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