Indoles

Contacts and URLs:

• Rhodium (homepage, more info)
  Drug chemistry and pharmacology
• Miscellaneous URLs
  • Indole Phyentech
    .MOL files and indole chemistry (related items...)

more...

Images:

• Strychnine 2D structure
  DMT frame highlighted in red

more...

Children:

• Beta-carbolines (Class of indole alkaloids found in P. harmala and B. caapi)
  • 6-MeO-THH (6-methoxy-1-methyl-1,2,3,4-tetrahydro-b-carboline)
    Aldosterone-stimulating hormone. Tihkal #44.
  • Harmaline (3,4-dihydro-7-methoxy-1-methyl-b-carboline)
    Tihkal #13; Primary agent of P. harmala
  • Harmine (7-methoxy-1-methyl-b-carboline)
    Tihkal #14; primary active agent in B. caapi
  • Tetrahydroharmine (7-methoxy-1-methyl-1,2,3,4-tetrahydro-b-carboline)
    Is a serotonin reuptake inhibitor. Tihkal #54.
• Corynantheine-related (Indole alkaloids from Yohimbe, Kratom, and others)
  • Corynantheidine
  • Corynantheine
  • Dihydrocorynantheine
  • Mitragynine (9-methoxy-corynantheidine)
    Primary active principle of Kratom
  • Paynanthine
  • Speciogynine
  • Yohimbine
• Ergolines (Includes LSD and LSA)
  • Agroclavine
  • AL-LAD (N-(6)-allylnorlysergic acid, N,N-diethylamide)
    Tihkal #1.
  • ALD-52 (N-acetyl-LSD)
  • Elymoclavine
  • Ergonovine (9,10-Didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8-carboxamide; Ergonovine)
  • Ergotamine (12-Hydroxy-2-methyl-5-(phenylmethyl)ergotaman-3,6,18-trione)
    Ergot alkaloid that is a precursor to LSD and related substances.
  • ETH-LAD (N-(6)-ethylnorlysergic acid, N,N-diethylamide)
    Tihkal #12.
  • Isoergine (D-isolysergic acid amide)
  • LSA (D-lysergic acid amide)
    Ergine
  • LSD (D-lysergic acid diethylamide)
    One of the most potent psychoactive drugs known, LSD is the prototypical psychedelic. Tihkal #26
  • Lysergene
  • Lysergic Acid
  • Lysergic acid hydroxyethylamide
  • Lysergine
  • Lysergol (9,10-Didehydro-8-hydroxymethyl-6-methyl-ergoline)
  • Methylergonovine (9,10-didehydro-N-[1(hydroxymethyl)propyl]-D-lysergamide)
  • Methysergide (1-methyl-D-lysergic acid butanolamide)
  • Penniclavine
  • PRO-LAD (6-propyl-nor-LSD)
    Tihkal #51.
  • Triseclavine
• Iboganes (Class of indole alkaloids including those derived from the West African shrub, Tabernanthe iboga.)
  • Ibogaine (12-methoxyibogamine)
    Tihkal #25. This indole alkaloid with a distinctive (and synthetically difficult) seven-membered ring is under investigation as a cure for addiction.
  • Voacangine (carbomethoxy-ibogaine)
• Tryptamines (Prototypical indole family including serotonin and such psychedelic drugs as DMT and psilocybin.)
  • 2,a-DMT (2,a-dimethyltryptamine)
    Tihkal #7.
  • 2-Me-DET (N,N-diethyl-2-methyl-tryptamine)
    Tihkal #33; noted for auditory and tactile distortion
  • 2-Me-DMT (2-N,N-trimethyltryptamine)
    Tihkal #34. Sensory stimulant, notably tactile.
  • 4,5-MDO-DIPT (N,N-diisopropyl-4,5-methylenedioxy-tryptamine)
    Tihkal #28.
  • 4,5-MDO-DMT (4,5-methylenedioxy-N,N-dimethyltryptamine)
    Tihkal #30.
  • 4-AcO-DIPT (4-acetoxy-N,N-diisopropyltryptamine)
    This ester of 4-OH-DIPT appeared on the gray market in late 1999.
  • 4-HO-DBT (4-hydroxy-N,N-dibutyltryptamine)
    Tihkal #15.
  • 4-HO-DET (4-hydroxy-N,N-diethyltryptamine)
    Tihkal #16.
  • 4-HO-DIPT (4-hydroxy-N,N-diisopropyltryptamine)
    Tihkal #17.
  • 4-HO-DPT (4-hydroxy-N,N-dipropyltryptamine)
