tryptamine

Tryptamine is the chemical structure from which many physiologically active chemicals are based upon. Tryptamine itself is shares the phenethylamine structure, which itself serves as the template for many other active chemicals including the neurotransmitter dopamine, and the psychedelic drug mescaline. Tryptamine is produced naturally from the amino acid l-tryptophan.

Tryptamine itself is not active orally. When administered parenterally, its effects are extremely short lived and include an increase in blood pressure, pupil dilation, an increase in the amplitude of the patellar reflex (knee-jerk) (qtd. in Shulgin). Most tryptamine-based compounds share these side-effects.

Chemical Properties

       R5       R6
        \      / 
         CH---CH 
       //      \\ 
   R4--CH       CH  
        \      /  
         C====C
         |     \
         |      NH
         |     /
         C====CH 
        /      \            
       CH2      R2
        \
         CH2--α
        /
        NH3

Melting Point: 114-119°C
Boiling Point: 137°C @ 0.15 mm Hg
Flash Point: 185°C
(ChemFinder)

Derivatives

Here is an extensive (yet incomplete) list of tryptamine derivatives. Most of these have entries in TiHKAL, or at least are mentioned. They are organized arbitrarily but hopefully intuitively.

Neurotransmitters and Endogenous Tryptamines

• serotonin (5-hydroxy-tryptamine)
• melatonin (N-acetyl-5-methoxytryptamine)
• DMT (N,N-dimethyltryptamine)
• 5-MeO-DMT (N,N-dimethyl-5-methoxytryptamine)

N,N-dialkyl Substitutions

• DMT (N,N-dimethyltryptamine)
• DET (N,N-diethyltryptamine)
• DPT (N,N-dipropyltryptamine)
• DiPT (N,N-diisopropyltryptamine)
• DBT (N,N-dibutyltryptamine)

Asymmetric N Substitutions

• Inactive: MBT (N-butyl-N-methyltryptamine), NMT (N-methyltryptamine), NET (N-ethyltryptamine), NPT (N-propyltryptamine), NIPT (N-ethyltryptamine)
• Unknown:PiPT (N-propyl-N-isopropyltryptamine), BiPT (N-butyl-N-isopropyltryptamine)
• MIPT (N-methyl-N-isopropyltryptamine)
• EIPT (N-ethyl-N-isopropyltryptamine)

α Substitutions

• AMT (α-methyltryptamine, indopan)
• AET (α-ethyltryptamine monase)
• 2,α-DMT (2,α-dimethyltryptamine
• 5-MeO-AMT (5-methoxy-αmethyltryptamine, α,O-dimethylserotonin)
• α,N-DMT (&alpha,N-dimethyltryptamine)
• a,N,O-TMS (5-methoxy-α,N-dimethyltryptamine)

4-hydroxy Substitutions

Phosphate and acetate esters are metabolized into the indolol. Their effects are similar but differ in dose, chronology, and chemical stability.

• Unknown: 4-HO-DPT (4-hydroxy-N,N-dipropyltryptamine), 4-HO-DBT (4-hydroxy-N,N-dibutyltryptamine), 4-HO-AMT (4-hydroxy-α-methyltryptamine)
• 4-HO-DMT (4-hydroxy-N,N-dimethyltryptamine, psilocin)
• 4-HO-DET (N,N-diethyl-4-hydroxytryptamine)
• 4-HO-DPT (4-hydroxy-N,N-dipropyltryptamine)
• 4-HO-DiPT (4-hydroxy-N,N-diisopropyltryptamine)
• 4-HO-pyr-T (4-hydroxy-N,N-tetramethylenetryptamine)
  
• 4-HO-MET (N-ethyl-4-hydroxy-N-methyltryptamine)
• 4-HO-MPT (4-hydroxy-N-methyl-N-propyltryptamine)
• 4-HO-MiPT (4-hydroxy-N-methyl-N-isopropyltryptamine)

5-methoxy Substitutions

Attaching a methoxy group to the five position alters the quality of the effects significantly, and results in an increase in potency. Many of these chemicals have been ascribed aphrodisiac properties.

• Unknown: 5-MeO-NMT (5-methoxy-N-methyltryptamine)
• 5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine)
• 5-MeO-DET (N,N-diethyl-5-methoxytryptamine)
• 5-MeO-DPT (5-methoxy-N,N-dipropyltryptamine)
• 5-MeO-DiPT (5-methoxy-N,N-diisopropyltryptamine)
• 5-MeO-MIPT (5-methoxy-N-methyl-N-isopropyltryptamine)
• 5-MeO-pyr-T (5-methoxy-N,N-tetramethylenetryptamine)
• 5-MeO-TMT (5-methoxy-2,N,N-trimethyltryptamine)

Other Tryptamine Derivatives of Interest

• bufotenine (5-hydroxy-N,N-dimethyltryptamine)
• 5-MeS-DMT (N,N-dimethyl-5-methylthiotryptamine)
• ergot alkaloids such as LSD, ergine, and lysergic acid amide
• 5-fluoro-α-methyltryptamine
• ibogaine
• harmala alkaloids
• Halogen-substituted tryptamines are similar in quality to their non-halogen-substituted counterparts.

References

Shulgin, Alexander. TiHKAL: The Continuation (Part II). http://www.erowid.org/library/books_online/tihkal/tihkal53.shtml

ChemFinder. accessed 14 April 2003. http://www.chemfinder.com.