4-chloro-3-indoxyl caprylate
B-7110 - 5-Bromo-4-chloro-3-indoxyl-beta-D-cellobioside
B-7116 - 5-Bromo-4-chloro-3-indoxyl choline phosphate
B-7141 - 5-Bromo-4-chloro-3-indoxyl-alpha-D-galactopyranoside
B-7150 - 5-Bromo-4-chloro-3-indoxyl-beta-D-galactopyranoside
B-7400 - 5-Bromo-4-chloro-3-indoxyl-beta-D-glucuronic acid, sodium salt
B-7404 - 5-Bromo-4-chloro-3-indoxyl-myo-inositol-1-phosphate, ammonium salt
B-7407 - 5-Bromo-4-chloro-3-indoxyl-alpha-D-maltotrioside
B-7409 - 5-Bromo-4-chloro-3-indoxyl-alpha-D-mannopyranoside
B-7414 - 5-Bromo-4-chloro-3-indoxyl palmitate
B-7470 - 5-Bromo-4-chloro-3-indoxyl phosphate, potassium salt
B-7748 - 5-Bromo-4-chloro-3-indoxyl-alpha-D-xylopyranoside
B-7750 - 5-Bromo-4-chloro-3-indoxyl-beta-D-xylopyranoside


Auxins

The plant hormone Indole-3-acetic acid (also termed IAA or Auxin) is also a derivative of Indole. It occurs naturally in plants and is also frequently used in horticulture. Read more.

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