    Tihkal #20.
  • 4-HO-MET (4-hydroxy-N-methyl-N-ethyltryptamine)
    Tihkal #21.
  • 4-HO-MIPT (4-hydroxy-N-methyl-N-isopropyltryptamine)
    Tihkal #22.
  • 4-HO-MPT (4-hydroxy-N-methyl-N-propyltryptamine)
    Tihkal #23.
  • 4-HO-pyr-T (4-hydroxy-N,N-tetramethylenetryptamine)
    Tihkal #24.
  • 4-MeO-MIPT (4-methoxy-N-methyl-N-isopropyltryptamine)
    Tihkal #39.
  • 4-PO-DET (4-phosphoryloxy-N,N-diethyltryptamine)
  • 5,6-MDO-DIPT (5,6-methylenedioxy-N,N-diisopropyltryptamine)
    Tihkal #29.
  • 5,6-MDO-DMT (5,6-methylenedioxy-N,N-dimethyltryptamine)
    Tihkal #31.
  • 5,6-MDO-MIPT (5,6-methylenedioxy-N-methyl-N-isopropyltryptamine)
    Tihkal #32.
  • 5,6-MeO-MIPT (5,6-dimethoxy-N-methyl-N-isopropyltryptamine)
    Tihkal #41.
  • 5-MeO-AMT (5-methoxy-a-methyltryptamine; a,O-DMS)
    Tihkal #5.
  • 5-MeO-DET (5-methoxy-N,N-diethyltryptamine)
    Tihkal #36.
  • 5-MeO-DIPT (5-methoxy-N,N-diisopropyltryptamine)
    Tihkal #37.
  • 5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine)
    Tihkal #38.
  • 5-MeO-MIPT (5-methoxy-N-methyl-N-isopropyltryptamine)
    Tihkal #40.
  • 5-MeO-NMT (5-methoxy-N-methyltryptamine)
    Tihkal #42.
  • 5-MeO-pyr-T (5-methxoy-N,N-tetramethylenetryptamine)
    Tihkal #43.
  • 5-MeO-TMT (5-methoxy-2,N,N-trimethyltryptamine)
    Tihkal #45.
  • 5-MeS-DMT (5-methylthio-N,N-dimethyltryptamine)
    Tihkal #46.
  • AET (a-ethyl-tryptamine)
    Tihkal #11
  • a,N,O-TMS (5-methoxy-a,N-dimethyltryptamine)
    Tihkal #55.
  • a,N-DMT (a,N-dimethyltryptamine)
    Tihkal #8.
  • AMDIPT (a-methyl-N,N-diisopropyltryptamine)
    A rare and novel substance, probably placebo
  • AMT (a-methyltryptamine)
    Tihkal #48. Also known as IT-290.
  • Baeocystine (4-PO-MT; 4-phosphoryloxy-N-methyltryptamine)
  • Bufotenine (5-HO-DMT; 5-hydroxy-N,N-dimethyltryptamine)
    Tihkal #19
  • DBT (N,N-dibutyltryptamine)
    Tihkal #2.
  • DET (N,N-diethyltryptamine)
    Tihkal #3.
  • DIPT (N,N-diisopropyltryptamine)
    Tihkal #4; Noted for its unique auditory effects
  • DMT (N,N-dimethyltryptamine)
    Tihkal #6.
  • DPT (N,N-dipropyltryptamine)
    Tihkal #9.
  • EIPT (N-ethyl-N-isopropyltryptamine)
    Tihkal #10.
  • MBT (N-butyl-N-methyl-tryptamine)
    Tihkal #27.
  • Melatonin (N-acetyl-5-methoxytryptamine)
    Tihkal #35.
  • MIPT (N-methyl-N-isopropyltryptamine)
    Tihkal #47.
  • NET (N-ethyltryptamine)
    Tihkal #49.
  • NIPT (N-isopropyltryptamine)
  • NMT (N-methyltryptamine)
    Tihkal #50.
  • Norbaeocystine (4-phosphoryloxytryptamine)
  • Psilocin (4-HO-DMT; 4-hydroxy-N,N-dimethyltryptamine)
    Tihkal #18
  • Psilocybin (4-PO-DMT; 4-phosphoryloxy-N,N-dimethyltryptamine)
  • pyr-T (N,N-tetramethylenetryptamine)
    Tihkal #52.
  • Serotonin (5-HT; 5-hydroxytryptamine)
    An important neuromodulatory neurotransmitter whose receptors are the site of action of most psychedelic drugs
  • Tryptamine (3-(2-Aminoethyl)indole; 1H-Indole-3-ethanamine)
    Structural basis of a large class of psychedelic drugs, as well as the neurotransmitter serotonin, although not itself psychoactive. Tihkal #53.
• 5-HTP (5-hydroxytryptophan)
  Metabolic precursor to Serotonin
• Indole (2,3-benzopyrrole)
  A commonly used precursor in tryptamine chemistry
• Strychnine
• Tryptophan (3-indol-3-ylalanine; L-tryptophan)
  Amino acid that is the biosynthetic precursor for tryptamines in vivo.